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 02:51:40 UTC |
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HMDB ID | HMDB0014566 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methylphenidate |
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Description | Methylphenidate is only found in individuals that have used or taken this drug. It is a central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy. Its mechanisms appear to be similar to those of dextroamphetamine. [PubChem]Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Alteration of serotonergic pathways via changes in dopamine transport may result. |
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Structure | COC(=O)C(C1CCCCN1)C1=CC=CC=C1 InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3 |
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Synonyms | Value | Source |
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alpha-Phenyl-2-piperidineacetic acid methyl ester | ChEBI | Methyl alpha-phenyl-alpha-(2-piperidyl)acetate | ChEBI | Methyl alpha-phenyl-alpha-2-piperidinylacetate | ChEBI | Methyl phenidylacetate | ChEBI | Methylphenidan | ChEBI | Daytrana | Kegg | a-Phenyl-2-piperidineacetate methyl ester | Generator | a-Phenyl-2-piperidineacetic acid methyl ester | Generator | alpha-Phenyl-2-piperidineacetate methyl ester | Generator | Α-phenyl-2-piperidineacetate methyl ester | Generator | Α-phenyl-2-piperidineacetic acid methyl ester | Generator | Methyl a-phenyl-a-(2-piperidyl)acetate | Generator | Methyl a-phenyl-a-(2-piperidyl)acetic acid | Generator | Methyl alpha-phenyl-alpha-(2-piperidyl)acetic acid | Generator | Methyl α-phenyl-α-(2-piperidyl)acetate | Generator | Methyl α-phenyl-α-(2-piperidyl)acetic acid | Generator | Methyl a-phenyl-a-2-piperidinylacetate | Generator | Methyl a-phenyl-a-2-piperidinylacetic acid | Generator | Methyl alpha-phenyl-alpha-2-piperidinylacetic acid | Generator | Methyl α-phenyl-α-2-piperidinylacetate | Generator | Methyl α-phenyl-α-2-piperidinylacetic acid | Generator | Methyl phenidylacetic acid | Generator | Methylphenidic acid | Generator | D-Methylphenidate HCL | HMDB | Methyl phenidyl acetate | HMDB | Methylphenidate HCL | HMDB | Methylphenidate hydrochloride | HMDB | Methylphenidylacetate hydrochloride | HMDB | Metilfenidat hydrochloride | HMDB | Phenidylate | HMDB | Methylin | HMDB | Novartis brand 1 OF methylphenidate hydrochloride | HMDB | Ritaline | HMDB | Centedrin | HMDB | Concerta | HMDB | Equasym | HMDB | Hydrochloride, methylphenidate | HMDB | Metadate | HMDB | Cephalon brand OF methylphenidate hydrochloride | HMDB | Ritalin | HMDB | Ritalin SR | HMDB | Tsentedrin | HMDB | Celltech brand OF methylphenidate hydrochloride | HMDB | Mallinckrodt brand OF methylphenidate hydrochloride | HMDB | Novartis brand 2 OF methylphenidate hydrochloride | HMDB | Ritalin-SR | HMDB | Methyl phenyl(piperidin-2-yl)acetic acid | HMDB | Methylphenidate | MeSH |
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Chemical Formula | C14H19NO2 |
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Average Molecular Weight | 233.3062 |
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Monoisotopic Molecular Weight | 233.141578857 |
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IUPAC Name | methyl 2-phenyl-2-(piperidin-2-yl)acetate |
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Traditional Name | methylphenidate |
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CAS Registry Number | 113-45-1 |
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SMILES | COC(=O)C(C1CCCCN1)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3 |
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InChI Key | DUGOZIWVEXMGBE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Amines |
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Direct Parent | Aralkylamines |
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Alternative Parents | |
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Substituents | - Aralkylamine
- Monocyclic benzene moiety
- Piperidine
- Benzenoid
- Methyl ester
- Amino acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Secondary amine
- Azacycle
- Organoheterocyclic compound
- Organopnictogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- 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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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 | 224 - 226 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.18 g/L | Not Available | LogP | 2.1 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
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[M+H]+ | CBM | 154.2 | 30932474 |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Methylphenidate,1TMS,isomer #1 | COC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C | 1813.3 | Semi standard non polar | 33892256 | Methylphenidate,1TMS,isomer #1 | COC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C | 1863.4 | Standard non polar | 33892256 | Methylphenidate,1TMS,isomer #1 | COC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C | 2544.4 | Standard polar | 33892256 | Methylphenidate,1TBDMS,isomer #1 | COC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C(C)(C)C | 2050.9 | Semi standard non polar | 33892256 | Methylphenidate,1TBDMS,isomer #1 | COC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C(C)(C)C | 2046.1 | Standard non polar | 33892256 | Methylphenidate,1TBDMS,isomer #1 | COC(=O)C(C1=CC=CC=C1)C1CCCCN1[Si](C)(C)C(C)(C)C | 2692.6 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Methylphenidate CI-B (Non-derivatized) | splash10-001i-0090000000-b461cd02e59ebf84d3f9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methylphenidate EI-B (Non-derivatized) | splash10-001i-9100000000-c75de12fbdae54dce658 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methylphenidate CI-B (Non-derivatized) | splash10-001i-0090000000-b461cd02e59ebf84d3f9 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methylphenidate EI-B (Non-derivatized) | splash10-001i-9100000000-c75de12fbdae54dce658 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methylphenidate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0089-9610000000-8e4c1241e36274356032 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methylphenidate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methylphenidate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methylphenidate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-001i-9100000000-1a9c5badbee827946da1 | 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 - Methylphenidate 10V, Positive-QTOF | splash10-001i-1190000000-8803b6fb1d54baf20a6f | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 20V, Positive-QTOF | splash10-001i-6390000000-63f6ddbd32540d6c0e4e | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 40V, Positive-QTOF | splash10-001i-9500000000-dab6b5667313005cbcd2 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 10V, Negative-QTOF | splash10-001i-0090000000-dbf1d73eb0c9410efbf6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 20V, Negative-QTOF | splash10-001i-2290000000-4a7ee5089439605a9759 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 40V, Negative-QTOF | splash10-00w9-9520000000-aa484f1df63a11905d5a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 10V, Positive-QTOF | splash10-001i-2190000000-aa6695fd8b35db2e4b41 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 20V, Positive-QTOF | splash10-001i-9440000000-3e2430ca32eb71f561e4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 40V, Positive-QTOF | splash10-001i-9300000000-2d49d7918e562aad8156 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 10V, Negative-QTOF | splash10-001i-0090000000-96a8c87419b47af6da2a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 20V, Negative-QTOF | splash10-00lr-4790000000-8bbed2d476f383bd9813 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methylphenidate 40V, Negative-QTOF | splash10-0006-9400000000-dabf09c5d3b6f3c788fe | 2021-09-25 | 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 DB00422 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00422 | | 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 | DB00422 |
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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 | 4015 |
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KEGG Compound ID | C07196 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Methylphenidate |
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METLIN ID | Not Available |
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PubChem Compound | 4158 |
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PDB ID | Not Available |
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ChEBI ID | 84276 |
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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 | - Fone KC, Nutt DJ: Stimulants: use and abuse in the treatment of attention deficit hyperactivity disorder. Curr Opin Pharmacol. 2005 Feb;5(1):87-93. [PubMed:15661631 ]
- Sharma RP, Javaid JI, Pandey GN, Easton M, Davis JM: Pharmacological effects of methylphenidate on plasma homovanillic acid and growth hormone. Psychiatry Res. 1990 Apr;32(1):9-17. [PubMed:2190251 ]
- Shults T, Kownacki AA, Woods WE, Valentine R, Dougherty J, Tobin T: Pharmacokinetics and behavioral effects of methylphenidate in Thoroughbred horses. Am J Vet Res. 1981 May;42(5):722-6. [PubMed:7258793 ]
- Keating GM, McClellan K, Jarvis B: Methylphenidate (OROS formulation). CNS Drugs. 2001;15(6):495-500; discussion 501-3. [PubMed:11524026 ]
- Markowitz JS, DeVane CL, Pestreich LK, Patrick KS, Muniz R: A comprehensive in vitro screening of d-, l-, and dl-threo-methylphenidate: an exploratory study. J Child Adolesc Psychopharmacol. 2006 Dec;16(6):687-98. [PubMed:17201613 ]
- (). FDA label . .
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