Tomscaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

Tomscaline is a serotonin 5-HT2 receptor modulator of the phenethylamine and scaline families related to TCB-2.[1] 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.[1]

Other namesTomscalin
Drug classSerotonin receptor modulator
ATC code
  • None
CAS Number
Quick facts Clinical data, Other names ...
Tomscaline
Clinical data
Other namesTomscalin
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 1-(2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine
CAS Number
ChemSpider
Chemical and physical data
FormulaC12H17NO3
Molar mass223.272 g·mol−1
3D model (JSmol)
  • NCC1Cc2c1cc(c(c2OC)OC)OC
  • InChI=1S/C12H17NO3/c1-14-10-5-8-7(6-13)4-9(8)11(15-2)12(10)16-3/h5,7H,4,6,13H2,1-3H3
  • Key:SEXAFWMJJMOSAF-UHFFFAOYSA-N
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Pharmacology

Pharmacodynamics

Tomscaline shows affinity for the serotonin 5-HT2A, 5-HT2C, and 5-HT1A receptors.[1] Its affinities (Ki) were 111 nM for the serotonin 5-HT2A receptor, 56 nM for the serotonin 5-HT2C receptor, and 160 nM for the serotonin 5-HT1A receptor.[1] 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.[1] Its functional activities at these serotonin receptors and its effects in animals and humans do not appear to have been studied.[1]

Chemistry

Analogues

Analogues of tomscaline include TCB-2, 2CBCB-NBOMe, jimscaline, and bromotomscaline, among others.[1] 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.[1]

History

Tomscaline was first described in the scientific literature by Daniel Trachsel and colleagues in their 2013 book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function).[1] 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.[1]

Society and culture

Canada

Tomscaline is not a controlled substance in Canada as of 2025.[2]

See also

References

External links

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