| Record Information |
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| Version | 4.0 |
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| Status | Detected 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 21:41:11 UTC |
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| HMDB ID | HMDB0015217 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Pilocarpine |
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| Description | Pilocarpine, also known as ocusert pilo-20 or adsorbocarpine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Pilocarpine is a drug which is used for the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with sjögrens syndrome. Pilocarpine is a very strong basic compound (based on its pKa). Pilocarpine is a potentially toxic compound. Pilocarpine is only found in individuals that have used or taken this drug. Bradycardia and tachycardia have both been reported with use of pilocarpine. It increase secretion by the exocrine glands, and produces contraction of the iris sphincter muscle and ciliary muscle (when given topically to the eyes) by mainly stimulating muscarinic receptors. It is a slowly hydrolyzed muscarinic agonist with no nicotinic effects. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (3S,4R)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone | ChEBI | | (3S-cis)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone | ChEBI | | Ocusert pilo-20 | Kegg | | Adsorbocarpine | HMDB | | beta-Pilocarpine hydrochloride | HMDB | | Pilocarpin | HMDB | | Pilocarpine chloride | HMDB | | Pilocarpine HCL | HMDB | | Pilocarpine hydrochloride | HMDB | | Pilocarpine monohydrochloride | HMDB | | Pilocarpine muriate | HMDB | | Pilokarpin | HMDB | | Pilokarpin monohydrochloride | HMDB | | Spersacarpine | HMDB | | Spersacarpine hydrochloride | HMDB | | Hydrochloride, pilocarpine | HMDB | | Isopilocarpine | HMDB | | Nitrate, pilocarpine | HMDB | | Pilocarpine mononitrate, (3S-cis)-isomer | HMDB | | Pilocarpine, monohydrochloride, (3S-cis)-isomer | HMDB | | Salagen | HMDB | | Ocusert | HMDB | | Isoptocarpine | HMDB | | Pilocarpine nitrate | HMDB | | Pilocarpine | ChEBI |
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| Chemical Formula | C11H16N2O2 |
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| Average Molecular Weight | 208.2569 |
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| Monoisotopic Molecular Weight | 208.121177766 |
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| IUPAC Name | (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one |
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| Traditional Name | pilocarpine |
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| CAS Registry Number | 54-71-7 |
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| SMILES | CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O |
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| InChI Identifier | InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1 |
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| InChI Key | QCHFTSOMWOSFHM-WPRPVWTQSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Not Available |
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| Sub Class | Not Available |
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| Direct Parent | Alkaloids and derivatives |
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| Alternative Parents | |
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| Substituents | - Alkaloid or derivatives
- Gamma butyrolactone
- N-substituted imidazole
- Azole
- Imidazole
- Heteroaromatic compound
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: 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 | 34 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 2.07 g/L | Not Available | | LogP | 1.1 | Not Available |
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| Predicted Properties | |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9500000000-dadfea39cdf9ef51bb38 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0690000000-786fb6f080bd545dbc39 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0cka-1920000000-56d387d24bcc6e2e3637 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9300000000-e57c52a1b125f83b1903 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0190000000-fc43dc1afe8440f3e607 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bt9-1930000000-b7fcb5510042754cd666 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4j-9800000000-0f44a4b4787f9e119567 | Spectrum |
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