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Details

Stereochemistry UNKNOWN
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
Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities.
1976 May 5
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 10:29:27 GMT 2023
Edited
by admin
on Sat Dec 16 10:29:27 GMT 2023
Record UNII
4NAV7SU9TR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRANDAMINE, (-)-
Common Name English
INDENO(2,1-C)PYRAN-1-ETHANAMINE, 1,3,4,9-TETRAHYDRO-N,N,1-TRIMETHYL-, (-)-
Systematic Name English
(-)-1,3,4,9-TETRAHYDRO-N,N,1-TRIMETHYLINDENO(2,1-C)PYRAN-1-ETHANAMINE
Common Name English
Code System Code Type Description
CAS
62157-13-5
Created by admin on Sat Dec 16 10:29:27 GMT 2023 , Edited by admin on Sat Dec 16 10:29:27 GMT 2023
PRIMARY
FDA UNII
4NAV7SU9TR
Created by admin on Sat Dec 16 10:29:27 GMT 2023 , Edited by admin on Sat Dec 16 10:29:27 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> ENANTIOMER
RACEMATE -> ENANTIOMER