Article · Wikipedia archive · Last revised Jun 17, 2026

2CLisaB

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. 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. The drug shows affinity for the serotonin 5-HT2A and 5-HT2C receptors. 2CLisaB was first described in the scientific literature by Michael Robert Braden of the lab of David E. Nichols at Purdue University in 2007.

Last revised
Jun 17, 2026
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≈ 1 min
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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.1234 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.12 The drug shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 45–1,580 nM and 270–77,680 nM, respectively).34 2CLisaB was first described in the scientific literature by Michael Robert Braden of the lab of David E. Nichols at Purdue University in 2007.12

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).12

See also

See also

References

References

  1. 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. 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. 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. 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.
External links