| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:32:35 UTC |
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| Update date | 2017-01-19 02:36:35 UTC |
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| FoodComEx ID | PC000768 |
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| FoodDB Record | FDB023069 |
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| Chemical Information |
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| Name | Methylimidazoleacetic acid |
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| Description | Methylimidazoleacetic 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] |
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| CAS Number | 2625-49-2 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 1-methyl-1H-Imidazole-4-acetate | hmdb | | 1-methyl-1H-Imidazole-4-acetic acid | hmdb | | 1-Methyl-4-imidazoleacetate | hmdb | | 1-Methyl-4-imidazoleacetic acid | hmdb | | 1-Methylimidazole-4-acetate | hmdb | | 1-Methylimidazole-4-acetic acid | Generator | | 1,4-Methyl-imidazoleacetate | Generator | | 1,4-methyl-imidazoleacetic acid | hmdb | | 1,4-Methylimidazoleacetate | hmdb | | Methylimidazole acetate | hmdb | | Methylimidazoleacetate | hmdb | | Methylimidazoleacetic acid | hmdb | | MIAA | HMDB | | N tau-methylimidazoleacetic acid | hmdb | | Tele-methylimidazoleacetate | hmdb | | Tele-methylimidazoleacetic acid | hmdb |
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| Chemical Formula | C6H8N2O2 |
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| IUPAC name | 2-(1-methyl-1H-imidazol-4-yl)acetic acid |
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| InChI Identifier | InChI=1S/C6H8N2O2/c1-8-3-5(7-4-8)2-6(9)10/h3-4H,2H2,1H3,(H,9,10) |
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| InChI Key | ZHCKPJGJQOPTLB-UHFFFAOYSA-N |
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| Isomeric SMILES | CN1C=NC(CC(O)=O)=C1 |
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| Average Molecular Weight | 140.1399 |
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| Monoisotopic Molecular Weight | 140.05857751 |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Azoles |
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| Sub Class | Imidazoles |
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| Direct Parent | Imidazolyl carboxylic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Imidazolyl carboxylic acid derivative
- N-substituted imidazole
- Heteroaromatic compound
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 20 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| AKSci | 2304AB |
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