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Metabolite(s)
16126N-desmethyl Loperamide
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Loperamide (hydrochloride)

Item No. 14875

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Synonyms
Synonyms
  • NSC 696356
  • PJ 185
  • R 18553
Technical Information
Formal Name
4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutanamide, monohydrochloride
CAS Number
34552-83-5
Molecular Formula
C29H33ClN2O2 • HCl
Formula Weight
513.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2.5 mg/mlDMSO: 2.5 mg/mlEthanol: 10 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
O=C(N(C)C)C(C1=CC=CC=C1)(C2=CC=CC=C2)CCN3CCC(C4=CC=C(Cl)C=C4)(O)CC3.Cl
InChi Code
InChI=1S/C29H33ClN2O2.ClH/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23;/h3-16,34H,17-22H2,1-2H3;1H
InChi Key
PGYPOBZJRVSMDS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Loperamide is an opiate which potently and selectively activates μ opioid receptors (Ki = 0.16 nM) exclusively in the periphery.1,2 It is a much weaker agonist of the δ opioid receptor (Ki = 50 nM).1 Through its actions in the gut wall, loperamide has antidiarrheal action by increasing transit time and by altering intestinal transport of water and electrolytes.2,3 It also blocks voltage-sensitive sodium channels (IC50 = 270 nM) and high voltage-activated calcium channels (IC50 = 900 nM), presumably through an inhibitory effect on calmodulin.4,5,2 Loperamide is comparable to morphine in blocking peripheral pain in rats.6

    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. Trinkley, K.E., and Nahata, M.C. Treatment of irritable bowel syndrome. J. Clin. Pharm. Ther. 36(3), 275-282 (2011).

    4. McNeal, E.T., Lewandowski, G.A., Daly, J.W., et al. [3H]Batrachotoxinin A 20α-benzoate binding to voltage-sensitive sodium channels: A rapid and quantitative assay for local anesthetic activity in a variety of drugs. J. Med. Chem. 28(3), 381-388 (1985).

    5. Church, J., Fletcher, E.J., Abdel-Hamid, K., et al. Loperamide blocks high-voltage-activated calcium channels and N-methyl-D-aspartate-evoked responses in rat and mouse cultured hippocampal pyramidal neurons. Mol. Pharmacol. 45, 747-757 (1994).

    6. Shannon, H.E., and Lutz, E.A. Comparison of the peripheral and central effects of the opioid agonists loperamide and morphine in the formalin test in rats. Neuropharmacology 42(2), 253-261 (2002).

    Product Citations

    Khan, S., Tyson, A.S., Ranjbar, M., et al. Structural snapshots capture nucleotide release at the μ-opioid receptor. Nature (2025).