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Home , Hallucinogenic mushroom, Panaeolus, Psilocybe, Psilocybe zapotecorum

Detection of in Species of , Panaeolu.s and

JONATHAN OTT Instituto de Investigaciones Biorneclicas, UNAM, Apartado Postal 70228, 20, D.F.l AND GASTON GUZMAN

Departamento de Botl.mica, Escuela Nacional de Ciencias Biologices, I.P.N., Apartado Postal 26-378, Mexico 4, D.F.

Since the ethnological and myco- based on information derived from logical studies of hallucinogenic mush- native sources in the Mazatec zone rooms conducted by Heim and Was- of the state of Oaxaca, where hallu- son (1), Singer and Smith (2-4) and cinogenic are still used in Guzman (5), a great deal of study has curing rituals. It has been observed been devoted to chemical analysis of that there is an association between supposed hallucinogenic species for the blueing phenomenon displayed by psilocybin, and related com- Psilocybe species of section Caeru- pounds. Thus far, psilocybin and/or lescentes and the presence of psi- psilocin have been detected in species locybin/psilocin in these species (7). of Psilocybe (1, 6, 7), So distinct is this phenomenon in (1, 8) and Conocy be (6, 7). Psi- some species, that many recreational locybin has also been reported as oc- users consider it to be an infallible curring in the genera Stropharia, identifying feature (11, 12, 13). and , these reports involving species more prop- PSATHYRELLA.-Psathyrella sep- perly classified in Psilocybe, Cono- ulchralis Singer, Smith and Guzman cybe and Panaeolus. The present was collected by Guzman in the study has been directed toward an- Zapotec zone of the Mexican state of alysis of recently described species of Oaxaca (an area where hallucino- Psilocy be, and resolution of prob- genic mushrooms are used ritually) lems concerning reports of the hal- and identified by native informants lucinogenic use of other species of as an hallucinogenic (4). Peilocy be, Panaeolus and Psa- Guzman had supposed that these in- tlcyrell e . formants had mistaken this mush- room for PSILOCYBE.-Two recently identi- Heim, an in fied species of Psilocybe section use in the Zapotec zone, which has Caerulescentes were analyzed for similar macroscopic features (5). the first time for the presence of psilocybin and psilocin. These spe- PANAEOLUs.-Ritual use of Panae- cies are: Psilocybe bolivarii Guz- olus sphinctrinus (Fr.) Quel. has man (9) and Psilocybe bonetii Guz- been reported from Mexico (14). man (10). Another species in section Use of this species as a ritual hal- Caerulescentes, not previously an- lucinogen in Mexico has been dis- alyzed chemically, Psilocybe candi- puted by some authors (1, 2), and dipes Singer and Smith, has been Guzman (5), despite intensive re- reported as being either inactive as search, has seen no evidence of its an , or as having toxic ritual employment anywhere in Mex- properties apart from the induction ico. This species, as well as Panae- of hallucinosis (2). This report was olus foenisecii (Fr.) Kuhner has been reported as being "latent psilo- 'Address reprint requests to: 2225 NW 26th St.. Olympia. WA 98502 cybian" (8), that is, some species 258 JUL-AUG 1976] NOTES 259 analyzed have been found to contain centrated to dryness. After being dissolved psilocybin, while others have been in approximately 3 ml of 70% methanol, all of the extracts were analyzed chromato- found to be devoid of this compound. graphically. The present study represents the first Spots of 50-100 ",1 of the extracts and chemical analysis published of wild standard solutions of psilocybin and psilocin P. sphinctrinus and P. foenisecii were spotted singly and in admixture on sheets of Whatman no. 3MM paper. These from Mexico. Another species, Pe- chromatograms were developed for approxi- naeolus subbalteatus (Berk. and mately 18 hr by the ascending method. Br.) Sacc., reported to reliably con- Three solvent systems were employed for tain psilocybin (8), is rather widely each sample: (A) water-saturated n-butanol; (B) ri-butanol-acetic acid-water (12:3 :5) and used as a recreational drug in the (C) n-propanol-1N ammonium hydroxide northwestern United States (11, 12), (5:1). Subsequent to development, the but specimens from Mexico have chromatograms were air dried and dipped in never been studied chemically. Fi- a modified Ehrlich's reagent (p-dimethyl- aminobenzaldehyde, 10% in con. HC1, di- nally, Panaeolus carnbodginiensis luted 1:4 with acetone). Psilocybin and Ola'h and Heirn has recently been psilocin were evident as violet and bluish- collected in and later grown violet zones respectively.' in artificial culture in the United States". This species has also been RESULTS AND DISCUSSION reported to reliably contain psilo- The results of the analysis of spe- cybin, based on analysis of Asian cies of Psilocybe, Panaeolus and specimens (8). Peat hyrelle are summarized in table

TABLE 1. Species examined and 4-substituted identified. .-

Species Locality Date I Herbarium I Psilocybin Psilocin ------'-- Peilocy be boliv erii, ...... Padmillas, Sinaloa 9/61 Guzman 4803 . - I ENCB Psilocybe bonetii.,. . - .. Rio Frio, Mexico 9/67 Arcos Mata 76 + - ENCB type Psilocy be candidipes. ... Huautla de Jimenez, 7/67 MEXU 5570 + - Oaxaca ENCB Panaeolus cambodginiensis .... San Antonio, Tx. 7/75 Pollock 001 + - (artificial) ENCB Panaeolus loenisecii. .... Mexico, D.F. 6/72 Garcia 161 - - ENCB Panaeolus sph inc trirurs . , .. Paso de Cortes, 8/63 Guzman 4712 - - Puebla ENCB Panaeolus subbalteatus". .... Oaxtepec, Morelos 4/71 Guzman 9813 + - ENCB

Psathyrella sepulchralis .. '" San Agustin Loxicha, 9/57 Guzman 1140 - - Oaxaca ENCB type Psathyrella sepulchra/is...... I Tepost lan, Morelos 7/68 Guzman 6658 - - ENCB

CHEMICAL STUDIES 1. Of the two newly described spe- All of the above-named species, with the cies of Psilocybe analyzed, only P. exception of Psilocybe zapotecorum have bonetii was found to contain psilo- been subjected to chemical analysis for the presence of psilocybin and psilocin. Quanti- cybin. P. bolivarii is the second ties of finely pulverized dried carpophores blueing species of Psilocybe reported (ca. 50-150 mg) were placed in small flasks not to contain psilocybin or psilocin. and extracted in cold 70% methanol ca. 5 Preliminary chromatographic studies ml/50 mg) by agitating overnight on magnetic stirrers. All extracts were filtered and con- of Psilocybe y urigeneis Singer and

2Personal communication, S. H. Pollock, 1975. Smith showed no detectable psilo- 3Representative RF values: Psilocybin, 0.04, 0.44 cybin or psilocin (1), but psilocybin and 0.05 in system A, Band C, respectively; psilocin. 0.50, 0.75 and 0.85 in these systems. was later isolated from wild carpo- 260 LLOYDIA [VOL. 39, No.4

phores of this species, and both com- locin. This work was supported, in part, by a grant from Centro Mexicano de Estudios pounds were detected in carpophores en Farmacodependencia (#BC9-75). grown in culture (15). The blueing reaction is probably due to oxidation Received 19 December 1975. of psilocin (16), and the advanced LITERATURE CITED age of the bolivarii specimen may ac- 1. HElM, R., R. G. WASSON and collaborators. 1958. Les Charnpignons Hallucinogenes count for the lack of detectable d u Mexique. Editions du Museum Na- tional d'Histoire Naturelle, Paris. psilocin. Unfortunately, no collec- 2. SINGER, R. 1958.Mycological investigations tions exist other than the type for this on reonanacat.l, the Mexican hallucinogenic mushroom. Part 1. The hist.ory of teona- species. The finding that P. candi- nacatl, field work and culture work. My- cologie 50(2): 239-261- dipes contains psilocybin disproves 3. SINGER. R. and A. H. SMITH. 1958. My- the report that this species is inactive cological investigations on reonanacatt, the Mexican hallucinogenic mushroom. Part as an hallucinogen. Psilocybin has II. A taxonomic monograph of Psilocybe, section Caerulescentes. Mycologia 50(2): been detected in two species of 262-303. Panaeolus, one of which has been 4. SINGER. R., A. H. SMITH and G. GUZMAN. 1958. A new species of Psathyrella. used in the United States as a recrea- Lloydia 21: 26-28. 5. GUZM..\N. G. 1959. Estudio taxon6mico y tional drug. Mexican specimens of eco16gico de Ios hongos neurotr6picos me xi- P. foenisecii and P. sphinctrinus canos. Escuela N acional de Ciencias Bio- logicas, LP.N., thesis. were shown to be devoid of psilocybin 6. BENEDICT. R. G., L. R. BRADY, A. H. SMITH and V. E. TYLER, JR. 1962.Occurrence of and psilocin. This finding is con- psilocybin and psilocin in certain sistent with the conception of these and PsiIocybe species. LIoydia 25: 156- 159. species as "latent psilocybian". Guz- 7. BENEDICT,R. G., V. E. TYLER and R. WATLING. 1967. Blueing in Coriocy be , Psilocybe man feels that the species sphinc- and a Stropharia species and the detection trinus should be split into two sepa- of psilocybin. LIoydia 30(2): 150-157. 8. OLA'H. G. M. 1969. Le Genre Panaeolus. rate entities based on size dif- Museum National d'Histoire NatureUe, Paris. ferences. The sample analyzed rep- 9.GUZMAN, G. 1968. Aportaciones sobre 105 hongos ajucinogenos mexlcanos y descripci6n resents the large-spored type. This de un nuevo Ps ilocy be, Cieneia (Mexico problem has been discussed at length City) 26(1): 25-28. 10. GUZMAN,G. 1970. Nueva especie de Peilocy be in an earlier paper (17). Failure to de la secci6n Caerulescentes de 10s bosques conifer-as de Mexico. An. Ese. Nac. Cienc. detect psilocybin in two samples of BioI. Mexico City 17: 9-16. Psathyrella sepulchralis would 11. OTT, J. 1976. Hallucinogenic plants of seem to support the contention that North Arrrer rce . Wingbow Press, Berkeley. 12.OTT, J. 1976. Recreational use of hallucino- the report of these species as being genic mushrooms in the United States. In hallucinogenic was due to a confusion SAl.ZMAN, E. (ed.). . eRe Press tin press). between this mushroom and Psilo- 13. POLLOCK,S. H. 1975. The psilocybin mush- cybe zapotecorurn. Failure to de- room pandemic. J. Psyched. Drugs 7(1): 73-84. tect psilocin in all of the species an- 14. SCHULTES.R. E. 1939. Plantae Mexicanae II. alyzed may be due rather to the age Bot. Mus. Leafl.Herv . Univ. 7(3): 37-54. 15. HElM, R. 1963. Champignons T'ox ic uee of the specimens than to absolute et Holl acinogenes . N. Boubee, Pans. lack of this compound in these species. 16. LEVINE. W. G. 1967. Formation of blue oxi- dation product from psilocybin. Nature 215: 1292-1293. ACKNOWLEDGMENTS 17. GUZMAN,G. and A. M. PEREZ-PATRACA. 1972. We are indebted to B. Ratcliffe for supply- Las especies conocidas del genero Panaeolus ing reference samples of psilocybin and psi- en Mexico. Bol. Soc.Mex. Mic. 6: 40.

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