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Ayahuasca: alkaloids, plants & analogs
assembled by Keeper of the Trout
Section 3 : Part 2 :
Analysis of Anadenanthera

Analyzing seeds, known to be used in preparing the snuff paricá, collected in Brazil during the first half of the 1800s, DeSmet & Rivier 1987, reported finding only bufotenine. They thought that any other tryptamines may have degraded over time. They noted that Schultes et al. 1977b, reported that 2 year old Anadenanthera seeds were observed to go through a similar change in composition while in storage and that Spruce's 1854 collection of A. peregrina seeds also yielded only bufotenine. [Identification of specific Anadenanthera species cannot be made from seeds alone.]

However, it might be also mentioned that Holmstedt & Lindgren 1967 detected both DMT and bufotenine in seeds that had been collected in 1948 and DMT and 5-MeO-DMT in seeds collected in 1956. Similarly, Torres et al. 1991 reported the detection of DMT, 5-MeO-DMT and Bufotenine in ancient Anadenanthera snuff which had been recovered from an archaeological site dated to 780 AD. Clearly more work is needed concerning DeSmet & Rivier's assertion.

Differential changes in alkaloid composition (enzymatic?) in post-harvest Phalaris and Desmodium species has also been reported. Phalaris strains also showed great variability during drying. Some much more than others. The reasons remain unclear.

Due to the abundant confusion historically surrounding the botanical identities of these snuffs, it has been proposed that Epena be reserved to refer to snuffs derived from Virola resin and Yopo and Paricá be applied to Anadenanthera derived snuffs.

While this is sound in both thought and principle, there is no such agreement among the people who actually make and use these snuffs; suggesting that such a convention might create more confusion than it alleviates.


"Epena" [Snuff prepared, by the Ma-hekodo-teri of the Rio Mavaca, from the seeds of an Anadenanthera species.]

DMT, DMT-N-oxide, Bufotenine and Bufotenine-N-oxide. Marini-Bettòlo et al. 1964


"Yopo"
[Snuff prepared, by the Pixasi-teri (or Bisashi-teri) of Upper Orinoco, from the seeds of an Anadenanthera species.]

Bufotenine and 5-MeO-DMT
Marini-Bettòlo et al. 1964


"Yopo" [Snuff collected in Colombia (collected 1956).]
DMT, Bufotenine and 5-MeO-DMT
Holmstedt & Lindgren 1967


"Paricà" [Snuff as prepared by Piaroa Indians (collected 1955).]
DMT, Bufotenine and 5-MeO-DMT
Holmstedt & Lindgren 1967


Seeds from unidentified or unspecified Anadenanthera species:
(all from Schultes et al. 1977b:
Biocca Cocco, 1963; Upper Orinoco, El Platanal, Machekototeri
Seeds: 0.001% DMT [1 mg/ 100 gm; Sole alkaloid.]
Biocca Cocco, 1965; Upper Orinoco, Rio Ocamo
Seeds: 0.006% DMT [6 mg/ 100 gm; Sole alkaloid.]
Caspar, 1964; Guaporé, Brazil; Tupari.
Seeds: 0.11% 5-MeO-DMT [85% of 13 mg of total alkaloid/ 100 gm] [0.002% DMT was also present]
G. Seitz, 1965
Seeds: 0.038% DMT [38 mg of total alkaloid/ 100 gm dry. Sole alkaloid]
Seedlings: 0.028% DMT [96% of 29 mg of total alkaloid/ 100 gm dry; 28 mg of DMT per 100 gm of dry seedlings.]
0.001% 5-MeO-DMT was also present.

2.1% yield of bufotenine from seeds of Anadenanthera colubrina collected in autumn near Rio de Janeiro. Voucher prepared. Pachter et al. 1959

Most accounts have found only bufotenine in the seeds but claims of the presence of DMT and/or 5-MeO-DMT exist.

Anadenanthera colubrina ? var. cebil?

Torres et al. 1991 reported the detection of all three in snuff powder recovered from archaeological sites in Argentina believed to have been derived from A. colubrina seeds. Both A. colubrina and A. colubrina var. cebil occur in Argentina. While it is not clear which Torres and coworkers referred to; the latter is implied. No analysis of seeds or verifiable plant material were reported in Torres et al. 1991. See below.

Anadenanthera colubrina (Lellozo) Brennan var. cebil (Grisebach) Altschul (= Piptadenia macrocarpa)

DMT as the sole alkaloid in pods. Not detected in seeds. Bufotenine, Bufotenine-N-oxide and DMT-N-oxide were present in seeds. Neither was detected in the pods. Fish et al. 1955. Material from both Florida and Brazil were used. Florida material gave weak results.
[It might be noted that this material was deliberately introduced and for many years was the only known occurrence of the species in Florida (the northernmost limit of its cold tolerances). It was destroyed during clearing of land for a building project some years ago.]

[Reported a total alkaloid concentration of ~ 1.5-2.0% in seeds. No indication was given of the actual amount of pure alkaloids. The pods were sometimes weaker but contained only DMT.]

DMT in both seeds and pods. Bufotenine was in seeds and lower in seed pods. Iacobucci & Rúveda 1964 (DMT was either the major alkaloid or only alkaloid in seed-pod (conflicting statements); no amounts given.) Bufotenine-N-oxide was reported in the seeds. 5-Methoxy-N-methyltryptamine was isolated (as oxalate) in 0.1% yield from the dry bark. Argentinean plants used.
Material recently collected in Argentina is said to have yielded only bufotenine from the seeds. [Unpublished work; Field worker requesting anonymity.] See the work of C.M. Torres.


Anadenanthera colubrina var. Cebil seeds
(% are dry wt.) nd indicates not detected.
Source Part DMT Bufotenine 4-OH-MMT
Cerro San
Bernardo Bark traces traces nd
Misión Wichi Seed 0.06% 12.4% 0.57%
Salta #1 Seed nd 4.41% nd
Salta #2 Seed nd 3.51% nd
Salta #2 Pods 0.05% 0.05% nd

No 5-Methoxy compounds, N-oxides or B-carbolines were detected in any samples. All were from Argentina. [Interestingly, the 12.4% seeds were collected from a shaman's garden.])
Salta #2 Seeds were small and poorly developed. Pods were said to be mature.


Anadenanthera colubrina var. Cebil
In northwestern Argentina, Anadenanthera colubrina var. Cebil seeds were smoked by the Abipones of the Cahaco (c. 1784), using combustion within a small structure, and were snuffed by the Lule of the Chaco (circa 1733). The Wichi (Mataco) still use the seeds both ways (seeds are smoked with tobacco). Torres & Repke 1996

An intriguing but still unanswered question comes up once again due to the report of Prosopis seeds being found in association with both Anadenanthera seeds and 2 feline-bone smoking pipes (in which DMT residue was detected) in a much older archeological site in NW Argentina. Torres & Repke 1996. [Pipes were dated to 2130 B.C. The archaeological evidence suggests that smoking preceded snuffing and was gradually replaced by it. (Page 314 in Torres 1996 citing Fernandez Distel 1980)] Other pipes were found with alkaloidal residue but were unaccompanied by plant material.


Anadenanthera excelsa Grisebach [Argentina]
DMT in seedpods (sole alkaloid present) Iacobucci and Rúveda 1964
Bufotenine and Bufotenine-N-oxide were in seeds. Lower concentration than P. macrocarpa. Iacobucci & Rúveda 1964

Anadenanthera falcata (as Piptadenia falcata)

Bufotenine was the major alkaloid in seeds. Giesbrecht 1960.

Snuff: "Yopo"
Believed to have originated from A. peregrina seeds; showed only bufotenine- 160 mg from 6 gm of snuff (2.67%). De Budowski et al. 1974. Another Yopo sample showed only 5-MeO-DMT and was thought to be derived from a Virola species instead.

Snuff: "Epena"
DMT, DMT-N-oxide, Bufotenine and Bufotenine-N-oxide reported in Yanomama snuff prepared from Piptadenia peregrina.
Marini-Bettòlo et al. 1964)


Anadenanthera peregrina
Seeds: southern Venezuela: 7.5% bufotenine
Schultes et al. 1977b citing Chagnon et al. 1970 and Chagnon et al. 1971

R.Spruce #119; Rio Negro, Brazil, collected in 1854 1977 analysis): 0.6% Bufotenine [614 mg/ 100 gm dry; Sole alkaloid.]

Schultes et al. 1977b.
western Brazil in the Rio Branco region during 1953: 5-MeO-DMT and DMT.
Holmstedt & Lindgren 1967.
Brazil: 1.1% Bufotenine in seeds.
Alvarez Periera 1957.
Haiti: Bufotenine was the major alkaloid in seeds.
Paris et al. 1967.
Abbott Lab., 1948; San Juan, Puerto Rico: 0.009% DMT [9 mg of DMT/ 100 gm; Sole alkaloid.]
Schultes et al. 1977b.
Puerto Rico during 1948: DMT and Bufotenine.
Holmstedt & Lindgren 1967
R.E. Schultes, S. von R. Altschul et B. Holmstedt, sin. num.; La Carolina, Barrio St. Just, near San Juan, Puerto Rico, December 1974. Same colony as Schultes 26363.

Mature seeds collected in March 1975; hill behind El Comandante horse-racing track.
1975 analysis (5 months after collection):
No quantification
Bufotenine- 80% of total alkaloid.
DMT- 19% of total alkaloid.
5-MeO-DMT- 1% of total alkaloid.
2-Methyl-1,2,3,4-tetrahydro-b-carboline- Traces.
1977 analysis of same material:
3.5% Bufotenine [3523 mg/ 100 gm dry; Bufotenine was sole alkaloid present.]
Schultes et al. 1977b.


Anadenanthera peregrina. [J. Yde, 1964, H4685]
Seedlings- 0.001% [1 mg of DMT/ 100 gm; Sole alkaloid.]
Schultes et al. 1977b.
Material from both Puerto Rico and Brazil. DMT was the sole alkaloid in pods. Not detected in seeds. Fish et al. 1955. Puerto Rican material gave variable results. [Reported a total alkaloid concentration of 1.6% in the seeds. No indication was given of the actual amount of pure alkaloids. The pods were weaker but contained only DMT.]


Anadenanthera peregrina [R.E. Schultes 26363; La Carolina, Barrio St. Just, near San Juan, Puerto Rico, Dec. 1972]

Immature seeds collected December 1972
0.16% DMT [75% of 209 mg of total alkaloid/ 100 gm dry; 156.75 mg of DMT per 100 gm of dried immature seeds]
[0.04% 5-MeO-DMT also present]
[0.01% Bufotenine also present]

Seedlings
0.001% DMT [4% of 25 mg of total alkaloid/ 100 gm dry]
[0.024% 5-MeO-DMT also present. 24 mg of 5-MeO-DMT per 100 grams of dried seedlings.]
[0.00025% Bufotenine also present]

Pods without seeds
0.012% 5-MeO-DMT. 12 mg of 5-MeO-DMT per 100 grams of dried pods without seeds.
0.001% DMT [8% of 13 mg of total alkaloid/ 100 gm dry.
0.00013% Bufotenine

Leaves
0.094% 5-MeO-DMT. 94 mg of 5-MeO-DMT per 100 grams of dried leaves.
0.013% DMT [12% of 107 mg of total alkaloid/ 100 gm dry]

Twigs
0.0357% 5-MeO-DMT. 36 mg of 5-MeO-DMT per 100 grams of dried twigs.
0.0019% DMT [5% of 38 mg of total alkaloid/ 100 gm dry.
0.0004% Bufotenine

Bark [0.41% total alkaloid]
0.39% 5-MeO-DMT. 390 mg of 5-MeO-DMT per 100 grams of dried bark.
0.02% DMT [5% of 410 mg of total alkaloid/ 100 gm dry.]

Roots [0.69% total alkaloid]
0.014% DMT [2% of 699 mg of total alkaloid/ 100 gm dry]
0.678% 5-MeO-DMT. 678 mg of 5-MeO-DMT per 100 grams of dried roots]
0.007% Bufotenine
Schultes et al. 1977b.


Anadenanthera peregrina (L.) Spegazzini [No. 24625; Origin: Boa Vista, Brazil]

Leaves:
0.0064% i.e. 6.37 mg DMT/ 100 gm dry leaves [49% of 13 mg. of total alkaloids/ 100 gm. of dry leaves:
0.006% [6 mg. of 5-Methoxy-N,N-dimethyltryptamine/ 100 gm. of dry leaves]
Traces of 5-MeO-MMT.
Agurell et al. 1969.

Bark:
0.025% 5-MeO-DMT [25 mg. of 5-Methoxy-N,N-dimethyltryptamine/ 100 gm. of dry bark]
0.0004% DMT i.e. 0.42 mg DMT / 100 gm dry bark [1% of 42 mg. of total alkaloids/ 100 gm. of dry bark]
0.0015% 5-MeO-MMT in bark [15 mg per 100 gm of dried bark]
Traces of bufotenine in dry bark.
Agurell et al. 1969.


Anadenanthera peregrina. [R.E.Schultes 24625; Boa Vista, Brazil]

Leaves
0.00637% DMT [49% of 13 mg of total alkaloid/ 100 gm dry
0.00624% 5-MeO-DMT

Bark
0.025% 5-MeO-DMT
0.015% 5-MeO-MMT
0.00042% DMT- [1% of 42 mg of total alkaloid/ 100 gm dry
0.00084% 6-Methoxy-1,2-dimethyl-1,2,3,4-tetrahydro-b-carboline
0.00084% 6-Methoxy-2-methyl-1,2,3,4-tetrahydro-b-carboline
Schultes et al. 1977b.
(Bark- as Piptadenia peregrina)
Legler & Tschesche 1963 examined bark and reported 5-MeO-DMT formed 32% of the crude base. A mixture of 5-MeO-MMT and MMT comprised 41%. Used Brazilian material.
as Piptadenia peregrina
Bark collected in Colombia during 1956
5-MeO-DMT, DMT, MMT, and 5-MeO-MMT
Holmstedt & Lindgren 1967.

See also:
Agurell et al. 1968 (Two b-carbolines; see above)
Stagno D'Alcontres & Cuzcocrea 1956-57 (what appeared to be bufotenine)
Grossa et al. 1975 (discusses some studies of seed based snuffs and compares with their analysis of Virola based material.).