Anadenanthera peregrina

Anadenanthera peregrina, also known as Yopo, Cohoba, Mopo, Nopo or Parica, is a perennial tree of the Anadenanthera genus native to the Caribbean and South America.^[1] It grows up to 20 m tall, having a thorny bark. Its flowers are pale yellow to white and spherical. It is not listed as being a threatened species. It is an entheogen used in healing ceremonies and rituals.

Additional recommended knowledge

Essential Laboratory Skills Guide

Safe Weighing Range Ensures Accurate Results

What is the Correct Way to Check Repeatability in Balances?

Related species

The usage complex of yopo is almost identical to that of a related tree, Anadenanthera colubrina, commonly known as Cebíl or Vilca. The beans of A. colubrina have a similar chemical makeup as Anadenanthera peregrina, with their primary constituent being 5-OH-DMT (bufotenin).

Botanical varieties

• Anadenanthera peregrina var. falcata
• Anadenanthera peregrina var. peregrina

Uses

Gum

The gum contains angicose, a sugar.^[2]

Traditional medicine

Bark

The bark is used to treat allergies, asthma, cough, diarrhea, dysentery, flatulence, hemorrhage and pneumonia.^[2]

Gum

The gum is used to treat asthma, bruises, cough, gonorrhea, pneumonia and ulcers.^[2]

Tannin

The tree's bark contains a high-quality tannin. It is said to be better than that of quebracho and mangrove.^[3]

Wood

The wood from A. peregrina is very hard and it is good for making furniture.^[4] It has a Janka rating of 3700 lb.^[5] and a density of around 0.86 g/cm³.^[6]

Warnings

Medicine from the tree definitely should not be used internally for pregnant women or infants. The beans (sometimes called seeds) and falling leaves are hallucinogenic and are toxic to cattle.^[2]

Chemical compounds

Chemical compounds contained in A. peregrina include:

• 1,2,3,4-Tetrahydro-6-methoxy-2,9-dimethyl-beta-carboline, Plant^[7]
• 1,2,3,4-Tetrahydro-6-methoxy-2-methyl-beta-carboline, Plant^[7]
• 5-Methoxy-N,N-dimethyltryptamine, Bark^[7]
• 5-Methoxy-N-methyltryptamine, Bark^[7]
• Bufotenin, Plant,^[7] beans^[8]
• Bufotenin N-oxide, Fruit^[7], beans^[8]
• Catechol, Plant^[7]
• Homoorientine, Leaf^[7]
• Leucoanthocyanin, Plant^[7]
• Leucopelargonidol, Plant^[7]
• N,N-Dimethyltryptamine, Fruit,^[7] beans, pods,^[8] bark^[9]
• N,N-Dimethyltryptamine-oxide, Fruit^[7][10]
• N-Methyltryptamine, Bark^[7]
• Orientin, Leaf^[7]
• Saponarentin, Leaf^[7]
• Viterine, Leaf^[7]

The bark and leaves contain tannin and the beans contain saponin.^[2]

Entheogenic uses

Traditional usage

Archeological evidence shows Anadenanthera beans have been used as hallucinogens for thousands of years. The oldest clear evidence of use comes from smoking pipes made of puma bone (Felis Concolor) found with Anadenanthera beans at Inca Cueva, a site in the northwest of Humahuaca in the Puna border of the Province of Jujuy, Argentina. The pipes were found to contain the hallucinogen DMT, one of the compounds found in Anadenanthera beans. Radiocarbon testing of the material gave a date of 2130 B.C., suggesting Anadenanthera use as a hallucinogen is over 4000 years old.^[11] Snuff trays and tubes similar to those commonly used for yopo were found in the central Peruvian coast dating back to 1200 B.C., suggesting that insufflation of Anadenanthera beans is a more recent method of use.^[12]

Some indigenous peoples of the Orinoco basin in Colombia, Venezuela and possibly in the southern part of the Brazilian Amazon make use of yopo snuff for spiritual healing. Yopo snuff was also widely used in ceremonial contexts in the Caribbean area, including Cuba and La Española, up to the Spanish Conquest.

Yopo snuff is usually blown into the user's nostrils by another person through bamboo tubes or sometimes snuffed by the user using bird bone tubes. Blowing is more effective as this method allows more powder to enter the nose and is said to be less irritating. In some areas the unprocessed ground beans are snuffed or smoked producing a much weaker effect with stronger physical symptoms. Some tribes use yopo along with Banisteriopsis caapi to increase and prolong the visionary effects, creating an experience similar to that of ayahuasca.

Snuff preparation

To make the psychedelic snuff called yopo, the black beans from the bean pods of these trees are first toasted until the beans pop like popcorn breaking the bean's husk. The roasting process facilitates removal of the husk and makes the beans easier to grind into a powder. The bean's husk is usually removed because it is difficult to powderise. The bean is then ground with a mortar and pestle into a powder and mixed with a natural form of calcium hydroxide (lime) or calcium oxide (from certain types of ashes, calcined shells, etc.). This mix is then moistened to a consistency similar to bread dough, using a small amount of water. If calcium oxide is used, the water will react with it to form calcium hydroxide. Once moistened, it is kneaded into a ball for several minutes. If given enough time, calcium hydroxide will react with bufotenine and replace the hydrogen bond at the five position of bufotenine (5-HO-DMT) with calcium, forming Ca + 5-O-DMT, also known as calcium bufotenate (or calcium bufotenoxide). This is a common chemical reaction that occurs with all phenolic compounds when reacted with calcium hydroxide for expended periods of time (see phenol for more information). Several hours are needed for the reaction to take place. Ca + 5-O-DMT is less toxic, and produces effects more like DMT and Psilocin than the classic toxic effects of bufotenine. Its effects last normally 2-3 hours. After kneading, it is then left to sit for several hours to several days, depending on the local customs. During this period most of the excess calcium hydroxide reacts with the carbon dioxide in the air to form less caustic calcium carbonate (carbonatation). The more modern non-traditional use of baking soda or ammonia as a substitute for calcium hydroxide has been used with limited success. A nearly identical snuff called Vilca, can be prepared from the related Anadenanthera colubrina.

Entheogenic effects

Shamans use yopo in a spiritual context much like ayahuasca is used. Use of yopo may actually predate Ayahuasca usage. Many shamans believe the visionary dream-state induced by yopo allows them to contact spirits in the spirit world to gain knowledge about medicinal plants, how to treat an illness, etc. The effects of properly made insufflated yopo are similar to the effects of vaporized DMT but much longer in duration. The effects begin approximately 15-30 minutes after insufflation and can last up to 2-3 hours. The insufflation process can be painful due to remaining calcium hydroxide, especially when using snuff that hasn’t been properly aged. The effects are can be visual in nature, causing the user to see colorful patterns, objects seen with the eyes may appear to be swirling, transforming into other objects, changing colors, etc. The user may see colorful 3-dimensional moving patterns with the eyes opened or closed. Some users experience more visual effects from yopo than from DMT. The user may hear dreamy sounds and voices. With the eyes closed or in a dark setting, users may experience full dream-like phenomena, interacting with imaginary places, people, etc. The visions are seen as dreamy or spiritual in nature and do not appear as though they are real. The over effects are generally relaxing. Users often feel a pleasant tingling sensation throughout the body similar to those felt while using Yohimbe. The mind normally remains clear and focused during the entire experience. Some users may experience transient nausea. At high doses, users may feel sweaty, become nervous, experience difficulty it walking, lose motor control, and may enter into a trance state.

Shamans sometimes combine yopo with Banisteriopsis caapi. The Banisteriopsis caapi is usually chewed before, during, and after yopo is insufflated. This intensifies and prolongs the visionary state produced by yopo. The combined effects are more dream-like and very similar to ayahuasca.

Active constituents

Bufotenin and Ca + 5-O-DMT

Bufotenine is the main active constituent of unprocessed yopo. Modern tests, prepared by the DEA and others, have shown that only bufotenin is present in active amounts in the beans.^{[13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29]} It must be noted that because bufotenine is a phenolic compound, the lengthy snuff processing with calcium hydroxide converts bufotenine into Ca + 5-O-DMT (calcium bufotenate/bufotenoxide). Ca + 5-O-DMT is a hallucinogen like DMT and psilocin and very unlike bufotenine. Snuff prepared without calcium hydroxide will contain large amount of bufotenine and no Ca + 5-O-DMT, and will produce nausea, tension, and a completely different hallucinogenic effect very unlike DMT and psilocin. Snuffs made with ammonia and other weak bases instead of calcium hydroxide, will create free base bufotenine and not Ca + 5-O-DMT. While free base bufotenine is psychoactive, it is very unlike DMT and somewhat toxic. Shamans typically prefer the effects of Ca + 5-O-DMT over bufotenine. This is why most shamans prepare yopo snuff using up to 33% calcium hydroxide and allow it to react overnight, kneading it over and over to ensure that all the bufotenine reacts with the calcium hydroxide.

The beans have been found to contain up to 7.4% bufotenin.^[30] At up to 7.4 % (74 mg per gram) bufotenin, an effective 40 mg dose of insufflated bufotenin^[30] requires little more than 0.5 grams of beans.

Bufotenin (5-hydroxy-dimethyltryptamine) is a positional isomer of psilocin (4-hydroxy-dimethyltryptamine), the more popular entheogen found in psilocybin mushrooms. Bufotenin is an amphoteric phenolic compound. It has a hydroxyl (HO) group on the 5 position similar to serotonin. At acidic pH its amine side chain is protonated while at basic pH the phenol is deprotonated.

The intraperitoneal LD₅₀ of bufotenin is between 200-300 mg/kg (in rodents) with death occurring by reparatory arrest. The LD₅₀ in rodents amounts to between 10,000 mg and 15,000 mg for a small 50 kg (110 lb) adult.^[31] Based on the intraperitoneal LD₅₀ for rodents, at 74 mg per gram, it would require approximately 135 grams of beans to reach the estimated LD₅₀of bufotenin for a 50 kg (110 lb) adult. The LD₅₀ for calcium bufotenate and free-base bufotenin in rodents is currently unknown. Human intravenous tests using bufotenin suggest the LD₅₀ may be much lower in humans with subjects showing signs of peripheral toxicity (purple face, tachycardia, difficulty breathing, etc.) at doses as little as 8 mg in some subjects.^[32] Free base bufotenin when insufflated, taken sublingually, orally, or intrarectally, elicits strong hallucinogenic effects with far less side effects^[30].

DMT and 5-MeO-DMT

The effects of insufflated DMT and 5-MeO-DMT are relatively short acting, lasting about 1 hour. While the effects of insufflated yopo typical lasts 2-3 hours. Of the three main compounds present, only insufflated bufotenine lasts 2-3 hours. Claims of Anadenanthera peregrina containing DMT and 5-MeO-DMT as their main active ingredients are based on rare cases where these compounds are found in larger quantities than bufotenine. Typical acid base extraction techniques utilizing strong bases such as sodium hydroxide solution will exclude bufotenin from the extraction, in favor of DMT and 5-MeO-DMT. It is believed^{[citation needed]} that such extractions have contributed to the misconception that bufotenin is a minor alkaloid in yopo. The majority of the extractions confirm that bufotenin is primarily responsible for the effects of yopo with the other compounds usually appearing in quantities too small to produce noticeable effects in an average yopo dose of 5-10 grams^{[citation needed]}.

The beans have been found to contain up to only 0.04% 5-MeO-DMT and 0.16% DMT.^[30] The leaves and bark also contain small amounts of DMT, 5-MeO-DMT and related compounds.^[33]

At up to 0.04% (0.4 mg per gram) 5-MeO-DMT, an effective light 5 mg dose of insufflated 5-MeO-DMT (5-MeO-DMT dosage, Erowid.org) would require over 12 grams of beans. It would be extremely difficult to insufflate the 12 grams of beans (approximately 72 beans) needed to reach the active dose of 5-MeO-DMT present in the beans. The body would begin to develop tolerance to 5-MeO-DMT before being able to insufflate all 12 grams of beans. Individual sensitivity to 5-MeO-DMT varies. Its been documented that the threshold dose in some individuals is as much as 10 mg insufflated^[34] requiring over 24 grams of beans for an effective dose of 5-MeO-DMT.

At up to 0.16% (1.6 mg per gram) DMT, an effective 40 mg dose of insufflated DMT would require 25 grams or more. It’s likely to be impossible to insufflate the 25 grams of beans required to reach the active dose of DMT present in the beans. An extract of 25 grams of beans could contain up to 1,850 mg of bufotenin, a potentially dangerous dose of bufotenin. With insufflated free-base bufotenin, the maximum published safe dose used has been 100 mg.^[30]

Unlike bufotenin, both DMT and 5-MeO-DMT are relatively unstable and begin to degrade rather quickly. Schultes and colleges (1977) examined a 120 year old bean collection and found 0.6% bufotenin with no DMT or 5-MeO-DMT present at all. They also examined a batch of beans that contained all three compounds when fresh, but found only bufotenin in the beans after only two years of storage.^[35]

Oral usage

When taken orally by some tribes in South America, small amounts are often combined with alcoholic chichas (maize based beer).^[36] Moderate doses are unpleasant, producing nausea and vomiting. The beans were a main ingredient in bilca tauri, an oral purge medicine used to induce ritual vomiting once a month.^[37] Large amounts are not usually consumed orally; as many tribes believe oral use is dangerous.

Use with MAOIs

Some South American tribes have been documented to use various bean preparations along with Banisteriopsis caapi, an herb containing MAOIs.^[31] Typically Banisteriopsis caapi is chewed in the mouth while the Anadenanthera beans are snuffed or smoked.^[31] Occasionally Banisteriopsis caapi is found mixed in with the snuff.^[31] Moderate amounts of Banisteriopsis caapi will effectively double the potency of the Anadenanthera beans. Larger amounts of Banisteriopsis caapi will not only double the potency of Anadenanthera beans but also alter the quality of the experience, producing a more relaxed dreamy effect, with possible increased nausea. There are no well documented reports of the beans being used as a major component in oral ayahuasca (a tea made with Banisteriopsis caapi).

See also

• List of plants of Caatinga vegetation of Brazil
• Psychedelic plants

References

Notes

1. ^ ^{a b} ILDIS LegumeWeb
2. ^ ^{a b c d e} PlantaMed (Portuguese)
3. ^ Anadenanthera: Visionary Plant of Ancient South America By Constantino Manuel Torres, David B. Repke, p. 97
4. ^ PDF Caracterização da Madeira de Angico-Vermelho
5. ^ J.G. Architectural
6. ^ FAO
7. ^ ^{a b c d e f g h i j k l m n o p} Dr. Duke's Phytochemical and Ethnobotanical Databases
8. ^ ^{a b c} UNO
9. ^ Medicina traditional Ergebnisse einethnomedizinischen ...(German)
10. ^ Psychedelics Encyclopedia By Peter G. Stafford, p. 313.
11. ^ M. L. Pochettino, A. R. Cortella, M. Ruiz. 1999
12. ^ Cortella, M. Ruiz. 1995
13. ^ Microgram Bulletin, VOL. XXXVII, NO. 4, DEA, April 2004
14. ^ Microgram Bulletin 32(2):83-89, DEA, 1999
15. ^ Torres & Repke 1996
16. ^ de Smet & Rivier 1987
17. ^ Sdvio Nunes et al. 1987
18. ^ Schultes et al. 1977
19. ^ Yamasato 1972
20. ^ Chagnon, Le Quesne & Cook 1971
21. ^ Fellows & Bell 1971
22. ^ Holmstedt & Lindgren 1967
23. ^ Paris, Saint-Firmin & Etchepare 1967
24. ^ Lacobucci & Rdveda 1964
25. ^ Giesbrecht 1960
26. ^ Pachter, Zacharias & Ribeiro 1959
27. ^ Alvares Pereira 1957
28. ^ Fish, Johnson & Horning 1955
29. ^ Stromberg 1954
30. ^ ^{a b c d e} Pharmanopo-Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine by Jonathan Ott, The Journal of Psychoactive Drugs, September 2001
31. ^ ^{a b c d} Anadenanthera: Visionary Plant Of Ancient South America, Constantino Manuel, Ph.D. Torres, David B. Repke, 2006, ISBN 0789026422
32. ^ TiKHAL, Alexander Shulgin, 1997
33. ^ Schultes 1976,1977; Pachter et al. 1959
34. ^ Shamanic Snuffs or Entheogenic Errhines by Jonathan Ott, Page 102, 2001, ISBN 1888755024
35. ^ Anadenanthera: Visionary Plant Of Ancient South America, Constantino Manuel, Ph.D. Torres, David B. Repke, 2006, page 123, ISBN 0789026422
36. ^ Anadenanthera: Visionary Plant Of Ancient South America, Constantino Manuel, Ph.D. Torres, David B. Repke, 2006, page 29, ISBN 0789026422
37. ^ Anadenanthera: Visionary Plant Of Ancient South America, Constantino Manuel, Ph.D. Torres, David B. Repke, 2006, page 28, ISBN 0789026422

General references

• Jonathan Ott - Shamanic Snuffs or Entheogenic Errhines (2001) ISBN 1-888755-02-4
• Richard Evans Schultes - Plants of the Gods (1992) ISBN 0-89281-979-0