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 15:16:49 UTC |
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Update Date | 2022-03-07 02:51:36 UTC |
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HMDB ID | HMDB0014390 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Benzatropine |
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Description | Benzotropine is a centrally-acting, antimuscarinic agent used as an adjunct in the treatment of Parkinson's disease. It may also be used to treat extrapyramidal reactions, such as dystonia and Parkinsonism, caused by antipsychotics (e.g. phenothiazines). Symptoms of Parkinson's disease and extrapyramidal reactions arise from decreases in dopaminergic activity which creates an imbalance between dopaminergic and cholinergic activity. Anticholinergic therapy is thought to aid in restoring this balance leading to relief of symptoms. In addition to its anticholinergic effects, benztropine also inhibits the reuptake of dopamine at nerve terminals via the dopamine transporter. Benzotropine also produces antagonistic effects at the histamine H1 receptor. |
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Structure | [H][C@]12CC[C@]([H])(C[C@@]([H])(C1)OC(C1=CC=CC=C1)C1=CC=CC=C1)N2C InChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19+,20+ |
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Synonyms | Value | Source |
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3alpha-(Diphenylmethoxy)-1alphah,5alphah-tropane | ChEBI | 3alpha-(Diphenylmethoxy)tropane | ChEBI | 3alpha-Benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane | ChEBI | 3ENdo-benzhydryloxytropane | ChEBI | Benzatropina | ChEBI | Benzatropinum | ChEBI | Benzhydryl 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ether | ChEBI | Benztropine | ChEBI | Tropine benzohydryl ether | ChEBI | 3a-(Diphenylmethoxy)-1alphah,5alphah-tropane | Generator | 3Α-(diphenylmethoxy)-1alphah,5alphah-tropane | Generator | 3a-(Diphenylmethoxy)tropane | Generator | 3Α-(diphenylmethoxy)tropane | Generator | 3a-Benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane | Generator | 3Α-benzhydryloxy-8-methyl-8-azabicyclo[3.2.1]octane | Generator | Benzatropine mesilate | HMDB | Benztropinum | HMDB |
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Chemical Formula | C21H25NO |
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Average Molecular Weight | 307.4293 |
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Monoisotopic Molecular Weight | 307.193614427 |
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IUPAC Name | (1R,3R,5S)-3-(diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane |
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Traditional Name | benzatropina |
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CAS Registry Number | 86-13-5 |
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SMILES | [H][C@]12CC[C@]([H])(C[C@@]([H])(C1)OC(C1=CC=CC=C1)C1=CC=CC=C1)N2C |
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InChI Identifier | InChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19+,20+ |
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InChI Key | GIJXKZJWITVLHI-PMOLBWCYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Diphenylmethanes |
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Direct Parent | Diphenylmethanes |
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Alternative Parents | |
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Substituents | - Diphenylmethane
- Benzylether
- Tropane alkaloid
- Piperidine
- N-alkylpyrrolidine
- Pyrrolidine
- Tertiary amine
- Tertiary aliphatic amine
- Dialkyl ether
- Ether
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Amine
- 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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0012 g/L | Not Available | LogP | 4.3 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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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 - Benzatropine GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-7910000000-522d5f59ab66fd491865 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzatropine 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 - Benzatropine 10V, Positive-QTOF | splash10-0a4i-0309000000-128b2c78aa7b0dd7d9e5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 20V, Positive-QTOF | splash10-0avi-1914000000-96ca5c9a7aea2b463b4d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 40V, Positive-QTOF | splash10-00rt-9600000000-6dda6384a6abcbd56c1f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 10V, Negative-QTOF | splash10-0a4i-0209000000-6ac5128c1f553f581afd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 20V, Negative-QTOF | splash10-0a4i-1619000000-5e54998dd75131048af5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 40V, Negative-QTOF | splash10-004i-6900000000-e13c6d55b6124ce3b733 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 10V, Negative-QTOF | splash10-0a4i-0009000000-362958de4b63235619b6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 20V, Negative-QTOF | splash10-0a4i-0809000000-7234c053d550e60a1abd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 40V, Negative-QTOF | splash10-0a59-0910000000-e6dc1d8e76e7c2a1274e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 10V, Positive-QTOF | splash10-0a4i-0009000000-f64e7cf22237a4e2aed0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 20V, Positive-QTOF | splash10-0a4i-0309000000-9c52d4b915a455b8641a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzatropine 40V, Positive-QTOF | splash10-014i-1900000000-ea82f96932aa4d054988 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00245 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00245 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00245 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 16736541 |
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KEGG Compound ID | C06846 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Benzatropine |
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METLIN ID | Not Available |
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PubChem Compound | Not Available |
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PDB ID | Not Available |
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ChEBI ID | 3048 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - van Harten PN, Hoek HW, Matroos GE, Koeter M, Kahn RS: Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curacao Extrapyramidal Syndromes Study III. Am J Psychiatry. 1998 Apr;155(4):565-7. [PubMed:9546009 ]
- Wszola BA, Newell KM, Sprague RL: Risk factors for tardive dyskinesia in a large population of youths and adults. Exp Clin Psychopharmacol. 2001 Aug;9(3):285-96. [PubMed:11534539 ]
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