Ayahuasca Analogues by Crazy Fingers

First of all, before I relate the tables, I will say a few words about what Ayahuasca is. Ayahuasca, also called Yaje or Yage, is a pan-Amazonian brew used shamanically. It most often involves the combination of Banisteriopsis caapi vine with other plants, usually plants containing tryptamines. B. caapi contains beta-carbolines which, in low doses, potentiate the effects of other entheogens. The basic chemical mechanism for Ayahuasca, as near as I can tell from my reading, and I'm no expert, is combination of a beta-carboline with a tryptamine, usually DMT.

Also below: Concentrations of DMT material in a few plant species and an extraction method for the Ayahuasca analogue.

Other sites of interest: Dimitri's Ayahuasca definition, Dimitri's Shamanism page which has lots of good information on the cultural use of Ayahuasca, Beta-Carbolines and the Tryptamines FAQ at the hyperreal.com drug archives.

IMPORTANT: Beta-carbolines are reversible MAO inhibitors. If you don't watch your diet six hours before and after using them, YOU COULD DIE!!!!! Check out the dietary restrictions for MAOI use at hyperreal.com.

Table I--Ayahuasca Additive Plants.

ACANTHACEAE Teliostachya lanceolata

AMARANTHACEAE Alternanthera lehmannii

Iresine sp.

APOCYNACEAE Himatanthus sucuuba

Malouetia tamaquarina

Mandevilla scabra

Tabernaemontana sp.

AQUIFOLIACEAE Ilex guayusa

ARACEAE Montrichardia arborescens

BIGNONIACEAE Mansoa alliacea

Tabebuia heteropoda

Tabebuia incana

Tabebuia sp.

Tynnanthus panurensis

BOMBACACEAE Cavanillesia hylogeiton

Cavanillesia umbellata

Ceiba pentandra

Chorisia insignis

Chorisia speciosa

Quararibea "ishpingo"

BORAGINACEAE Tournefortia angustifolia

CACTACEAE Epiphyllum sp.

Opuntia sp.

CARYOCARACEAE Anthodiscus pilosus

CELASTRACEAE Maytenus ebenifola

CYCLANTHACEAE Carludovica divergens

DRYOPTERIDACEAE Lomariopsis japurensis

DRYOPTERIDACEAE Erythroxylum coca

ERYTHROXYLACEAE Erythroxylum coca

EUPHORBIACEAE Alchornea castaneifolia

Hura crepitans

GNETACEAE Gnetum nodiflorum

GUTTIFERAE Clusia sp.

Tovomita sp.

LABIATAE Ocimum micranthum

LECYTHIDACEAE Couroupita guianensis

LEGUMINOSAE Bauhinia guianensis

Caesalpinia echinata

Calliandra angustifolia

Campsiandra laurifolia

Cedrelinga castaneiformis

Erythrina glauca

Erythrina poeppigiana

Pithecellobium laetum

Sclerobium setiferum

Vouacapoua americana

LORANTHACEAE Phrygilanthus eugenioides

Phtirusa pyrifolia

MALPIGHIACEAE Diplopterys cabrerana

Diplopterys involuta (=Mezia includens)

Mascagnia psilophylla (var. antifebrilis = Cabi paraensis; Callaeum antifebrile)

Stigmaphyllon fulgens

MARANTACEAE Calathea veitchiana

MENISPERMACEAE Abuta grandifolia

MORACEAE Coussapa tessmannii

Ficus insipida

Ficus ruiziana

Ficus sp.

MYRISTICACEAE Virola sp.

Virola surinamensis

NYMPHIACEAE Caboma aquatica

PHYTOLACCACEAE Petiveria alliaceae

PIPERACEAE Piper sp.

POLYGONACEAE Triplaris surinamensis

Triplaris surinamensis var. chamissoana

PONTEDERIACEAE Pontederia cordata

RUBIACEAE Calycophyllum spruceanum

Capirona decoriticans

Guettarda ferox

Psychotria carthaginensis

Psychotria psychotriaefolia

Psychotria "batsikawa"

Psychotria "nai kawa"

Psychotria "pishikawa"

Psychotria viridis

Rudgea retifolia

Sabicea amazonensis

Uncaria guianensis

SAPINDACEAE Paullinia yoco

SCHIZAEACEAE Lygodium venustum

SCROPHULARIACEAE Scoparia dulcis

SOLANACEAE Brugmansia insignis

Brugmansia suaveolens

Brunfelsia chiricaspi

Brunfelsia grandiflora

Brunfelsia grandiflora subsp schultesii

Capsicum sp.

Iochroma fuchsioides

Juanulloa ochracea

Nicotiana rustica

Nicotiana tabacum

VERBENACEAE Cornutia odorata

Vitex triflora

VIOLACEAE Rinorea viridiflora

Table II-A--Reported Analyses of Ayahuasca [B. caapi] Plants (Dried Stems)

.........................................Alkaloid Range.............Average Hochstein & Paradies 1957 (1) --- 0.30% Poisson 1965 (1 sample) --- 0.21% Schultes et al 1969 (2 samples) 0.40-0.50% 0.45% Rivier & Lindgren 1972 (15 samples) 0.05-0.83% 0.35% McKenna et al 1984 (6 samples) 0.17-1.36% 0.78% Overall Average (all 25 samples) 0.05-1.36% 0.45%

Table II-B--Reported Analyses of Ayahuasca Leaf Admixture.

..........................................DMT Range.................Average Diplopterys cabrerana Poisson 1965 (1 sample) --- 0.64% Der Marderosian et al 1968 (1) 1.33-1.75% 1.46% Agurell et al 1968 (1 sample) --- 0.46% McKenna et al 1984 (1 sample) --- 0.17% Overall Average (all 4 samples) 0.17-1.75% 0.68% Psychotria species (P. viridis, P. carthaginensis, nai kawa) Der Marderosian et al 1970 1970 (4) 0.16-0.22% 0.19% Rivier & Lindgren 1972 (3) 0.00-0.66% 0.33% McKenna et al 1984 (4) 0.00-0.16% 0.10% Overall average (all 11 samples) 0.00-0.66% 0.20%

Table II-C--Reported Analyses of Ayahuasca Potions (Average Per Dose)

...........................................Beta-Carbolines..........DMT Der Marderosian et al 1970 (1) 20 mg 30 mg Rivier & Lindgren 1972 (9) 40 mg 25 mg McKenna et al 1984 (5) 401 mg 36 mg Liwszyc et al 1992 (1, Santo Daime) 144 mg 26 mg Overall Average (all 16 samples) 158 mg 29 mg

References:

Agurell, S. et al. 1968. "Alkaloid content of Bansteriopsis rusbyana." American Journal of Pharmacy 140(5): 148-151.

Agurell, S. et al. 1969. "Alkaloids in certain species of Virola and other South American plants of ethnopharmacologic interest." Acta Chemica Scandinavica 23(3): 903-916.

Der Marderosian, A. H. et al. 1968. "Native use and occurence [sic] of N,N- dimethyltryptamine in the leaves of Banisteriopsis rusbyana." American Journal of Pharmacy 140(5): 137-147.

Hochstein, F. A. and A. M. Paradies. 1957. "Alkaloids of Banisteria caapi and Prestonia amazonicum [sic]." Journal of the American Chemical Society 79: 5735-5736.

Liwszyc, G. E. et al. 1992. "Daime--A ritual herbal potion." Journal of Ethnopharmacology 36(1): 91-92.

McKenna, D. J. et al. 1984. "Monoamine oxidase inhibitors in South American hallucinogenic plants: Tryptamine and Beta-Carboline constituents of ayahuasca." Journal of Ethnopharmacology 10(2): 195-223.

Poisson, J. 1965. "Note surle 'Natem', boisson toxique peruvienne et es alcaloides" Annales Pharmaceutiques Francaises 23(4): 241-244.

Schultes, R. E. 1969. "De plantis toxicariis e mundo novo tropicale commentationes V. Virola as an orally administered hallucinogen" Botanical Museum Leaflets, Harvard University 22(6): 229-240.



Table IV-B--Plants Containing Entheogenic Tryptamines.

Letters in square brackets refer to DMT and 5-MeO-DMT [5MD] in leaves [l], seeds [s], pods [p], stems [st], bark [b], roots [r], flowers [f], fruit [fr], root bark [rb], or whole plant [w]. ACANTHACEAE * Justicia pectoralis [DMT,l] AGARICACEAE * Amanita citrina [DMT,5MD,w] * Amanita porphyria [5MD,w] AIZOACEAE * Delosperma sp. [DMT] GRAMINEAE * Arundo donax [DMT,l,r,f] - ALKALOIDS Plant 5,000 ppm (0.5 % - propably dry material) - 5-METHOXY-N-METHYLTRYPTAMINE Plant, BUFOTENIDINE Rhizome, BUFOTENINE Leaf, DEHYDROBUFOTENINE Rhizome, DONAXARIDINE Plant, DONAXERINE Rhizome, DONAXINE Rhizome, ELEAGNINE Flower, FRIEDELIN Leaf, GRAMINE Rhizome, GRAMINE-METHOHYDROXIDE Flower, GRAMINE-N-OXIDE Plant 700 ppm, N,N-DIMETHYLTRYPTAMINE Leaf, N,N-DIMETHYLTRYPTAMINE-METHOHYDROXIDE Flower * Phalaris arundinacea [DMT,5MD,l,w] From the usenet (dry material): Source 1. DMT 0.060% Source 2. Alkaloids 0.004-0.121% * Phalaris tuberosa (= P. aquatica) [DMT,5MD,l] From the usenet (dry material): Source 1. DMT 0.100% 5-MeO-DMT 0.022% 5-OH-DMT 0.005% Source 2. DMT 0.170% 5-MeO-DMT 0.060% Source 3. Alkaloids 0.007-0.18% * Phragmites australis [DMT,r] LEGUMINOSAE * Acacia confusa [DMT,st] * Acacia maidenii [DMT,b] * Acacia nubica [DMT,l] * Acacia phlebophylla [DMT,l] * Acacia polyacantha subsp. campylacantha [DMT,l] * Acacia senegal [DMT,l] - CYSTEINE Plant, D-PINITOL Leaf, DIMETHYLTRYPTAMINE Plant, ERYTHRODIOL Plant, LEUCINE Plant * Acacia simplicifolia [DMT,b,l,st] * Anadenanthera colubrina var. cebil (= Piptadenia macrocarpa) [DMT,s,p] - BUFOTENINE Seed, N,N-DIMETHYLTRYPTAMINE Seed, TRYPTAMINES Seed * Anadenanthera excelsa [DMT,s,p] * Anadenanthera peregrina [DMT,5MD,b,l,s,p] - 1,2,3,4-TETRAHYDRO-6-METHOXY-2,9-DIMETHYL-BETA-CARBOLINE Plant, 1,2,3,4-TETRAHYDRO-6-METHOXY-2-METHYL-BETA-CARBOLINE Plant, 5-METHOXY-N,N-DIMETHYLTRYPTAMINE Bark, 5-METHOXY-N-METHYLTRYPTAMINE Bark, BUFOTENINE Plant, BUFOTENINE-OXIDE Fruit, N,N-DIMETHYLTRYPTAMINE Fruit, N,N-DIMETHYLTRYPTAMINE-OXIDE Fruit, N-METHYLTRYPTAMINE Bark, HOMOORIENTINE Leaf, LEUCOANTHOCYANIN Plant, LEUCOPELARGONIDOL Plant, ORIENTIN Leaf, SAPONARETIN Leaf, VITERINE Leaf * Desmanthus illineonsis [DMT,r,rb] - DMT (root) 0.200% (dry material) DMT (root bark) 0.340% (dry material) * Desmodium caudatum [DMT,r,st] * Desmodium gangeticum [DMT,5MD,w,r,st,l] - 2'HYDROXYGENISTEIN Leaf Diffusate 14 ppm, GENISTEIN Leaf Diffusate 8 ppm * Desmodium gyrans [DMT,5MD,l,r] * Desmodium pulchellum [DMT,5MD,w,r,st,l,f] - BETULIN Root * Desmodium racemosum [5MD,w] * Desmodium triflorum [DMT-N-oxide,r] * Lespedeza bicolor var. japonica [DMT,5MD,l,rb] 5-METHOXY-N-METHYLTRYPTAMINE Bark, BUFOTENINE Plant, BUFOTENINE-OXIDE Fruit, N,N-DIMETHYLTRYPTAMINE Fruit, N,N-DIMETHYLTRYPTAMINE-OXIDE Fruit, N-METHYLTRYPTAMINE Bark, HOMOORIENTINE Leaf, LEUCOANTHOCYANIN Plant, LEUCOPELARGONIDOL Plant, ORIENTIN Leaf, SAPONARETIN Leaf, VITERINE Leaf * Desmanthus illineonsis [DMT,r,rb] - DMT (root) 0.200% (dry material) DMT (root bark) 0.340% (dry material) * Desmodium caudatum [DMT,r,st] * Desmodium gangeticum [DMT,5MD,w,r,st,l] - 2'HYDROXYGENISTEIN Leaf Diffusate 14 ppm, GENISTEIN Leaf Diffusate 8 ppm * Desmodium gyrans [DMT,5MD,l,r] * Desmodium pulchellum [DMT,5MD,w,r,st,l,f] - BETULIN Root * Desmodium racemosum [5MD,w] * Desmodium triflorum [DMT-N-oxide,r] * Lespedeza bicolor var. japonica [DMT,5MD,l,rb] * Mimosa hostilis [DMT,r] - N,N-DIMETHYLTRYPTAMINE Plant, NIGERINE Plant - DMT root 0.57% (propably fresh (=wet) material) * Mimosa scabrella [DMT,b] * Mimosa tenuiflora [DMT,5MD,b] * Mucuna pruriens [DMT,5MD,l,s,st,r] - GENISTEIN Leaf Diffusate 6 ppm, HYDROXYGENISTEIN Leaf Diffusate 14 ppm * Petalostylis labicheoides var. casseoides [DMT,l,st] MALPIGHIACEAE * Banisteriopsis muricata (= B. argentea) [DMT,st,l] * Diplopterys cabrerana (=Banisteriopsis rusbyana) [DMT,5MD,l] MYRISTICACEAE * Iryanthera ulei [5MD,b] * Osteophloem platyspermum [DMT,5MD,b] * Virola calophylla [DMT,5MD,b,r,l,s,f] - 5-METHOXY-N,N-DIMETHYLTRYPTAMINE Bark, N,N-DIMETHYLTRYPTAMINE Bark, N-MONOMETHYLTRYPTAMINE Bark - Origin: Manaus Brazil (dry plant material) Bark: - DMT 0.008% - 5-MeO-DMT trace Root: - DMT and 5-MeO-DMT trace Flow, shoots: - DMT 0.185% - N-Methyltryptamine (MMT) 0.008% Leaves: - DMT 0.149% - MMT 0.006% * Virola carinata [DMT,l] * Virola divergens [DMT,l] * Virola elongata [DMT,5MD,b,l] * Virola melinonii [DMT,b] * Virola multinervia [DMT,5MD,b,r] * Virola pavonis [DMT,l] * Virola peruviana [DMT,5MD,b] - Mainly 5-MeO-DMT [b], small amounts DMT and 5-Methoxy-tryptamine [b] * Virola rufula [DMT,5MD,b,r,l] - Origin: Manaus Brazil (dry plant material) Bark: - 5-MeO-DMT 0.190% - DMT 0.008% - 5-MeO-MMT trace - 2-Methyl-6-MeO-1,2,3,4-tetrahydro-_-carboline (6-MeO-THC) trace Root: - 5-MeO-DMT 0.135% - 5-MeO-MMT 0.006% - DMT 0.001% - 6-MeO-THC trace Leaves: - DMT 0.092% - MMT 0.006% * Virola sebifera [DMT,b] * Virola theiodora [DMT,5MD,b,r,l,f] - Origin: Manaus Brazil (dry plant material) Bark: - DMT 0.130% - 5-Meo-DMT 0.110% - 6-MeO-THC 0.010% - N-Methyltryptamine (MMT) 0.003% Root: - 5-MeO-DMT 0.010% - DMT 0.004% - 5-MeO-MMT 0.003% Flow, shoots: - DMT 0.440% - MMT 0.033% Leaves: - DMT 0.044% - 5-MeO-DMT trace - Origin: Tototobi Brazil (dry plant material) Bark: - DMT 0.033% - 5-Meo-DMT 0.062% Leaves: - DMT 0.021% - Methyl-THC trace * Virola venosa [DMT,5MD,r,l] OCHNACEAE * Testulea gabonensis [DMT,b,rb] POLYGONACEAE * Erigonum sp. [DMT] RUBIACEAE * Psychotria carthaginensis [DMT,l] - Also N-methyltryptamine and N-methyltetrahydro-_-carboline * Psychotria viridis (= P. psychotriaefolia) [DMT,l] - Also N-methyltryptamine and N-methyltetrahydro-_-carboline Average DMT contents on leaves of different P. species is 0.2% (dry material) RUTACEAE * Dictyoloma incanescens [5MD,l] * Dutaillyea drupacea [5MD,l] * Dutaillyea oreophila [5MD,l] * Evodia rutaecarpa [5MD,l] * Limonia acidissima [5MD,st] - ESTRAGOLE Leaf 6,570 ppm, ISOPIMPINELLIN Root, MARMESIN Bark 160 ppm, ORIENTIN Leaf, PECTIN Fruit 30,000 - 160,000 ppm, PSORALEN Leaf, SPONARIN Leaf, STIGMASTEROL Fruit 150 ppm, STIGMASTEROL Leaf 120 ppm, VITEXIN Leaf * Melicope leptococca [5MD,l,st] * Pilocarpus organensis [5MD,l] * Vepris ampody [DMT,l] * Zanthoxylum arborescens [DMT,l] * Zanthoxylum procerum [DMT,l]

Table IV-A--Plants Containing MAO-Inhibiting Beta-Carbolines.

AGARICACEAE Coriolus maximus [Harman]

APOCYNACEAE Amsonia tabernaemontana [Harmine etc.]

Apocynum cannabinum [Harmalol]

Ochrosia nakaiana [Harman]

BIGNONIACEAE Newbouldia laevis [Harman]

CALYCANTHACEAE Calycanthus occidentalis [Harmine]

CHENOPODIACEAE Hammada leptoclada [Tetrahydroharman etc.]

Kochia scoparia [Harmine etc.]

COMBRETACEAE Guiera senegalensis [Harman etc.]

CYBERACEAE Carex brevicollis [Harmine etc.]

ELAEAGNACEAE Elaeagnus augustifolia [Harman etc.]

Elaeagnus hortensis [Tetrahydroharman etc.]

Elaeagnus orientalis [Tetrahydroharman]

Elaeagnus spinosa [Tetrahydroharman]

Hippophae rhammoides [Harman etc.]

Shepherdia argentea [Tetrahydroharmol]

Shepherdia canadensis [Tetrahydroharmol]

GRAMINEAE Arundo donax [Tetrahydroharman]

Festuca arundinacea [Harman etc.]

Lolium perenne [Harman etc.]

LEGUMINOSAE Acacia baileyana [Tetrahydroharman]

Acacia complanata [Tetrahydroharman etc.]

Burkea africana [Harman etc.]

Desmodium pulchellum [Harman etc.]

Mucuna pruriens [6-Methoxy-Harman]

Petalostylis labicheoides [Tetrahydroharman]

Prosopis nigra [Harman etc.]

LOGANIACEAE Strychnos usambarensis [Harman]

MALPIGHIACEAE Banisteriopsis caapi [Harmine etc.]

Banisteriopsis lutea [Harmine]

Banisteriopsis muricata [Harmine]

Callaeum antifebrile (= Cabe paraensis) [Harmine]

MYRISTICACEAE Virola cuspidata [6-Methoxy-Harman]

PASSIFLORACEAE Passiflora actinea [Harman = Passiflorine]

Passiflora alata [Harman]

Passiflora alba [Harman]

Passiflora bryonoides [Harman]

Passiflora caerulea [Harman]

Passiflora capsularis [Harman]

Passiflora decaisneana [Harman]

Passiflora edulis [Harman]

Passiflora eichleriana [Harman]

Passiflora foetida [Harman]

Passiflora incarnata [Harmine, Harmaline, Harman, etc.]

Passiflora quadrangularis [Harman]

Passiflora ruberosa [Harman]

Passiflora subpeltata [Harman]

Passiflora warmingii [Harman]

POLYGONACEAE Leptactinia densiflora [Leptaflorine, etc.]

Nauclea diderrichii [Harman etc.]

Ophiorrhiza japonica [Harman]

Pauridiantha callicarpoides [Harman]

Pauridiantha dewevrei [Harman]

Pauridiantha lyalli [Harman]

Pauridiantha viridiflora [Harman]

Simira klugii [Harman]

Simira rubra [Harman]

Uncaria attenuata [Harman]

Uncaria canescens [Harman]

Uncaria orientalis [Harman]

SAPOTACEAE Chrysophyllum lacouritianum [Norharman etc.]

SYMPLOCACEAE Symplocos racemosa [Harman]

ZYGOPHYLLACEAE Fagonia cretica [Harman]

Peganum harmala [Harmaline, Harmine, etc.]

Tribulus terrestris [Harmine etc.]

Zaygophyllum fabago [Harmine etc.]