Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2020-02-26 21:41:27 UTC |
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HMDB ID | HMDB0015346 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Estazolam |
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Description | Estazolam is only found in individuals that have used or taken this drug. It is a benzodiazepine with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam. [PubChem]Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell. |
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Structure | ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1 InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2 |
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Synonyms | Value | Source |
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8-Chloro-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine | ChEBI | Estazolamum | ChEBI | ProSom | Kegg | D40TA | HMDB | Hormona brand OF estazolam | HMDB | Abbott brand OF estazolam | HMDB | Nuctalon | HMDB | D-40TA | HMDB | Takeda brand OF estazolam | HMDB | Tasedan | HMDB |
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Chemical Formula | C16H11ClN4 |
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Average Molecular Weight | 294.738 |
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Monoisotopic Molecular Weight | 294.067224079 |
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IUPAC Name | 12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene |
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Traditional Name | estazolam |
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CAS Registry Number | 29975-16-4 |
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SMILES | ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2 |
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InChI Key | CDCHDCWJMGXXRH-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring. |
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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 | 1,2,4-triazolo[4,3-a][1,4]benzodiazepines |
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Alternative Parents | |
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Substituents | - 1,2,4-triazolo[4,3-a][1,4]benzodiazepine
- Aryl chloride
- Aryl halide
- Monocyclic benzene moiety
- Benzenoid
- Azole
- 1,2,4-triazole
- Heteroaromatic compound
- Ketimine
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Azacycle
- Organopnictogen compound
- Organic nitrogen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Imine
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 228.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.042 g/L | Not Available | LogP | 4.7 | 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 - Estazolam GC-MS (Non-derivatized) - 70eV, Positive | splash10-016r-2190000000-7bceaaf0dfe0270e210a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Estazolam GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Estazolam GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0a4u-4590000000-dbd088d66293b3b539c3 | 2014-09-20 | Not Available | 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 - Estazolam 10V, Positive-QTOF | splash10-0002-0090000000-8b0f7d04b982deb5a038 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 20V, Positive-QTOF | splash10-0002-0090000000-6608de192721b2ce8c75 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 40V, Positive-QTOF | splash10-03xu-8690000000-2b0a33869a0469e8d7b5 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 10V, Negative-QTOF | splash10-0006-0090000000-3bf04c7178bea5e8dea2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 20V, Negative-QTOF | splash10-0006-0090000000-4b4a11f4e7a928221cff | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 40V, Negative-QTOF | splash10-0a5c-1090000000-7609bb7b371102913ae0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 10V, Positive-QTOF | splash10-0002-0090000000-7f5d232a357b1b41cae8 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 20V, Positive-QTOF | splash10-0002-0090000000-7f5d232a357b1b41cae8 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 40V, Positive-QTOF | splash10-014j-0090000000-b88d0c4f35949ad6a7ab | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 10V, Negative-QTOF | splash10-0006-0090000000-1901824a83af80ea7083 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 20V, Negative-QTOF | splash10-0006-0090000000-1901824a83af80ea7083 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Estazolam 40V, Negative-QTOF | splash10-0006-0090000000-f5fb876690ac80360a52 | 2021-10-11 | Wishart Lab | View Spectrum |
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General References | - Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. [PubMed:3089825 ]
- Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5. [PubMed:11995921 ]
- Watanabe S, Ohta H, Sakurai Y, Takao K, Ueki S: [Electroencephalographic effects of 450191-S and its metabolites in rabbits with chronic electrode implants]. Nihon Yakurigaku Zasshi. 1986 Jul;88(1):19-32. [PubMed:3758874 ]
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