Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:36:18 UTC |
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Update Date | 2023-02-21 17:19:33 UTC |
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HMDB ID | HMDB0030353 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Arecoline |
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Description | Arecoline is found in nuts. Arecoline is isolated from betel nuts Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). It is an oily liquid that is soluble in water, alcohols, and ether. Owing to its muscarinic and nicotinic agonist properties, arecoline has shown improvement in the learning ability of healthy volunteers. Since one of the hallmarks of Alzheimer's disease is a cognitive decline, arecoline was suggested as a treatment to slow down this process and arecoline administered via i.v. route did indeed show modest verbal and spatial memory improvement in Alzheimer's patients, though due to arecoline's possible carcinogenic properties, it is not the first drug of choice for this degenerative disease |
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Structure | InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3 |
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Synonyms | Value | Source |
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Arecaidine methyl ester | ChEBI | Arecaline | ChEBI | Arecholine | ChEBI | Arekolin | ChEBI | Methylarecaiden | ChEBI | Methylarecaidin | ChEBI | 1,2,5,6-Tetrahydro-1-methylnicotinic acid, methyl ester | HMDB | Arecholin | HMDB | Arecolin | HMDB | Arecoline base | HMDB | Arecoline hydrobromide | HMDB | Methyl 1,2,5, 6-tetrahydro-1-methylnicotinate | HMDB | Methyl 1,2,5,6-tetrahydro-1-methylnicotinate | HMDB | Methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate | HMDB | Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate | HMDB | Methyl 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylate | HMDB | Methyl N-methyl-1,2,5, 6-tetrahydronicotinate | HMDB | Methyl N-methyl-1,2,5,6-tetrahydronicotinate | HMDB | Methyl N-methyltetrahydronicotinate | HMDB | N-Methyl-beta -carboxylic acid methyl ester | HMDB | N-Methyltetrahydronicotinic acid, methyl ester | HMDB | Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester | HMDB |
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Chemical Formula | C8H13NO2 |
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Average Molecular Weight | 155.1943 |
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Monoisotopic Molecular Weight | 155.094628665 |
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IUPAC Name | methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate |
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Traditional Name | arecoline |
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CAS Registry Number | 63-75-2 |
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SMILES | COC(=O)C1=CCCN(C)C1 |
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InChI Identifier | InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3 |
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InChI Key | HJJPJSXJAXAIPN-UHFFFAOYSA-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
- Hydropyridine
- Methyl ester
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Amino acid or derivatives
- Carboxylic acid ester
- Tertiary amine
- Tertiary aliphatic amine
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Azacycle
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Amine
- Organic oxide
- Hydrocarbon derivative
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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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 | Not Available |
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Experimental Molecular Properties | |
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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 - Arecoline GC-MS (Non-derivatized) - 70eV, Positive | splash10-006w-9400000000-98b26a9d2867d710059e | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Arecoline GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0006-9400000000-c2ac70d939302e3f979b | 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 - Arecoline 10V, Positive-QTOF | splash10-0a4i-0900000000-13bcb3825f7244e9bfd3 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 20V, Positive-QTOF | splash10-05fr-5900000000-4c54ca467a6647c61870 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 40V, Positive-QTOF | splash10-00rw-9000000000-ff7785df405dc6c7b136 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 10V, Negative-QTOF | splash10-0udi-0900000000-1de11420c61028c65308 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 20V, Negative-QTOF | splash10-0udi-1900000000-ff4ff3298d65bc8e1a2b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 40V, Negative-QTOF | splash10-05fu-9300000000-f368ae9f151a5d63114c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 10V, Negative-QTOF | splash10-0udi-2900000000-938088a337b250c4c45d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 20V, Negative-QTOF | splash10-0fdk-7900000000-eacff4cd88f94b61cec0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 40V, Negative-QTOF | splash10-0a5c-9000000000-39cbbf9119989e64dd6e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 10V, Positive-QTOF | splash10-0a4i-2900000000-9d51360c21b50a4980fc | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 20V, Positive-QTOF | splash10-05fs-8900000000-84101b2b84e59517def6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Arecoline 40V, Positive-QTOF | splash10-0007-9100000000-330ea72f81622bbe2ec1 | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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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 | DB04365 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB002198 |
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KNApSAcK ID | C00002020 |
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Chemspider ID | 13872064 |
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KEGG Compound ID | C10129 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Arecoline |
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METLIN ID | Not Available |
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PubChem Compound | 2230 |
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PDB ID | Not Available |
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ChEBI ID | 2814 |
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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 | rw1389511 |
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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 | - Shih YT, Chen PS, Wu CH, Tseng YT, Wu YC, Lo YC: Arecoline, a major alkaloid of the areca nut, causes neurotoxicity through enhancement of oxidative stress and suppression of the antioxidant protective system. Free Radic Biol Med. 2010 Nov 30;49(10):1471-9. doi: 10.1016/j.freeradbiomed.2010.07.017. Epub 2010 Aug 4. [PubMed:20691257 ]
- Yang YR, Chang KC, Chen CL, Chiu TH: Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor. Chin J Physiol. 2000 Mar 31;43(1):23-8. [PubMed:10857465 ]
- Wang SW, Hwang GS, Chen TJ, Wang PS: Effects of arecoline on testosterone release in rats. Am J Physiol Endocrinol Metab. 2008 Aug;295(2):E497-504. doi: 10.1152/ajpendo.00045.2008. Epub 2008 Jun 17. [PubMed:18559981 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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