BD1018

BD1018
Identifiers
	IUPAC name (S)-2-[2-(3,4-dichlorophenyl)ethyl]octahydropyrrolo[1,2-a]pyrazine;
CAS Number	150208-42-7;
PubChem CID	9796317;
ChemSpider	7972083;
CompTox Dashboard (EPA)	DTXSID80430866 ;
Chemical and physical data
Formula	C15H20Cl2N2
Molar mass	299.24 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1Cl)CCN3C[C@H]2N(CCC2)CC3;
	InChI InChI=1S/C15H20Cl2N2/c16-14-4-3-12(10-15(14)17)5-7-18-8-9-19-6-1-2-13(19)11-18/h3-4,10,13H,1-2,5-9,11H2/t13-/m0/s1; Key:IGVDQXLOMXGWKN-ZDUSSCGKSA-N;

BD1018 or (S)-2-[2-(3,4-dichlorophenyl)ethyl]octahydropyrrolo[1,2-a]pyrazine is a selective sigma receptor ligand, with a reported binding affinity of K_i = 5 ± 0.7 nM for the sigma-1 receptor and approximately 10 times selectivity over the sigma-2 receptor.^[1] Unlike its enantiomer, BD1031, BD1018 acts as a sigma receptor antagonist.^[1]

Consistent with other reported sigma receptor antagonists, BD1018 decreases the behavioural toxicity of cocaine in Swiss Webster mice.^[1]

References

^ ^a ^b ^c Matsumoto RR, McCracken KA, Friedman MJ, Pouw B, De Costa BR, Bowen WD (2001). "Conformationally restricted analogs of BD1008 and an antisense oligodeoxynucleotide targeting sigma1 receptors produce anti-cocaine effects in mice". Eur. J. Pharmacol. 419 (2–3): 163–74. doi:10.1016/s0014-2999(01)00968-2. PMID 11426838.