Anadenanthera peregrina
Anadenanthera peregrina (known as Yopo, Cohoba, Mopo, Nopo or Parica), is a perennial tree native to the Caribbean and South America.  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.

# Related species
The usage complex of Yopo is almost identical to that of a related tree, Anadenanthera colubrina, commonly known as Cebil 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.

## Traditional medicine

### Bark
The bark is used to treat allergies, asthma, cough, diarrhea, dysentery, flatulence, hemorrhage and pneumonia.

### Gum
The gum is used to treat asthma, bruises, cough, gonorrhea, pneumonia and ulcers.

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

## Wood
The wood from A. peregrina is very hard and it is good for making furniture.  It has a Janka rating of 3700 lb. and a density of around 0.86 g/cm3.

## 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.

# Chemical compounds
Chemical compounds contained in A. peregrina include:
- 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
- Bufotenin,	Plant, beans
- Bufotenin N-oxide, Fruit, beans
- Catechol, Plant
- Homoorientine, Leaf
- Leucoanthocyanin, Plant
- Leucopelargonidol, Plant
- N,N-Dimethyltryptamine, Fruit, beans, pods, bark
- N,N-Dimethyltryptamine-oxide, Fruit
- N-Methyltryptamine, Bark
- Orientin, Leaf
- Saponarentin, Leaf
- Viterine, Leaf
The bark and leaves contain tannin and the beans contain saponin.

# 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.  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.
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 Espanola, 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 so that all the bufotenin comes into contact with the moistened calcium hydroxide and reacts with it to form calcium bufotenate (5-CaO-DMT).  The calcium hydroxide also reacts with any DMT and 5-MeO-DMT present to form free-base DMT and free-base 5-MeO-DMT.  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 calcium carbonate (carbonatation). Calcium hydroxide is caustic in the presence of water, and is very irritating to the nasal passages, so it is desirable to allow any left over calcium hydroxide to convert to calcium carbonate.  It is then thoroughly dried and ready for use.  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 especially when using snuff that hasnt been properly aged (if aged a week, most of the excess calcium hydroxide combines with the carbon dioxide in the air to form calcium carbonate).  Yopo produces more bodily sensations, and more auditory effects than vaporized DMT, and the experience is usually seen as more deeply spiritual and meaningful.  The effects are primarily 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.
If the Yopo is poorly made, it may contain little or no calcium bufotenate, instead containing the unprocessed acidic salt form of bufotenin, producing strong unpleasant physical side effects (tight feeling in the throat and chest, nausea, vomiting, increased blood pressure, sweating, paresthesia, heaviness in the limbs, headache, muscle tension, etc.) and much less pronounced visual effects.

## Active Constituents

### Bufotenin
Calcium bufotenate (the calcium salt of bufotenoxide) is the main active constituent of properly prepared Yopo.  An acidic salt form of bufotenin (often spelled bufotenine) is the main active constituent of the unprocessed beans.  The acidic salt form is often incorrectly attributed to the effects of Yopo.  Although the basic salt calcium bufotenate is made from the acidic salt form of bufotenin, the two chemicals vary on a molecular basis and vary dramatically in their effects.  In the past researchers believed that DMT must have been the main active constituent of Yopo due to the fact that the effects of Yopo seemed to be more similar to DMT than the natural acidic salt form of bufotenin present in the beans.  Modern tests, prepared by the DEA and others, have shown that only bufotenin is present in active amounts in the beans.
The beans have been found to contain up to 7.4% bufotenin. At up to 7.4 % (74 mg per gram) bufotenin, an effective 40 mg dose of insufflated bufotenin 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.  In low pH levels, its amine side chain is able to react with acids forming an acidic salt. For example, bufotenin can react with hydrochloric acid (HCl) forming bufotenin hydrochloride (5-hydroxy-dimethyltryptamine + HCl), an acidic salt of bufotenin.  As with other phenolic compounds (phenol, morphine, etc.) bufotenins hydroxyl (HO) group is unstable at high pH levels, and can decompose losing its hydrogen atom forming a phenoxide based compound called bufotenoxide (5-oxy-dimethyltryptamine). When in its phenoxide form, bufotenoxides oxygen atom at the 5 position is able to form salts with bases. For example the base calcium hydroxide used in the preparation of Yopo causes bufotenin (5-hydroxy-dimethyltryptamine) to decompose into bufotenoxide (5-oxy-dimethyltryptamine). Bufotenoxide then forms calcium bufotenate (Ca + 5-oxy-dimethyltryptamine), the calcium salt of bufotenoxide.  Yopo preparations made with baking soda or dilute ammonia are not very effective at decomposing bufotenin into bufotenoxide and will simply create free-base bufotenin.  Free-base bufotenin is weakly acidic and very polar. Calcium bufotenate is weakly alkaline and less polar. Bufotenin hydrochloride, calcium bufotenate, and free-base bufotenin are all water soluble, with bufotenin hydrochloride being the most water soluble and calcium bufotenate being the least water soluble.
The intraperitoneal LD50 of water soluble acidic salt forms 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.  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 tests using water soluble acidic salt forms intravenously 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.  However, the pharmacological effects of calcium bufotenate and free-base bufotenin in humans are on many levels very different from those produced by highly water soluble acidic salt forms. In humans, calcium bufotenate and free-base bufotenin show far less toxic bodily symptoms than water soluble acidic forms.  For example, in humans, 10 mg of the water soluble acidic salt bufotenin hydrochloride inhaled via vaporization typically produces a tight feeling in the throat, strong nausea, vomiting, a feeling of pressure and tension in the body, and only very slight hallucinogenic effects.  The same vaporized dose of calcium bufotenate produces very strong hallucinogenic effects and none of the other effects of bufotenin hydrochloride.  Even the hallucinogenic effects are qualitatively different to such a degree that human test subjects often believe it to be a different drug.  While human tests seem to show that calcium bufotenate and free-base bufotenin are relatively low in toxicity compared to their water soluble acidic salt forms, the actual LD50 for all forms of bufotenin in humans is unknown.

### DMT and 5-MeO-DMT
Claims of Anadenanthera peregrina containing DMT and 5-MeO-DMT as the main active ingredients are unsubstantiated.Template:Disputable  The effects of DMT and 5-MeO-DMT are very short acting, while the effects of Yopo last a good 2 hours.  Modern tests confirm that bufotenin is responsible for the effects of Yopo with the other compounds appearing in quantities too small to produce noticeable effects in an average Yopo dose of 1-3 grams.Template:Disputable
The beans have been found to contain up to only 0.04% 5-MeO-DMT and 0.16% DMT.  The leaves and bark also contain small amounts of DMT, 5-MeO-DMT and related compounds.
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 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.  Its 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.
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.

## Oral Usage
The beans are not normally ingested orally because the hydrochloric acid in the human digestive system reacts with bufotenin producing the very water soluble bufotenin hydrochloride, a compound producing strong physical side effects.  However, use of very small oral doses produces a mild pleasant stimulant effect, very mild visual effects, euphoria, and is said by some users to have aphrodisiac properties.  When taken orally by some tribes in South America, small amounts are often combined with alcoholic chichas (maize based beer).  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.  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.  Typically Banisteriopsis caapi is chewed in the mouth while the Anadenanthera beans are snuffed or smoked.  Occasionally Banisteriopsis caapi is found mixed in with the snuff.  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).  This practice may be dangerous.  The side effects of bufotenin hydrochloride may increase dramatically and may be fatal do to potentially dangerous interactions with the MAOI compounds present in ayahuasca brews.