96795-89-0

Basic information

• Product Name: (+/-)-MCN 5652
• Synonyms: (+/-)-MCN 5652;rel-(6R*,10bS*)-6α*-[4-(Methylthio)phenyl]-1,2,3,5,6,10bβ*-hexahydropyrrolo[2,1-a]isoquinoline;trans-McN-5652;(-)-McN-5652Z;(-)-McN-5652-Z;1,2,3,5,6,10bβ-Hexahydro-6α-[4-(methylthio)phenyl]pyrrolo[2,1-a]isoquinoline;(6S)-1,2,3,5,6,10bβ-Hexahydro-6β-(4-methylthiophenyl)pyrrolo[2,1-a]isoquinoline;(6R,10bS)-rel-1,2,3,5,6,10b-Hexahydro-6-[4-(methylthio)phenyl]-pyrrolo[2,1-a]isoquinoline
• CAS NO: 96795-89-0
• Molecular Formula: C₁₉H₂₁NS
• Molecular Weight: 295.448
• Mol File: 96795-89-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 433.1°Cat760mmHg
• Flash Point: 215.7°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 1.05E-07mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: Store at -20°C
• CAS DataBase Reference: (+/-)-MCN 5652(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-MCN 5652(96795-89-0)
• EPA Substance Registry System: (+/-)-MCN 5652(96795-89-0)

Safety Data

• Hazardous Substances Data: 96795-89-0(Hazardous Substances Data)

Usage

Uses

McN 5652, (+/-) is a 5-HT uptake inhibitor.

Biological Activity

Potent, high affinity serotonin re-uptake inhibitor that is selective in vivo . In vitro, displays moderate selectivity over noradrenalin and dopamine re-uptake (K i values are 0.68, 2.9 and 36.8 nM for inhibition of serotonin, noradrenalin and dopamine uptake respectively in rat brain synaptosomes). Potently potentiates 5-HT-induced effects in vivo following oral administration. Biological activity resides predominantly in (+)-enantiomer.

InChI:InChI=1/C19H21NS/c1-21-15-10-8-14(9-11-15)18-13-20-12-4-7-19(20)17-6-3-2-5-16(17)18/h2-3,5-6,8-11,18-19H,4,7,12-13H2,1H3/t18-,19+/m1/s1

Upstream product

• 125330-79-2 1-[2-hydroxy-2-(4-methylthiophenyl)]ethanoyl-2-phenylpyrrolidine 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 109086-16-0 2-hydroxy-2-(4-methylthiophenyl)ethanoic acid 
• 93-89-0 benzoic acid ethyl ester 
• 1006-64-0 2-(phenyl)pyrrolidine 
• 700-91-4 2-phenyl-1-pyrroline 
• 370102-66-2 6-(4-(methylthio)phenyl)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one 

Downstream Products

• 96795-90-3 (+)-trans-1,2,3,5,6,10b-hexahydro-6-<4-(methylthio)phenyl>pyrrolo<2,1-a>isoquinoline perchlorate salt 
• 96795-90-3 (-)-trans-1,2,3,5,6,10b-hexahydro-6-<4-(methylthio)phenyl>pyrrolo<2,1-a>isoquinoline perchlorate 
• 129540-10-9 cis-1,2,3,5,6,10b-hexahydro-6-<4-(methylsulfinyl)phenyl>pyrrolo<2,1-a>isoquinoline 
• 129540-10-9 trans-1,2,3,5,6,10b-hexahydro-6-<4-(methylsulfinyl)phenyl>pyrrolo<2,1-a>isoquinoline 

Relevant articles and documents

The structure of McN-5652

The configuration of the diastereoisomers of 6-(4-methylthiophenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline 1 (McN-5652) is determined and unequivocally assigned by NMR spectroscopy (NOE measurements) and an X-ray structural analysis of the trans diastereoisomer. The enantiomers of cis-1 are separated by preparative HPLC on a chiral phase. One of the enantiomers of cis-1 represents the precursor for imaging the serotonin 5-HT transporter with positron emission tomography (PET).