Igmesine
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
| (E)-N-(cyclopropylmethyl)-N-ethyl-3,6-diphenylhex-5-en-3-amine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 140850-73-3  |
| ATC code | None |
| PubChem | CID 6438340 |
| ChemSpider | 4942823  |
| UNII | XA3745J38K |
| Chemical data | |
| Formula | C23H29N |
| Mol. mass | 319.483 g/mol |
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Igmesine (JO-1,784) is a sigma receptor agonist.[1] It has neuroprotective and antidepressant effects in animal studies,[2][3] as well as nootropic effects in models of age-related cognitive decline.[4] It showed good results in phase I human clinical trials but has not been continued further.[5]
Synthesis [edit]
Particularly worth mentioning is the Curtius rearrangement whereby the acid azide spontaneously rearranges to the isocyanate functional group upon heating in an aprotic solvent.
Aubard, G. G.; De Faux, J.-P.; Gouret, C. J.; Grouhel, A. M.; Jacobelli, H. M.; et al.; 1991, U.S. Patent 5,034,419.
References [edit]
- ^ Roman FJ, Pascaud X, Martin B, Vauché D, Junien JL (June 1990). "JO 1784, a potent and selective ligand for rat and mouse brain sigma-sites". The Journal of Pharmacy and Pharmacology 42 (6): 439–40. PMID 1979628.
- ^ O'Neill M, Caldwell M, Earley B, Canney M, O'Halloran A, Kelly J, Leonard BE, Junien JL (September 1995). "The sigma receptor ligand JO 1784 (igmesine hydrochloride) is neuroprotective in the gerbil model of global cerebral ischaemia". European Journal of Pharmacology 283 (1-3): 217–25. doi:10.1016/0014-2999(95)00356-P. PMID 7498313.
- ^ Akunne HC, Zoski KT, Whetzel SZ, Cordon JJ, Brandon RM, Roman F, Pugsley TA (July 2001). "Neuropharmacological profile of a selective sigma ligand, igmesine: a potential antidepressant". Neuropharmacology 41 (1): 138–49. doi:10.1016/S0028-3908(01)00049-1. PMID 11445194.
- ^ Maurice T, Roman FJ, Su TP, Privat A (September 1996). "Beneficial effects of sigma agonists on the age-related learning impairment in the senescence-accelerated mouse (SAM)". Brain Research 733 (2): 219–30. doi:10.1016/0006-8993(96)00565-3. PMID 8891305.
- ^ Volz HP, Stoll KD (November 2004). "Clinical trials with sigma ligands". Pharmacopsychiatry. 37 Suppl 3: S214–20. doi:10.1055/s-2004-832680. PMID 15547788.
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