1.02011-09-21 00:24:13 UTC2015-10-09 22:32:35 UTCFDB023069Methylimidazoleacetic acidMethylimidazoleacetic acid is the main metabolite of histamine. This end product of histamine catabolism is formed by N-methylation in the imidazole ring to methylhistamine by histamine methyltransferase (EC 2.1.1.8) and a subsequent oxidative deamination in the side chain by type B monoamine oxidase (EC 1.4.3.4). From studies is known that as much as 70 to 80 percent of the histamine metabolized in the body is excreted in the urine as Methylimidazoleacetic acid. Thus, urinary Methylimidazoleacetic acid being the major and specific histamine metabolite is a clear marker of any changes in histamine metabolism in the body. The urinary excretion of methylimidazoleacetic acid is considered a reliable indicator of histamine turnover rate in the body. The excretion of Methylimidazoleacetic acid is higher in men than women however; this gender difference is abolished when corrected for creatinine excretion. A possible explanation is that basal histamine turnover is related to body size. There is no significant difference in Methylimidazoleacetic acid excretion between smokers and non-smokers when analysing absolute values (mg/24 h). When using Methylimidazoleacetic acid values corrected for creatinine excretion female smokers have significantly higher Methylimidazoleacetic acid excretion compared to nonsmokers. (PMID: 11411609, 7130180, 10350179, 10202992) [HMDB]1-methyl-1H-Imidazole-4-acetate1-methyl-1H-Imidazole-4-acetic acid1-Methyl-4-imidazoleacetate1-Methyl-4-imidazoleacetic acid1-Methylimidazole-4-acetate1-Methylimidazole-4-acetic acid1,4-Methyl-imidazoleacetate1,4-methyl-imidazoleacetic acid1,4-MethylimidazoleacetateMethylimidazole acetateMethylimidazoleacetateMethylimidazoleacetic acidMIAAN tau-methylimidazoleacetic acidTele-methylimidazoleacetateTele-methylimidazoleacetic acidC6H8N2O2140.1399140.058577512-(1-methyl-1H-imidazol-4-yl)acetic acidmethylimidazoleacetic acid2625-49-2CN1C=NC(CC(O)=O)=C1InChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)ZHCKPJGJQOPTLB-UHFFFAOYSA-N belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.Imidazolyl carboxylic acids and derivativesOrganic compoundsOrganoheterocyclic compoundsAzolesImidazolesAromatic heteromonocyclic compoundsAzacyclic compoundsCarbonyl compoundsCarboxylic acidsHeteroaromatic compoundsHydrocarbon derivativesMonocarboxylic acids and derivativesN-substituted imidazolesOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsAromatic heteromonocyclic compoundAzacycleCarbonyl groupCarboxylic acidCarboxylic acid derivativeHeteroaromatic compoundHydrocarbon derivativeImidazolyl carboxylic acid derivativeMonocarboxylic acid or derivativesN-substituted imidazoleOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundimidazolyl carboxylic acidSolidlogp-0.22logs-1.38solubility5.88e+00 g/llogp-1.2pka_strongest_acidic3.68pka_strongest_basic6.45iupac2-(1-methyl-1H-imidazol-4-yl)acetic acidaverage_mass140.1399mono_mass140.05857751smilesCN1C=NC(CC(O)=O)=C1formulaC6H8N2O2inchiInChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10)inchikeyZHCKPJGJQOPTLB-UHFFFAOYSA-Npolar_surface_area55.12refractivity34.85polarizability13.69rotatable_bond_count2acceptor_count3donor_count1physiological_charge-1formal_charge0Histidine MetabolismSMP00044map00340Specdb::NmrTwoD1841Specdb::MsIr1835Specdb::MsIr1836Specdb::MsIr1837Specdb::CMs1223Specdb::CMs9982Specdb::CMs31426Specdb::CMs38481Specdb::CMs145952Specdb::NmrOneD1906Specdb::NmrOneD149360Specdb::NmrOneD149361Specdb::NmrOneD149362Specdb::NmrOneD149363Specdb::NmrOneD149364Specdb::NmrOneD149365Specdb::NmrOneD149366Specdb::NmrOneD149367Specdb::NmrOneD149368Specdb::NmrOneD149369Specdb::NmrOneD149370Specdb::NmrOneD149371Specdb::NmrOneD149372Specdb::NmrOneD149373Specdb::NmrOneD149374Specdb::NmrOneD149375Specdb::NmrOneD149376Specdb::NmrOneD149377Specdb::NmrOneD149378Specdb::NmrOneD149379Specdb::MsMs2140Specdb::MsMs2141Specdb::MsMs2142Specdb::MsMs288073Specdb::MsMs288074Specdb::MsMs288075Specdb::MsMs327070Specdb::MsMs327071Specdb::MsMs327072Specdb::MsMs1448478Specdb::MsMs2237962Specdb::MsMs2239626Specdb::MsMs2244150Specdb::MsMs2245961Specdb::MsMs2246296Specdb::MsMs2247968Specdb::MsMs2248421Specdb::MsMs2249967Specdb::MsMs2250385Specdb::MsMs2251988Specdb::MsMs2456046Specdb::MsMs2456047Specdb::MsMs2456048Specdb::MsMs2478787Specdb::MsMs2478788HMDB02820#<Reference:0x0000555673739898>#<Reference:0x0000555673739500>#<Reference:0x0000555673739190>#<Reference:0x0000555673738e48>#<Reference:0x0000555673738c40>#<Reference:0x0000555673738948>#<Reference:0x0000555673738678>#<Reference:0x00005556737383a8>#<Reference:0x0000555673737e08>#<Reference:0x0000555673737c28>#<Reference:0x00005556737379d0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823