Avitriptan

Avitriptan is an antimigraine drug of the triptan family which was never marketed. It acts as a serotonin 5-HT_1B and 5-HT_1D receptor agonist. The drug reached phase 3 clinical trials prior to the discontinuation of its development.

Pharmacology

Avitriptan acts as a selective serotonin 5-HT_1B and 5-HT_1D receptor agonist. It is also notable in being a weak serotonin 5-HT_2A receptor agonist, albeit with about two orders of magnitude lower activational potency than at the serotonin 5-HT_1B and 5-HT_1D receptors.
Besides its activities at serotonin receptors, avitriptan has been found to act as a weak aryl hydrocarbon receptor agonist.

Chemistry

Avitriptan is a triptan and a modified analogue of tryptamines like the psychedelic drug dimethyltryptamine. However, avitriptan itself is not technically a tryptamine as it features a propyl amine side chain instead of the ethyl amine 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.