| Revision as of 11:05, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 464352342 of page Methylphenidate for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 11:56, 18 September 2023 edit KoIobok (talk | contribs)Extended confirmed users1,350 edits Added Category:Beta-Amino acids |
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{{short description|Major metabolite of the psychostimulant drug methylphenidate}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{drugbox |
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{{drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 464194286 |
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| verifiedrevid = 464371569 |
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| IUPAC_name = methyl phenyl(piperidin-2-yl)acetate |
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| IUPAC_name = Phenyl(piperidin-2-yl)acetic acid <!-- the locant ‘2’ for acetic acid is not cited --> |
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| image = Methylphenidate-2D-skeletal.svg |
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| image = Ritalinic acid-2D-skeletal.svg |
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| width = 160 |
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<!--Clinical data-->| legal_US = Unscheduled and Uncontrolled |
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| image2 = Methylphenidate-enantiomers-3D-balls.png |
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<!--Identifiers--> |
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| width2 = 240 |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 19395-41-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = GT4165RS9H |
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| PubChem = 86863 |
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| ATC_prefix = None |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 78360 |
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<!--Chemical data-->| C = 13 |
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| H = 17 |
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| N = 1 |
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| O = 2 |
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| smiles = C1CCNC(C1)C(C2=CC=CC=C2)C(=O)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = InChI=1S/C13H17NO2/c15-13(16)12(10-6-2-1-3-7-10)11-8-4-5-9-14-11/h1-3,6-7,11-12,14H,4-5,8-9H2,(H,15,16) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = INGSNVSERUZOAK-UHFFFAOYSA-N |
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}} |
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'''Ritalinic acid''' is a ] and an inactive major ] of the ] ], ] and ].<ref name="faraj1974">{{cite journal | vauthors = Faraj BA, Israili ZH, Perel JM, Jenkins ML, Holtzman SG, Cucinell SA, Dayton PG | title = Metabolism and disposition of methylphenidate-14C: studies in man and animals | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 191 | issue = 3 | pages = 535–47 | date = December 1974 | pmid = 4473537 }}</ref><ref>{{cite journal | vauthors = Negreira N, Erratico C, van Nuijs AL, Covaci A | title = Identification of in vitro metabolites of ethylphenidate by liquid chromatography coupled to quadrupole time-of-flight mass spectrometry | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 117 | issue = 5 | pages = 474–84 | date = January 2016 | pmid = 26454340 | doi = 10.1016/j.jpba.2015.09.029 | hdl-access = free | hdl = 10067/1301870151162165141 }}</ref> When administered orally, methylphenidate is extensively metabolized in the liver by hydrolysis of the ] yielding ritalinic acid.<ref name="faraj1974" /> The hydrolysis was found to be catalyzed by ] (CES1).<ref name="sun2004">{{cite journal | vauthors = Sun Z, Murry DJ, Sanghani SP, Davis WI, Kedishvili NY, Zou Q, Hurley TD, Bosron WF | s2cid = 24233422 | display-authors = 6 | title = Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 310 | issue = 2 | pages = 469–76 | date = August 2004 | pmid = 15082749 | doi = 10.1124/jpet.104.067116 }}</ref> |
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<!--Clinical data--> |
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| tradename = Concerta, Methylin, Ritalin |
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| Drugs.com = {{drugs.com|monograph|methylphenidate-hydrochloride}} |
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| MedlinePlus = a682188 |
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| licence_US = Methylphenidate |
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| pregnancy_category = C |
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| legal_AU = Schedule 8 |
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| legal_CA = Schedule III |
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| legal_UK = POM |
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| legal_US = Schedule II |
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| routes_of_administration = Oral, Transdermal |
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Etymologically, ritalinic acid shares its roots with ''Ritalin'', a common brand name for methylphenidate. |
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<!--Pharmacokinetic data--> |
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| bioavailability = 11–52% |
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| protein_bound = 30% |
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| metabolism = ] (80%) |
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| elimination_half-life = 2–4 hours |
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| excretion = ] |
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==Uses== |
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<!--Identifiers--> |
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Ritalinic acid is used as an intermediate in the synthesis of methylphenidate and its analogues, such as ] and ]. |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 113-45-1 |
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| ATC_prefix = N06 |
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| ATC_suffix = BA04 |
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| PubChem = 4158 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00422 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4015 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 207ZZ9QZ49 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D04999 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 6887 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 796 |
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== References == |
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<!--Chemical data--> |
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{{reflist}} |
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| C=14 | H=19 | N=1 | O=2 |
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| molecular_weight = 233.31 g/mol |
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== External links == |
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| smiles = O=C(OC)C(c1ccccc1)C2NCCCC2 |
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* on ] |
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| InChI = 1/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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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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] |
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| StdInChI = 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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] |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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] |
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| StdInChIKey = DUGOZIWVEXMGBE-UHFFFAOYSA-N |
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] |
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| melting_point = 214 |
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}} |
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