U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H23NO
Molecular Weight 257.3706
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRANDAMINE

SMILES

CN(C)CCC1(C)OCCC2=C1CC3=C2C=CC=C3

InChI

InChIKey=AMJPIGOYWBNJLP-UHFFFAOYSA-N
InChI=1S/C17H23NO/c1-17(9-10-18(2)3)16-12-13-6-4-5-7-14(13)15(16)8-11-19-17/h4-7H,8-12H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C17H23NO
Molecular Weight 257.3706
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Pirandamine is the potential antidepressant drug. It is a relatively selective inhibitor of the serotonin uptake mechanism and does not exhibit appreciable norepinephrine uptake blocking activity in contrast to the tricyclic antidepressant drugs imipramine and amitriptyline. Pirandamine is equivalent to amitriptyline and greater than imipramine in potency as a serotonin uptake blocker and a potentiator of central serotonin pharmacological actions, and in contrast, does not exhibit appreciable central anticholinergic effects. Pirandamine potentiated the behavioral effects of 5-hydroxytryptophan in mice. Pirandamine, in contrast to desimipramine and imipramine, did not prevent reserpine-induced hypothermia. The (-)-enantiomer of pirandamine retained the activity of the racemate; the (+I-enantiomer was much less effective.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pirandamine, a relatively selective 5-hydroxytryptamine uptake inhibitor.
1976 Aug
Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities.
1976 May 5
Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat.
1977 Apr 15
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:00 UTC 2023
Edited
by admin
on Fri Dec 15 16:20:00 UTC 2023
Record UNII
WC6V8L1Z13
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRANDAMINE
INN  
INN  
Official Name English
INDENO(2,1-C)PYRAN-1-ETHANAMINE, 1,3,4,9-TETRAHYDRO-N,N,1-TRIMETHYL-
Systematic Name English
pirandamine [INN]
Common Name English
1,3,4,9-TETRAHYDRO-N,N,1-TRIMETHYLINDENO(2,1-C)PYRAN-1-ETHYLAMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C94725
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL2110982
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
FDA UNII
WC6V8L1Z13
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
PUBCHEM
431429
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
CAS
42408-79-7
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
MESH
C013202
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
EVMPD
SUB09893MIG
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
NCI_THESAURUS
C84064
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
WIKIPEDIA
Pirandamine
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID10866093
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
CAS
62099-43-8
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
SUPERSEDED
INN
3638
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
SMS_ID
100000081638
Created by admin on Fri Dec 15 16:20:00 UTC 2023 , Edited by admin on Fri Dec 15 16:20:00 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY