Avitriptan (; development code BMS-180048) is an antimigraine drug of the triptan family which was never marketed. It acts as a serotonin 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptor agonist. The drug reached phase 3 clinical trials prior to the discontinuation of its development.
Avitriptan acts as a selective serotonin 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptor agonist. It is also notable in being a weak serotonin 5-HT<sub>2A</sub> receptor agonist ( = 123nM), albeit with about two orders of magnitude lower activational potency than at the serotonin 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptors.
Besides its activities at serotonin receptors, avitriptan has been found to act as a weak aryl hydrocarbon receptor agonist.
Avitriptan is a triptan and a modified analogue of tryptamines like the psychedelic drug dimethyltryptamine (DMT). However, avitriptan itself is not technically a tryptamine as it features a propylamine side chain instead of the ethylamine side chain present in tryptamines. Besides this difference, avitriptan is substituted at the 5 position of the indole ring system and the amine moiety has been cyclized and extended.
The predicted log P of avitriptan is 1.8.