Tomscaline
Tomscaline is a serotonin 5-HT2 receptor modulator of the phenethylamine and scaline families related to TCB-2. It is a cyclized phenethylamine and derivative of the psychedelic drug mescaline where the side chain has been cyclized with the benzene ring to form a benzocyclobutene ring system.Pharmacology
Pharmacodynamics
Tomscaline shows affinity for the serotonin 5-HT2A, 5-HT2C, and 5-HT1A receptors. Its affinities were 111nM for the serotonin 5-HT2A receptor, 56nM for the serotonin 5-HT2C receptor, and 160nM for the serotonin 5-HT1A receptor. Compared to mescaline, tomscaline showed 3.3-fold higher affinity for the serotonin 5-HT2A receptor, 6.8-fold higher affinity for the serotonin 5-HT2C receptor, and 18.4-fold higher affinity for the serotonin 5-HT1A receptor. Its functional activities at these serotonin receptors and its effects in animals and humans do not appear to have been studied.Chemistry
Analogues
s of tomscaline include TCB-2, 2CBCB-NBOMe, jimscaline, and bromotomscaline, among others. Bromotomscaline, which is a derivative of tomscaline, shows dramatically or more than 10-fold higher affinities for the serotonin 5-HT2A and 5-HT2C receptors than tomscaline itself.History
Tomscaline was first described in the scientific literature by Daniel Trachsel and colleagues in their 2013 book Phenethylamine: von der Struktur zur Funktion. It was originally synthesized and studied by David E. Nichols and colleagues at Purdue University, who provided information about tomscaline to Trachsel and colleagues via personal communication in 2010.Tomscaline is not a controlled substance in Canada as of 2025.