O-Desmethyltramadol (O-DT) or 3-[2-(1-Amino-1-methylethyl)-1-hydroxycyclohexyl]phenol is an opioid analgesic and the main active metabolite of tramadol. O-Desmethyltramadol is the most important metabolite of tramadol produced in the liver after tramadol is consumed. This metabolite is considerably more potent as a µ opioid agonist than the parent compound. The two enantiomers of O-desmethyltramadol show quite distinct pharmacological profiles; both (+) and (-)-O-desmethyltramadol are inactive as serotonin reuptake inhibitors, but (-)-O-desmethyltramadol retains activity as a noradrenaline reuptake inhibitor and so the mix of both the parent compound and metabolites produced contributes significantly to the complex pharmacological profile of tramadol. O-Desmethyltramadol is metabolized in the liver into the active metabolite N,O-didesmethyltramadol via CYP2D6. The inactive tramadol metabolite N-desmethyltramadol is also metabolized into the active metabolite N,O-didesmethyltramadol by the same enzyme.
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