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Details

Stereochemistry UNKNOWN
Molecular Formula C23H29N
Molecular Weight 319.4831
Optical Activity ( + )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of IGMESINE

SMILES

CCC(C\C=C\C1=CC=CC=C1)(N(C)CC2CC2)C3=CC=CC=C3

InChI

InChIKey=VCZSWYIFCKGTJI-JLHYYAGUSA-N
InChI=1S/C23H29N/c1-3-23(22-14-8-5-9-15-22,24(2)19-21-16-17-21)18-10-13-20-11-6-4-7-12-20/h4-15,21H,3,16-19H2,1-2H3/b13-10+

HIDE SMILES / InChI

Molecular Formula C23H29N
Molecular Weight 319.4831
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Igmesine is a sigma-1 receptor agonist. It was assayed in clinical trials targeting major depressive disorder. Igmesine is the only antisecretory agent that we have tested to date that inhibits both cholera toxin and the E. coli enterotoxins. Sigma receptors are known to be present on nerves in the enteric nervous system and this would seem to be a potentially useful class of drugs to pursue for the treatment of secretory diarrhoea in humans. It was shown that when Alzheimer's disease rats were submitted to the conditioned fear stress test, igmesine can significantly reduce the stress-induced motor suppression, indicating exogenous σ-1 receptor agonists may alleviate Alzheimer's disease-associated depressive symptoms.

Originator

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/1979628

Approval Year

Doses

Doses

DosePopulationAdverse events​
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
healthy
Health Status: healthy
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
The SigmaR1 chaperone drives breast and colorectal cancer cell migration by tuning SK3-dependent Ca2+ homeostasis.
2017-06-22
Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands.
2015-01-07
Behavioural phenotyping of knockout mice for the sigma-1 (σ₁) chaperone protein revealed gender-related anxiety, depressive-like and memory alterations.
2011-07
Effects of PB190 and PB212, new σ receptor ligands, on glucocorticoid receptor-mediated gene transcription in LMCAT cells.
2011
Pharmacological interaction with the sigma1 (σ1)-receptor in the acute behavioral effects of antidepressants.
2011
Patents

Sample Use Guides

25, 50, 100 or 200 mg per day
Route of Administration: Oral
In Vitro Use Guide
Igmesine is a potent ligand for (+)-[3H]SKF 10,047 (2'-hydroxy-5,9-dimethyl-2-allyl-6,7-benzomorphan) binding sites in rat brain membrane preparations with an IC50 of 39 +/- 8 nM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:48:13 GMT 2025
Edited
by admin
on Mon Mar 31 18:48:13 GMT 2025
Record UNII
XA3745J38K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IGMESINE
INN  
INN  
Official Name English
(+)-Igmesine
Preferred Name English
Benzenemethanamine, N-(cyclopropylmethyl)-?-ethyl-N-methyl-?-[(2E)-3-phenyl-2-propen-1-yl]-, (+)-
Systematic Name English
igmesine [INN]
Common Name English
(+)-N-(Cyclopropylmethyl)-?-ethyl-N-methyl-?-[(2E)-3-phenyl-2-propen-1-yl]benzenemethanamine
Systematic Name English
Code System Code Type Description
PUBCHEM
6438340
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
CAS
140850-73-3
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL2110660
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
MESH
C065310
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
INN
6995
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID801028764
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
NCI_THESAURUS
C170052
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
WIKIPEDIA
IGMESINE
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
FDA UNII
XA3745J38K
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
EVMPD
SUB08128MIG
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
SMS_ID
100000083702
Created by admin on Mon Mar 31 18:48:14 GMT 2025 , Edited by admin on Mon Mar 31 18:48:14 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Ki
Related Record Type Details
ACTIVE MOIETY