Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 12:13:52 UTC |
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Update Date | 2021-09-26 23:06:49 UTC |
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HMDB ID | HMDB0253540 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Iomazenil |
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Description | Iomazenil, also known as iomazenil (123i) or (123i)iomazenil, belongs to the class of organic compounds known as imidazo[1,5-a][1,4]benzodiazepines. Imidazo[1,5-a][1,4]benzodiazepines are compounds containing an imidazole ring and a 1,4-benzodiazepine ring system, both sharing one nitrogen atom. Iomazenil is a strong basic compound (based on its pKa). The compound was introduced in 1989 by pharmaceutical company Hoffmann-La Roche as an Iodine-123-labelled SPECT tracer for imaging benzodiazepine receptors (GABAA receptors) in the brain. The effect of iomazenil of reducing levels of GABA in the brain was used by researchers to exacerbate symptoms in patients with schizophrenia in a laboratory study, supporting the theory that a GABA deficiency underlies that disease. Iomazenil is an analogue of flumazenil (Ro15-1788).123I-labelled iomazenil can be used to image epileptic seizure foci as an alternative to 18F-fludeoxyglucose PET imaging. Researcher Deepak D'Souza and colleagues at Yale University and Veterans Affairs Connecticut Healthcare System are testing iomazenil as a potential treatment for drunkenness due to its ability to bind alcohol receptors in the brain. This compound has been identified in human blood as reported by (PMID: 31557052 ). Iomazenil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Iomazenil is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | CCOC(=O)C1=C2CN(C)C(=O)C3=C(I)C=CC=C3N2C=N1 InChI=1S/C15H14IN3O3/c1-3-22-15(21)13-11-7-18(2)14(20)12-9(16)5-4-6-10(12)19(11)8-17-13/h4-6,8H,3,7H2,1-2H3 |
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Synonyms | Value | Source |
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Iomazenil (123I) | MeSH | (123I)iomazenil | MeSH | Ethyl 7-iodo-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate | MeSH | Iomazenil I-123 | MeSH | Iomazenil | MeSH |
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Chemical Formula | C15H14IN3O3 |
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Average Molecular Weight | 411.199 |
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Monoisotopic Molecular Weight | 411.00799 |
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IUPAC Name | ethyl 11-iodo-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(14),3,5,10,12-pentaene-5-carboxylate |
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Traditional Name | ethyl 11-iodo-8-methyl-9-oxo-2,4,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(14),3,5,10,12-pentaene-5-carboxylate |
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CAS Registry Number | Not Available |
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SMILES | CCOC(=O)C1=C2CN(C)C(=O)C3=C(I)C=CC=C3N2C=N1 |
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InChI Identifier | InChI=1S/C15H14IN3O3/c1-3-22-15(21)13-11-7-18(2)14(20)12-9(16)5-4-6-10(12)19(11)8-17-13/h4-6,8H,3,7H2,1-2H3 |
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InChI Key | FRIZVHMAECRUBR-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as imidazo[1,5-a][1,4]benzodiazepines. Imidazo[1,5-a][1,4]benzodiazepines are compounds containing an imidazole ring and a 1,4-benzodiazepine ring system, both sharing one nitrogen atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzodiazepines |
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Sub Class | 1,4-benzodiazepines |
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Direct Parent | Imidazo[1,5-a][1,4]benzodiazepines |
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Alternative Parents | |
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Substituents | - Imidazo[1,5-a][1,4]benzodiazepine
- Para-diazepine
- Imidazole-4-carbonyl group
- Aryl halide
- Aryl iodide
- Benzenoid
- N-substituted imidazole
- Azole
- Heteroaromatic compound
- Vinylogous amide
- Vinylogous halide
- Tertiary carboxylic acid amide
- Imidazole
- Carboxamide group
- Carboxylic acid ester
- Lactam
- Azacycle
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organonitrogen compound
- Organooxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organoiodide
- Organic oxygen compound
- Organohalogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Iomazenil GC-MS (Non-derivatized) - 70eV, Positive | splash10-004j-4049000000-97801e7083c4dd7365ff | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Iomazenil GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 10V, Positive-QTOF | splash10-03di-0003900000-e358826f97b67d489288 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 20V, Positive-QTOF | splash10-02t9-2009400000-50baa7d7cbb2a9b2b035 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 40V, Positive-QTOF | splash10-0fre-7296000000-905bef309974a447663e | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 10V, Negative-QTOF | splash10-03di-2009800000-8119e1e0f351fa041041 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 20V, Negative-QTOF | splash10-03di-2009300000-42ee6be19b1ee880dca2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 40V, Negative-QTOF | splash10-0002-4179000000-933ee6deb8b580e5e9b8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 10V, Positive-QTOF | splash10-03di-0002900000-04c42bb69a24f01f19e5 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 20V, Positive-QTOF | splash10-02t9-0009500000-de1a934b4c4f77a803e2 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 40V, Positive-QTOF | splash10-000b-2039000000-5ce9ae338518aa965f18 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 10V, Negative-QTOF | splash10-03di-0001900000-962fcb4c89b24ed7316f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 20V, Negative-QTOF | splash10-03di-0109300000-d65417b4ea4f23c5ff1f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Iomazenil 40V, Negative-QTOF | splash10-0229-0129000000-3b84364974e79325e696 | 2021-10-12 | Wishart Lab | View Spectrum |
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