JNJ-7925476

JNJ-7925476
Identifiers
	IUPAC name (6S,10bR)-6-(4-Ethynylphenyl)-1H,2H,3H,5H,6H,10bH-pyrrolo[2,1-a]isoquinoline;
CAS Number	129540-12-1 ; HCl: 109085-56-5 ;
PubChem CID	13903191;
ChemSpider	23130640;
UNII	VSM44B5G3G; HCl: IQ02SF57WP ;
ChEMBL	ChEMBL286312;
CompTox Dashboard (EPA)	DTXSID001134549 ;
Chemical and physical data
Formula	C20H19N
Molar mass	273.379 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C#CC1=CC=C(C=C1)[C@@H]2CN3CCC[C@@H]3C4=CC=CC=C24;
	InChI InChI=1S/C20H19N/c1-2-15-9-11-16(12-10-15)19-14-21-13-5-8-20(21)18-7-4-3-6-17(18)19/h1,3-4,6-7,9-12,19-20H,5,8,13-14H2/t19-,20+/m0/s1; Key:YPFCCQUUZJDQAM-VQTJNVASSA-N;
	(verify)

JNJ-7925476 is a triple reuptake inhibitor antidepressant discovered by Johnson & Johnson, but never marketed.

These molecules were first prepared by Bruce E. Maryanoff and coworkers during the late 1970s–1980s. The structure is a pyrroloisoquinoline core, with an overlaid benzhydryl motif.

Incorporating the pyrrolidino ring onto the tetrahydroisoquinoline scaffolding markedly improves potency, although this only works for one of the available stereoisomers. JNJ-7925476 is a racemic preparation of the more potent diastereomer. Of these enantiomers, the eutomer is the (6R,10bS) stereoisomer, known as JNJ-39836966, and the distomer, (6S,10bR), is JNJ-39836732

There is some confusion over the nomenclature and cis/trans isomeric relationship at the piperidine ring. The compounds as depicted have the carbon of the pyrrolidine carbon and the phenyl cis, but Maryanoff and coworkers are of the opinion that the compound is trans. (see abstract)

The reason for this is not known because it was referred to as "cis" in earlier reports, and then later reassigned.