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
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+
| 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.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15547788
25, 50, 100 or 200 mg per day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1979628
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
Edited
Mon Mar 31 18:48:13 GMT 2025
by
admin
on
Mon Mar 31 18:48:13 GMT 2025
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| Record UNII |
XA3745J38K
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| Record Status |
Validated (UNII)
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| Record Version |
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6438340
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140850-73-3
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CHEMBL2110660
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C065310
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6995
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DTXSID801028764
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C170052
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IGMESINE
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XA3745J38K
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SUB08128MIG
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100000083702
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
Ki
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ACTIVE MOIETY |
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