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Igmesin

С Википедије, слободне енциклопедије
Igmesin
IUPAC ime
(E)-N-(cyclopropylmethyl)-N-ethyl-3,6-diphenylhex-5-en-3-amine
Identifikatori
CAS broj140850-73-3 ДаY
ATC kodnone
PubChemCID 6438340
Hemijski podaci
FormulaC23H29N
Molarna masa319.483 g/mol

Igmesin (JO-1,784) je agonist sigma receptora.[1] On ima neuroprotektivno i antidepresivno dejstvo u studijama na životinjama,[2][3], kao i nootropske efekte u modelima gubljenja kognitivnih sposobnosti usled starenja.[4] On se dobro pokazao u kliničkim ispitivanja faze I, ali njegov razvoj nije nastavljen.[5]

Posebno vredan pomena je Kurtiusov rearanžman, gde se kiseli azid sponatano rearanžira u izocijanatnu funkcionalnu grupu nakon zagrevanja u aprotičnom rastvaraču.[6]

  1. ^ Roman FJ, Pascaud X, Martin B, Vauché D, Junien JL (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. 
  2. ^ O'Neill M, Caldwell M, Earley B, Canney M, O'Halloran A, Kelly J, Leonard BE, Junien JL (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. PMID 7498313. doi:10.1016/0014-2999(95)00356-P. 
  3. ^ Akunne HC, Zoski KT, Whetzel SZ, Cordon JJ, Brandon RM, Roman F, Pugsley TA (2001). „Neuropharmacological profile of a selective sigma ligand, igmesine: a potential antidepressant”. Neuropharmacology. 41 (1): 138—49. PMID 11445194. doi:10.1016/S0028-3908(01)00049-1. 
  4. ^ Maurice T, Roman FJ, Su TP, Privat A (1996). „Beneficial effects of sigma agonists on the age-related learning impairment in the senescence-accelerated mouse (SAM)”. Brain Research. 733 (2): 219—30. PMID 8891305. doi:10.1016/0006-8993(96)00565-3. 
  5. ^ Volz HP, Stoll KD (2004). „Clinical trials with sigma ligands”. Pharmacopsychiatry. 37 Suppl 3: S214—20. PMID 15547788. doi:10.1055/s-2004-832680. 
  6. ^ 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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