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Parent Compound(s)
14875Loperamide (hydrochloride)
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N-desmethyl Loperamide

Item No. 16126

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Synonyms
Synonyms
  • R 20905
Technical Information
Formal Name
4-(4-chlorophenyl)-4-hydroxy-N-methyl-α,α-diphenyl-1-piperidinebutanamide
CAS Number
66164-07-6
Molecular Formula
C28H31ClN2O2
Formula Weight
463.0
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 1 mg/ml
SMILES
O=C(NC)C(C1=CC=CC=C1)(C2=CC=CC=C2)CCN3CCC(C4=CC=C(Cl)C=C4)(O)CC3
InChi Code
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)
InChi Key
ZMOPTLXEYOVARP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Loperamide (Item No. 14875) is an opiate which potently and selectively activates μ opioid receptors (Ki = 0.16 nM) exclusively in the periphery.1,2 N-desmethyl Loperamide is a major metabolite of loperamide.3,4 Like loperamide, N-desmethyl loperamide is a substrate of the ATP-dependent efflux transporter, P-glycoprotein.4,5 As a result, both the parent compound and the metabolite display restricted passage through the blood-brain barrier.5,6 N-desmethyl Loperamide in biological samples can be analyzed by a variety of methods.3,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Breslin, H.J., Miskowski, T.A., Rafferty, B.M., et al. Rationale, design, and synthesis of novel phenyl imidazoles as opioid receptor agonists for gastrointestinal disorders. J. Med. Chem. 47(21), 5009-5020 (2004).

    2. Regnard, C., Twycross, R., Mihalyo, M., et al. Loperamide. J. Pain Symptom Manage. 42(2), 319-323 (2011).

    3. Sklerov, J., Levine, B., Moore, K.A., et al. Tissue distribution of loperamide and N-desmethylloperamide following a fatal overdose. J. Anal. Toxicol. 29(7), 750-754 (2005).

    4. Kalgutkar, A.S., and Nguyen, H.T. Identification of an N-methyl-4-phenylpyridinium-like metabolite of the antidiarrheal agent loperamide in human liver microsomes: Underlying reason(s) for the lack of neurotoxicity despite the bioactivation event. Drug Metab. Dispos. 32(9), 943-952 (2004).

    5. Kannan, P., Brimacombe, K.R., Zoghbi, S.S., et al. N-desmethyl-loperamide is selective for P-glycoprotein among three ATP-binding cassette transporters at the blood-brain barrier. Drug Metab. Dispos. 38(6), 917-922 (2010).

    6. Hsiao, P., and Unadkat, J.D. P-glycoprotein-based loperamide-cyclosporine drug interaction at the rat blood-brain barrier: Prediction from in vitro studies and extrapolation to humans. Mol. Pharm. 9(3), 629-633 (2012).

    7. Johansen, S.S., and Jensen, J.L. Liquid chromatography-tandem mass spectrometry determination of loperamide and its main metabolite desmethylloperamide in biological specimens and application to forensic cases. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 811(1), 31-36 (2004).