Igmesin

Igmesin

(IUPAC) ime
(E)-N-(cyclopropylmethyl)-N-ethyl-3,6-diphenylhex-5-en-3-amine
Klinički podaci
Identifikatori
CAS broj	140850-73-3
ATC kod	nije dodeljen
PubChem[1][2]	6438340
Hemijski podaci
Formula	C23H29N
Mol. masa	319.483 g/mol
InChI 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+^Y Key: VCZSWYIFCKGTJI-JLHYYAGUSA-N^Y
Farmakoinformacioni podaci
Trudnoća	?
Pravni status

Igmesin (JO-1,784) je agonist sigma receptora.^[3] On ima neuroprotektivno i antidepresivno dejstvo u studijama na životinjama,^[4][5], kao i nootropske efekte u modelima gubljenja kognitivnih sposobnosti usled starenja.^[6] On se dobro pokazao u kliničkim ispitivanja faze I, ali njegov razvoj nije nastavljen.^[7]

Sinteza

Posebno vredan pomena je Kurtiusov rearanžman, gde se kiseli azid sponatano rearanžira u izocijanatnu funkcionalnu grupu nakon zagrevanja u aprotičnom rastvaraču.^[8]

Literatura

1. Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
2. Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1. 
3. 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. 
4. 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. 
5. 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. 
6. 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. 
7. 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. 
8. Aubard, G. G.; De Faux, J.-P.; Gouret, C. J.; Grouhel, A. M.; Jacobelli, H. M.; et al.; 1991, US Patent 5,034,419.

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