1.02011-09-21 00:16:34 UTC2019-11-26 03:21:04 UTCFDB022593VaporoleIsoamyl nitrite (IAN) has been used as antianginal agents for more than 100 years. It is now established that IAN cause direct vasorelaxation through vascular generation of NO and relaxation via a cyclic guanosine monophosphate-dependent process. (PMID: 8996213)
IAN is a member of the family of volatile organic nitrites that exert vasodilatory effects and have recently exhibited a considerable potential for inhalation abuse. (PMID: 9829558)
All nitrovasodilators act intracellularly by a common molecular mechanism. This is characterized by the release of nitric oxide (NO). This process basically depends on the presence of oxygen as electron acceptor from the sydnonimine molecule. Organic nitrites (such as IAN) require the interaction with a mercapto group to form a S-nitrosothiol intermediate, from which finally NO radicals are liberated. In the presence of thiol compounds organic nitrites (e.g., IAN) and nitrosothiols may act as intermediary products of NO generation. (PMID: 1683227) [HMDB]3-Methylbutanol nitrite3-Methylbutyl nitriteAmilnitriteAmyl nitritAmyl nitriteAmyl nitrite (JP15/USP)Amyl nitrite (van)Amyl nitrite [usan]Amyl nitrite Iamyl nitrite(mixed isomers)Amyl nitrosumAspiralAspiral (TN)IPNIsoamyl nitriteisopentyl ester Nitrous acidIsopentyl nitriteNitramylNitramyl (van)Nitrite Isopentyl alcoholNitrous acid 3-methylbutyl esterNitrous acid, 3-methylbutyl esterNitrous acid, isopentyl esterPentanoli nitrisPentyl nitriteVaporoleVaporole (TN)Vaporole amyl nitriteC5H11NO2117.1463117.0789786013-methylbutyl nitriteaspiral110-46-3CC(C)CCON=OInChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3OWFXIOWLTKNBAP-UHFFFAOYSA-N belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O.Organic O-nitroso compoundsOrganic compoundsOrganic nitrogen compoundsOrganonitrogen compoundsOrganic nitroso compoundsAliphatic acyclic compoundsAlkyl nitritesHydrocarbon derivativesOrganic oxidesOrganooxygen compoundsAliphatic acyclic compoundAlkyl nitriteHydrocarbon derivativeOrganic nitriteOrganic o-nitroso compoundOrganic oxideOrganic oxygen compoundOrganooxygen compoundnitrite estersSolidlogp1.87logs-1.61solubility2.88e+00 g/llogp2.16pka_strongest_basic-1.8iupac3-methylbutyl nitriteaverage_mass117.1463mono_mass117.078978601smilesCC(C)CCON=OformulaC5H11NO2inchiInChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3inchikeyOWFXIOWLTKNBAP-UHFFFAOYSA-Npolar_surface_area38.66refractivity31.63polarizability12.63rotatable_bond_count4acceptor_count2donor_count0physiological_charge0formal_charge0Specdb::MsIr1234Specdb::MsIr1235Specdb::CMs16351Specdb::CMs155646Specdb::NmrOneD147610Specdb::NmrOneD147611Specdb::NmrOneD147612Specdb::NmrOneD147613Specdb::NmrOneD147614Specdb::NmrOneD147615Specdb::NmrOneD147616Specdb::NmrOneD147617Specdb::NmrOneD147618Specdb::NmrOneD147619Specdb::NmrOneD147620Specdb::NmrOneD147621Specdb::NmrOneD147622Specdb::NmrOneD147623Specdb::NmrOneD147624Specdb::NmrOneD147625Specdb::NmrOneD147626Specdb::NmrOneD147627Specdb::NmrOneD147628Specdb::NmrOneD147629Specdb::MsMs46707Specdb::MsMs46708Specdb::MsMs46709Specdb::MsMs176397Specdb::MsMs176398Specdb::MsMs176399Specdb::MsMs2275395Specdb::MsMs2275396Specdb::MsMs2275397Specdb::MsMs3093199Specdb::MsMs3093200Specdb::MsMs3093201HMDB01382#<Reference:0x00005556741124a0>#<Reference:0x00005556741122e8>#<Reference:0x0000555674112130>Cherry tomatoType 1specificSolanum lycopersicum var. cerasiforme195583Garden tomatoType 1specificSolanum lycopersicum4081Garden tomato (var.)Type 1specificSolanum lycopersicum var. lycopersicum397755