N,O-Didesmethyltramadol

Metabolite of tramadol

N,O-Didesmethyltramadol
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CAS Number	36282-47-0
PubChem	3083540
DrugBank
ChemSpider	2340865
KEGG

N,O-Didesmethyltramadol is a metabolite of the opioid analgesic tramadol. It is formed in the body through the metabolic pathway involving the cytochrome P450 enzyme system. This compound is one of the active metabolites that contribute to the pharmacological effects of tramadol.

Chemical Structure and Properties

Chemical structure of N,O-Didesmethyltramadol

N,O-Didesmethyltramadol is characterized by the removal of two methyl groups from the parent compound, tramadol. The chemical structure consists of a cyclohexanol ring with a methoxyphenyl group and a dimethylamino group. The molecular formula is C₁₃H₁₉NO₂, and it has a molecular weight of 221.3 g/mol.

Pharmacology

N,O-Didesmethyltramadol retains some of the analgesic properties of tramadol, although it is generally less potent. The compound acts on the central nervous system by binding to opioid receptors, primarily the mu-opioid receptor. It also inhibits the reuptake of serotonin and norepinephrine, contributing to its analgesic effects.

Metabolism

Tramadol is metabolized in the liver by the cytochrome P450 enzyme system, particularly by CYP2D6 and CYP3A4. N,O-Didesmethyltramadol is produced through the demethylation of tramadol, a process that involves the removal of methyl groups. This metabolite is further processed and eventually excreted in the urine.

Clinical Significance

The presence of N,O-Didesmethyltramadol in the body can influence the overall efficacy and side effect profile of tramadol. Variability in the metabolism of tramadol, due to genetic differences in cytochrome P450 enzymes, can lead to differences in the levels of this metabolite among individuals. This can affect both the therapeutic and adverse effects experienced by patients.

Related Compounds

• Tramadol
• O-Desmethyltramadol
• N-Desmethyltramadol

Related Pages

• Opioid analgesic
• Cytochrome P450
• Metabolite