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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

Molecular Formula C19H21NS
Molecular Weight 295.442
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClHO4
Molecular Weight 100.459
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:38:25 GMT 2025
Edited
by admin
on Mon Mar 31 23:38:25 GMT 2025
Record UNII
2BB56N9061
Record Status Validated (UNII)
Record Version
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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
Related Record Type Details
ACTIVE MOIETY