View source for Anadenanthera peregrina

{{Short description|Species of plant}}
{{redirect|Ebene|the city in Mauritius|Ebene City}}
{{Multiple issues|
{{more citations needed|date=October 2014}}
{{original research|date=October 2014}}
{{confusing|date=October 2014}}
}}
{{Speciesbox
|image = Anadenanthera peregrina.jpg
|taxon = Anadenanthera peregrina
|authority = ([[Carl Linnaeus|L.]]) [[Carlo Luigi Spegazzini|Speg.]]
|status = LC
|status_system = IUCN3.1
|status_ref = <ref name="iucn status 18 November 2021">{{cite iucn |author=Botanic Gardens Conservation International (BGCI). |author2=IUCN SSC Global Tree Specialist Group |date=2019 |title=''Anadenanthera peregrina'' |volume=2019 |article-number=e.T144262459A149021134 |doi=10.2305/IUCN.UK.2019-2.RLTS.T144262459A149021134.en |access-date=18 November 2021}}</ref>
|range_map = Anadenanthera-peregrina-range-map.png
|range_map_caption = Range of ''Anadenanthera peregrina''
|synonyms = ''Acacia angustiloba'' <small>[[A. P. de Candolle|DC.]]</small><br />
''Acacia microphylla'' <small>[[Carl Ludwig Willdenow|Willd.]]</small><br />
''Acacia peregrina'' <small>([[Carl Linnaeus|L.]]) Willd.</small><br />
''Inga niopo'' <small>Willd.</small><br />
''Mimosa acacioides'' <small>[[Benth.]]</small><br />
''Mimosa niopo'' <small>(Willd.) [[Poir.]]</small><br />
''Mimosa parvifolia'' <small>Poiret</small><br />
''Mimosa peregrina'' <small>L.</small><br />
''Niopa peregrina'' <small>(L.)&nbsp;[[Nathaniel Lord Britton|Britton]]&nbsp;&&nbsp;[[Joseph Nelson Rose|Rose]]</small><br />
''Piptadenia niopo'' <small>(Willd.) [[Richard Spruce|Spruce]]</small><br />
''Piptadenia peregrina'' <small>(L.) [[Benth.]]</small><ref name="ILDIS">{{Cite web
|url=http://www.ildis.org/LegumeWeb?sciname=Anadenanthera+peregrina
|title=Anadenanthera peregrina - ILDIS LegumeWeb
|publisher=www.ildis.org
|access-date=2008-05-17
}}</ref>
}}

'''''Anadenanthera peregrina''''', also known as '''yopo''', '''jopo''', '''cohoba''', '''parica''' or  '''calcium tree''', is a perennial tree of the genus ''[[Anadenanthera]]'' native to the [[Caribbean]] and [[South America]].<ref name="ILDIS"/> It grows up to {{convert|20|m|ft|abbr=on}} tall, and has a thorny bark. Its flowers grow in small, pale yellow to white spherical clusters resembling Acacia (e.g. wattle) inflorescences.  It is an [[entheogen]] which has been used in healing ceremonies and [[ritual]]s for thousands of years in northern South America and the Caribbean.<ref>{{Cite journal|last1=Carod-Artal|first1=F. J.|last2=Vázquez Cabrera|first2=C. B.|date=July 2007|title=[Ritual use of Anadenanthera seeds among South America natives]|journal=Neurologia (Barcelona, Spain)|volume=22|issue=6|pages=410–415|issn=0213-4853|pmid=17610173}}</ref> Although the seeds of the yopo tree were originally gathered from the wild, increased competition between tribes over access to the seeds led to it being intentionally cultivated and transported elsewhere, expanding the plant's distribution through introduction to areas beyond its native range.<ref name="tropical.theferns.info">{{Cite web |title=Anadenanthera peregrina - Useful Tropical Plants |url=http://tropical.theferns.info/viewtropical.php?id=Anadenanthera+peregrina |access-date=2022-08-26 |website=tropical.theferns.info}}</ref>

==Related species==
This plant is almost identical to that of a related tree, ''[[Anadenanthera colubrina]]'',<ref name="PLOS ONE">{{Cite journal|last1=Mota|first1=Graciene S.|last2=Sartori|first2=Caroline J.|last3=Miranda|first3=Isabel|last4=Quilhó|first4=Teresa|last5=Mori|first5=Fábio Akira|last6=Pereira|first6=Helena|date=2017|title=Bark anatomy, chemical composition and ethanol-water extract composition of Anadenanthera peregrina and Anadenanthera colubrina|journal=PLOS ONE|volume=12|issue=12|article-number=e0189263|doi=10.1371/journal.pone.0189263|issn=1932-6203|pmid=29281656|pmc=5744935|bibcode=2017PLoSO..1289263M|doi-access=free}}</ref> commonly known as ''cebíl'' or ''vilca''.<ref name=":0">{{Cite web|url=https://azarius.net/smartshop/herbs/psychedelic_herbs/anadenanthera_colubrina/|title=Cebil (Anadenanthera colubrina) seeds|website=Azarius|language=en|access-date=2017-12-30|archive-url=https://web.archive.org/web/20171230225838/https://azarius.net/smartshop/herbs/psychedelic_herbs/anadenanthera_colubrina/|archive-date=2017-12-30}}</ref> The beans of ''A. colubrina'' have a similar chemical makeup as ''Anadenanthera peregrina'', with their primary constituent being [[bufotenin]].<ref name=":0" />

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

==Uses==

===Wood===
The wood from ''A. peregrina'' produces very hard timber that is used for making [[furniture]].<ref>[http://www.ibama.gov.br/ojs/index.php/braflor/article/view/89/88 PDF] Caracterização da Madeira de Angico-Vermelho  {{webarchive |url=https://web.archive.org/web/20071213093902/http://www.ibama.gov.br/ojs/index.php/braflor/article/view/89/88 |date=December 13, 2007 }}</ref> It has a [[Janka Wood Hardness Rating|Janka]] rating of 3700&nbsp;lb.<ref>{{Cite web |url=http://www.jgarchitectural.com/species.htm |title=J.G. Architectural |access-date=2007-05-26 |archive-date=2007-09-29 |archive-url=https://web.archive.org/web/20070929073931/http://www.jgarchitectural.com/species.htm }}</ref>{{Failed verification|date=June 2021}} and a density of around 0.86 g/cm<sup>3</sup>.<ref>[http://www.fao.org/docrep/W4095E/w4095e0c.htm FAO]</ref> Tannins have also been derived from this plant.<ref name="tropical.theferns.info"/>

===Toxicity===
The beans (sometimes called seeds) and falling leaves are hallucinogenic and are toxic to [[cattle]].<ref>{{cite journal |last1=Monteiro |first1=Júlio Marcelino |last2=de Fátima |first2=Cecília |last3=de Almeida |first3=Rangel |last4=de Albuquerque |first4=Ulysses Paulino |last5=Farias Paiva de Lucena |first5=Reinaldo |last6=Florentino |first6=Alissandra Trajano N |last7=de Oliveira |first7=Rodrigo Leonardo C |title=Use and traditional management of Anadenanthera colubrina (Vell.) Brenan in the semi-arid region of northeastern Brazil |journal=Journal of Ethnobiology and Ethnomedicine |date=18 January 2006 |volume=2 |article-number=6 |doi=10.1186/1746-4269-2-6 |pmid=16420708 |publisher=PubMed Central |doi-access=free |pmc=1382198}}</ref>

==Chemical compounds==
[[Chemical compound]]s contained in ''A. peregrina'' include:
* [[Tryptoline|2,9-dimethyltryptoline]] – plant<ref name="drduke">[http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=72 Dr. Duke's] {{webarchive |url=https://web.archive.org/web/20130219223907/http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=72 |date=February 19, 2013 }} Phytochemical and Ethnobotanical Databases</ref>
* [[Tryptoline|2-methyltryptoline]] – plant<ref name="drduke" />
* [[5-MeO-DMT]] – bark,<ref name="drduke" /> beans
* 5-Methoxy-''N''-methyltryptamine – bark<ref name="drduke" />
* [[Bufotenin]] – plant<ref name="drduke" /> beans<ref name="uno">{{Cite web |url=http://www.unodc.org/unodc/en/bulletin/bulletin_1965-01-01_2_page006.html?print=yes |title=UNO |access-date=2007-06-10 |archive-url=https://web.archive.org/web/20050120023802/http://www.unodc.org/unodc/en/bulletin/bulletin_1965-01-01_2_page006.html |archive-date=2005-01-20 }}</ref>
* [[Bufotenin]]-[[amine oxide|oxide]] – fruit,<ref name="drduke" /> beans<ref name="uno" />
* [[Catechol]] – plant<ref name="drduke" />
* [[Leucoanthocyanin]] – plant<ref name="drduke" />
* Leucopelargonidol – plant<ref name="drduke" />
* [[Dimethyltryptamine|DMT]] – fruit,<ref name="drduke" /> beans, pods,<ref name="uno" /> bark<ref>[http://deposit.ddb.de/cgi-bin/dokserv?idn=981893406&dok_var=d1&dok_ext=pdf&filename=981893406.pdf Medicina traditional Ergebnisse einethnomedizinischen ...(German)] {{webarchive |url=https://web.archive.org/web/20120205184910/http://deposit.ddb.de/cgi-bin/dokserv?idn=981893406&dok_var=d1&dok_ext=pdf&filename=981893406.pdf |date=February 5, 2012 }}</ref>
* [[Dimethyltryptamine|DMT]]-[[amine oxide|oxide]] – fruit<ref name="drduke" /><ref>{{Cite book
|title=Psychedelics Encyclopedia
|author=Peter Stafford , Jeremy Bigwood
|year=1993
|publisher=Ronin Publishing
|isbn=0-914171-51-8
|pages=420 pages
|url=https://books.google.com/books?id=Ec5hNgYWHtkC
}}</ref>
* [[N-Methyltryptamine]] – bark<ref name="drduke" />
* [[Orientin]] – leaf<ref name="drduke" />
* [[Isovitexin|Saponarentin]] – leaf<ref name="drduke" />
* Viterine – leaf<ref name="drduke"/>

The bark contains a high percentage of [[tannin]]s, 587&nbsp;mg CE/g extract.<ref name="PLOS ONE"/>

==Entheogenic uses==
{{More citations needed section|date=August 2007}}

===Traditional usage===
[[File:Anadenanthera-peregrina-bw.png|right|thumb|250px|''Anadenanthera peregrina'' 1916]]
[[File:Yopo Seeds.jpg|thumb|right|Yopo seeds]]

[[Archaeological]] evidence shows ''Anadenanthera'' beans have been used as [[hallucinogens]] for thousands of years. The oldest clear evidence of use comes from pipes made of [[Puma concolor|puma]] bone (''Puma concolor'') found with ''Anadenanthera'' beans presumably of the sister species ''A. colubrina'', at Inca Cueva, a site in the [[Humahuaca]] gorge at the edge of the [[Altiplano|Puna]] of [[Jujuy Province]], Argentina. The pipes were found to contain the hallucinogen [[Dimethyltryptamine|DMT]], one of the compounds found in ''Anadenanthera'' beans. [[Radiocarbon]] testing of the material gave a date of 2130 BC, suggesting that ''Anadenanthera'' use as a hallucinogen is over 4,000 years old.<ref>{{cite journal|last1=Pochettino|first1=M. L.|last2=Cortella|first2=A. R.|last3=Ruiz|first3=M.|title=Hallucinogenic Snuff from Northwestern Argentina: Microscopical Identification of Anadenanthera colubrina var. cebil (Fabaceae) in Powdered Archaeological Material|journal=Economic Botany|date=1999|volume=53|issue=2|pages=127–132|jstor=4256172|doi=10.1007/bf02866491|bibcode=1999EcBot..53..127P |s2cid=13153575|url=http://sedici.unlp.edu.ar/handle/10915/139078 }}</ref> [[Snuff tray]]s and tubes similar to those commonly used for yopo were found in the central Peruvian coast dating back to 1200 BC, suggesting that [[Insufflation (medicine)|insufflation]] of ''Anadenanthera'' beans is a more recent method of use.<ref>Cortella, M. Ruiz. 1995 {{full citation needed|date=September 2016}}</ref> Archaeological evidence of insufflation use within the period 500-1000 AD, in northern Chile, has been reported.<ref>{{cite journal |author1=Juan P. Ogalde |author2=Bernardo T. Arriaza |author3=Elia C. Soto | title = Uso de plantas psicoactivas en el north de Chile: evidencia química del consumo de ayahuasca durante el periodo medio (500-1000 d.C.) | journal = Latin American Antiquity | volume = 21 | issue = 4 | year = 2010 | pages = 441–450 | doi=10.7183/1045-6635.21.4.441|s2cid=163915994 }}</ref>

Some Indigenous peoples of the Orinoco basin in Colombia, Venezuela, and Brazil prepare yopo snuff for ritual and healing purposes. Among the Piaroa of the Venezuelan Orinoco, yopo is reserved primarily for shamanic specialists known as ''meñeruá''.<ref name="Mansutti2012">Mansutti Rodríguez, A. (2012). Yuruparí: máscaras y poder entre los piaroas del Orinoco. ''Espaço Ameríndio'', 6(2), 46–75.</ref> These shamans use yopo in visionary rituals to diagnose illness, mediate with spiritual beings, and access ancestral knowledge encoded in myth and cosmology. The yopo experience is considered essential to shaping future realities and maintaining the ethical balance between human and non-human worlds.<ref name="Rodd2011">Rodd, R., & Sumabila, A. (2011). Yopo, Ethnicity and Social Change: A Comparative Analysis of Piaroa and Cuiva Yopo Use. ''Journal of Psychoactive Drugs'', 43(1), 36–45. [https://doi.org/10.1080/02791072.2011.566499 doi:10.1080/02791072.2011.566499]</ref>

[[File:Instrumentos de yopo piaroa, ñuaba, pisador, brocha.jpg|thumb|Piaroa yopo instruments, bird bones tubes for sniffing, brush and masher.]]

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. In some areas the unprocessed ground beans are snuffed or smoked producing a much weaker effect with stronger physical symptoms. Some tribes as Piaroas, also prepare yopo by integrating cuttings of ''Banisteriopsis caapi'' (capi), and they may ingest capi decoctions or chew its inner bark shortly before inhaling yopo, with the intention of prolonging and intensifying the visionary experience.<ref name="Rodd2002">Rodd, R. (2002). Snuff synergy: preparation, use and pharmacology of yopo and ''Banisteriopsis caapi'' among the Piaroa of southern Venezuela. ''Journal of Psychoactive Drugs'', 34(3), 273–279. [https://doi.org/10.1080/02791072.2002.10399963 doi:10.1080/02791072.2002.10399963]</ref>

=== Effects ===
The first report of the effects of [[hallucinogenic snuff]] prepared from the beans of ''Anadenanthera peregrina'' dates back to 1496 when it was observed by Friar Ramon Pane, who was commissioned by Christopher Columbus, among the Taino Indians of Hispaniola. Pane's report was first published in 1511 in Martyr's descriptions of the New World. The description of its effects reads in part: "This ''kohobba'' powder," described as "an intoxicating herb, is so strong that those who take it lose consciousness; when the stupefying action begins to wane, the arms and legs become loose and the head droops." It is administered with a cane about one foot long of which they introduce one end "in the nose and the other in the powder and ...draw it into themselves through the nose". It worked quickly: "almost immediately they believe they see the room turn upside-down and men walking with their heads downwards". The administering witch-doctor took the drug along with his patients, intoxicating "them so that they do not know what they do and ... speak of many things incoherently", believing that they are in communication with spirits.<ref>{{Cite web|url=https://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1969-01-01_4_page004.html|title=UNODC - Bulletin on Narcotics - 1969 Issue 4 - 003|last=EVANS-SCHULTES|first=Richard|website=www.unodc.org|access-date=2017-12-30}}</ref>

===Active constituents===
{{multiple issues|section=y|{{Page numbers needed|section|date=September 2010}}
{{Confusing section|date=August 2007}}
{{Original research|section|date=September 2007}}}}

====Bufotenin====
The beans have been found to contain up to 7.4% [[bufotenin]].<ref name="PharmanopoPsychonautics">[http://entheology.org/edoto/anmviewer.asp?a=9&z=8 Pharmanopo-Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine] {{Webarchive|url=https://web.archive.org/web/20160303175808/http://entheology.org/edoto/anmviewer.asp?a=9&z=8 |date=2016-03-03 }} by Jonathan Ott, The Journal of Psychoactive Drugs, September 2001</ref> At up to 7.4% (74&nbsp;mg per gram) bufotenin, an effective 40&nbsp;mg dose of insufflated bufotenin<ref name="PharmanopoPsychonautics" /> requires little more than 0.5&nbsp;grams of beans.

The [[intraperitoneal]] {{LD50}} of bufotenin is between 200 and 300&nbsp;mg/kg (in rodents) with death occurring by respiratory arrest.<ref name="VisionaryPlantofAncientSouthAmerica">{{Cite book|title= Anadenanthera: Visionary Plant of Ancient South America|last= Torres|first= Constantino Manuel|author2= David B. Repke|year= 2006|publisher= Haworth Herbal Press|location= New York, New York|isbn= 0-7890-2642-2}}</ref> Human intravenous tests using [[bufotenin]] suggest the LD<sub>50</sub> 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&nbsp;mg in some subjects.<ref>TiKHAL, Alexander Shulgin, 1997</ref> Free base bufotenin when insufflated, taken sublingually, orally, or intrarectally, elicits strong hallucinogenic effects with far less side effects.<ref name="PharmanopoPsychonautics" />

====Dimethyltryptamine and 5-MeO-DMT====
{{more citations needed section|date=October 2014}}

The beans have been found to contain up to only 0.04% 5-MeO-DMT and 0.16% DMT.<ref name="PharmanopoPsychonautics" /> The leaves and bark also contain small amounts of DMT, 5-MeO-DMT and related compounds.<ref>Schultes 1976 {{full citation needed|date=September 2016}}</ref><ref>Schultes 1977 {{full citation needed|date=September 2016}}</ref><ref>Pachter et al. 1959  {{full citation needed|date=September 2016}}</ref>

At up to 0.04% (0.4&nbsp;mg per gram) 5-MeO-DMT, an effective light 5&nbsp;mg dose of insufflated 5-MeO-DMT would require over 12 grams of beans. It would be extremely difficult to insufflate such a quantity, as tolerance would likely develop before the 12-gram nasal intake could be completed. Individual sensitivity to 5-MeO-DMT varies. It has been documented that the threshold dose in some individuals is as much as 10&nbsp;mg insufflated<ref name="ShamanicSnuffsOrEntheogenicErrhines-Page-102">Shamanic Snuffs or Entheogenic Errhines by Jonathan Ott, Page 102, 2001, {{ISBN|1-888755-02-4}}</ref> requiring over 24 grams of beans for an effective dose of 5-MeO-DMT.

At up to 0.16% (1.6&nbsp;mg per gram) DMT, an effective 40&nbsp;mg dose of insufflated DMT would require 25 grams or more. Because of its volume, 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&nbsp;mg of bufotenin, a potentially dangerous dose. With insufflated freebase bufotenin, the maximum published safe dose used has been 100&nbsp;mg.<ref name="PharmanopoPsychonautics" />

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 [[Metalocalypse|storage]].<ref name=" VisionaryPlantofAncientSouthAmerica"/>

===Oral usage===
When taken orally by some tribes in South America, small amounts are often combined with alcoholic ''chichas'' ([[maize beer]]).<ref name=" VisionaryPlantofAncientSouthAmerica"/>{{rp|29}} 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.<ref name=" VisionaryPlantofAncientSouthAmerica"/> 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 [[monoamine oxidase inhibitor]]s (MAOIs).<ref name="VisionaryPlantofAncientSouthAmerica"/> Typically ''Banisteriopsis caapi'' is chewed in the mouth while the Anadenanthera beans are snuffed or smoked.<ref name="VisionaryPlantofAncientSouthAmerica"/> Occasionally ''Banisteriopsis caapi'' is found mixed in with the snuff.<ref name="VisionaryPlantofAncientSouthAmerica"/>

==See also==
* ''[[Anadenanthera colubrina]]''
* [[Cohoba]]
* [[List of plants of Caatinga vegetation of Brazil]]
* [[Nu-nu]], a psychotropic snuff used by Matsés people
* [[Psychedelic plants]]

==References==
{{Reflist}}

===Further reading===
* {{cite book | author = Richard Evans Schultes | author-link = Richard Evans Schultes | title = Plants of the Gods | date = 1992 | publisher = Inner Traditions/Bear | isbn = 0-89281-979-0 }}

==External links==
{{Commons}}
{{Wikispecies |Anadenanthera peregrina}}
* [http://www.erowid.org/plants/anadenanthera/anadenanthera.shtml Erowid Anadenanthera Vault]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Taxonbar|from=Q150584}}

[[Category:Anadenanthera|peregrina]]
[[Category:5-HT2A agonists]]
[[Category:Ayahuasca analogs]]
[[Category:Entheogens]]
[[Category:Herbal and fungal hallucinogens]]
[[Category:Plants described in 1753]]
[[Category:Psychedelic drugs]]
[[Category:Psychedelic tryptamine carriers]]
[[Category:Serotonin receptor agonists]]
[[Category:Botanical taxa named by Carl Linnaeus]]
[[Category:Taxa named by Carlo Luigi Spegazzini]]
[[Category:Trees of Brazil]]
[[Category:Trees of Colombia]]
[[Category:Trees of the Dominican Republic]]
[[Category:Trees of South America]]
[[Category:Trees of Venezuela]]