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Tuesday, 13 November 2012

Chemistry

Psilocybin (PY, 4-phosphoryloxy-N,N-dimethyltryptamine) is the main psychoactive principle of hallucinogenic mushrooms. After ingestion, psilocybin is converted into the pharmacologically active form psilocin. Psilocin itself is also present in the mushroom, but in smaller amounts. Psilocybin and psilocin are both indolealkylamines and structurally similar to the neurotransmitter serotonin (5-hydroxytryptamine or 5-HT). Besides psilocybin and psilocin, two further tryptamines — baeocystin and norbaeocystin — could also be present but are thought to be less active than the former two. Psilocybin (psilocybine, psilocibina, psilocybinum, psylosybiini) (CAS-number: 520-52-5) is 4-phosphoryloxy-NN-dimethyltryptamine. According to IUPAC, the fully systematic chemical name is [3-(2-dimethylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate. Psilocybin is the dihydrogen phospate of psilocin. Psilocybin is soluble in water, moderately soluble in methanol and ethanol, and insoluble in most organic solvents. Psilocybin is a prodrug of psilocin, in vivo the molecule is metabolised into psilocin by dephosphorylation. Molecular structure of psilocybin
Molecular formula: C12H17N204P Molecular weight: 284.3 g/mol Psilocin (psilocine, psilocyn) (CAS-number 520-53-6) is 4-hydroxy-NN-dimethyltryptamine (4-OH-DMT) or alternatively 3-(2-dimethylaminoethyl)indol-4-ol. According to IUPAC, the fully systematic chemical name is 3-(2-dimethylaminoethyl)-1H-indol-4-ol. Psilocin is an isomer of bufotenine, it differs only in the position of the hydroxylgroup. Psilocin is relatively unstable in solution. Under alkaline conditions in the presence of oxygen it immediately forms bluish and black degradation products. Molecular structure of psilocin