To address the gap of information, studies were conducted with 17 tryptamines containing a variety of symmetrical and asymmetrical N, N-dialkyl substituents and either a 4-hydroxy or 4-acetoxy group. In addition, structural analogs of psilocybin containing a 4-acetoxy group, such as 4-acetoxy- N, N-dimethyltryptamine (4-AcO-DMT), have appeared as new designer drugs, but almost nothing is known about their pharmacological effects. Although a large amount of experimental work has been conducted to characterize the pharmacology of psilocybin and its dephosphorylated metabolite psilocin (4-hydroxy- N, N-dimethyltryptamine), there has been little systematic investigation of the structure-activity relationships (SAR) of 4-substituted tryptamine derivatives. The 5-HT 2A receptor is thought to be the primary target for psilocybin (4-phosphoryloxy- N, N-dimethyltryptamine) and other serotonergic hallucinogens (psychedelic drugs).
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