<unk>  and its phosphorylated cousin, psilocybin, were first isolated and named in 1958 by Swiss chemist Albert Hofmann. Hofmann obtained the chemicals from laboratory-grown specimens of the entheogenic mushroom Psilocybe mexicana. Hofmann also succeeded in finding synthetic routes to these chemicals.<unk>  can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis). Another synthetic route uses the Speeter–Anthony tryptamine synthesis starting from 4-hydroxyindole.<unk>  is relatively unstable in solution due to its phenolic hydroxy (-OH) group. In the presence of oxygen it readily forms bluish and dark black degradation products. Similar products are also formed under acidic conditions in the presence of oxygen and Fe3+ ions (Keller's reagent). Structural analogs Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. 1-Methylpsilocin is a functionally 5-HT2C receptor preferring agonist. 4-Fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin (4-AcO-DMT) is an acetylated analog of<unk> . Additionally, replacement of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-hydroxy-N-methyl-N-isopropyltryptamine) and 4-HO-MET (4-hydroxy-N-methyl-N-ethyltryptamine), respectively. 4-Acetoxy-MET (4-Acetoxy-N-methyl-N-ethyltryptamine), also known as 4-AcO-MET, is the acetate ester of 4-HO-MET, and a homologue of 4-AcO-DMT.
Psilocin
Oxytocin 
Oxytocin
Progestogen
Progestogen 
Prolene
Antigonadotropin
Progonadotropin