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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NS.ClHO4
Molecular Weight 395.9
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MCN-5652W68

SMILES

OCl(=O)(=O)=O.CSC1=CC=C(C=C1)[C@H]2CN3CCC[C@H]3C4=C2C=CC=C4

InChI

InChIKey=PBALTVQMQFVDBV-VOMIJIAVSA-N
InChI=1S/C19H21NS.ClHO4/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;2-1(3,4)5/h2-3,5-6,8-11,18-19H,4,7,12-13H2,1H3;(H,2,3,4,5)/t18-,19+;/m1./s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11391781

MCN-5652W68 is pharmacologically inactive enantiomer of an selective serotonin reuptake MCN-5652. The enantiomers of McN-5652 differed in their ability to inhibit ex vivo binding of paroxetine in rat frontal cortex and hypothalamus, in vitro uptake of 5-HT in rat blood platelets, and 5-HT-induced contraction of rat vascular smooth muscle, with (+)-McN-5652-Z being most active. No difference was observed between the effects of (+)- and (-)-McN-5652-Z on 5-HT metabolism by rat brain monoamine oxidase. MCN-5652, as enantiomeric mixture, is currently being used for positron emission tomography studies.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
712.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
A new single-photon emission computed tomography imaging agent for serotonin transporters: [123I]IDAM, 5-iodo-2-((2-((dimethylamino)methyl)phenyl)thio)benzyl alcohol.
1999-02-11
Patents

Patents

Sample Use Guides

injection of 455.1 to 728.2 (mean, 625.9 ± 138.2) MBq [11C](−)McN5652
Route of Administration: Intravenous
Binding affinity for (-)-McN5652 was determined at 21°C and 37°C in a final volume of 300 ml of buffer 3, which contained 50 ml of membrane suspension and (-)-McN5652 at one of eight concentrations between 1nM and 10 mkM Nonspecific binding was determined using 1 mM paroxetine as inhibitor. The binding at each concentration was determined with two samples for total binding and one for nonspecific binding. After 3.5 h incubation the samples were filtered using a 24-channel cell harvester Five ml of buffer 3 (20°C) was added to each sample, which was then filtered through Whatman GF/B glass-fiber filters and washed with 20 ml buffer 3. The filters had been soaked with 0.5% polyethylenimine prior to filtration in order to reduce and stabilize nonspecific binding to the filters. The filters were dried overnight and counted in Ultima Gold
Name Type Language
MCN-5652W68
Common Name English
PYRROLO(2,1-A)ISOQUINOLINE, 1,2,3,5,6,10B-HEXAHYDRO-6-(4-(METHYLTHIO)PHENYL)-, (6R,10BS)-, PERCHLORATE (1:1)
Preferred Name English
Code System Code Type Description
PUBCHEM
9952587
Created by admin on Mon Mar 31 23:38:25 GMT 2025 , Edited by admin on Mon Mar 31 23:38:25 GMT 2025
PRIMARY
CAS
109278-13-9
Created by admin on Mon Mar 31 23:38:25 GMT 2025 , Edited by admin on Mon Mar 31 23:38:25 GMT 2025
PRIMARY
FDA UNII
2BB56N9061
Created by admin on Mon Mar 31 23:38:25 GMT 2025 , Edited by admin on Mon Mar 31 23:38:25 GMT 2025
PRIMARY