N-Didesmethyl Loperamide
N-Didesmethyl Loperamide is a demethylated analog of loperamide, characterized by the absence of two methyl groups on the terminal piperidine nitrogen, resulting in a primary amine functionality. Structurally, it retains the phenylpiperidine core and α-methylbenzyl side chain of the parent compound, with a fully exposed nitrogen atom in the piperidine ring. This structural modification reduces lipophilicity and alters binding affinity at opioid receptors. The compound arises as a synthetic byproduct during loperamide production via N-demethylation pathways. It serves as a critical HPLC reference standard for quantifying process-related impurities in loperamide APIs.
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Molecular Formula
C27H29ClN2O2
Molecular Weight
449.0000
CAS Number
66164-06-5
PubChem CID
25129795 ↗
IUPAC Name
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanamide
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📝 Synonyms
N-Didesmethyl Loperamide
66164-06-5
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanamide
4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-2,2-diphenylbutanamide
Loperamid-M didesmethyl
Loperamide Impurity 20
orb1979966
SCHEMBL2310814
CHEMBL4449669
DTXSID10648790
🔬 Chemical Identifiers
C1CN(CCC1(C2=CC=C(C=C2)Cl)O)CCC(C3=CC=CC=C3)(C4=CC=CC=C4)C(=O)N
InChI=1S/C27H29ClN2O2/c28-24-13-11-21(12-14-24)26(32)15-18-30(19-16-26)20-17-27(25(29)31,22-7-3-1-4-8-22)23-9-5-2-6-10-23/h1-14,32H,15-20H2,(H2,29,31)
PXJHDOGGBLQFRX-UHFFFAOYSA-N
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