McN-5558

McN-5558
Identifiers
	IUPAC name (6S,10bR)-6-[3-(trifluoromethyl)phenyl]-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline;
PubChem CID	13646491;
ChemSpider	23130492;
ChEMBL	ChEMBL286849;
Chemical and physical data
Formula	C19H18F3N
Molar mass	317.355 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C[C@@H]2C3=CC=CC=C3[C@@H](CN2C1)C4=CC(=CC=C4)C(F)(F)F;
	InChI InChI=1S/C19H18F3N/c20-19(21,22)14-6-3-5-13(11-14)17-12-23-10-4-9-18(23)16-8-2-1-7-15(16)17/h1-3,5-8,11,17-18H,4,9-10,12H2/t17-,18+/m0/s1; Key:LWXKKDYZAXBAPH-ZWKOTPCHSA-N;

FormulaC₁₉H₁₈F₃N

McN-5558 is a drug which acts as a selective noradrenaline reuptake inhibitor. It was investigated for potential application as an antidepressant, but was never developed for clinical use.^[1]^[2]

Compound 37b	norepinephrine transporter (NE)	dopamine transporter (DAT)	serotonin transporter (SERT)
racemic	1.0	54.3	23.0
(+)	1.5	25.7	9.1
(-)	2570	7690	2920

SAR

Identifiers

IUPAC name (6S,10bR)-6-[3-(trifluoromethyl)phenyl]-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
PubChem CID	13646491
ChemSpider	23130492
ChEMBL	ChEMBL286849
Chemical and physical data
Formula	C₁₉H₁₈F₃N
Molar mass	317.355 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1C[C@@H]2C3=CC=CC=C3[C@@H](CN2C1)C4=CC(=CC=C4)C(F)(F)F
InChI InChI=1S/C19H18F3N/c20-19(21,22)14-6-3-5-13(11-14)17-12-23-10-4-9-18(23)16-8-2-1-7-15(16)17/h1-3,5-8,11,17-18H,4,9-10,12H2/t17-,18+/m0/s1 Key:LWXKKDYZAXBAPH-ZWKOTPCHSA-N