Tomscaline

Last updated

Tomscaline
Tomscaline.svg
Clinical data
Other namesTomscalin
Drug class Serotonin 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
Formula C12H17NO3
Molar mass 223.272 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

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]

Contents

Pharmacology

The drug 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]

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]

Analogs

A derivative of tomscaline, bromotomscaline, shows dramatically (more than 10-fold) higher affinities for the serotonin 5-HT2A and 5-HT2C receptors than tomscaline itself. [1]

See also

References

  1. 1 2 3 4 5 6 7 8 9 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 909–910. ISBN   978-3-03788-700-4. OCLC   858805226 . Retrieved 31 January 2025. Die beiden Benzocycloalkenderivate Bromotomscalin (60) und Bromojimscalin (61) wurden ebenfalls durch die Gruppe von Nichols untersucht [27]; sie sind Bromoderivate von rigidisierten Mescalinanaloga (Tomscalin (62) und Jimscalin (63), siehe auch Kapitel 8.4.7). Bromotomscalin (60) zeigte hohe Affinitäten zu [125I]DOI markierten 5-HT1A- und 5-HT Rezeptoren und war jeweils rund 10-mal affiner als das bromfreie Tomscalin (62. Ki-Werte Sind unter den Strukturen gegeben) [27]. Bromojimscalin (61) war etwas weniger affin zu den 5-HT2A- und 5-HT2C-Bindungsstellen, jedoch zeigte es zusammen mit Jimscalin (63) recht hohe Affinitäten zum [3H]8-OH-DPAT markierten 5-HT1A-Rezeptor [27]. Die bei den Subs- tanzen 53, 55, 56 und 59 (Tabelle 2) beobachteten erhöhten 5-HT1A-Rezeptoraffinitäten im Vergleich zu Mescalin (2) könnten von einer (durch sterische Repulsion bedingten) günstigeren Konformation der Ethylaminseitenkette herrühren; das zum 5-HT1A-Rezeptor hochaffine Jimscalin (63) könnte durch seine konformationelle Einschränkung der Seitenkette diese günstige Bindungsorientierung aufweisen. [...] [27] D. E. Nichols. Persönliche Mitteilung, 2010.


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