2CLisaB

2CLisaB
Clinical data
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline
Chemical and physical data
FormulaC19H22BrNO2
Molar mass376.294 g·mol−1
3D model (JSmol)
  • COc1cc(Br)c(cc1CCN1CCc2c(C1)cccc2)OC
  • InChI=1S/C19H22BrNO2/c1-22-18-12-17(20)19(23-2)11-15(18)8-10-21-9-7-14-5-3-4-6-16(14)13-21/h3-6,11-12H,7-10,13H2,1-2H3
  • Key:FUQOBJZWVZVGDO-UHFFFAOYSA-N

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

References

  1. ^ a b c d 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. 837–840, 866–867. ISBN 978-3-03788-700-4. OCLC 858805226.
  2. ^ a b c d e Braden MR (2007). Towards a Biophysical Understanding of Hallucinogen Action (Ph.D. thesis). Purdue University. ProQuest 304838368. Archived from the original on 2025-01-21. Retrieved 2025-08-01.{{cite thesis}}: CS1 maint: bot: original URL status unknown (link)
  3. ^ a b 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. ^ a b Juncosa JI, Hansen M, Bonner LA, Cueva JP, Maglathlin R, McCorvy JD, Marona-Lewicka D, Lill MA, Nichols DE (January 2013). "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. doi:10.1021/cn3000668. PMC 3547484. PMID 23336049.
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