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

Details

Stereochemistry RACEMIC
Molecular Formula C17H23NO.ClH
Molecular Weight 293.832
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRANDAMINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=OZWMTVPSSFWHIM-UHFFFAOYSA-N
InChI=1S/C17H23NO.ClH/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;1H

HIDE SMILES / InChI
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
Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat.
1977-04-15
Pirandamine, a relatively selective 5-hydroxytryptamine uptake inhibitor.
1976-08
Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities.
1976-05-05
Patents

Patents

Name Type Language
AY-23,713
Preferred Name English
PIRANDAMINE HYDROCHLORIDE
MART.   USAN  
USAN  
Official Name English
PIRANDAMINE HYDROCHLORIDE [MART.]
Common Name English
INDENO(2,1-C)PYRAN-1-ETHANAMINE, 1,3,4,9-TETRAHYDRO-N,N,1-TRIMETHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
PIRANDAMINE HYDROCHLORIDE [USAN]
Common Name English
PIRANDAMINE HCL
Common Name English
N,N-DIMETHYL-2-(1-METHYL-1,3,4,9-TETRAHYDROINDENO(2,1-C)PYRAN-1-YL)ETHANAMINE HYDROCHLORIDE
Systematic Name English
AY-23713
Code English
NSC-293164
Code English
INDENO(2,1-C)PYRAN-1-ETHANAMINE, 1,3,4,9-TETRAHYDRO-N,N,1-TRIMETHYL-, HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C94725
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
NCI_THESAURUS C265
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
Code System Code Type Description
MESH
C013202
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY
FDA UNII
Y4F9MIF6M1
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY
SMS_ID
300000055532
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL2110982
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY
NSC
293164
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY
PUBCHEM
3047850
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY
NCI_THESAURUS
C66411
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY
CAS
62099-44-9
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
SUPERSEDED
CAS
42408-78-6
Created by admin on Mon Mar 31 18:06:31 GMT 2025 , Edited by admin on Mon Mar 31 18:06:31 GMT 2025
PRIMARY