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Record Information |
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Version | 4.0 |
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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 21:41:15 UTC |
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HMDB ID | HMDB0015245 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Papaverine |
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Description | Papaverine, also known as mesotina or cerespan, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Papaverine has also been demonstrated to be a selective phosphodiesterase inhibitor for the PDE10A subtype found mainly in the striatum of the brain. Papaverine is a drug. Papaverine is a very strong basic compound (based on its pKa). Papaverine is a bitter tasting compound. Outside of the human body, papaverine has been detected, but not quantified in, opium poppies. This could make papaverine a potential biomarker for the consumption of these foods. It is not a first line drug such as a few beta blockers, calcium channel blockers, tricyclic antidepressants, and some anticonvulsants such as divalproex, but rather when these first line drugs and secondary drugs such as SSRIs, angiotensin II receptor antagonists, etc. fail in the prophylaxis of migraines, have intolerable side effects or are contraindicated. It is used in the treatment of acute mesenteric ischemia. Frequent side effects of papaverine treatment include polymorphic ventricular tachycardia, constipation, interference with sulphobromophthalein retention test (used to determine hepatic function), increased transaminase levels, increased alkaline phosphatase levels, somnolence, and vertigo. It is also commonly used in cryopreservation of blood vessels along with the other glycosaminoglycans and protein suspensions. The hydrochloride salt is available for intramuscular, intravenous, rectal and oral administration. |
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Structure | |
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Synonyms | Value | Source |
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Mesotina | Kegg | Chlorhydrate de papaverine | HMDB | Papavarine chlorhydrate | HMDB | Papaverin | HMDB | Papaverine chlorohydrate | HMDB | Papaverine monohydrochloride | HMDB | Papaverinium chloride | HMDB | Cerespan | HMDB | Hydrochloride, papaverine | HMDB | Pavatym | HMDB | Pavabid | HMDB | Papaverine hydrochloride | HMDB |
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Chemical Formula | C20H21NO4 |
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Average Molecular Weight | 339.385 |
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Monoisotopic Molecular Weight | 339.147058165 |
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IUPAC Name | 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline |
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Traditional Name | papaverine |
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CAS Registry Number | 61-25-6 |
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SMILES | COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1 |
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InChI Identifier | InChI=1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3 |
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InChI Key | XQYZDYMELSJDRZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Isoquinolines and derivatives |
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Sub Class | Benzylisoquinolines |
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Direct Parent | Benzylisoquinolines |
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Alternative Parents | |
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Substituents | - Benzylisoquinoline
- O-dimethoxybenzene
- Dimethoxybenzene
- Phenoxy compound
- Anisole
- Phenol ether
- Methoxybenzene
- Alkyl aryl ether
- Monocyclic benzene moiety
- Pyridine
- Benzenoid
- Heteroaromatic compound
- Ether
- Azacycle
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- 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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.013 g/L | Not Available | LogP | 3 | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0079-4569000000-42d74df972bf1280fb29 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0079-4569000000-42d74df972bf1280fb29 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05fs-0279000000-6a8c8886127d693c8567 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0006-0009000000-376bdab66f9ada8143f2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0f6x-0049000000-fbf8945b1b40a8e629ff | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0779000000-37837168aff5cb2db6db | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0006-0019000000-175d5d7601656bade9be | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-00dl-0569000000-1f7e7c97dcea64bf274a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0009000000-5adf8eed4c99ef024ca8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0009000000-90f688022df6ca82e68d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-0092000000-d2012c62f8a18f28d8e0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-14a648b12b81f2d898df | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0019000000-3f207d6944b0d0c476ad | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0gbc-0090000000-218cfc775f1db8beaf69 | 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 DB01113 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01113 | | details |
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Abnormal Concentrations |
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| Not Available |
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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 | DB01113 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000447 |
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KNApSAcK ID | C00027467 |
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Chemspider ID | 4518 |
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KEGG Compound ID | C06533 |
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BioCyc ID | CPD-15742 |
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BiGG ID | Not Available |
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Wikipedia Link | Papaverine |
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METLIN ID | Not Available |
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PubChem Compound | 4680 |
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PDB ID | Not Available |
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ChEBI ID | 28241 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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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 | - Tang Y, Luan J, Zhang X: Accelerating tissue expansion by application of topical papaverine cream. Plast Reconstr Surg. 2004 Oct;114(5):1166-9. [PubMed:15457029 ]
- Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J: Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting. Eur J Cardiothorac Surg. 2004 Nov;26(5):956-9. [PubMed:15519189 ]
- Liu JK, Couldwell WT: Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. Neurocrit Care. 2005;2(2):124-32. [PubMed:16159054 ]
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