Bromotomscaline

Bromotomscaline, or 5-bromotomscaline, is a serotonin 5-HT₂ receptor modulator of the phenethylamine and scaline families related to TCB-2.^[1] It is the 5-bromo derivative tomscaline, a cyclized phenethylamine analogue of mescaline with a benzocyclobutene ring system.^[1] Bromotomscaline shows more than 10-fold higher affinities for the serotonin 5-HT_2A and 5-HT_2C receptors than tomscaline.^[1] It was developed by David E. Nichols and colleagues at Purdue University and was subsequently reported by Daniel Trachsel in 2013, who obtained the information via personal communication with Nichols in 2010.^[1] It is not a controlled substance in Canada as of 2025.^[2]

Other namesBromotomscalin; 5-Bromotomscaline

Drug classSerotonin receptor modulator; Serotonin 5-HT₂ receptor modulator

ATC code

• None

FormulaC₁₂H₁₆BrNO₃

Quick facts Clinical data, Other names ...

Bromotomscaline

Clinical data
Other names	Bromotomscalin; 5-Bromotomscaline
Drug class	Serotonin receptor modulator; Serotonin 5-HT2 receptor modulator
ATC code	None
Identifiers
IUPAC name 1-(5-bromo-2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine
Chemical and physical data
Formula	C12H16BrNO3
Molar mass	302.168 g·mol−1
3D model (JSmol)	Interactive image
SMILES NCC1Cc2c1c(Br)c(c(c2OC)OC)OC
InChI InChI=1S/C12H16BrNO3/c1-15-10-7-4-6(5-14)8(7)9(13)11(16-2)12(10)17-3/h6H,4-5,14H2,1-3H3 Key:FGAILPHQFDPSQN-UHFFFAOYSA-N

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