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Tramadol

Synthetic opioid pain medicationPharmaceutical compoundClinical dataPronunciation/ˈtræməˌdɒl/ Trade namesTramal, othersAHFS/Drugs.comMonographMedlinePlusa695011License dataUS DailyMed: TramadolPregnancycategoryAU: CRoutes ofadministrationBy mouth, intravenous, intramuscular, rectalDrug classOpioid;Serotonin–norepinephrine reuptake inhibitorATC codeN02AX02 (WHO) N02AJ13 (WHO)Legal statusLegal statusAU: S4 (Prescription only)BR: Class A2 (Narcotic drugs)CA: Schedule INZ: Class C2 UK: POM (Prescription only) / Class CUS: Schedule IVUN: UnscheduledEU: Rx-onlySE: Förteckning IIIIn general: Prescription onlyPharmacokinetic dataBioavailability68% (by mouth), 77% (rectal), 100% (IM)Protein binding20%MetabolismLiver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4MetabolitesO-desmethyltramadolN-desmethyltramadolOnset of action< 1 hour (by mouth)Elimination half-life6.3 ± 1.4 hDuration of action6 hoursExcretionUrine (95%)IdentifiersIUPAC name2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-olCAS Number27203-92-5PubChemCID33741DrugBankDB00193ChemSpider31105UNII39J1LGJ30JKEGGD08623as HCl: D01355ChEBICHEBI:9648ChEMBLChEMBL1066CompTox Dashboard(EPA)DTXSID401167150 DTXSID90858931, DTXSID401167150ECHA InfoCard100.043.912Chemical and physical dataFormulaC16H25NO2Molar mass263.381 g·mol3D model (JSmol)Interactive imageMelting point180 to 181 °C (356 to 358 °F)SMILESCN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)OInChIInChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3/t14-,16+/m1/s1Key:TVYLLZQTGLZFBW-ZBFHGGJFSA-N (verify)Tramadol, sold under the brand name Tramal among others, is an opioidpain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderate to severe pain.

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