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2CLisaB

From Wikipedia, the free encyclopedia
Pharmaceutical compound
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 as2-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline, is aserotonin receptor modulator of thephenethylamine,2C, andN-benzylphenethylamine families.[1][2][3][4] It is acyclized phenethylamineanalogue of theserotonergic psychedelic25B-NBOMe in which theN-benzyl group has beencyclized with theamine to form atetrahydroisoquinolinering.[1][2] The drug showsaffinity for theserotonin5-HT2A and5-HT2C receptors (Ki = 45–1,580 nM and 270–77,680 nM, respectively).[3][4] 2CLisaB was first described in thescientific literature by Michael Robert Braden of the lab ofDavid E. Nichols atPurdue University in 2007.[1][2]

The compound without the 4-bromosubstitution 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

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References

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  1. ^abcdTrachsel 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. ^abcdeBraden MR (2007).Towards a Biophysical Understanding of Hallucinogen Action (Ph.D. thesis). Purdue University.ProQuest 304838368.
  3. ^abHansen 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. ^abJuncosa 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

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