2CJP

2CJP
Identifiers
	IUPAC name 4-(4-bromo-2,5-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-2-benzazepine;
Chemical and physical data
Formula	C18H20BrNO2
Molar mass	362.267 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(Br)c(cc1C1CNCc2c(C1)cccc2)OC;
	InChI InChI=1S/C18H20BrNO2/c1-21-17-9-16(19)18(22-2)8-15(17)14-7-12-5-3-4-6-13(12)10-20-11-14/h3-6,8-9,14,20H,7,10-11H2,1-2H3; Key:FQAXYSXGRJQKMV-UHFFFAOYSA-N;

2CJP, also known as 4-(4-bromo-2,5-dimethoxyphenyl)-2,3,4,5-tetrahydro-1H-2-benzazepine, is a serotonin receptor modulator of the phenethylamine, 2C, and N-benzylphenethylamine families.^[1]^[2]^[3]^[4] It is a cyclized phenethylamine analogue of 25B-NBOMe in which the N-benzyl ethyl amine side chain has been cyclized to form a tetrahydrobenzazepine ring.^[1]^[2] The drug shows affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = 19–457 nM and 227–3,240 nM, respectively).^[3]^[4] 2CJP 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]

References

^ ^a ^b ^c 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 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.

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