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Details

Stereochemistry RACEMIC
Molecular Formula C19H21NS
Molecular Weight 295.442
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MCN-5652

SMILES

[H][C@]12CCCN1C[C@@H](C3=CC=C(SC)C=C3)C4=C2C=CC=C4

InChI

InChIKey=YVKDUIAAPBKHMJ-RBUKOAKNSA-N
InChI=1S/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+/m0/s1

HIDE SMILES / InChI
McN-5652 is one of a series of substituted pyrrolo-isoquinolines that, as a group, potently inhibit the uptake of one or more of the monoamines, norepinephrine, serotonin and dopamine. Receptor binding experiments indicated that McN-5652 has a weak affinity for serotonin 5-HT2 and alpha-1 adrenergic receptors. Abnormalities of the 5-HT transporter have been suggested in mood disorders, since it is one of the major binding sites of antidepressants. (+)-[11C]McN 5652 is an appropriate radiotracer to quantify 5-HT transporters in regions with relatively high concentration of 5-HT transporters, such as the midbrain, thalamus, and basal ganglia, and should prove useful in elucidating abnormalities of 5-HT transmission in neuropsychiatric conditions.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.6 nM [Ki]
3.04 nM [Ki]
208.0 nM [Ki]
314.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
McN-5652: a highly potent inhibitor of serotonin uptake.
1988 Dec
Patents

Sample Use Guides

(+)-[11C]McN5652 injected dose (ID) was 580±128 MBq and the injected mass was 13.3±4.4 nmol. For (-)-[11C]McN 5652 the ID was 625±88 MBq and the injected mass was 18.6±16.1 nmol.
Route of Administration: Intravenous
In Vitro Use Guide
When tested at concentrations of 34 nM to 3.4 uM, McN-5652-Z-68 gave no indication of competitive antagonism against acetylcholine or histamine. A nonparallel shift of the acetylcholine concentration-response curve occurred when McN-5652-Z-68 was tested at concentrations of 340 nM and higher. A moderate but statistically significant increase in ED50 values for histamine was observed with McN-5652-Z-68 at 34 and 340 nM, but this inhibition was not competitive as indicated by the slope of the Schild plot (about 0.5). At 3.4 uM, McN-5652-Z-68 marginally relaxed smooth muscle.
Name Type Language
MCN-5652
Common Name English
PYRROLO(2,1-A)ISOQUINOLINE, 1,2,3,5,6,10B-HEXAHYDRO-6-(4-(METHYLTHIO)PHENYL)-, (6R,10BS)-REL-
Systematic Name English
REL-(6R,10BS)-1,2,3,5,6,10B-HEXAHYDRO-6-(4-(METHYLTHIO)PHENYL)PYRROLO(2,1-A)ISOQUINOLINE
Common Name English
TRANS-MCN 5652
Code English
MCN-5652, (±)-
Code English
PYRROLO(2,1-A)ISOQUINOLINE, 1,2,3,5,6,10B-HEXAHYDRO-6-(4-(METHYLTHIO)PHENYL)-, TRANS-
Common Name English
MCN-5652Z
Code English
Code System Code Type Description
WIKIPEDIA
McN5652
Created by admin on Sat Dec 16 11:05:48 GMT 2023 , Edited by admin on Sat Dec 16 11:05:48 GMT 2023
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CAS
96795-89-0
Created by admin on Sat Dec 16 11:05:48 GMT 2023 , Edited by admin on Sat Dec 16 11:05:48 GMT 2023
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EPA CompTox
DTXSID901026892
Created by admin on Sat Dec 16 11:05:48 GMT 2023 , Edited by admin on Sat Dec 16 11:05:48 GMT 2023
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PUBCHEM
3036461
Created by admin on Sat Dec 16 11:05:48 GMT 2023 , Edited by admin on Sat Dec 16 11:05:48 GMT 2023
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FDA UNII
21MT8QF2LI
Created by admin on Sat Dec 16 11:05:48 GMT 2023 , Edited by admin on Sat Dec 16 11:05:48 GMT 2023
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