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2CLisaB
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| Clinical data | |
|---|---|
| Drug class | Serotonin receptor modulator |
| ATC code |
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| Identifiers | |
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| Chemical and physical data | |
| Formula | C19H22BrNO2 |
| Molar mass | 376.294 g·mol−1 |
| 3D model (JSmol) | |
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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
[edit]References
[edit]- ^ 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.
- ^ a b c d e Braden MR (2007). Towards a Biophysical Understanding of Hallucinogen Action (Ph.D. thesis). Purdue University. ProQuest 304838368.
- ^ 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.
- ^ 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.
External links
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