2CB-Ind

2CB-Ind
Clinical data
Other names	2CB-Indane
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code	None;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name (5-bromo-4,7-dimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine;
CAS Number	912342-23-5 ;
PubChem CID	16086368;
ChemSpider	17245022 ;
UNII	ZMP92SN5X2;
ChEMBL	ChEMBL424890 ;
CompTox Dashboard (EPA)	DTXSID70582080 ;
Chemical and physical data
Formula	C12H16BrNO2
Molar mass	286.169 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C2=C1C(CC2)CN)OC)Br;
	InChI InChI=1S/C12H16BrNO2/c1-15-10-5-9(13)12(16-2)8-4-3-7(6-14)11(8)10/h5,7H,3-4,6,14H2,1-2H3 ; Key:HCLPGYNQMVSQIM-UHFFFAOYSA-N ;
	(what is this?) (verify)

2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B which was developed by David E. Nichols and colleagues. It acts as a moderately potent and selective agonist for the 5-HT_2A and 5-HT_2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a K_i of 47nM at the human 5-HT_2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.^[1]^[2]

References

↑ McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE (September 2006). "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry. 49 (19): 5794–803. CiteSeerX 10.1.1.688.9849. doi:10.1021/jm060656o. PMID 16970404.
↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.

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