Psilocybin (Molecule of the Month for July 2001)
Psilocybin is the main active ingredient in magic mushrooms, obtained in Mexico and Central America. It has hallucinogenic properties.
Psilocybin has been known for centuries by the Aztecs in Mexico, and has been used by tribes and natives for many reasons. The Aztecs thought that hallucinations had religious significance and were important in tribal rites. In fact the drug was considered so important that it was called "God's Flesh". More recently Psilocybin has been used in Europe and America in psychotherapy. However Psilocybin is now commonly known as a constituent in the drug Magic Mushrooms. The mushroom in its natural form is legal to grow and process though when dried or purified to Psilocybin it is an illegal Class A drug.
Once ingested most of the Psilocybin is converted into Psilocin within an hour. The alkyl group attached to the indole ring makes the molecule more lipophillic and therefore able to penetrate the central nervous system. It is the phosphoric acid group attached to this ring that is oxidised in the body to the hydroxyl group in Psilocin. It is this Psilocin that is the highly psycho-active compound that actually effects the brain. The structure of psilocybin mirrors that of some neurotransmitters in the brain as it contains the indole ring. This mirroring leads to the psilocybin molecules fitting into receptors in the brain causing over stimulation (trips). Other hallucinogens, such as LSD, contain indole rings and produce similar effects.
The laboratory preparation of Psilocybin is possible, though difficult. This is why it is taken in the mushroom form when consumed as a drug.
Psilocybin mushrooms are consumed either in their natural form or crushed into a fine, white powder for consumption. They are not generally habit-forming and do have a long history of use. Dried mushrooms contain about 0.2 to 0.4 percent psilocybin and only trace amounts of psilocin. The hallucinogenic dose of both substances is about 4 to 8 milligrams or about 2 grams of mushrooms with effects lasting for about six hours. Most of the Psilocin is excreted within 8 hours although portions do remain in the system for several hours after and Psilocybin is believed to build up in body fat. Used correctly, they have pleasant effects and are completely non-toxic. However they are capable of producing vivid hallucinations and can be very dangerous when combined with other drugs
Formal Chemical Name (IUPAC)
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol dihydrogen phosphate ester
Update by Karl Harrison
(Molecule of the Month for July 2001 )