An active metabolite of loperamide
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N-didesmethyl Loperamide

Item No. 39559

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(4-chlorophenyl)-4-hydroxy-α,α-diphenyl-1-piperidinebutanamide
CAS Number
66164-06-5
Synonyms
  • R 21345
Molecular Formula
C27H29ClN2O2
Formula Weight
449.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: slightly solubleChloroform: sparingly soluble
SMILES
NC(C(C1=CC=CC=C1)(C2=CC=CC=C2)CCN3CCC(C4=CC=C(Cl)C=C4)(O)CC3)=O
InChi Code
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)
InChi Key
PXJHDOGGBLQFRX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    N-didesmethyl Loperamide is an active metabolite of the peripheral μ1-opioid receptor agonist loperamide.1 It inhibits electricity-induced contractions in isolated guinea pig myenteric plexus (IC50 = 370 nM).2 N-didesmethyl Loperamide sensitizes a chloroquine-resistant P. falciparum strain to chloroquine (EC50 = 482 nM) without inducing toxicity in A-10 vascular smooth muscle cells (IC50 = >10,000 nM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoshida, K., Nambu, K., Arakawa, S., et al. Metabolites of loperamide in rats. Biomed. Mass Spectrom. 6(6), 253-259 (1979).

    2. Wüster, M., and Herz, A. Opiate agonist action of antidiarrheal agents in vitro and in vivo - findings in support for selective action. Naunyn Schmiedebergs Arch. Pharmacol. 301(3), 187-194 (1978).

    3. Boudhar, A., Ng, X.W., Loh, C.Y., et al. Overcoming chloroquine resistance in malaria: Design, synthesis and structure-activity relationships of novel chemoreversal agents. Eur. J. Med. Chem. 119, 231-249 (2016).