Desmethyl Loperamide
Desmethyl Loperamide is an N-demethylated derivative of loperamide, characterized by a 4-phenylpiperidine core linked to a phenoxypropanolamine side chain. The absence of the methyl substituent at the piperidine nitrogen distinguishes it from the parent compound, altering its lipophilicity and metabolic stability. This impurity arises during synthetic processes via oxidative N-demethylation or as a primary metabolite in biotransformation pathways. Structurally, it retains the ether and secondary amine functionalities critical for opioid receptor interaction but exhibits reduced μ-opioid agonist activity. It serves as a reference standard for HPLC-based quantification of process-related impurities in loperamide API batches.
On Request📝 Synonyms
🔬 Chemical Identifiers
CNC(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4
InChI=1S/C28H31ClN2O2/c1-30-26(32)28(23-8-4-2-5-9-23,24-10-6-3-7-11-24)18-21-31-19-16-27(33,17-20-31)22-12-14-25(29)15-13-22/h2-15,33H,16-21H2,1H3,(H,30,32)
ZMOPTLXEYOVARP-UHFFFAOYSA-N
