O-Acetylbufotenine
O-Acetylbufotenine, or bufotenine O''-acetate, also known as 5-acetoxy-N,''N-dimethyltryptamine or O-acetyl-N,''N-dimethylserotonin, is a synthetic tryptamine derivative and putative serotonergic psychedelic. It is the O''-acetylated analogue of the naturally occurring peripherally selective serotonergic tryptamine bufotenine and is thought to act as a centrally penetrant prodrug of bufotenine.
Use and effects
The effects of O-acetylbufotenine in humans have not been assessed or reported. Alexander Shulgin speculated about O-acetylbufotenine in his 1997 book TiHKAL, but did not personally synthesize or test it.Interactions
Pharmacology
has low lipophilicity, limitedly crosses the blood–brain barrier in animals, does not produce psychedelic-like effects in animals except at very high doses or administered directly into the brain, and produces inconsistent and weak psychedelic effects accompanied by pronounced peripheral side effects in humans. O-Acetylbufotenine, which is much more lipophilic than bufotenine due to its acetyl group, was developed in an attempt to overcome bufotenine's limitations and allow for the drug to efficiently cross the blood–brain barrier. In contrast to peripherally administered bufotenine, O-acetylbufotenine readily enters the brain in animals and produces robust psychedelic-like effects. In addition, O-acetylbufotenine was more potent than N,''N-dimethyltryptamine or 5-methoxy-N'',N-dimethyltryptamine in animals.O-Acetylbufotenine is thought to be a prodrug of bufotenine, which is a non-selective agonist of many of the serotonin receptors, including of the serotonin 5-HT2A receptor. However, O-acetylbufotenine has also unexpectedly been found to act directly as an agonist of certain serotonin receptors, including of the serotonin 5-HT1A and 5-HT1D receptors.
The O-acetyl substitution of O-acetylbufotenine is expected to be cleaved quite rapidly in vivo, which may hinder the ability of O-acetylbufotenine to cross the blood–brain barrier and deliver bufotenine into the central nervous system. This might be overcome with other O-acyl bufotenin derivatives.