Chemistry:2CLisaB

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2CLisaB, also known as 2-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline, is a serotonin receptor modulator of the phenethylamine, 2C, and N-benzylphenethylamine families.[1][2][3][4] It is a cyclized phenethylamine analogue of the serotonergic psychedelic 25B-NBOMe in which the N-benzyl group has been cyclized with the amine to form a tetrahydroisoquinoline ring.[1][2] The drug shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 45–1,580 nM and 270–77,680 nM, respectively).[3][4] 2CLisaB was first described in the scientific literature by Michael Robert Braden of the lab of David E. Nichols at Purdue University in 2007.[1][2]

The compound without the 4-bromo substitution is known as 2CLisaH.[2] It shows much lower affinities for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 690–1,158 nM and 1,303–1,404 nM, respectively).[1][2]

See also

  • Substituted methoxyphenethylamine
  • Cyclized phenethylamine
  • 25-NB
  • 2CBecca
  • 2CJP

References

  1. ↑ 1.0 1.1 1.2 1.3 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 837–840, 866–867. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 Braden MR (2007). Towards a Biophysical Understanding of Hallucinogen Action (Ph.D. thesis). Purdue University. ProQuest 304838368.
  3. ↑ 3.0 3.1 Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
  4. ↑ 4.0 4.1 "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience 4 (1): 96–109. January 2013. doi:10.1021/cn3000668. PMID 23336049. 



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