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{{Taxobox
| color = lightgreen
| name = ''Anadenanthera peregrina''
| image = Anadenanthera peregrina.jpg
| image_width = 300px
| regnum = [[Plantae]]
| divisio = [[Flowering plant|Magnoliophyta]]
| classis = [[Magnoliopsida]]
| ordo = [[Fabales]]
| familia = [[Fabaceae]]
| subfamilia = [[Mimosoideae]]
| genus = [[Anadenanthera]]
| species = '''''A. peregrina'''''
| binomial = ''Anadenanthera peregrina''
| binomial_authority = [[Carlo Luigi Spegazzin|Speg.]]
| range_map = Anadenanthera-peregrina-range-map.png
| range_map_width = 300px
| range_map_caption = Range of ''Anadenanthera peregrina''
| synonyms =
''Acacia angustiloba'' [[A. P. de Candolle|DC.]] 
''Acacia microphylla'' [[Carl Ludwig Willdenow|Willd.]] 
''Acacia peregrina'' ([[Carolus Linnaeus|L.]]) Willd. 
''Inga niopo'' Willd. 
''Mimosa acacioides'' [[Benth.]] 
''Mimosa niopo'' (Willd.) [[Poiret]] 
''Mimosa parvifolia'' Poiret 
''Mimosa peregrina'' L. 
''Niopa peregrina'' (L.) [[Britton]] & [[Rose]] 
''Piptadenia niopo'' (Willd.) [[Spruce]] 
''Piptadenia peregrina'' (L.) [[Benth.]] <ref name="ILDIS">[http://www.ildis.org/LegumeWeb?sciname=Anadenanthera+peregrina ILDIS LegumeWeb]
</ref>
}}

'''''Anadenanthera peregrina''''' (known as '''''Yopo''''', '''Cohoba''', '''Mopo''', '''Nopo''' or '''Parica'''), is a perennial tree native to the [[Carribean]] and [[South America]].<ref name="ILDIS">Text</ref> It grows up to 20m 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 [[ritual]]s.

==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]]). The traditional use of the leaves of these two trees has been discussed in detail by [[Jonathan Ott]].

== Botanical varieties ==
*[[Anadenanthera peregrina var. falcata|''Anadenanthera peregrina'' var. ''falcata'']]
*[[Anadenanthera peregrina var. peregrina|''Anadenanthera peregrina'' var. ''peregrina'']]

== Uses ==
===Gum===
The gum contains [[angicose]], a sugar.<ref name="plantamed">[http://www.plantamed.com.br/plantaservas/especies/Anadenanthera_peregrina.htm PlantaMed (Portuguese)]</ref>

===Traditional medicine===
====Bark====
The bark is used to treat [[allergy|allergies]], [[asthma]], [[cough]], [[diarrhea]], [[dysentery]], [[flatulence]], [[hemorrhage]] and [[pneumonia]].<ref name="plantamed">.</ref>

====Gum====
The gum is used to treat [[asthma]], [[bruise]]s, [[cough]], [[gonorrhea]], [[pneumonia]] and [[ulcer]]s.<ref name="plantamed">.</ref>

===Tannin===
The tree's bark contains a high-quality [[tannin]]. It is said to be better than that of [[quebracho]] and [[mangrove]].<ref>[http://books.google.com/books?hl=en&lr=&id=cMSFT5K3C9wC&oi=fnd&pg=PR9&dq=Anadenanthera+peregrina+falcata&ots=YxsJ1pJmIc&sig=cz-JSXhgUDeHieDOmCq2gseSQ3w#PPA97,M1 Anadenanthera: Visionary Plant of Ancient South America By Constantino Manuel Torres, David B. Repke, p. 97]</ref>

===Wood===
The wood from ''A. peregrina'' is very hard and it is good for making [[furniture]].<ref>[http://www.ibama.gov.br/ojs/index.php/braflor/article/view/89/88 PDF]
Caracterização da Madeira de Angico-Vermelho</ref> It has a Janka rating of 3700 lb.<ref>[http://www.jgarchitectural.com/species.htm J.G. Architectural]</ref> and a density of around 0.86 g/cm3.<ref>[http://www.fao.org/docrep/W4095E/w4095e0c.htm FAO]</ref>

===Warnings===
Medicine from the tree definitely should not be used internally for pregnant women or infants. The seeds and falling leaves are hallucinogenic and are toxic to [[cattle]].<ref name="plantamed">.</ref>

== Chemical compounds ==

[[Chemical compound]]s contained in ''A. peregrina'' include:

*1,2,3,4-Tetrahydro-6-methoxy-2,9-dimethyl-[[beta-carboline]], Plant<ref name="drduke">[http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=72 Dr. Duke's] Phytochemical and Ethnobotanical Databases</ref>
*1,2,3,4-Tetrahydro-6-methoxy-2-methyl-beta-carboline, Plant<ref name="drduke">.</ref>
*[[5-MeO-DMT|5-Methoxy-N,N-dimethyltryptamine]], Bark<ref name="drduke">.</ref>
*5-Methoxy-N-methyltryptamine, Bark<ref name="drduke">.</ref>
*[[Bufotenin]], Plant<ref name="drduke">.</ref>, seeds<ref name="uno">[http://www.unodc.org/unodc/en/bulletin/bulletin_1965-01-01_2_page006.html?print=yes UNO]</ref>
*Bufotenine [[N-oxide]], Fruit<ref name="drduke">.</ref>, seeds<ref name="uno">.</ref>
*[[Catechol]], Plant<ref name="drduke">.</ref>
*[[Homoorientine]], Leaf<ref name="drduke">.</ref>
*[[Leucoanthocyanin]], Plant<ref name="drduke">.</ref>
*[[Leucopelargonidol]], Plant<ref name="drduke">.</ref>
*N,N-[[Dimethyltryptamine]], Fruit<ref name="drduke">.</ref>, seeds, pods<ref name="uno">.</ref>
*N,N-Dimethyltryptamine-oxide, Fruit<ref name="drduke">.</ref><ref>[http://books.google.com/books?id=Ec5hNgYWHtkC&pg=RA2-PA313&lpg=RA2-PA313&dq=%22dmt+n+oxide%22&source=web&ots=BqP13bWy2d&sig=YDxzS2LNTLuBTLU8F3bPdEX0oWY Psychedelics Encyclopedia By Peter G. Stafford, p. 313.]</ref>
*N-[[Methyltryptamine]], Bark<ref name="drduke">.</ref>
*[[Orientin]], Leaf<ref name="drduke">.</ref>
*[[Saponarentin]], Leaf<ref name="drduke">.</ref>
*[[Viterine]], Leaf<ref name="drduke">.</ref>

The bark and leaves contain [[tannin]] and the seeds contain [[saponin]].<ref name="plantamed">.</ref>

== Entheogenic uses ==
To make a [[psychedelic]] snuff called [[Yopo]], the black beans from the seed 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]] ([[Limestone|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 [[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]]. [[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. Some indigenous peoples of the [[Orinoco]] basin in [[Colombia]], [[Venezuela]] and possibly in the southern part of the [[Brazil]]ian [[Amazon Basin|Amazon]] make use of [[Yopo]] snuff for spiritual healing. [[Yopo]] snuff was also widely used in ceremonial contexts by the aborigines of the [[Caribbean]] area, including [[Cuba]] and [[La Española]], up to the [[Spanish Conquest]]. [[Yopo]] snuff is blown into the nostrils through [[bamboo]] tubes or snuffed by bird bone tubes. In some areas the unprocessed ground beans are 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]]. A nearly identical, more potent snuff called [[Vilca]], can be prepared from the related [[Anadenanthera colubrina]]).

The effects of properly made [[insufflation|insufflated]] [[Yopo]] are nearly identical to the effects of [[vaporized]] [[dimethyltryptamine|DMT]] with little physical side effects. However, [[Yopo]] has a slower onset (20-30 minutes), and a much longer duration (up to 2 hours), and the [[insufflation]] process can be painful. Poorly made [[Yopo]] will contain large amounts of [[bufotenin]] and little or no calcium bufotenate, producing strong unpleasant physical side effects (nausea, increased blood pressure, sweating, tingling sensations, heaviness in the limbs, headache, muscle tension, etc.) and much less impressive visionary effects.

Calcium bufotenate is the main active constituent of properly prepared [[Yopo]]. [[Bufotenin]] (often spelled [[bufotenine]]) is the main active constituent of the unprocessed beans. [[Bufotenin]] is often incorrectly attributed to the effects of [[Yopo]]. Although calcium bufotenate is made from [[bufotenin]], these two chemicals vary dramatically in their effects. In the past researchers believed that DMT must have been the main active constituent of [[Yopo]] do to the fact that the effects of [[Yopo]] were more similar to [[DMT]] than [[bufotenin]]. Modern tests, prepared by the DEA and others, have shown that only [[bufotenin]] is present in active amounts in the beans (Microgram Bulletin, VOL. XXXVII, NO. 4, DEA, April 2004; Microgram Bulletin 32(2):83-89, DEA, 1999; Torres & Repke 1996; de Smet & Rivier 1987; Sdvio Nunes et al. 1987; Rend6n 1984; Schultes et al. 1977; Yamasato 1972; Chagnon, Le Quesne & Cook 1971; Fellows & Bell 1971; Holmstedt & Lindgren 1967; Paris, Saint-Firmin & Etchepare 1967; lacobucci & Rdveda 1964; Giesbrecht 1960; Pachter, Zacharias & Ribeiro 1959; Alvares Pereira 1957; Fish, Johnson & Horning 1955; Stromberg 1954). The leaves, bark and seeds also contain small amounts of [[dimethyltryptamine|DMT]], [[5-MeO-DMT]] and related compounds (Schultes 1976,1977; Pachter et al. 1959). [[Bufotenin]] (5-[[OH]]-[[DMT]]) is a positional [[isomer]] of [[psilocin]] (4-[[OH]]-[[DMT]]), the more popular [[entheogen]] found in [[psilocybin mushrooms]]. [[Bufotenin]] is an [[amphoteric]] [[phenols|phenolic]] compound. It has a [[hydroxyl]] ([[OH]]) group on the 5 position similar to [[serotonin]]. As with other [[phenols|phenolic]] compounds ([[phenol]], [[morphine]], etc.) its [[hydroxyl]] ([[OH]]) group is unstable at high [[pH]] levels, and can react with a base forming a salt. For example the base [[calcium hydroxide]] used in the preparation of [[Yopo]] causes the [[hydroxyl]] group's oxygen hydrogen bond to break, replacing the hydrogen with calcium, effectively forming calcium bufotenate (5-[[CaO]]-[[DMT]]), the calcium salt of [[bufotenin]]. Its [[amine]] side chain is able to react with acids, such as [[hydrochloric acid]] forming [[bufotenin]] [[hydrochloride]], the [[hydrochloric]] salt of [[bufotenin]]. Because [[bufotenin]] is weakly acetic, preparations made with [[baking soda]] or dilute [[ammonia]] are not very effective at breaking the [[hydroxyl]] ([[OH]]) group and will simply create [[free-base]] [[bufotenin]].

In general, the physical side effects of [[bufotenine]] based compounds increase dramatically as their water solubility increases. The more water soluble compounds are also less effective at penetrating the [[blood brain barrier]] and produce less psychoactive effects. For example, highly water soluble [[bufotenin]] [[hydrochloride]] produces strong physical side effects (nausea, increased blood pressure, sweating, tingling sensations, heaviness in the limbs, headache, muscle tension, etc.) and is only weakly psychoactive. The less water soluble [[free-base]] [[bufotenin]] produces stronger psychoactive effects and less physical side effects. While the very weakly water soluble calcium bufotenate, found in [[Yopo]], produces the strongest psychoactive effects with very little physical side effects. Of the three compounds, only calcium bufotenate is capable of producing psychoactive effects that rival those of [[DMT]].

[[Yopo]] is never ingested orally because the [[hydrochloric acid]] in the stomach reacts with calcium bufotenate producing the very water soluble [[bufotenin]] [[hydrochloride]], a compound producing dangerous physical side effects when taken orally. The side effects of [[bufotenin]] [[hydrochloride]] increase dramatically and may me fatal if taken orally with an MAOI.

==See also==
*[[List of plants of Caatinga vegetation of Brazil]]

==References==
=== Notes ===
<References/>
{{commons}}
{{wikispecies |Anadenanthera peregrina}}

=== 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

==External links==
* [http://images.google.com/images?svnum=10&hl=en&ie=ISO-8859-1&oe=ISO-8859-1&gbv=1&q=%22Anadenanthera+peregrina%22&btnG=Search+Images '''''Anadenanthera peregrina''''' -- Google Images]
* [http://www.erowid.org/plants/anadenanthera/anadenanthera.shtml Erowid Anadenanthera Vault]
* [http://www.plot55.com/growing/a.colubrina.html Growing Anadenanthera colubrina (Plot55.com)]
* [http://www.plot55.com/usage/anadenanthera.html The Preparation of Anadenanthera Snuffs (Plot55.com)]

[[Category:Anadenanthera]]
[[Category:Entheogens]]
[[Category:Mimosoideae]]
[[Category:Herbal and fungal hallucinogens]]
[[Category:Psychedelic tryptamine carriers]]
[[Category:Trees of Brazil]]
[[Category:Trees of Colombia]]
[[Category:Trees of Venezuela]]
[[Category:Trees of South America]]
[[Category:Trees]]

Anadenanthera peregrina - Revision history

MediaWiki default at 09:36, 16 June 2007