Ayahuasca Analogues
This is a file by Crazy Fingers, aka Ryan M. Hastings ( rhasting@copper.ucs.indiana.edu)

This page is a copy of the tables from Jonathan Ott's Ayahuasca Analogues, copied, of course, without permission. If Mr. Ott or his publishers would like me to remove this, I ask that they e-mail me before threatening me legally, and I'll be happy to delete this page. This is for informational purposes, for those of us who do not have access to the Amazon but still want to explore the entheogenic properties of Ayahuasca. All standard disclaimers apply.

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.

All notes have been removed, this is just the barest essentials of information.

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

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.

Table I--Ayahuasca Additive Plants.

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

Alkaloid RangeAverage
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 RangeAverage
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-CarbolinesDMT
Der Marderosian et al 1970 (1)20 mg30 mg
Rivier & Lindgren 1972 (9)40 mg25 mg
McKenna et al 1984 (5)401 mg36 mg
Liwszyc et al 1992 (1, Santo Daime)144 mg26 mg
Overall Average (all 16 samples)158 mg29 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.]
Below is information on alkaloid content of various analogues which I've gleaned from Ott's text.

  • Peganum harmala (seeds): 2-7% beta-carboline
  • (3g P. harmala + 20 g Acacia phlebophylla leaves work well, according to the text, for a 3.5h experience)
  • Acacia maidenii (bark): 0.36% DMT
  • Acacia phlebophylla (leaf): 0.3% DMT
  • Acacia simplicifolia (bark): 0.81% DMT
  • Desmanthus illinoensis (root bark): 0.34% DMT
  • Mimosa hostilis (roots): 0.57% DMT
  • Virola theiodora (flowers): 0.44% DMT
  • Pilocarpus organensis (unspecified): 1.06% tryptamines, chiefly 5-MeO-DMT
  • Vepris ampody (leafy branches): 0.22% DMT
  • Melicope leptococca (leafy branches): 0.21% 5-MeO-DMT
To prepare the harmala seeds, Ott ground them in a mortar, placed the groundings in enough of a 30% solution of lime juice in water to suspend the seeds in a pot, and brought it rapidly to a boil with stirring. He then filtered the suspension with a coffee filter. The residual solid matter was then added back to the pot and again extracted by the same means, using minimal lime/water. He recommends not using prolonged heating or an excess of water. After filtration, he rinses the pot out with water, and places water over the remaining solid material. He got about 150 mL of extract from 15 g of seeds. He uses the extraction method on combined constituents--D. illinoensis, A. phlebophylla, and P. viridis, each separately with P. harmala--and this seems to work at the proper doses.

 
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