list of psicoactive plants

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list of psicoactive plants

ContentsList of psychoactive plants 1Tryptamine 30Dimethyltryptamine 34Monoamine oxidase inhibitor 45Acanthaceae 52Fittonia albivenis 60Justicia pectoralis 62Aceraceae 64Acer saccharinum 65Aizoaceae 69Delosperma cooperi 76Apocynaceae 78Prestonia amazonica 86Voacanga africana 87Fabaceae 89Acacia acuminata 97Acacia alpina 99Acaciella angustissima 100Vachellia aroma 105Acacia auriculiformis 107Acacia baileyana 110Acacia beauverdiana 113Senegalia berlandieri 114Senegalia catechu 117Vachellia caven 121Senegalia chundra 123Acacia colei 125Acacia complanata 127Acacia confusa 128Vachellia cornigera 131Acacia cultriformis 133Acacia cuthbertsonii 135Acacia decurrens 137Acacia delibrata 141Acacia falcata 142Vachellia farnesiana 144

Acacia flavescens 148Acacia floribunda 149Acacia georginae 151Vachellia horrida 153Acacia implexa 155Mimosa tenuiflora 156Vachellia karroo 161Senegalia laeta 165Acacia longifolia 167Acacia sophorae 171Acacia macradenia 172Acacia maidenii 175Acacia mangium 178Acacia melanoxylon 181Senegalia mellifera 185Vachellia nilotica 187Vachellia nilotica subsp. adstringens 191Acacia obtusifolia 192Vachellia oerfota 194Acacia penninervis 195Acacia phlebophylla 197Acacia podalyriifolia 199Senegalia polyacantha 201Vachellia rigidula 203Acacia sassa 206Acacia schaffneri 207Senegalia senegal 210Vachellia seyal 214Vachellia sieberiana 217Acacia simplex 220Vachellia tortilis 222Acacia vestita 225Acacia victoriae 226Albizia inundata 228Anadenanthera colubrina 230Anadenanthera colubrina var. cebil 235Anadenanthera peregrina 238Anadenanthera peregrina var. peregrina 244

Bufotenin 245Desmanthus illinoensis 250Desmanthus leptolobus 252Desmodium caudatum 254Codariocalyx motorius 255Desmodium triflorum 257Leonurus sibiricus 259Lespedeza capitata 261Lespedeza bicolor 263Mimosa ophthalmocentra 265Mimosa scabrella 266Mimosa somnians 268Mimosa verrucosa 270Mucuna pruriens 272Phyllodium pulchellum 279Caesalpinioideae 280Lauraceae 282Malpighiaceae 289Diplopterys cabrerana 291Myristicaceae 292Horsfieldia superba 295Virola calophylla 296Virola callophylloidea 297Virola carinata 298Virola cuspidata 299Virola divergens 300Virola elongata 301Virola melinonii 303Virola multinervia 304Virola pavonis 305Virola peruviana 307Virola rufula 308Virola sebifera 309Virola surinamensis 312Virola venosa 314Ochnaceae 315Testulea gabonensis 318Pandanus 319

Poaceae 324Arundo donax 332Phalaris aquatica 341Phalaris arundinacea 343Phalaris brachystachys 346Phragmites 348Polygonaceae 353Punica 356Pomegranate 358Rubiaceae 373Mitragyna speciosa 379Psychotria carthagenensis 385Psychotria expansa 387Psychotria forsteriana 388Psychotria insularum 389Psychotria poeppigiana 390Psychotria rostrata 393Psychotria rufipilis 394Psychotria viridis 395Rutaceae 399Limonia acidissima 402Zanthoxylum procerum 406Urticaceae 407

ReferencesArticle Sources and Contributors 410Image Sources, Licenses and Contributors 417

Article LicensesLicense 429

List of psychoactive plants 1

List of psychoactive plants

Salvia divinorum, a psychedelic sage

A list of plants that are used as hallucinogens. Some of themhave been used for thousands of years for religious purposes.The plants are listed according to the substances they contain.

THC

Cannabis plant

Cannabis (Marijuana) is a popular psychoactive plant that is often used recreationally.Cannabis is also unique in that it contains a psychoactive substance, THC, whichcontains no nitrogen and is not an indole, tryptamine, phenethylamine, anticholinergic(deliriant), or a dissociative drug. Cannabis plants tend to vary, with different strainsproducing dynamic balances of psychoactive cannabinoids (THC, CBD, etc.) that causedifferent strains to produce markedly different effects, popular strains often beinghybrids of both Cannabis sativa and Cannabis indica. Some universities and researchfirms currently study the medicinal effects of cannabis. Many jurisdictions have lawsregulating (or outright prohibiting) the sale and use of medical cannabis to treat pain,insomnia, and stimulate appetite.

Tryptamines

DMT Molecule in 2D

Many of the psychedelic plants contain dimethyltryptamine (DMT), which iseither snorted (Virola, Yopo snuffs), smoked, or drunk with MAOIs(Ayahuasca). It cannot simply be eaten as it is not orally active without anMAOI and it needs to be extremely concentrated to be smokable.


DMT Molecule in 3D

Acanthaceae

Species, Alkaloid content, where given, refers to dried material Fittonia albivenis, a common ornamental plant from South America. It is

useful in the treatment of headaches, etc. Justicia pectoralis, DMT in leaves

Aceraceae

Acer saccharinum (Silver Maple Tree) was found to contain the indole alkaloid gramine (not active and extremelytoxic) 0.05% in the leaves, so it is possible that other members of this plant family contain active compounds.[1]

Aizoaceae Delosperma acuminatum, DMT, 5-MEO-DMT[2]

Delosperma cooperi, DMT, 5-MEO-DMT Delosperma ecklonis, DMT Delosperma esterhuyseniae, DMT Delosperma hallii, 5-MEO-DMT Delosperma harazianum, DMT, 5-MEO-DMT Delosperma harazianum

Shibam, DMT Delosperma hirtum, DMT Delosperma hallii

aff. litorale Delosperma lydenbergense, DMT, 5-MEO-DMT

Delosperma nubigenum, 5-MEO-DMT

Delosperma pageanum, DMT, 5-MEO-DMT Delosperma pergamentaceum, Traces of DMT Delosperma tradescantioides, DMT


Apocynaceae Prestonia amazonica: DMT Voacanga africana: Iboga alkaloids

Fabaceae (Leguminosae) Acacia acuminata, Up to 1.5% alkaloids, mainly consisting of dimethyltryptamine in bark & leaf Also, Harman,

Tryptamine, NMT, other alkaloids in leaf. Acacia alpina, Active principles in leaf[3]

Acacia angustissima, -methyl-phenethylamine, NMT and DMT in leaf (1.1-10.2 ppm)[4]

Acacia aroma, Tryptamine alkaloids.[5] Significant amount of tryptamine in the seeds.[6]

Acacia auriculiformis, 5-MeO-DMT in stem bark[7]

Acacia baileyana, 0.02% tryptamine and -carbolines, in the leaf, Tetrahydroharman

Acacia beauverdiana, Psychoactive[8] Ash used in Pituri.[9]

Acacia berlandieri, DMT, amphetamines, mescaline, nicotine[10]


Acacia catechu, DMT[2] and other tryptamines in leaf, bark

Acacia caven, Psychoactive[11]

Acacia chundra, DMT and other tryptamines in leaf, bark Acacia colei, DMT[12]

Acacia complanata, 0.3% alkaloids in leaf and stem, almost allN-methyl-tetrahydroharman, with traces of tetrahydroharman, some oftryptamine[13][14][15]

Acacia confusa, DMT & NMT in leaf, stem & bark 0.04% NMT and 0.02% DMT in stem. AlsoN,N-dimethyltryptamine N-oxide[16]

Acacia cornigera, Psychoactive, Tryptamines[17]

DMT according to C. Rastch. Acacia cultriformis, Tryptamine, in the leaf, stem and seeds. Phenethylamine in leaf and

seeds

Acacia cuthbertsonii, Psychoactive Acacia decurrens, Psychoactive, but less than 0.02% alkaloids[]


Acacia delibrata, Psychoactive Acacia falcata, Psychoactive, but less than 0.02% alkaloids Psychoactive 0.2-0.3%

alkaloids Acacia farnesiana, Traces of 5-MeO-DMT[18] in fruit. -methyl-phenethylamine,

flower.[19] Ether extracts about 2-6% of the dried leaf mass.[20] Alkaloids are present inthe bark[21] and leaves.[22] Amphetamines and mescaline also found in tree.

Acacia flavescens, Strongly Psychoactive, Bark. Acacia floribunda, Tryptamine, phenethylamine, in flowers other tryptamines,

DMT,tryptamine,NMT 0.3-0.4% phyllodes.[23]

Acacia georginae, Psychoactive, plus deadly toxins Acacia horrida, Psychoactive

Acacia implexa, Psychoactive[24]

Acacia jurema, DMT, NMT Acacia karroo, Psychoactive

Acacia laeta, DMT, in the leaf Acacia longifolia, 0.2% tryptamine in bark, leaves, some in flowers, phenylethylamine in

flowers, 0.2% DMT in plant. Histamine alkaloids.

Acacia sophorae, Tryptamine in leaves, bark Acacia macradenia, Tryptamine Acacia maidenii, 0.6% NMT and DMT in about a 2:3 ratio in the stem bark, both present

in leaves


Acacia mangium, Psychoactive

Acacia melanoxylon, DMT, in the bark and leaf,[25] but less than 0.02% total alkaloids

Acacia mellifera, DMT, in the leaf

Acacia nilotica, DMT, in the leaf

Acacia nilotica subsp. adstringens, Psychoactive, DMT in the leaf Acacia neurophylla DMT in bark, Harman in leaf.[26]

Acacia obtusifolia, Tryptamine, DMT, NMT, other tryptamines,[24] 0.4-0.5% in driedbark,0.15-0.2% in leaf, 0.07% in branch tips.[27]

Acacia oerfota, Less than 0.1% DMT in leaf,[28] NMT Acacia penninervis, Psychoactive Acacia phlebophylla, 0.3% DMT in leaf, NMT


Acacia podalyriaefolia, Tryptamine in the leaf, 0.5% to 2% DMT in fresh bark,phenethylamine, trace amounts. Although this species is claimed to contain 0.5% to 2%DMT in fresh bark the reference for this is invalid as there is no reference to AcaciaPodalyriffolia anywhere in the reference article. Additionally, well known and provenextraction techniques for DMT have failed to produce any DMT or alkaloids from freshbark or the leaves on multiple sample taken at various seasons. Should DMT actually exist

in this species of Acacia then it exists in extremely small amounts and have failed to produce any alkaloids withAcid/Base extraction techniques using HCl/Na(OH)2. On the same note, more academic research is definitelyrequired into the DMT content of this and other Australian Acacia species with proper chemical analysis ofsample.[citation needed]

Acacia polyacantha, DMT in leaf and other tryptamines in leaf, bark

Acacia polyacantha ssp. campylacantha, Less than 0.2% DMT in leaf, NMT; DMT andother tryptamines in leaf, bark

Acacia rigidula, DMT, NMT, tryptamine, traces of amphetamines, mescaline, nicotineand others

Acacia sassa, Psychoactive Acacia schaffneri, -methyl-phenethylamine, Phenethylamine[29] Amphetamines and

mescaline also found.

Acacia senegal, Less than 0.1% DMT in leaf, NMT, other tryptamines. DMT in plant,DMT in bark.

Acacia seyal, DMT, in the leaf. Ether extracts about 1-7% of the dried leaf mass. Acacia sieberiana, DMT, in the leaf


Acacia simplex

, DMT and NMT, in the leaf, stem and trunk bark, 0.81% DMT in bark, MMT[30]

Acacia tortilis, DMT, NMT, and other tryptamines

Acacia vestita, Tryptamine, in the leaf and stem, but less than 0.02% total alkaloids

Acacia victoriae, Tryptamines, 5-MeO-alkyltryptamine List of Acacia Species Having Little or No Alkaloids in the Material Sampled: (0%

C 0.02%, Concentration of Alkaloids)

Acacia acinacea Acacia baileyana Acacia decurrens Acacia dealbata

Acacia mearnsii Acacia drummondii Acacia elata Acacia falcata Acacia leprosa Acacia linearis Acacia melanoxylon Acacia pycnantha Acacia retinodes Acacia saligna Acacia stricta Acacia verticillata Acacia vestita

Albizia inundata leaves contain DMT. Anadenanthera colubrina, Bufotenin, Beans,[31][32] Bufotenin oxide, Beans, N,N-Dimethyltryptamine, Beans,

pods,


Anadenanthera colubrina var. cebil - Bufotenin and Dimethyltryptamine have beenisolated from the seeds and seed pods, 5-MeO-DMT from the bark of the stems.[33] Theseeds were found to contain 12.4% bufotenine, 0.06% 5-MeO-DMT and 0.06% DMT.

Anadenanthera peregrina, 1,2,3,4-Tetrahydro-6-methoxy-2,9-dimethyl-beta-carboline,Plant,[32] 1,2,3,4-Tetrahydro-6-methoxy-2-methyl-beta-carboline, Plant,

5-Methoxy-N,N-dimethyltryptamine, Bark, 5-Methoxy-N-methyltryptamine, Bark, Bufotenin, plant, beans,Bufotenin N-oxide, Fruit, beans, N,N-Dimethyltryptamine-oxide, Fruit[34]

Anadenanthera peregrina var. peregrina, Bufotenine is in the seeds.[35]

Desmanthus illinoensis, 0% - 0.34% DMT in root bark, highly variable.[36] Also NMT,N-hydroxy-N-methyltryptamine, 2-hydroxy-N-methyltryptamine, and gramine (toxic).

Desmanthus leptolobus, 0.14% DMT in root bark, more reliable than D. illinoensis

Desmodium caudatum (syn. Ohwia caudata ), Roots: 0.087% DMT, Desmodium intortum, Bufotentine, DMT[37]

Codariocalyx motorius(syn. Desmodium gyrans), DMT, 5-MEO-DMT, leaves, roots

Desmodium racemosum, 5-MEO-DMT Desmodium triflorum, 0.0004% DMT-N-oxide, roots,[38] less in stems and trace in leaves.

Leonurus sibiricus', Alkaloids Lespedeza capitata,


Lespedeza bicolor, DMT, 5-MEO-DMT in leaves and roots

Lespedeza bicolor var. japonica, DMT, 5-MEO-DMT in leaves and root bark Mimosa ophthalmocentra, Dried root: DMT 1.6%, NMT 0.0012% and hordenine 0.0065% Mimosa scabrella, Tryptamine, NMT, DMT and N-methyltetrahydrocarboline in bark

Mimosa somnians, Trytamines and MMT Mimosa tenuiflora (syn. "Mimosa hostilis"), 0.31-0.57% DMT (dry root bark).[39]

mimosa hostilis contains dmt and 5-meo-dmt.

Mimosa verrucosa, DMT in root bark Mucuna pruriens, "The leaves, seeds, stems and roots contain L-Dopa, Serotonin, 5-HTP,

and Nicotine, as well as N,N-DMT, Bufotenine, and 5-MeO-DMT."[40]

Petalostylis casseoides, 0.4-0.5% tryptamine, DMT, etc. in leaves and stems Petalostylis labicheoides var. casseoides, DMT in leaves and stems Phyllodium pulchellum(syn. Desmodium pulchellum), 0.2% 5-MeO-DMT, small

quantities of DMT DMT (dominates in seedlings and young plants), 5-MEO-DMT(dominates in mature plant), whole plant, roots, stems, leaves, flowers

Erythrina flabelliformis, other Erythrina species, seeds contain the alkaloids Erysodin andErysovin


Caesalpinioideae subfamily Petalostylis cassioides [41]: 0.4-0.5% tryptamine, DMT, etc. in leaves and stems[41]

Petalostylis labicheoides [43], Tryptamines in leaves and stems, MAO's up to 0.5%[42]

Lauraceae Nectandra megapotamica, NMT[42]

Malpighiaceae Diplopterys cabrerana: DMT 0.17-1.74%, average of 0.47% DMT[43]

Myristicaceae Horsfieldia superba: 5-MeO-DMT and beta-carbolines Iryanthera macrophylla: 5-MeO-DMT in bark Iryanthera ulei: 5-MeO-DMT in bark Osteophloem platyspermum: DMT, 5-MeO-DMT in bark Virola calophylla, Leaves 0.149% DMT, leaves 0.006% MMT 5-MeO-DMT in bark Virola callophylloidea, DMT Virola carinata, DMT in leaves Virola cuspidata, DMT Virola divergens, DMT in leaves Virola elongata(syn. Virola theiodora), DMT, 5-MEO-DMT in bark, roots, leaves and flowers

Virola melinonii, DMT in bark Virola multinervia, DMT, 5-MEO-DMT in bark and roots Virola pavonis, DMT in leaves Virola peruviana, 5-MEO-DMT, traces of DMT and 5-MeO-tryptamine in bark Virola rufula, Alkaloids in bark and root, 95% of which is MeO-DMT[44] 0.190%

5-MeO-DMT in bark, 0.135% 5-MeO-DMT in root, 0.092% DMT in leaves. Virola sebifera, The bark contains 0.065% to 0.25% alkaloids, most of which are DMT and 5-MeO-DMT.[45]

Virola surinamensis, DMT in bark Virola venosa, DMT, 5-MEO-DMT in roots, leaves DMT

Ochnaceae Testulea gabonensis: 0.2% 5-MeO-DMT, small quantities of DMT, DMT in bark and root bark, NMT

Ochnaceae Genus Pandanus (Screw Pine): DMT in nuts

Poaceae (Gramineae)Some Graminae (grass) species contain gramine, which can cause brain damage, other organ damage, centralnervous system damage and death in sheep. Arundo donax, 0.0057% DMT in dried rhizome, no stem, 0.026% bufotenine, 0.0023% 5-MeO-MMT[46]


Phalaris aquatica, 0.0007-0.18% Total alkaloids, 0.100% DMT,[47] 0.022%5-MeO-DMT, 0.005% 5-OH-DMT

Phalaris arundinacea, 0.0004-0.121% Total alkaloids[]

Phalaris brachystachys, Aerial parts up to 3% total alkaloids, DMT present[citation needed]

Phragmites australis, DMT in roots. None of the above alkaloids are said to have beenfound in Phalaris californica, Phalaris canariensis, Phalaris minor and hybrids of P.arundinacea together with P. aquatica.

Polygonaceae

Erigonum sp.: DMT

Punicaceae

Punica granatum "DMT in root cortex;" The dried stem and root bark of the tree containabout 0.4-0.9% alkaloids.[48]

Rubiaceae Mitragyna speciosa, 7-hydroxymitragynine Psychotria carthagenensis, 0.2% average DMT in dried leaves Psychotria expansa, DMT Psychotria forsteriana, DMT Psychotria insularum, DMT Psychotria poeppigiana, DMT


Psychotria rostrata, DMT Psychotria rufipilis, DMT Psychotria viridis, DMT 0.1-0.61% dried mass.[49]

Rutaceae

Dictyoloma incanescens, 5-MeO-DMT in leaves, 0.04% 5-MeO-DMT in bark[]

Dutaillyea drupacea, > 0.4% 5-MeO-DMT in leaves Dutaillyea oreophila, 5-MeO-DMT in leaves Tetradium ruticarpum(syn. Evodia rutaecarpa), 5-MeO-DMT in leaves, fruit and roots

Limonia acidissima, 5-MeO-DMT in stems

Euodia leptococca (formerly Melicope), 0.2% total alkaloids, 0.07% 5-MeO-DMT;5-MeO-DMT in leaves and stems, also "5-MeO-DMT-Oxide and a beta-carboline"

Pilocarpus organensis, 5-MeO-DMT in leaves Vepris ampody, Up to 0.2% DMT in leaves and branches Zanthoxylum arborescens, DMT in leaves Zanthoxylum procerum, DMT in leaves


Urticaceae Urtica pilulifera: Bufotenin

PhenethylaminesSpecies, Alkaloid Content (Fresh) - Alkaloid Content (Dried)

Echinopsis lageniformis (syn. Trichocereus bridgesii), Mescaline > 0.025%, also3,4-dimethoxyphenylethylamine < 1%, 3-methoxytyramine < 1%, tyramine < 1% -Mescaline 2%[50]

Echinopsis scopulicola (syn. Trichocereus scopulicola), Mescaline[51]

Echinopsis pachanoi

(syn. Trichocereus pachanoi), Mescaline 0.006-0.12%, 0.05% Average - Mescaline0.01%-2.375%

Echinopsis spachiana

(syn. Trichocereus spachianus), Mescaline[52] - Mescaline Lophophora williamsii

(Peyote), 0.4% Mescaline[51] - 3-6% Mescaline Opuntia acanthocarpa

Mescaline[52]

Opuntia basilaris


Mescaline 0.01%, plus 4-hydroxy-3-5-dimethoxyphenethylamine Austrocylindropuntia cylindrica (syn. Opuntia cylindrica),[53] Mescaline Cylindropuntia echinocarpa

(syn. Opuntia echinocarpa), Mescaline 0.01%, 3-4-dimethoxyphenethylamine 0.01%,4-hydroxy-3-5-dimethoxyphenethylamine 0.01%

Cylindropuntia spinosior (syn. Opuntia spinosior),[54] Mescaline 0.00004%,3-methoxytyramine 0.001%, tyramine 0.002%, 3-4-dimethoxyphenethylamine.

Echinopsis macrogona

(syn. Trichocereus macrogonus), > 0.01-0.05% Mescaline[55]

Echinopsis peruviana

(syn. Trichocereus peruvianus), Mescaline 0.0005%-0.12%[] - Mescaline Echinopsis tacaquirensis subsp. taquimbalensis (syn. Trichocereus taquimbalensis),[56] >

0.005-0.025% Mescaline Echinopsis terscheckii

(syn. Trichocereus terscheckii, Trichocereus werdemannianus)[57] > 0.005-0.025%Mescaline - Mescaline 0.01%-2.375%

Echinopsis valida, 0.025% Mescaline[51]

Pelecyphora aselliformis, Mescaline[51]


Beta-carbolines

Harmaline, aBeta-carboline

Beta-carbolines are "reversible" MAO-A inhibitors. They are found in some plants usedto make Ayahuasca. In high doses the harmala alkaloids are somewhat hallucinogenic ontheir own.

Apocynaceae

Amsonia tabernaemontana, Harmine Aspidosperma exalatum, Beta-carbolines[58]

Aspidosperma polyneuron, Beta-carbolines Apocynum cannabinum, Harmalol

Ochrosia nakaiana, Harman Pleicarpa mutica, Beta-carbolines

Bignoniaceae

Newbouldia laevis, Harman

Calycanthaceae Calycanthus occidentalis, Harmine

Chenopodiaceae

Hammada leptoclada, Tetrahydroharman, etc. Kochia scoparia, Harmine, etc.

Combretaceae Guiera senegalensis, Harman, etc.

Cyperaceae Carex brevicollis, Harmine, etc. Carex parva, Beta-carbolines

Elaeagnaceae Elaeagnus angustifolia, Harman, etc.

Elaeagnus commutata, Beta-carbolines


Elaeagnus hortensis, Tetrahydroharman, etc. Elaeagnus orientalis, Tetrahydroharman Elaeagnus spinosa, Tetrahydroharman Hippophae rhamnoides, Harman, etc. Shepherdia argentea, Tetrahydroharmol

Shepherdia canadensis, Tetrahydroharmol

Gramineae

Arundo donax, Tetrahydroharman

Festuca arundinacea, Harman, etc.

Lolium perenne, (Perennial Ryegrass), Harman, etc.

Phalaris aquatica, Beta-carbolines Phalaris arundinacea, Beta-carbolines

Lauraceae

Nectandra megapotamica, Beta-carbolines


Leguminosae Acacia baileyana, Tetrahydroharman Acacia complanata, Tetrahydroharman, etc. Burkea africana, Harman, etc. Desmodium gangeticum, Beta-carbolines Desmodium gyrans, Beta-carbolines Desmodium pulchellum, Harman, etc. Mucuna pruriens, 6-Methoxy-Harman Petalostylis labicheoides, Tetrahydroharman; MAO's up to 0.5% Prosopis nigra, Harman, etc. Shepherdia pulchellum, Beta-carbolines

Loganiaceae Strychnos melinoniana, Beta-carbolinesStrychnos usambarensis, Harman

Malpighiaceae Banisteriopsis argentia, 5-methoxytetrahydroharman, (-)-N(6)-methoxytetrahydroharman,

dimethyltryptamine-N(6)-oxide Banisteriopsis caapi, Harmine 0.31-0.84%,[59] tetrahydroharmine, telepathine, dihydroshihunine,[60]

5-MeO-DMT in bark Banisteriopsis inebrians, Beta-carbolines Banisteriopsis lutea, Harmine, telepathine Banisteriopsis metallicolor, Harmine, telepathine Banisteriopsis muricata, Harmine up to 6%, harmaline up to 4%, plus DMT Diplopterys cabrerana, Beta-carbolines

Cabi pratensis, Beta-carbolines Callaeum antifebrile(syn. Cabi paraensis), Harmine Tetrapterys methystica(syn. Tetrapteris methystica), Harmine[61]

Myristicaceae Gymnacranthera paniculata, Beta-carbolines Horsfieldia superba Beta-carbolines Virola cuspidata, 6-Methoxy-Harman Virola rufula, Beta-carbolines Virola theiodora, Beta-carbolines


Ochnaceae Testulea gabonensis, Beta-carbolines

Palmae Plectocomiopsis geminiflora, Beta-carbolines

Papaveraceae Meconopsis horridula, Beta-carbolines Meconopsis napaulensis, Beta-carbolines

Meconopsis paniculata, Beta-carbolines Meconopsis robusta, Beta-carbolines Meconopsis rudis, Beta-carbolines Papaver rhoeas, Beta-carbolines

Passifloraceae

Passiflora actinia, Harman Passiflora alata, Harman

Passiflora alba, Harman Passiflora bryonoides, Harman Passiflora caerulea, Harman

Passiflora capsularis, Harman Passiflora decaisneana, Harman Passiflora edulis, Harman, 0-7001 ppm in fruit

Passiflora eichleriana, Harman


Passiflora foetida, Harman Passiflora incarnata (with bee), Harmine, Harmaline, Harman, etc. 0.03%.[62] Alkaloids

in rind of fruit 0.25%

Passiflora quadrangularis, Harman

Passiflora ruberosa, Harman Passiflora subpeltata, Harman

Passiflora warmingii, Harman

Polygonaceae

Calligonum minimum, Beta-carbolines Leptactinia densiflora, Leptaflorine, etc.

Ophiorrhiza japonica, Harman Pauridiantha callicarpoides, Harman Pauridiantha dewevrei, Harman Pauridiantha lyalli, Harman Pauridiantha viridiflora, Harman Simira klugei, Harman Simira rubra, Harman

Rubiaceae Borreria verticillata, Beta-carbolines Leptactinia densiflora, Beta-carbolines Nauclea diderrichii, Beta-carbolines Ophiorrhiza japonica, Beta-carbolines Pauridiantha callicarpoides, Beta-carbolines Pauridiantha dewevrei, Beta-carbolines Pauridiantha yalli, Beta-carbolines Pauridiantha viridiflora, Beta-carbolines Pavetta lanceolata, Beta-carbolines Psychotria carthagenensis, Beta-carbolines Psychotria viridis, Beta-carbolines Simira klugei, Beta-carbolines


Simira rubra, Beta-carbolines Uncaria attenuata, Beta-carbolines Uncaria canescens, Beta-carbolines Uncaria orientalis, Beta-carbolines

Rutaceae Tetradium (syn. Evodia) species: Some contain carbolines Euodia leptococca Beta-carboline Araliopsis tabouensis, Beta-carbolines Flindersia laevicarpa, Beta-carbolines Xanthoxylum rhetsa, Beta-carbolines

Sapotaceae Chrysophyllum lacourtianum, Norharman etc. Scutellaria Scutellaria nana

Simaroubaceae Ailanthus malabarica, Beta-carbolines. See also Nag Champa. Perriera madagascariensis, Beta-carbolines Picrasma ailanthoides, Beta-carbolines Picrasma crenata, Beta-carbolines Picrasma excelsa, Beta-carbolines Picrasma javanica, Beta-carbolines

Solanaceae Vestia foetida, (Syn V. lycioides) Beta-carbolines

Vestia foetida

Symplocaceae

Symplocos racemosa, Harman

Tiliaceae

Grewia mollis, Beta-carbolines

Zygophyllaceae

Fagonia cretica, Harman

Nitraria schoberi, Beta-carbolines Peganum harmala, (Syrian Rue), The seeds contain about 2-6% alkaloids, most of which

is harmaline.[63] Peganum harmala is also an abortifacient.


Peganum nigellastrum, Harmine Tribulus terrestris, Harman

Zygophyllum fabago, Harman, harmine

Plants containing other psychoactive substances

Acoraceae: Acorus calamus, asarone

Salvinorin A Salvia divinorum

Salvinorin A, 0.89-3.87mg/g, also Salvinorin B andSalvinorin C[64]

Cathinone Catha edulis

Khat

Unknown Foeniculum

vulgare

Unknown

Unknown

Justicia pectoralis Unknown


Pukateine

Laurelianovae-zelandiae

Pukateine

Thujone

Artemisia vulgaris

Thujone

Damianin

Turnera diffusa

Damianin

unknown

Magnoliavirginiana

The leaves or bark have been placed in cupped hands overthe nose and inhaled as a mild hallucinogen

Bulbocapnine Corydalis solida,

Corydalis cava

Bulbocapnine, Nantenine, Tetrahydropalmatine

Kavalactones

Piper methysticum

Kavalactones


Lagochilin

Lagochilusinebrians

Lagochilin is thought to be responsible for the sedative,hypotensive and hemostatic effects of this plant.

Unknown

Tagetes lucida

Anethole, Chavicol, Coumarin, Estragole, Isorhamnetin,Methyleugenol, Quercitin

Lactucarium

Lactuca virosa

Lactucarium

Glaucine Glaucium flavum

Glaucine

Muscarinic Galbulimima belgraveana

Galbulimima belgraveana is rich in alkaloids andtwenty-eight alkaloids have been isolated. Himbacine,himbeline, himandravine, himgravine, himbosine,himandridine, himandrine, G.B. 1, G. B. 2, G. B. 3, G. B. 4,G. B. 5, G. B. 6, G. B. 7, G. B. 8, G. B. 9, G. B. 10, G. B. 11,G. B. 12, himgaline, himbadine, G. B. 13, himgrine, G. B. 14,G. B. 15, G. B. 16, G. B. 17 and G. B. 18.

Unknown Zornia latifolia

Zornia latifolia, is mentioned in Food of the Gods as "anhallucinogenic substitute for cannabis". It's nicknamedMaconha brava because locals use it as a cannabis substitute.

Unknown Argemone mexicana

Used by Chinese residents of Mexico during the early 20thcentury as a legal substitute for opium and currently smokedas a marijuana substitute.

Ergine

Argyreia nervosa(Hawaiian Baby Woodrose)

Seeds contain high amounts of LSA (also known asd-lysergic acid amide, d-lysergamide, ergine, and LA-111),often 50-150X the amounts found in Ipomoea violacea.


Ibogaine

Tabernanthe iboga

Ibogaine in root bark[65]

Ibogaine

Tabernanthe orientalis Ibogaine in root leaves

Ibogaine

Tabernanthe pubescens Ibogaine and similar alkaloids

Ibogaine

Tabernaemontana sp. Ibogaine

Ibogaine Trachelospermum

jasminoides

Ibogaine[66]

Aporphine

Nymphaea caerulea

Recent studies have shown Nymphaea caerulea to havepsychedelic properties, and may have been used as asacrament in ancient Egypt and certain ancient SouthAmerican cultures. Dosages of 5 to 10grams of the flowersinduces slight stimulation, a shift in thought processes,enhanced visual perception, and mild closed-eye visuals.Nymphaea caerulea is related to, and possesses similaractivity as Nelumbo nucifera, the Sacred Lotus. BothNymphaea caerulea and Nelumbo nucifera contain thealkaloids nuciferine and apomorphine, which have beenrecently isolated by independent labs.[citation needed]

These psychoactive effects make Nymphaea caerulea a likelycandidate (among several) for the lotus plant eaten by themythical Lotophagi in Homer's Odyssey.

Used in aromatherapy, Nymphaea caerulea is purported tohave a "divine" essence, bringing euphoria, heightenedawareness and tranquility.[citation needed]

Other sources cite anti-spasmodic and sedative, purifying andcalming properties.


Leonurine

Leonotis leonurus

Both leaves and flowers (where most concentrated) containLeonurine. (Effects reminiscent of marijuana)

Leonurine

Leonotis nepetifolia

Both leaves and flowers (where most concentrated) containLeonurine. (Effects reminiscent of marijuana)

Active Chemical Unknown

Calea zacatechichi

Produces vivid dreams after smoking. It is also employed bythe Chontal people as a medicinal herb againstgastrointestinal disorders, and is used as an appetizer,cathartic anti-dysentery remedy, and as a fever-reducingagent. Its psychedelic properties do not become apparentuntil the user is asleep.

Unknown

Silene capensis

Produces vivid dreams after smoking.

Convolvulaceae:


Ipomoea tricolor & Ipomoea violacea

D-lysergic acid amide and lysergic acid amides in the seeds; up to 0.12% total

Rivea corymbosa Seeds contain D-lysergic acid amide, lysergol, and turbicoryn; lysergic acid alkaloids up to0.03%

Some Mirabilis sp. (Actually in Nyctaginaceaefamily)

LSA[citation needed]

Apocynaceae family: Catharanthus roseus is (perhaps unpleasantly) "hallucinogenic."[67]

Vinca minorAquifoliaceae family: Ilex guayusa, which is used as an additive to some versions of Ayahuasca. According to the Ecuadorian

indigenous, it is also slightly hallucinogenic on its own, when drunk in high enough quantities.Euphorbiaceae family: Alchornea floribunda, YohimbineLoganaceae family: Desfontainia spinosa, causes visions[68]

Lythraceae family: Heimia myrtifolia, auditory[69]

Heimia salicifolia, auditory

References[1] IJ PACHTER, DE ZACHARIAS, O RIBEIRO - The Journal of Organic Chemistry, 1959 - (http:/ / pubs. acs. org/ cgi-bin/ abstract. cgi/

joceah/ 1959/ 24/ i09/ f-pdf/ f_jo01091a032. pdf?sessid=6006l3)[2] Trouts Notes on Sacred Cacti (http:/ / www. entheogen. com/ component/ option,com_docman/ task,doc_download/ gid,6/ Itemid,42/ )[3] Shaman Australis (http:/ / shaman-australis. com. au/ shop/ index. php?cPath=21_26_72)[4][4] Nutritive value assessment of the tropical shrub legume Acacia angustissima: anti-nutritional compounds and in vitro digestibility. Personal

Authors: McSweeney, C. S., Krause, D. O., Palmer, B., Gough, J., Conlan, L. L., Hegarty, M. P.Author Affiliation: CSIRO LivestockIndustries, Long Pocket Laboratories, 120 Meiers Road, Indooroopilly, Qld 4068, Australia. Document Title: Animal Feed Science andTechnology, 2005 (Vol. 121) (No. 1/2) 175-190

[5] Maya Ethnobotanicals (http:/ / www. maya-ethnobotanicals. com/ product_info. phtml/ herbid_340/ category_ayahuasca)[6] Acacia (Polish) (http:/ / herbarium. 0-700. pl/ Akacje. html)[7] Lycaeum (http:/ / leda. lycaeum. org/ ?ID=15931)[8] www.bushfood.net (http:/ / www. bushfood. net/ viewtopic. php?p=3443)[9] Duboisia hopwoodii - Pituri Bush - Solanaceae - Central America (http:/ / www. entheology. org/ edoto/ anmviewer. asp?a=47)[10] Ask Dr. Shulgin Online: Acacias and Natural Amphetamine (http:/ / www. cognitiveliberty. org/ shulgin/ adsarchive/ acacia. htm)[11] Index of Rtsch, Christian. Enzyklopdie der psychoaktiven Pflanzen, Botanik, Ethnopharmakologie und Anwendungen, 7. Auflage. AT

Verlag, 2004, 941 Seiten. ISBN 3-85502-570-3 at (http:/ / www. deutschesfachbuch. de/ info/ detail. php?isbn=3855025703& part=4&word=)

[12] www.abc.net.au (http:/ / www. abc. net. au/ science/ k2/ stn/ q& a/ notes/ 051027-9. htm)[13] Acacia Complanata Phytochemical Studies (http:/ / users. lycaeum. org/ ~mulga/ acacia/ comphy. html)[14] Lycaeum -- Acacias and Entheogens (http:/ / users. lycaeum. org/ ~mulga/ acacia/ entheo. html)[15] Lycaeum (http:/ / leda. lycaeum. org/ ?ID=15796)


[16] NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa (http:/ / doi. wiley. com/ 10. 1002/mrc. 1959) Malcolm S. Buchanan, Anthony R. Carroll, David Pass, Ronald J. Quinn Magnetic Resonance in Chemistry Volume 45, Issue 4 ,Pages359 - 361. John Wiley & Sons, Ltd.

[17] Naturheilpraxis Fachforum (German) (http:/ / web. archive. org/ web/ 20080626102405/ http:/ / www. naturheilpraxis. de/ exclusiv/nh-online/ 2005/ nhp05/ a_nh-ff02. html)

[18] Lycaeum (http:/ / leda. lycaeum. org/ ?ID=15965)[19] Dr. Duke's Phytochemical and Ethnobotanical Databases (http:/ / www. ars-grin. gov/ duke/ plants. html)[20] Wattle Seed Workshop Proceedings 12 March 2002, Canberra March 2003 RIRDC Publication No 03/024, RIRDC Project No WS012-06

(http:/ / www. rirdc. gov. au/ reports/ AFT/ 03-024. pdf)[21] www.bpi.da.gov.ph (http:/ / www. bpi. da. gov. ph/ Publications/ mp/ pdf/ a/ aroma. pdf)[22] Purdue University (http:/ / www. hort. purdue. edu/ newcrop/ duke_energy/ Acacia_farnesiana. html)[23][23] Voogelbreinder, S. "Garden Of Eden" 2009[24] wiki.magiskamolekyler.org (Swedish) (http:/ / wiki. magiskamolekyler. org/ index.

php?title=Lista_ver_hallucinogena_vxter,_svampar_och_djur)[25] extentech.sheetster.com (http:/ / extentech. sheetster. com/ knowledgebase/ wiki_search. jsp?search=acacia)[26][26] S. Voogelbreinder "Garden Of Eden" 2009[27] Acacia obtusifolia Phytochemical Studies (http:/ / users. lycaeum. org/ ~mulga/ acacia/ obtuphy. html)[28] Plants Containing DMT (German) (http:/ / www. drogen-forum. com/ wiki/ index. php/ DMT-haltige_Pflanzen)[29] Chemistry of Acacias from South Texas (http:/ / uvalde. tamu. edu/ pdf/ chemtdaf. pdf)[30] Arbeitsstelle fr praktische Biologie (APB) (http:/ / www. factorey. ch/ Eins. htm)[31] UNO (http:/ / www. unodc. org/ unodc/ en/ bulletin/ bulletin_1965-01-01_2_page006. html?print=yes)[32] Dr. Duke's (http:/ / sun. ars-grin. gov:8080/ npgspub/ xsql/ duke/ plantdisp. xsql?taxon=71) Phytochemical and Ethnobotanical Databases[33] Herbotechnica (Spanish) (http:/ / www. herbotecnia. com. ar/ aut-curupay. html)[34] Psychedelics Encyclopedia By Peter G. Stafford, p. 313. (http:/ / books. google. com/ books?id=Ec5hNgYWHtkC& pg=RA2-PA313&

lpg=RA2-PA313& dq="dmt+ n+ oxide"& source=web& ots=BqP13bWy2d& sig=YDxzS2LNTLuBTLU8F3bPdEX0oWY)[35] PubMed (http:/ / www. ncbi. nlm. nih. gov/ entrez/ query. fcgi?cmd=Retrieve& db=PubMed& list_uids=11718320& dopt=Citation)[36] Desmanthus (Ayahuasca: alkaloids, plants & analogs) (http:/ / www. erowid. org/ library/ books_online/ ayahuasca_apa/

aya_sec3_part2_desmanthus. shtml)[37] Pharmaceutical-Neutraceutical Bulletin, Final (http:/ / www. crcsalinity. com/ documents/ key_publications/ Pharma-neutra bull final. pdf)[38] Trout's Notes on Desmodium (http:/ / trout. yage. net/ sc/ D2_2004_Trout. pdf)[39] Ask Erowid ID 75 (http:/ / www. erowid. org/ ask/ ask. php?ID=75)[40] Erowid entry(2002) (http:/ / www. erowid. org/ plants/ mucuna_pruriens/ )[41] Bluezoo Tryptamines (http:/ / bluezoo. org/ tryptamines/ plants. html)[42] Plants Containing DMT (http:/ / www. dmt-nexus. com/ phpBB2/ viewtopic. php?t=26)[43] DMT Plants List (http:/ / www. psychonaut. com/ index. php?Itemid=11& option=com_forum& page=viewtopic& t=25189& lang=nl)[44] www.tryptamines.com (http:/ / www. tryptamines. com/ )[45] Committee for veterinary medicinal products virola sebifera summary report (http:/ / www. emea. europa. eu/ pdfs/ vet/ mrls/ 060499en.

pdf)[46] Erowid Arundo Donax Info Page 1 (http:/ / www. erowid. org/ plants/ arundo_donax/ arundo_donax_info1. shtml)[47] Erowid Phalaris FAQ (http:/ / www. erowid. org/ plants/ phalaris/ phalaris_faq. shtml)[48] Pomegranate (Herbdata New Zealand) (http:/ / www. herbdatanz. com/ pomeganate. htm)[49] Amazing Nature (http:/ / www. amazing-nature. com/ -i-36. html?osCsid=38ad41e62a454589a0afd2d17ae0fa40)[50] Trichocereus (http:/ / www. a1b2c3. com/ drugs/ var014. htm)[51][51] Lycaeum[52] Visionary Cactus Guide (http:/ / users. lycaeum. org/ ~iamklaus/ botany. htm#)[53] Austrocylindropuntia cylindrica (http:/ / www. desert-tropicals. com/ Plants/ Cactaceae/

Opuntia_cylindrica. html)[54] Cylindropuntia spinosior (www.desert-tropicals.com) (http:/ / www. desert-tropicals. com/ Plants/ Cactaceae/ Opuntia_spinosior. html)[55] Partial List of Alkaloids in Trichocereus Cacti (http:/ / www. thenook. org/ archives/ tek/ alklist. htm)[56] Echinopsis tacaquirensis ssp. taquimbalensis (http:/ / www. desert-tropicals. com/ Plants/ Cactaceae/ Echinopsis_taquimb. html)[57] www.desert-tropicals.com (http:/ / www. desert-tropicals. com/ Plants/ Cactaceae/ Echinopsis_terscheckii. html)[58] Angiosperm Families Containing Beta-Carbolines (http:/ / www. ansci. cornell. edu/ plants/ toxicagents/ betacarbolines/ bcarbfams. html)[59] Callaway JC, Brito GS & Neves ES (2005). Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis. Journal of Psychoactive

Drugs 37(2): 145-150.[60] John Stephen Glasby, Dictionary of Plants Containing Secondary Metabolites, Published by CRC Press (http:/ / books. google. com/

books?id=te53VV5u8YMC& pg=RA1-PA124& lpg=RA1-PA124& dq=erythrina+ alkaloids& source=web& ots=e5SBqn4GS7&sig=JdEQoIKcYwAM7N_cTUtCQNhl6Hc)

[61] Erowid - Ayahuasca: alkaloids, plants & analogs


[62] www.drugs.com (http:/ / www. drugs. com/ npp/ passion-flower. html)[63] www.amazing-nature.com (http:/ / www. amazing-nature. com/ -i-43. html)[64] Clones of Salvia divinorum (http:/ / www. sagewisdom. org/ clones. html)[65] Tihkal (http:/ / www. erowid. org/ library/ books_online/ tihkal/ tihkal25. shtml)[66] Trachelospermum jasminoides (www.giftpflanzen.com) (http:/ / www. giftpflanzen. com/ trachelospermum_jasminoides. html)[67] Catharanthus roseus (http:/ / sliceoftheday. wordpress. com/ 2007/ 05/ 13/ madagascar-periwinkle-catharanthus-roseus/ )[68][68] Schultes, Richard Evans, Iconography of New World Plant Hallucinogens. p. 101[69] Sinicuichi FAQ (http:/ / www. erowid. org/ plants/ sinicuichi/ sinicuichi_faq. shtml)

External links The Salvia Divinorum Blog Research And Information (http:/ / www. salviadivinorumblog. com) The Salvia Divinorum Mass Distribution Project (http:/ / forum. salviadivinorumblog. com) Descriptions of psychoactive Cacti. Lycaeum Visionary Cactus Guide (http:/ / users. lycaeum. org/ ~iamklaus/

botany. htm#) "Herbal Highs Legal Buds Reviews" (http:/ / drugreviews. info) Components of street drug alternatives sold and

used legally. Erowid Tryptamine FAQ More Plants Containing Tryptamines (http:/ / www. erowid. org/ psychoactives/ faqs/

faqs_tryptamine. shtml) John Stephen Glasby, Dictionary of Plants Containing Secondary Metabolites, Published by CRC Press (http:/ /

books. google. com/ books?id=te53VV5u8YMC& pg=RA1-PA124& lpg=RA1-PA124& dq=erythrina+alkaloids& source=web& ots=e5SBqn4GS7& sig=JdEQoIKcYwAM7N_cTUtCQNhl6Hc)

Golden Guide to Hallucinogenic Plants (http:/ / www. erowid. org/ library/ books_online/ golden_guide/ g91-100.shtml)

Hallucinogens on the Internet: A Vast New Source of Underground Drug Information John H. Halpern, M.D. andHarrison G. Pope, Jr., M.D. (http:/ / ajp. psychiatryonline. org/ cgi/ content/ full/ 158/ 3/ 481)

Peter L. Katavic, Chemical Investigations of the Alkaloids From the Plants Of The Family [[Elaeocarpaceae(http:/ / www4. gu. edu. au:8080/ adt-root/ uploads/ approved/ adt-QGU20070710. 160928/ public/ 02Whole.pdf)]], School of Science/Natural Product Discovery (NPD), Faculty of Science, Griffith University

Alexander T. Shulgin, Psychotomimetic Drugs: Structure-Activity Relationships (http:/ / www. erowid. org/archive/ rhodium/ chemistry/ shulgin. pea. sar. hop. html)

UNODC The plant kingdom and hallucinogens (part II) (http:/ / www. unodc. org/ unodc/ en/ bulletin/bulletin_1969-01-01_4_page004. html)

UNODC The plant kingdom and hallucinogens (part III) (http:/ / www. unodc. org/ unodc/ bulletin/bulletin_1970-01-01_1_page005. html?print=yes)

Virola Dried Herbarium Specimens (http:/ / www. bio. uu. nl/ ~herba/ Guyana/ VTGG/ Myristicaceae/ Virola/index. html)

Virola Species Pictures USGS (http:/ / images. nbii. gov/ search_results. php) Desmanthus illinoensis USDA (http:/ / plants. usda. gov/ java/ profile?symbol=DEIL) A General Introduction to Ayahuasca (http:/ / www. ayahuasca-info. com/ ) Psychedelic Reader (Google Books) (http:/ / books. google. com/ books?id=iEVeFOLc_FUC& pg=PA93&

lpg=PA93& dq="Prestonia+ amazonica"& source=web& ots=WWANl44f-H&sig=7EuWEQsMW3yVHi56Ks0BfjJhf44& hl=en#PPA92,M1)

Tryptamine 30

Tryptamine

Tryptamine

Identifiers

CAS number 61-54-1 [1]

PubChem 1150 [2]

ChEMBL CHEMBL6640 [3]

IUPHAR ligand 125 [4]

Jmol-3D images Image 1 [5]

Properties

Molecular formula C10H12N2Molar mass 160.22 g mol1

Appearance white to orange crystalline powder[1]

Melting point 113-116C

Boiling point 137C

Solubility in water negligible solubility in water

Hazards

Flash point 185C

(verify) [7](what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25C (77F), 100kPa)

Infobox references

Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It contains an indole ring structure, and isstructurally similar to the amino acid tryptophan, from which it derives its name. Tryptamine is found in traceamounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.The tryptamine chemical structure is the backbone for a group of compounds termed collectively tryptamines. Thisgroup includes many biologically active compounds, including neurotransmitters and psychedelic drugs.The concentration of tryptamine in rat brains is about 3.5 pmol/g.

Tryptamine 31

Plants containing tryptamineMany plants contain small amounts of tryptamine, for example, as a possible intermediate in one biosyntheticpathway to the plant hormone indole-3-acetic acid. Higher concentrations can be found in many Acacia species.

Role in vertebratesTryptamine acts as a serotonin releasing agent and a serotonergic activity enhancer. It is metabolised by MAO-A andMAO-B.

Tryptamine derivativesWell-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved inregulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are sometimes used byhumans and other animals, notably, the Jaguar, for their psychotropic effects. A Jaguar is seen eating yage(banisteriopsis caapi), a plant with high concentrations of the tryptamines harmine and harmaline, in an interestingclip borrowed from the "Peculiar Potions" episode of BBC's series "Weird Nature". Prominent examples oftryptamines include psilocybin (from "Psilocybin mushrooms") and DMT (from numerous plant sources, e.g.chacruna, often used in ayahuasca brews). Many synthetic tryptamines have also been made, including the migrainedrug sumatriptan and its relatives. The tables below list some tryptamines.

General structure of substituted tryptamines

The tryptamine structure, in particular its indole ring, may be part ofthe structure of some more complex compounds, for example: LSD,ibogaine and yohimbine. A thorough investigation of dozens oftryptamine compounds was published by Ann and Alexander Shulginunder the title TiHKAL.

Short Name Origin R R4 R5 RN1 RN2 Full Name

Tryptamine Natural H H H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine

Bufotenin Natural H H OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine

N-methylserotonin(norbufotenin)

Natural H H OH CH3 H 5-hydroxy-N-methyltryptamine

Serotonin Natural H H OH H H 5-hydroxytryptamine

DMT Natural H H H CH3 CH3 N,N-dimethyltryptamine

Melatonin Natural H H OCH3 O=C-CH3 H 5-methoxy-N-acetyltryptamine

5-Bromo-DMT Natural H H Br CH3 CH3 5-bromo-N,N-dimethyltryptamine

5-MeO-DMT Natural H H OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine

5-MeO-NMT Natural H H OCH3 CH3 H 5-methoxy-N-methyltryptamine

NMT Natural H H H H CH3 N-methyltryptamine

Norbaeocystin Natural H OPO3H2 H H H 4-phosphoryloxy-tryptamine

Baeocystin Natural H OPO3H2 H CH3 H 4-phosphoryloxy-N-methyl-tryptamine

Tryptamine 32

Psilocybin Natural H PO4 H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine

Psilocin Natural H OH H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine

Tryptophan Natural COOH H H H H -carboxyltryptamine

ET artificial CH2CH3 H H H H -ethyltryptamine

MT artificial CH3 H H H H -methyltryptamine

DALT artificial H H H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine

DET artificial H H H CH2CH3 CH2CH3 N,N-diethyltryptamine

DiPT artificial H H H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine

DPT artificial H H H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine

5-MeO-MT artificial CH3 H OCH3 H H 5-methoxy--methyltryptamine

5-MeO-DALT artificial H H OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine

4-HO-DET artificial H OH H CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine

4-AcO-DMT artificial H OCOCH3 H CH3 CH3 4-acetoxy-N,N-dimethyltryptamine

4-HO-MET artificial H OH H CH3 CH2CH3 4-hydroxy-N-methyl-N-ethyltryptamine

4-HO-DIPT artificial H OH H CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine

5-MeO-DIPT artificial H H OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine

4-HO-MiPT artificial H OH H CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine

Sumatriptan artificial H H CH2SO2NHCH3 CH3 CH3 5-(methylaminosulfonylmethylene)-N,N-dimethyltryptamine

Zolmitriptan artificial H H -(CHNHC=OOCH2) CH3 CH3 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine

Short Name Origin R R4 R5 RN1 RN2 Full Name

|+ Selected tryptamines |+ (see also Table of naturally occurring tryptamines)

SynthesisThe AbramovitchShapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamines startingfrom a -carboline.

Tryptamine 33

References[1] "http:/ / www. chemicalbook. com/ ProductChemicalPropertiesCB8192006_EN. htm"

External links Tryptamine FAQ (http:/ / www. erowid. org/ psychoactives/ faqs/ faqs_tryptamine. shtml) Tryptamine Hallucinogens and Consciousness (http:/ / www. tryptamind. com/ tryptamine. html) Tryptamind Psychoactives (http:/ / www. tryptamind. com/ ), reference site on tryptamine and other

psychoactives. Tryptamine (T) entry in TiHKAL info (http:/ / tihkal. info/ read. php?domain=tk& id=53)

Dimethyltryptamine 34

Dimethyltryptamine

Dimethyltryptamine

Systematic (IUPAC) name

2-(1H-indol-3-yl)-N,N-dimethylethanamine

Clinical data

Legal status Prohibited (S9) (AU) Schedule III (CA) CD Lic (UK) Schedule I (US)

Routes Oral (with an MAOI), Insufflated, Rectal, vaporized, IM, IV

Identifiers

CAS number 61-50-7 [1]

ATC code None

PubChem CID 6089 [2]

IUPHAR ligand 141 [3]

DrugBank DB01488 [4]

ChemSpider 5864 [5]

UNII WUB601BHAA [6]

KEGG C08302 [7]

ChEBI CHEBI:28969 [8]

ChEMBL CHEMBL12420 [9]

Chemical data

Formula C12H16N2

Mol. mass 188.269 g/mol

Physical data

Density 1.099g/mlg/cm


Melt. point 40C (104F)

Boiling point 160C (320F)@ 0.6Torr (80Pa)also reported as80135C (176275F)@ 0.03Torr (4.0Pa)

(what is this?) (verify) [10]

N,N-Dimethyltryptamine (DMT or N,N-DMT) is a compound of the tryptamine family. Its presence is widespreadthroughout the plant kingdom. DMT occurs in trace amounts in mammals, including humans, where it putativelyfunctions as a trace amine neurotransmitter/neuromodulator. It is originally derived from the essential amino acidtryptophan and ultimately produced by the enzyme INMT during normal metabolism. The significance of itswidespread natural presence remains undetermined. DMT is structurally analogous to the neurotransmitter serotonin(5-HT) and the hormone melatonin, and furthermore functionally analogous to other psychedelic tryptamines, suchas 5-MeO-DMT, bufotenin, psilocin, and psilocybin.When ingested, DMT acts as a psychedelic drug. Depending on the dose and method of administration, its subjectiveeffects can range from short-lived milder psychedelic states to powerful immersive experiences; these are oftendescribed as a total loss of connection to external reality and an experience of encountering indescribablespiritual/alien realms. Indigenous Amazonian Amerindian cultures consume DMT as the primary psychoactive inayahuasca, a shamanistic brew used for divinatory and healing purposes. Pharmacologically, ayahuasca combinesDMT with an MAOI, an enzyme inhibitor that allows DMT to be orally active.

HistoryDMT was first synthesized in 1931 by Canadian chemist Richard Helmuth Fredrick Manske (19011977). Itsdiscovery as a natural product is generally credited to Brazilian chemist and microbiologist Oswaldo Gonalves deLima (19081989) who, in 1946, isolated an alkaloid he named nigerina (nigerine) from the root bark of juremapreta, that is, Mimosa tenuiflora.[1] However, in a careful review of the case Jonathan Ott shows that the empiricalformula for nigerine determined by Gonalves de Lima, which notably contains an atom of oxygen, can only match apartial, "impure" or "contaminated" form of DMT. It was only in 1959, when Gonalves de Lima provided Americanchemists a sample of Mimosa tenuiflora roots, that DMT was unequivocally identified in this plant material. Lessambiguous is the case of isolation and formal identification of DMT in 1955 in seeds and pods of Anadenantheraperegrina by a team of American chemists led by Evan Horning (19161993). Since 1955 DMT has been found in ahost of organisms: in at least fifty plant species belonging to ten families, and in at least four animal species,including one gorgonian and three mammalian species.Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive tothe vine Banisteriopsis caapi to make ayahuasca decoctions. In 1957, American chemists Francis Hochstein andAnita Paradies identified DMT in an "aqueous extract" of leaves of a plant they named Prestonia amazonicum (sic)and described as "commonly mixed" with B. caapi. The lack of a proper botanical identification of Prestoniaamazonica in this study led American ethnobotanist Richard Evans Schultes (19152001) and other scientists toraise serious doubts about the claimed plant identity. A better evidence is produced in 1965 by Frenchpharmacologist Jacques Poisson who isolated DMT as sole alkaloid from leaves, provided and used by AguarunaIndians, identified as pertaining to the vine Diplopterys cabrerana (then known as Banisteriopsis rusbyana).Published in 1970, the first identification of DMT in the other commonly used additiveWikipedia:Please clarify plantPsychotria viridis was made by a team of American researchers led by pharmacologist Ara der Marderosian. Notonly did they detect DMT in leaves of P. viridis obtained from Cashinahua Indians, but they also were the first toidentify it in a sample of an ayahuasca decoction, prepared by the same Indians.


Biosynthesis

Biosynthetic pathway forN,N-dimethyltryptamine

Dimethyltryptamine is an indole alkaloid derived from the shikimate pathway. Itsbiosynthesis is relatively simple and summarized in the picture to the left. In plants,the parent amino acid L-tryptophan is produced endogenously where in animalsL-tryptophan is an essential amino acid coming from diet. No matter the source ofL-tryptophan, the biosynthesis begins with its decarboxylation by an aromatic aminoacid decarboxylase (AADC) enzyme (step 1). The resulting decarboxylatedtryptophan analog is tryptamine. Tryptamine then undergoes a transmethylation (step2): the enzyme indolethylamine-N-methyltransferase (INMT) catalyzes the transfer ofa methyl group from cofactor S-adenosyl-methionine (SAM), via nucleophilic attack,to tryptamine. This reaction transforms SAM into S-adenosylhomocysteine (SAH),and gives the intermediate product N-methyltryptamine (NMT). NMT is in turntransmethylated by the same process (step 3) to form the end productN,N-dimethyltryptamine. Tryptamine transmethylation is regulated by two productsof the reaction: SAH, and DMT were shown ex vivo to be among the most potentinhibitors of rabbit INMT activity.

This transmethylation mechanism has been repeatedly and consistently proven byradiolabeling of SAM methyl group with carbon-14 (14C-CH3)SAM).

Evidence in mammals

Published in Science in 1961, Julius Axelrod found an N-methyltransferase enzymecapable of mediating biotransformation of tryptamine into DMT in a rabbit's lung.This finding initiated a still ongoing scientific interest in endogenous DMTproduction in humans and other mammals. From then on, two major complementarylines of evidence have been investigated: localization and further characterization of

the N-methyltransferase enzyme, and analytical studieslooking for endogenously produced DMT in body fluids andtissues.

In 2013, researchers first reported DMT in the pineal gland microdialysate of rodents.

INMT

Before techniques of molecular biology were used to localize indolethylamine N-methyltransferase (INMT),characterization and localization went on a par: samples of the biological material where INMT is hypothesized to beactive are subject to enzyme assay. Those enzyme assays are performed either with a radiolabeled methyl donor like(14C-CH3)SAM to which known amounts of unlabeled substrates like tryptamine are added, or with addition of aradiolabeled substrate like (14C)NMT to demonstrate in vivo formation. As qualitative determination of theradioactively tagged product of the enzymatic reaction is sufficient to characterize INMT existence and activity (orlack of), analytical methods used in INMT assays aren't required to be as sensitive as those needed to directly detectand quantify the minute amounts of endogenously formed DMT (see DMT subsection below). The essentiallyqualitative method thin layer chromatography (TLC) was thus used in a vast majority of studies. Also, robustevidence that INMT can catalyze transmethylation of tryptamine into NMT and DMT could be provided withreverse isotope dilution analysis coupled to mass spectrometry for rabbit and human lung during the early 1970s.Selectivity rather than sensitivity proved to be an Achilles heel for some TLC methods with the discovery in 19741975 that incubating rat blood cells or brain tissue with (14C-CH3)SAM and NMT as substrate mostly yields tetrahydro--carboline derivatives, and negligible amounts of DMT in brain tissue. It is indeed simultaneously realized that the TLC methods used thus far in almost all published studies on INMT and DMT biosynthesis are


incapable to resolve DMT from those tetrahydro--carbolines. These findings are a blow for all previous claims ofevidence of INMT activity and DMT biosynthesis in avian and mammalian brain, including in vivo, as they all reliedupon use of the problematic TLC methods: their validity is doubted in replication studies that make use of improvedTLC methods, and fail to evidence DMT-producing INMT activity in rat and human brain tissues. Published in1978, the last study attempting to evidence in vivo INMT activity and DMT production in brain (rat) with TLCmethods finds biotransformation of radiolabeled tryptamine into DMT to be real but "insignificant". Capability of themethod used in this latter study to resolve DMT from tetrahydro--carbolines is questioned later. To localize INMT, a qualitative leap is accomplished with use of modern techniques of molecular biology, and ofimmunohistochemistry. In humans, a gene encoding INMT is determined to be located on chromosome 7. Northernblot analyses reveal INMT messenger RNA (mRNA) to be highly expressed in rabbit lung, and in human thyroid,adrenal gland, and lung.[2] Intermediate levels of expression are found in human heart, skeletal muscle, trachea,stomach, small intestine, pancreas, testis, prostate, placenta, lymph node, and spinal cord. Low to very low levels ofexpression are noted in rabbit brain, and human thymus, liver, spleen, kidney, colon, ovary, and bone marrow. INMTmRNA expression is absent in human peripheral blood leukocytes, whole brain, and in tissue from 7 specific brainregions (thalamus, subthalamic nucleus, caudate nucleus, hippocampus, amygdala, substantia nigra, and corpuscallosum). Immunohistochemistry showed INMT to be present in large amounts in glandular epithelial cells of smalland large intestines, and to be absent in neurons.

Endogenous DMT

The first claimed detection of mammalian endogenous DMT was published in June 1965: German researchers F.Franzen and H. Gross report to have evidenced and quantified DMT, along with its structural analog bufotenin(5-OH-DMT), in human blood and urine. In an article published four months later, the method used in their study isstrongly criticized, and credibility of their results challenged.A 2013 study found DMT in microdialysate obtained from a rat's pineal gland, providing evidence of endogenousDMT in the mammalian brain.In 2001, surveys, made in research articles, point that few of the analytical methods previously used to measurelevels of endogenously formed DMT had enough sensitivity and selectivity to produce reliable results. Gaschromatography, preferably coupled to mass spectrometry (GC-MS), is considered a minimum requirement. A studypublished in 2005 implements the most sensitive and selective method ever used to measure endogenous DMT:liquid chromatography-tandem mass spectrometry with electrospray ionization (LC-ESI-MS/MS) allows to reachlimits of detection (LODs) 12 to 200 fold lower (that is, better) than those attained by the best methods employed inthe 1970s. The data summarized in the table below are from studies conforming to the abovementioned requirements(abbreviations used: CSF = cerebrospinal fluid; LOD = limit of detection; n = number of samples; ng/L and ng/kg =nanograms (109 g) per litre, and nanograms per kilogram, respectively):

DMT in body fluids and tissues (NB: units have been harmonized)

Species Sample Results

Human Blood serum < LOD (n = 66)

Blood plasma < LOD (n = 71) < LOD (n = 38); 1,000 & 10,600ng/L (n = 2)

Whole blood < LOD (n = 20); 50790ng/L (n = 20)

Urine < 100ng/L (n = 9) < LOD (n = 60); 160540ng/L (n = 5) Detected in n = 10 by GC-MS

Feces < 50ng/kg (n= 12); 130ng/kg (n = 1)

Kidney 15ng/kg (n = 1)

Lung 14ng/kg (n = 1)

Lumbar CSF 100,370ng/L (n = 1); 2,3307,210ng/L (n = 3); 350 & 850ng/L (n = 2)


Rat Kidney 12 &16ng/kg (n = 2)

Lung 22 & 12ng/kg (n = 2)

Liver 6 & 10ng/kg (n = 2)

Brain 10 &15ng/kg (n = 2) Measured in synaptic vesicular fraction

Rabbit Liver < 10ng/kg (n = 1)

Physical and chemical properties

DMT crystals

DMT is commonly handled and stored as a fumarate,[citation needed] asother DMT acid salts are generally very hygroscopic and will notreadily crystallize. Its freebase form, although less stable than DMTfumarate, is favored by recreational users choosing to vaporize thechemical because it has a lower boiling point.[citation needed] In contrastto DMT's base, its salts are water-soluble. DMT in solution degradesrelatively quickly and should be stored protected from air, light, andheat in a freezer.[citation needed]

Pharmacology

PharmacokineticsDMT peak level concentrations (Cmax) measured in whole blood after intramuscular (IM) injection (0.7mg/kg, n =11) and in plasma following intravenous (IV) administration (0.4mg/kg, n = 10) of fully psychedelic doses are in therange of 14 to 154 g/L and 32 to 204 g/L, respectively. The corresponding molar concentrations of DMT aretherefore in the range of 0.0740.818 M in whole blood and 0.1701.08 M in plasma. However, several studieshave described active transport and accumulation of DMT into rat and dog brain following peripheral administration.Similar active transport, and accumulation processes likely occur in human brain and may concentrate DMT in brainby several-fold or more (relatively to blood), resulting in local concentrations in the micromolar or higher range.Such concentrations would be commensurate with serotonin brain tissue concentrations which have beenconsistently determined to be in the 1.5-4 M range.Closely coextending with peak psychedelic effects, mean time to reach peak concentrations (Tmax) was determinedto be 1015 minutes in whole blood after IM injection, and 2 minutes in plasma after IV administration. When takenorally mixed in an ayahuasca decoction, and in freeze-dried ayahuasca gel caps, DMT Tmax is considerably delayed:107.59 32.5 minutes, and 90120 minutes, respectively. The pharmacokinetics for vaporizing DMT have not beenstudied or reported.

PharmacodynamicsDMT binds non-selectively with affinities < 0.6 M to the following serotonin receptors: 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT6, and 5-HT7. An agonist action has been determined at 5-HT1A, 5-HT2A and 5-HT2C. Its efficacies at other serotonin receptors remain to be determined. Of special interest will be the determination of its efficacy at human 5-HT2B receptor as two in vitro assays evidenced DMT high affinity for this receptor: 0.108 M and 0.184 M. This may be of importance because chronic or frequent uses of serotonergic drugs showing preferential high affinity and clear agonism at 5-HT2B receptor have been causally linked to valvular heart


disease.It has also been shown to possess affinity for the dopamine D1, 1-adrenergic, 2-adrenergic, imidazoline-1, sigma-1(1), and trace amine-associated receptors. Agonism was demonstrated at 1 M at the rat trace amine-associatedreceptor 1 (TAAR1) and converging lines of evidence established activation of the 1 receptor at concentrations of50100 M. Its efficacies at the other receptor binding sites are unclear. It has also been shown in vitro to be asubstrate for the cell-surface serotonin transporter (SERT) and the intracellular vesicular monoamine transporter 2(VMAT2), inhibiting SERT-mediated serotonin uptake in human platelets at an average concentration of 4.00 0.70M and VMAT2-mediated serotonin uptake in vesicles (of army worm Sf9 cells) expressing rat VMAT-2 at anaverage concentration of 93 6.8 M.As with other so-called "classical hallucinogens", a large part of DMT psychedelic effects can be attributed to afunctionally selective activation of the 5-HT2A receptor. DMT concentrations eliciting 50% of its maximal effect(half maximal effective concentration = EC50 or Kact) at the human 5-HT2A receptor in vitro are in the 0.1180.983M range. This range of values coincides well with the range of concentrations measured in blood and plasma afteradministration of a fully psychedelic dose (see Pharmacokinetics).As DMT has been shown to have slightly better efficacy (EC50) at human serotonin 2C receptor than at 2A receptor,5-HT2C highly likely also is implicated in DMT's overall effects. Other receptors, such as 5-HT1A 1, and TAAR1may also play a role.In 2009 it was hypothesized that DMT may be an endogenous ligand for the 1 receptor. The concentration of DMTneeded for 1 activation in vitro (50100 M) is similar to the behaviorally active concentration measured in mousebrain of approximately 106 M This is minimally 4 orders of magnitude (104) higher than the average concentrationsmeasured in rat brain tissue or human plasma under basal conditions (see Endogenous DMT), so 1 receptors arelikely to be activated only under conditions of high local DMT concentrations. If DMT is stored in synaptic vesicles,such concentrations might occur during vesicular release. To illustrate, while the average concentration of serotoninin brain tissue is in the 1.5-4 M range, the concentration of serotonin in synaptic vesicles was measured at 270 mM.Following vesicular release, the resulting concentration of serotonin in the synaptic cleft, to which serotoninreceptors are exposed, is estimated to be about 300 M. Thus, while in vitro receptor binding affinities, efficacies,and average concentrations in tissue or plasma are useful, they are not likely to predict DMT concentrations in thevesicles or at synaptic or intracellular receptors. Under these conditions, notions of receptor selectivity are moot, andit seems probable that most of the receptors identified as targets for DMT (see above) participate in producing itspsychedelic effects.

Psychedelic properties"So I did it and...there was a something, like a flower, like a chrysanthemum in orange and yellow that was sort of spinning,spinning, and then it was like I was pushed from behind and I fell through the chrysanthemum into another place that didn't seem likea state of mind, it seemed like another place. And what was going on in this place aside from the tastefully soffited indirect lighting,and the crawling geometric hallucinations along the domed walls, what was happening was that there were a lot of beings in there,what I call self-transforming machine elves. Sort of like jewelled basketballs all dribbling their way toward me. And if they'd hadfaces they would have been grinning, but they didn't have faces. And they assured me that they loved me and they told me not to beamazed; not to give way to astonishment."

Terence McKenna, on his first experience with DMT[3]

DMT is produced naturally in many species of plants often in conjunction with its close chemical relatives 5-MeO-DMT and bufotenin (5-OH-DMT). DMT-containing plants are commonly used in South American Shamanic practices. It is usually one of the main active constituents of the drink ayahuasca, however ayahuasca is sometimes brewed with plants which don't produce DMT. It occurs as the primary psychoactive alkaloid in several plants including Mimosa tenuiflora, Diplopterys cabrerana, and Psychotria viridis. DMT is found as a minor alkaloid in snuff made from Virola bark resin in which 5-MeO-DMT is the main active alkaloid. DMT is also found as a minor


alkaloid in bark, pods, and beans of Anadenanthera peregrina and Anadenanthera colubrina used to make Yopo andVilca snuff in which bufotenin is the main active alkaloid. Psilocin, an active chemical in many psychedelicmushrooms, is structurally similar to DMT.The psychotropic effects of DMT were first studied scientifically by the Hungarian chemist and psychologist Dr.Stephen Szra who performed research with volunteers in the mid-1950s. Szra, who later worked for the USNational Institutes of Health, had turned his attention to DMT after his order for LSD from the Swiss companySandoz Laboratories was rejected on the grounds that the powerful psychotropic could be dangerous in the hands ofa communist country.

DMT during various stages ofpurification

DMT can produce powerful psychedelic experiences including intense visuals,euphoria and hallucinations. DMT is generally not active orally unless it iscombined with a monoamine oxidase inhibitor (MAOI) such as a reversibleinhibitor of monoamine oxidase A (RIMA), for example, harmaline. Withoutan MAOI, the body quickly metabolizes orally administered DMT, and ittherefore has no hallucinogenic effect unless the dose exceeds monoamineoxidase's metabolic capacity. Other means of ingestion such as vaporizing,injecting, or insufflating the drug can produce powerful hallucinations andentheogenic activity for a short time (usually less than half an hour), as theDMT reaches the brain before it can be metabolized by the body's naturalmonoamine oxidase. Taking a MAOI prior to vaporizing or injecting DMTprolongs and potentiates the effects.

Inhalation

A standard dose for vaporized DMT is between 1560mg. This is generallyinhaled in a few successive breaths. The effects last for a short period of time,usually 5 to 15 minutes, dependent on the dose. The onset after inhalation isvery fast (less than 45 seconds) and peak effects are reached within a minute. In the 1960s, DMT was known as a"businessman's lunch" in the US because of the relatively short duration (and rapid onset) of action when inhaled.

InsufflationInsufflating DMT (commonly as a freebase or fumarate) requires a higher dose than inhalation. The duration ismarkedly increased, and some users report diminished euphoria but an intensified otherworldly experience. A doseof approximately 70 to 120mg of insufflated DMT will induce medium to strong effects. If successful in containingthis pain-inducing insufflation, the trip can last anywhere from 20 to 50 minutes, with undefinable peak(s).

InjectionInjected DMT produces an experience that is similar to inhalation in duration, intensity, and characteristics.In a study conducted from 1990 through 1995, University of New Mexico psychiatrist Rick Strassman found thatsome volunteers injected with high doses of DMT reported experiences with perceived alien entities. Usually, thereported entities were experienced as the inhabitants of a perceived independent reality the subjects reported visitingwhile under the influence of DMT.[1] In a September 2009 interview with Examiner.com, Strassman described theeffects on participants in the study: "Subjectively, the most interesting results were that high doses of DMT seemedto allow the consciousness of our volunteers to enter into non-corporeal, free-standing, independent realms ofexistence inhabited by beings of light who oftentimes were expecting the volunteers, and with whom the volunteersinteracted. While 'typical' near-death and mystical states occurred, they were relatively rare."


Oral ingestionDMT is broken down by the digestive enzyme monoamine oxidase through a process called deamination, and istherefore inactive if taken orally unless combined with a monoamine oxidase inhibitor (MAOI). The traditionalSouth American beverage ayahuasca, or yage, is derived by boiling the ayahuasca vine (Banisteriopsis caapi) withleaves of one or more plants containing DMT, such as Psychotria viridis, Psychotria carthagenensis, or Diplopteryscabrerana. The Ayahuasca vine contains harmala alkaloids, highly active reversible inihibitors of monoamineoxidase A (RIMAs), rendering the DMT orally active by protecting it from deamination. A variety of differentrecipes are used to make the brew depending on the purpose of the ayahuasca session, or local availability ofingredients. Two common sources of DMT in the western US are reed canary grass (Phalaris arundinacea) andHarding grass (Phalaris aquatica). These invasive grasses contain low levels of DMT and other alkaloids. Inaddition, Jurema (Mimosa tenuiflora) shows evidence of DMT content: the pink layer in the inner rootbark of thissmall tree contains a high concentration of N,N-DMT.[citation needed]

Taken orally with an RIMA, DMT produces a long lasting (over 3 hour), slow, deep metaphysical experience similarto that of psilocybin mushrooms, but more intense. RIMAs should be used with caution as they can have lethalcomplications with some prescription drugs such as SSRI antidepressants, and some over-the-counter drugs.Induced DMT experiences can include profound time-dilation, visual and auditory illusions, and other experiencesthat, by most firsthand accounts, defy verbal or visual description. Some users report intense erotic imagery andsensations and utilize the drug in a ritual sexual context.

Distinguish from 5-MeO-DMT5-MeO-DMT, a psychedelic drug structurally similar to N,N-DMT, is sometimes referred to as DMT throughabbreviation. As a white, crystalline solid, it is also similar in appearance to DMT. However, it is considerably morepotent (5-MeO-DMT typical vaporized dose: 520mg), and care should be taken to clearly differentiate between thetwo drugs to avoid accidental overdose.

Detection in body fluidsDMT may be quantitated in blood, plasma or urine using chromatographic techniques as a diagnostic tool in clinicalpoisoning situations or to aid in the medicolegal investigation of suspicious deaths. Blood or plasma DMT levels inrecreational users of the drug are generally in the 1030 g/L range during the first several hourspost-ingestion.[citation needed] Less than 0.1% of an oral dose is eliminated unchanged in the 24-hour urine ofhumans.[4]


Side effectsAccording to a "Dose-response study of N,N-dimethyltryptamine in humans" by Rick Strassman,"Dimethyltryptamine dose slightly elevated blood pressure, heart rate, pupil diameter, and rectal temperature, inaddition to elevating blood concentrations of beta-endorphin, corticotropin, cortisol, and prolactin. Growth hormoneblood levels rose equally in response to all doses of DMT, and melatonin levels were unaffected."

Conjecture

DMT crystal at 400x magnification

Several speculative and yet untested hypotheses suggest thatendogenous DMT is produced in the human brain and is involved incertain psychological and neurological states. DMT is naturallyoccurring in small amounts in rat brain, human cerebrospinal fluid, andother tissues of humans and other mammals. A biochemicalmechanism for this was proposed by the medical researcher J. C.Callaway, who suggested in 1988 that DMT might be connected withvisual dream phenomena: brain DMT levels would be periodicallyelevated to induce visual dreaming and possibly other natural states ofmind. A new hypothesis proposed is that in addition to being involvedin altered states of consciousness, endogenous DMT may be involvedin the creation of normal waking states of consciousness. It is proposed that DMT and other endogenoushallucinogens mediate their neurological abilities by acting as neurotransmitters at a sub class of the trace aminereceptors; a group of receptors found in the CNS where DMT and other hallucinogens have been shown to haveactivity. Wallach further proposes that in this way waking consciousness can be thought of as a controlledpsychedelic experience. It is when the control of these systems becomes loosened and their behavior no longercorrelates with the external world that the altered states arise.

Dr. Rick Strassman, while conducting DMT research in the 1990s at the University of New Mexico, advanced thecontroversial hypothesis that a massive release of DMT from the pineal gland prior to death or near death was thecause of the near death experience (NDE) phenomenon. Several of his test subjects reported NDE-like audio orvisual hallucinations. His explanation for this was the possible lack of panic involved in the clinical setting andpossible dosage differences between those administered and those encountered in actual NDE cases. Several subjectsalso reported contact with "other beings", alien like, insectoid or reptilian in nature, in highly advanced technologicalenvironments where the subjects were "carried", "probed", "tested", "manipulated", "dismembered", "taught","loved" and even "raped" by these "beings". Basing his reasoning on his belief that all the enzymatic material neededto produce DMT is found in the pineal gland (see evidence in mammals), and moreover in substantially greaterconcentrations than in any other part of the body, Strassman ( p.69) has speculated that DMT is made in the pinealgland. Currently there was no published reliable scientific evidence supporting this hypothesis. Until Rick Strassmanpublished his data showing DMT found in the pineal glands of live mice.In the 1950s, the endogenous production of psychoactive agents was considered to be a potential explanation for thehallucinatory symptoms of some psychiatric diseases as the transmethylation hypothesis (see also adrenochrome),though this hypothesis does not account for the natural presence of endogenous DMT in otherwise normal humans,rats and other laboratory animals.In 2011, Nicholas V. Cozzi, of the University of Wisconsin School of Medicine and Public Health, concluded that INMT, an enzyme that may be associated with the biosynthesis of DMT and endogenous hallucinogens, is present in the primate (rhesus macaque) pineal gland, retinal ganglion neurons, and spinal cord.[5] In August 2012, Steven Barker, Ethan McIlHenny, and Rick Strassman, developed a new method to measure the three known endogenous hallucinogens and their major N-oxide metabolites in blood, urine, cerebrospinal fluid, ocular fluid and/or other


tissues by using state-of-the-art liquid chromatography-mass spectrometry (LC/MS) equipment. For the first time inhistory, they were able to detect the DMT-N-oxide metabolite in blood and urine.

Legal status

International lawDMT is classified as a Schedule I drug under the UN 1971 Convention on Psychotropic Substances, meaning thatuse of DMT is supposed to be restricted to scientific research and medical use and international trade in DMT issupposed to be closely monitored. Natural materials containing DMT, including ayahuasca, are explicitly notregulated under the 1971 Psychotropic Convention.

AustraliaBetween 2011 and 2012, the Australian Federal Government was considering changes to the Australian CriminalCode that would classify any plants containing any amount of DMT as "controlled plants". DMT itself was alreadycontrolled under current laws. The proposed changes included other similar blanket bans for other substances, suchas a ban on any and all plants containing Mescaline or Ephedrine. The proposal was not pursued after politicalembarrassment on realisation that this would make Australia's national flower, Acacia pycnantha (Golden Wattle),illegal. The Therapeutic Goods Administration and federal authority had considered a motion to ban the same, butthis was withdrawn in May 2012 (as DMT may still hold potential entheogenic value to native and/or religiouspeoples).[6]

CanadaDMT is classified in Canada as a Schedule III drug.

FranceDMT, along with most of its plant sources, is classified in France as a stupfiant (narcotic).

New ZealandDMT is classified in New Zealand as a Class A drug under the Misuse of Drugs Act 1975.

United KingdomDMT is classified in the United Kingdom as a Class A drug.

United StatesDMT is classified in the United States as a Schedule I drug under the Controlled Substances Act of 1970.In December 2004, the Supreme Court lifted a stay, thereby allowing the Brazil-based Unio do Vegetal (UDV)church to use a decoction containing DMT in their Christmas services that year. This decoction is a tea made fromboiled leaves and vines, known as hoasca within the UDV, and ayahuasca in different cultures. In Gonzales v. OCentro Espirita Beneficente Uniao do Vegetal, the Supreme Court heard arguments on November 1, 2005, andunanimously ruled in February 2006 that the U.S. federal government must allow the UDV to import and consumethe tea for religious ceremonies under the 1993 Religious Freedom Restoration Act.In September 2008, the three Santo Daime churches filed suit in federal court to gain legal status to import DMT-containing ayahuasca tea. The case, Church of the Holy Light of the Queen v. Mukasey,[7] presided over by Judge Owen M. Panner, was ruled in favor of the Santo Daime church. As of March 21, 2009, a federal judge says members of the church in Ashland can import, distribute and brew ayahuasca. U.S. District Judge Owen Panner


issued a permanent injunction barring the government from prohibiting or penalizing the sacramental use of "Daimetea". Panner's order said activities of The Church of the Holy Light of the Queen are legal and protected underfreedom of religion. His order prohibits the federal government from interfering with and prosecuting churchmembers who follow a list of regulations set out in his order.

CultureIn South America, there are a number of indigenous traditions and more recent religious movements based on the useof ayahuasca, usually in an animistic context that may be mixed with Christian imagery. There are three main groupsusing DMT-MAOI based sacraments in South America.The Amazon Basin's indigenous population

There are many indigenous cultures in South America, mostly in the Upper Amazon Basin whose traditionalreligious practices include the use of ayahuasca. These are the oldest cultures in the whole of South Americathat continue to use ayahuasca or analogue brews, such as the ones made from Jurema in the Pernambuco, nearRecife or Iquitos in Peru.

Santo Daime ("Holy Give Unto Me") and Barquinha ("Little Boat")A syncretic religion from Brazil. The former was founded by Raimundo Irineu Serra in the early 1930s, as anesoteric Christian religion with shamanic tendencies. The Barquinha was derived from this one. The SantoDaime also includes children in their Entheogenic rituals; studies done by the Brazilian government concludedthat there were no physical or mental damage caused by this practice, so it is allowed.

Unio do Vegetal ("Union of the Plants" or UDV)Another Christian ayahuasca religion from Brazil, a single unified organization with a structure resemblingFreemasonry.

Popular cultureDMT was the subject of a 2010 American documentary titled DMT: The Spirit Molecule.[8] DMT was one of thepsychedelic drugs used in the 2009 French movie, titled Enter The Void. In 2012, electronic producer Flying Lotusreleased the song DMT on his album Until the Quiet Comes., featuring Thundercat. DMT is also mentioned in anepisode of Adventure Time. [9]

References[1][1] ()[2] General annotation of Human INMT (O95050) entry in UniProtKB/Swiss-Prot (http:/ / www. uniprot. org/ uniprot/ O95050)[3] Alien Dreamtime a multimedia event recorded live. (27 February 1993)[4] R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 9th edition, Biomedical Publications, Seal Beach, CA, 2011, pp. 525526.[5] http:/ / www. neurophys. wisc. edu/ ~cozzi/

Indolethylamine%20N-methyltransferase%20expression%20in%20primate%20nervous%20tissue. pdf[6] http:/ / connection. ebscohost. com/ c/ articles/ 79564875/ aussie-dmt-ban[7] Church of the Holy Light of the Queen v. Mukasey (http:/ / csp. org/ society/ docs/ SantoDaimeAshland20090318. pdf)[8] http:/ / www. imdb. com/ title/ tt1340425/[9] http:/ / www. dosenation. com/ listing. php?id=8252


External links Identifying Spiritual Content in First-Person Reports from Ayahuasca Sessions (http:/ / www. neuroquantology.

com/ index. php/ journal/ article/ view/ 410) DMT Vault (http:/ / www. erowid. org/ chemicals/ dmt/ ) Erowid DMT (http:/ / www. thesite. org/ drinkanddrugs/ drugsafety/ drugsatoz/ dmt) TheSite.org DMT chapter from TiHKAL (http:/ / www. erowid. org/ library/ books_online/ tihkal/ tihkal06. shtml) DMT: The Spirit Molecule (http:/ / www. rickstrassman. com/ index. php?option=com_content& view=article&

id=54& Itemid=54), an overview by its author, Rick Strassman DMT: The Spirit Molecule (http:/ / www. imdb. com/ title/ tt1340425/ ) at the Internet Movie Database CRFDL (http:/ / www. crfdl. org), a database of scientific research on psychedelics

Monoamine oxidase inhibitor

Monoamine oxidase

Monoamine oxidase inhibitors (MAOIs) are chemicals which inhibitthe activity of the monoamine oxidase enzyme family. They have along history of use as medications prescribed for the treatment ofdepression. They are particularly effective in treating atypicaldepression. They are also used in the treatment of Parkinson's Diseaseand several other disorders.

Because of potentially lethal dietary and drug interactions, monoamineoxidase inhibitors have historically been reserved as a last line oftreatment, used only when other classes of antidepressant drugs (forexample selective serotonin reuptake inhibitors and tricyclicantidepressants) have failed.[1] New research into MAOIs indicate thatmuch of the concern over their dangerous dietary side effects stemsfrom misconceptions and misinformation, and that despite proven effectiveness of this class of drugs, it isunderutilized and misunderstood in the medical profession. New research also questions the validity of the perceivedseverity of dietary reactions, which has historically been based on outdated research.

IndicationsNewer MAOIs such as selegiline (typically used in the treatment of Parkinson's disease) and the reversible MAOImoclobemide provide a safer alternative and are now sometimes used as first-line therapy.MAOIs have been found to be effective in the treatment of panic disorder with agoraphobia,[2] social phobia,[3][4][5]

atypical depression[6][7] or mixed anxiety and depression, bulimia,[8][9][10][11] and post-traumatic stress disorder,[12]

as well as borderline personality disorder.[13] MAOIs appear to be particularly effective in the management ofbipolar depression according to a recent retrospective-analysis.[14] There are reports of MAOI efficacy inobsessive-compulsive disorder (OCD), trichotillomania, dysmorphophobia, and avoidant personality disorder, butthese reports are from uncontrolled case reports.MAOIs can also be used in the treatment of Parkinson's disease by targeting MAO-B in particular (thereforeaffecting dopaminergic neurons), as well as providing an alternative for migraine prophylaxis. Inhibition of bothMAO-A and MAO-B is used in the treatment of clinical depression and anxiety.MAOIs appear to be particularly indicated for outpatients with "neurotic depression" complicated by panic disorderor hysteroid dysphoria, which involves repeated episodes of depressed mood in response to feeling rejected.[15]

Monoamine oxidase inhibitor 46

Mechanism of actionMAOIs act by inhibiting the activity of monoamine oxidase, thus preventing the breakdown of monoamineneurotransmitters and thereby increasing their availability. There are two isoforms of monoamine oxidase, MAO-Aand MAO-B. MAO-A preferentially deaminates serotonin, melatonin, epinephrine, and norepinephrine. MAO-Bpreferentially deaminates phenylethylamine and trace amines. Dopamine is equally deaminated by both types.

ReversibilityThe early MAOIs inhibited monoamine oxidase irreversibly. When they react with monoamine oxidase, theypermanently deactivate it, and the enzyme cannot function until it has been replaced by the body, which can takeabout two weeks. A few newer MAOIs, a notable one being moclobemide, are reversible, meaning that they are ableto detach from the enzyme to facilitate usual catabolism of the substrate. The level of inhibition in this way isgoverned by the concentrations of the substrate and the MAOI.Harmaline found in Peganum harmala, as well as the Ayahuasca vine, Banisteriopsis caapi, and Passiflora incarnatais a reversible inhibitor of MAO-A (RIMA).[16]

SelectivityIn addition to reversibility, MAOIs differ by their selectivity of the MAO receptor. Some MAOIs inhibit bothMAO-A and MAO-B equally, other MAOIs have been developed to target one over the other.MAO-A inhibition reduces the breakdown of primarily serotonin, norepinephrine, and dopamine; selective inhibitionof MAO-A allows for tyramine to be metabolised via MAO-B. Agents that act on serotonin if taken with anotherserotonin-enhancing agent may result in a potentially fatal interaction called serotonin syndrome or with irreversibleand unselective inhibitors (such as older MAOIs), of MAO a hy

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