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Pril:cybin forns white crystals saich ars fairly solubla ia water, bat
practieally insoluble in the usual organic solvents. It is eaphotaric, i.e. it fors
salte with both aside and alkalis. Analysis of psilocybin and a study of its spsctrs
and color reastions, havs revealed that it is an indole darivativa, substituted in tho
bezceno nucleus, It was provisionally assigmed tho forula: $\bar { \mathsf { C } } _ { 1 3 } \bar { \mathsf { E } } _ { 1 3 } \bar { \mathsf { s } } ( 2 0 ) ^ { 3 } \bar { \mathsf { s } } ^ { \dagger } \bar { \mathsf { z } } ^ { 3 } \bar { \mathsf { z } } ^ { 3 } = :$ tut $a _ { 2 } ^ { 3 } = 2 ^ { n } , 2 ^ { n } = 3 ^ { n } 2 ^ { p }$ Cn hrdrolysis the
Ictor degrodsticn stadias have shoxa it to be
psiloeybin zolosule ia cleaved in tho, givingt 4-hydroxy-dinethyltryptánize and phosphoris acid. Thes psilccybin possesses the structural formula I.

It is ths phosphoric ester of 4-bydrory-dimethyltryptamine. This constitution has been ccnfirmed by tho synthesis of psilocybin as dezonstrated by the following schamat

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Ta aath o crzpuucd as idonzical ia every roopset with natural pailoeybin.

Poiloopsin is yet another exapls of the importanes of the indols stricturo in peychotropie coapounds. It is closely related to biocheaically inportant naturaliyoccuring hydrottryptuine derivatives such as: serotonin (5-Hydrozytryptaaine), bafotonin (5-hydroxydirethyltryptazine), bufotenidine(çiarterary base of bufotenin) .dllrdro-bufotnin snd bufothionino. The structure analogy with bufothionino(formula II) 7) hich has been.icslated from saphibian skin is striking.

Eoth compounds ars acidie esters of a hydrory-dinethyltryptsaine dorivative, the ons kaing an estor of phosphoric acid, tho other of sulfuric acid.

às it is an indole derivative, pailocydin is furthermore related to tho poychotropic iudols alkaloids, such as taberanthine, harins and raserpine.

A'spscial relaticnship erists betwsen pailocybin and lysergic acid

disMylanido (LsD),hitherto the rost notent. psychotomimstie kmown. Both thess coap cunds are indolo dorivatives substitutad in position 4. Psilocybin and the orgot alkaloids, vhich iacludo LSd, are wique in possessing this special struetural featura.

The Ciscovery of a naturally ocearriug irdole derivative with a phosphorplcted

hydrayl group in position 4 may lead to a new concopt of the bioganesis of tho lysorgio acid coiety of the ergot alkaloids. The proposals put forward alrsady are o, stogother satisfactory in that no explanation has been offared for ring closurs in Fositicn à ef the tryptsina zoisty. As ths phosphorylated hydroxyl group in the poilseybin wolccule impliss astivation of position 4, it does not seem unreasenabla to cessidez bydrozylation, and phosphorylation at positios 4 as an ieportant step in tho bioyaaecis or the ergot alkaleids.

4

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3) R. Z nd R. CAILLEU, C.. Acad.Sei 244,3109 (1957); 245,597,1761 (1957).

5) . EI, A. RAC, . OL, A. HOMAN, . CALLEU, C.B. Acad.Sci 246, 1346 (1958).

6) A. HOFMANN, A. FREY, H. OT, TH. PETAZILKA, F. TROKLER, Ezperientia 14,... (1958)in press.

7) . WLD, 7. V0, A. 421,216 (1930).

Iiteravics

Hedieal Danartaant Cndoz Fharnceuticals Hansvar, N.J.

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o-phospkoyl-k-hyeroy-i-dinethyl-tryptmins

Pazsieal and Cenical Data: Epirieal foa: G1e174gPCg Molecular Height: 254.332 ltirz foint: 200 - 2100vith decopesition Sohubility: In 120 pmts o2 vater st 20°c.

5.3

Keller Colo: Eesction:

C.l rz. of Pailocybin dissolve in l cc. O.Olp feric chtcriãa - contsinins scetic acid and stratify vith l ca. concentreted culfuric acid. After nixding a pernanent violet, color is obtained.

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