Venlafaxine EP Impurity D, also designated Venlafaxine Related Compound A and rac N-Desmethyl Venlafaxine (Free Base), CAS 149289-30-5, is the racemic secondary amine metabolite and process-related impurity of venlafaxine. With molecular formula C16H25NO2 and molecular weight 263.38 g/mol, it lacks the O-methyl tertiary amine present in the parent drug and therefore exhibits distinct chromatographic polarity and ionization behavior. Formation may arise from N-demethylation during synthesis or oxidative degradation. Its assay typically requires LC-MS/MS, LC-HRMS, or chiral LC when enantiomeric separation is needed. Although not a nitrosamine, its impurity profile is relevant to specification setting and degradation pathway evaluation.
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