Occurrence of 5-hydroxytryptamine and 5-hydroxytryptophan in Panaeolus sphinctrinus
โ Scribed by V. E. Tyler Jr.; D. Groger
- Publisher
- John Wiley and Sons
- Year
- 1964
- Tongue
- English
- Weight
- 176 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0022-3549
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โฆ Synopsis
Occurrence of 5-Hydroxytryptamine and 5 -Hydroxytryptophan in
Panaeolus sphirzctririus
The status of Pnnaeolus sphinclrinits (Fr.) Qukl. as a hallucinogenic mushroom is currently a matter of dispute Specimens of this species collected in hlexico by Schultes approximately 5.5 years ago were said to be employed there as ps)-chotomimetic agents (1). The possibility of such application was seemingly verified when IIrini and Ilofmann reported the isolation of psilocybin from cultivated sporocarps o f the fungus (?). However, their recent investigations of other samples of P. sphinctrinits iailed to detect psilocybin (3). In neither caSe did the authors present experimental details or sources of the fungi examined, and herbarium reference specimens were apparently not retained.
An investigation of nine species and forms of P , i w e o l u s by Tyler and Smith (4) revealed the presence of 5-substituted tryptamine derivatives but no 4-substituted derivatives. I3ecause of its relative scarcity, P. sphinctrinus was not included i n that study, but the possibility that it might contain psilocybin or psilocin appeared remote 0 1 1 chemotaxonomic grounds Investigation of an authentic sample of the fungus was clearly required to settle the ethnological, phytochernical, and chemotaxonomic prohlems raised by this apparent discrepancy in the type of tryptaminc derivatives reported to t x contained in a single species of the genus Pnnrzeolus.
Kemntly, we. obtained through the courtesy of I>r. K. Singer' a small sample of P. sphzncfrinus (Fr.) QuCl. collected in Argentina (collection No.
M 3514) and determined by Singer to be the same species as the Mexican material originally collected by Schultes (1). The powdered specimen (95 mg.) was extracted with 5 ml. of methanol and 100-150-pl. quantities of the extract subjected to circular chromatography on S. and S. 2043-bm filter paper in three solvent svstems essentially as described by Benedict, et a l . (5).
Spraying the chromatograms with p dimethyl-
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## Abstract Convenient and efficient syntheses of ^13^C and ^2^H sidechain labelled Lโtryptophan, racemic 5โhydroxytryptophan and 5โhydroxytryptamine (serotonin) from indole and 5โbenzyloxyindole are described.