Psilocin

H. Eindenblatt, E. Ki amer, P. Holzmann-Erens, E. Gouzoulis-Mayfrank and K.-A. Kovai, Quantitation of psilocin in human plasma by high-perfomance liquid... 

Such alkaloids can be found particularly in the Myristicaceae, Malpighiaceae, Rutaceae, Apocynaceae, Rubiaceae, Loganiaceae, and Convolvulaceae. Such compounds are also found in mushrooms from the genera Conocybe, Panaeolus, Psilocybe, and Stropharia (Agaricaceae), which where used by the Aztecs of pre-Columbian America for their psilocin. 

Psychotropic indol derivatives (psilo-cin, bufetonine, V-methyl-, 5-methyl- and a-methyltryptamine) 0.6-140 pmol 138-230 pmol 1.5-2.2 Psilocin was quantified in specimens of the fungal species Psylocibe semilanceata 44... 

Using tactile startle, bufotenin, a hallucinogen that does not cross the blood-brain barrier readily, also produced biphasic dose-response effects when given intraventricularly (76). After systemic administration, however, low doses of indole hallucinogens have not been reported to increase tactile startle (73). Thus LSD (20-80 Mg/kg), DMT (0.25-1.0 mg/kg), and psilocin (2.5-5.0 mg/kg) did not increase tactile startle. A slightly higher dose of LSD (100 Mg/kg) did increase startle toward the end of the test session, perhaps because of blocking habituation (see below). 

The natural prototype for the phenylalkylamines is mescaline (Structure 1), isolated from the peyote cactus (Lophophora williamsii) by Heffter in 1896 (100) and subsequently obtained synthetically by Spath in 1919 (218). Used for many centuries in the form of peyote by Indians in Mexico and the American Southwest (3), it is often referred to as one of the classic hallucinogens, along with psilocybin, psilocin, and LSD. Little structure-activity work was directed toward mescaline or its congeners until 1955, when Peretz et al. (174) reported that a-methyl mescaline (TMA) (8), which represented a hybrid of the structure... 

There are only two reports of the human evaluation of a 6-hydroxylated N,N-dialkyltryptamine. Szara and Hearst (223) studied the effects of 6-hydroxy-N,N-diethyltryptamine (6-OH-DET 56) in a single subject. Doses of 1 and 2 mg were inactive a 5-mg dose produced a short-lasting perceptual disturbance and a 10-mg dose, after 1 hr, produced some psychotomimetic disturbances. Rosenberg et al. (182) compared the activity of DMT with that of 6-OH-DMT (55) in five human subjects. While DMT was active, the 6-hydroxy derivative was found to be inactive at intramuscular doses of approximately 50 to 75 mg. At a dose of 10 mg/kg, 6-OH-DMT (55) increased spontaneous activity in mice more so than a comparable dose of DMT 6-OH-DET (36) was essentially equiactive with DET in this respect (224). In most other animal studies, however, 6-hydroxylation of DMT has been observed to result in a decrease or complete loss of behavioral activity (228,236-238). The behavioral potency of 5-OMeDMT (59) was also reduced by 6-hydroxylation (226). 7-Hydroxy-N,N-dimethyltrypt-amine (7-OH-DMT 57) has not been evaluated in man. At an intraperitoneal dose of 33 jtM/kg, 7-OH-DMT displayed no behavioral effects in rats (228). The pharmacologic effects of all four hydroxylated derivatives of DMT, psilocin (49), bufotenine (53), 6-OH-DMT (55), and 7-OH-DMT (57) have been compared in studies by Taborsky et al. (228) and by Cerletti et al. (29). 

Psilocin has also been the object of considerable investigation using animals as subjects. Much of the initial work with psilocin, as well as other 4-hydroxy-tryptamine derivatives with alterations in the side chain and/or terminal amine, was performed at Sandoz Laboratories in Switzerland (29,245). Subsequent investigations have shown that psilocin produces hyperthermia in rabbits (113), induces the head-twitch in mice (43), disrupts acquisition of avoidance behavior in rats (240), increases startle response magnitudes in rats (68), increases limb-flick behavior in cats (120), and produces discriminative stimulus effects in rats similar to those of 5-OMeDMT (59) (93). 

Gessner, P. K., Godse, D. D., Krull, A. H., and McMullan, J. M. (1968) Structure-activity relationships among 5-methoxy-N,N-dimethyltryptamine, 4-hydroxy-N,N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 7 267-277. 

Compounds with a low relative activity (e.g., DMT, DET, 5 methoxy-DMT) have very little activity orally and must be smoked or sniffed. Unfortunately, these compounds taste and smell like burning plastic when smoked and are harder to smoke than hash. There is, however, no evidence for the notion that they are damaging. With the exception of DMT, DET, psilocin and psilocybin, most of these compounds are probably legal in most states. 

---