Loperamide HCl | CAS#53179-11-6 | Opiate Agonist

MedKoo Cat#: 318160 | Name: Loperamide HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Loperamide is an opiate agonist with selectivity for the MOR (μ-opiod receptor). This specificity for μ-opioid receptors and limited penetrability into the brain prevent Loperamide from demonstrating central systemic effects generally associated with opiates. Loperamide is shown to have an effect on the Ca2+ flux through high-voltage-activated calcium channels in response to high levels of extracellular K+, and at higher concentrations Loperamide is also a calcium channel protein inhibitor via the N-methyl-D-aspartate (NMDA) receptor-operated ion channel.

Chemical Structure

Loperamide HCl

CAS#34552-83-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 318160

Name: Loperamide HCl

CAS#: 34552-83-5 (HCl)

Chemical Formula: C29H34Cl2N2O2

Exact Mass: 0.0000

Molecular Weight: 513.50

Elemental Analysis: C, 67.83; H, 6.67; Cl, 13.81; N, 5.46; O, 6.23

Price and Availability

Size	Price	Availability
2g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks
10g	USD 750.00	2 Weeks
25g	USD 1,350.00	2 Weeks

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Related CAS #

34552-83-5 (HCl) 53179-11-6 (free)

Synonym

Loperamide Hydrochloride; Loperamide HCl; Imodium; Dissenten; Fortasec;Loperamide Monohydrochloride; Monohydrochloride, Loperamide; R 18553; R-18553; R18553;

IUPAC/Chemical Name

4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide;hydrochloride

InChi Key

PGYPOBZJRVSMDS-UHFFFAOYSA-N

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

SMILES Code

CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4.Cl

Appearance

White to light yellow solid powder.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Loperamide (hydrochloride) (R-18553 (hydrochloride)) is an opioid receptor agonist.

In vitro activity:

The effect of loperamide on tachykinin NK(2)- and NK(3)-receptor-mediated 5-HT outflow from guinea pig colonic mucosa was investigated in vitro. Loperamide concentration-dependently suppressed the senktide-evoked 5-HT outflow, but failed to affect the betaAla-NKA-evoked 5-HT outflow. Reference: J Pharmacol Sci. 2005 Jun;98(2):175-80. https://pubmed.ncbi.nlm.nih.gov/15942125/

In vivo activity:

Peripheral opioids act as analgesics in bone cancer pain in mice. The aim of this report was to characterize the analgesic responses obtained by activating peripheral opioid receptors in bone cancer pain. Loperamide, an opioid agonist unable to cross the blood-brain barrier, inhibits both thermal and mechanical hyperalgesia when s.c. injected, locally over the tibial tumoral mass (7.5-75 microg) or distantly, under the fur of the neck (4 mg/kg). Reference: Pharmacol Biochem Behav. 2005 May;81(1):114-21. https://pubmed.ncbi.nlm.nih.gov/15894068/

	Solvent	mg/mL	mM
Solubility
	DMF	2.5	4.87
	DMSO	21.7	42.24
	Ethanol	8.1	15.75
	Ethanol:PBS (pH 7.2) (1:1)	0.5	0.97
	Water	1.0	1.95

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 513.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kojima S, Ikeda M, Kamikawa Y. Loperamide inhibits tachykinin NK3-receptor-triggered serotonin release without affecting NK2-receptor-triggered serotonin release from guinea pig colonic mucosa. J Pharmacol Sci. 2005 Jun;98(2):175-80. doi: 10.1254/jphs.fpj05011x. Epub 2005 Jun 8. PMID: 15942125. 2. Church J, Fletcher EJ, Abdel-Hamid K, MacDonald JF. Loperamide blocks high-voltage-activated calcium channels and N-methyl-D-aspartate-evoked responses in rat and mouse cultured hippocampal pyramidal neurons. Mol Pharmacol. 1994 Apr;45(4):747-57. PMID: 8183255. 3. Menéndez L, Lastra A, Meana A, Hidalgo A, Baamonde A. Analgesic effects of loperamide in bone cancer pain in mice. Pharmacol Biochem Behav. 2005 May;81(1):114-21. doi: 10.1016/j.pbb.2005.02.007. Epub 2005 Apr 25. PMID: 15894068. 4. DeHaven-Hudkins DL, Burgos LC, Cassel JA, Daubert JD, DeHaven RN, Mansson E, Nagasaka H, Yu G, Yaksh T. Loperamide (ADL 2-1294), an opioid antihyperalgesic agent with peripheral selectivity. J Pharmacol Exp Ther. 1999 Apr;289(1):494-502. PMID: 10087042.

In vitro protocol:

In vivo protocol:

1. Menéndez L, Lastra A, Meana A, Hidalgo A, Baamonde A. Analgesic effects of loperamide in bone cancer pain in mice. Pharmacol Biochem Behav. 2005 May;81(1):114-21. doi: 10.1016/j.pbb.2005.02.007. Epub 2005 Apr 25. PMID: 15894068. 2. DeHaven-Hudkins DL, Burgos LC, Cassel JA, Daubert JD, DeHaven RN, Mansson E, Nagasaka H, Yu G, Yaksh T. Loperamide (ADL 2-1294), an opioid antihyperalgesic agent with peripheral selectivity. J Pharmacol Exp Ther. 1999 Apr;289(1):494-502. PMID: 10087042.

1: Kim JE, Song HJ, Choi YJ, Jin YJ, Roh YJ, Seol A, Park SH, Park JM, Kang HG, Hwang DY. Improvement of the intestinal epithelial barrier during laxative effects of phlorotannin in loperamide-induced constipation of SD rats. Lab Anim Res. 2023 Jan 3;39(1):1. doi: 10.1186/s42826-022-00152-1. PMID: 36597137; PMCID: PMC9808941. 2: Wang L, Xie S, Jiang X, Xu C, Wang Y, Feng J, Yang B. Therapeutic effects of Bombax ceiba flower aqueous extracts against loperamide-induced constipation in mice. Pharm Biol. 2023 Dec;61(1):125-134. doi: 10.1080/13880209.2022.2157841. PMID: 36582187; PMCID: PMC9809371. 3: Lammoglia BC, Hasselmann G, Pires-Oliveira M, Duarte Nicolau LA, Rolim Medeiros JV, Sabia Tallo F, Omar Taha M, Yamaguti Lima R, Caricati-Neto A, Menezes-Rodrigues FS. Risk of Cardiac Lesion with Chronic and Acute Use of Loperamide-An Integrative Review. J Cardiovasc Dev Dis. 2022 Dec 2;9(12):431. doi: 10.3390/jcdd9120431. PMID: 36547428; PMCID: PMC9782787. 4: Li R, Li M, Li B, Chen WH, Liu Z. Cannabis sativa L. alleviates loperamide-induced constipation by modulating the composition of gut microbiota in mice. Front Pharmacol. 2022 Dec 2;13:1033069. doi: 10.3389/fphar.2022.1033069. PMID: 36532754; PMCID: PMC9755208. 5: Cao J, Wang K, Li N, Zhang L, Qin L, He Y, Wang J, Qu C, Miao J. Soluble dietary fiber and cellulose from Saccharina japonica by-product ameliorate Loperamide-induced constipation via modulating enteric neurotransmitters, short- chain fatty acids and gut microbiota. Int J Biol Macromol. 2023 Jan 31;226:1319-1331. doi: 10.1016/j.ijbiomac.2022.11.243. Epub 2022 Nov 26. PMID: 36511265. 6: Zhao Y, Zhang C, Yu L, Tian F, Zhao J, Zhang H, Chen W, Zhai Q. Strain- specific effect of Limosilactobacillus fermentum with distinct genetic lineages on loperamide-induced constipation in mice: attributing effects to certain genes. Food Funct. 2022 Dec 13;13(24):12742-12754. doi: 10.1039/d2fo02675a. PMID: 36411976. 7: Park SH, Lee MR, Yang SY, Lee JY, Lee HH, Seong YJ, Kim B, Kim HJ, Jin H, Johnston TV, Ku S, Park MS. In vivo functional effects of Weissella confusa VP30 exopolysaccharides on loperamide-induced constipation in rats. Food Sci Biotechnol. 2022 Sep 6;31(13):1703-1715. doi: 10.1007/s10068-022-01159-z. PMID: 36312995; PMCID: PMC9596668. 8: Gao X, Hu Y, Tao Y, Liu S, Chen H, Li J, Zhao Y, Sheng J, Tian Y, Fan Y. Cymbopogon citratus (DC.) Stapf aqueous extract ameliorates loperamide- induced constipation in mice by promoting gastrointestinal motility and regulating the gut microbiota. Front Microbiol. 2022 Oct 4;13:1017804. doi: 10.3389/fmicb.2022.1017804. PMID: 36267178; PMCID: PMC9578511. 9: Yang C, Bai X, Hu T, Xue X, Su X, Zhang X, Wu T, Zhang M, Shen X, Dong X. Integrated metagenomics and targeted-metabolomics analysis of the effects of phenylalanine on loperamide-induced constipation in rats. Front Microbiol. 2022 Sep 30;13:1018008. doi: 10.3389/fmicb.2022.1018008. PMID: 36246281; PMCID: PMC9561758. 10: Qiu B, Zhu L, Zhang S, Han S, Fei Y, Ba F, Berglund B, Li L, Yao M. Prevention of Loperamide-Induced Constipation in Mice and Alteration of 5-Hydroxytryotamine Signaling by Ligilactobacillus salivarius Li01. Nutrients. 2022 Oct 1;14(19):4083. doi: 10.3390/nu14194083. PMID: 36235735; PMCID: PMC9571718. 11: Zhou X, Chen Y, Ma X, Yu Y, Yu X, Chen X, Suo H. Efficacy of Bacillus coagulans BC01 on loperamide hydrochloride-induced constipation model in Kunming mice. Front Nutr. 2022 Sep 21;9:964257. doi: 10.3389/fnut.2022.964257. PMID: 36211526; PMCID: PMC9533339. 12: Jung SM, Ha AW, Choi SJ, Kim SY, Kim WK. Effect of Bacillus coagulans SNZ 1969 on the Improvement of Bowel Movement in Loperamide-Treated SD Rats. Nutrients. 2022 Sep 8;14(18):3710. doi: 10.3390/nu14183710. PMID: 36145085; PMCID: PMC9500726. 13: Feng X, Shi Y, Zhou Z, Ji Z, Zhou W, Chen S, Mao J. Alleviation of loperamide-induced constipation with sticky rice fermented huangjiu by the regulation of serum neurotransmitters and gut microbiota. J Sci Food Agric. 2023 Jan 30;103(2):692-704. doi: 10.1002/jsfa.12181. Epub 2022 Sep 19. PMID: 36121332. 14: Heitmann PT, Keightley L, Wiklendt L, Wattchow DA, Brookes SSJ, Spencer NJ, Costa M, Dinning PG. The effects of loperamide on excitatory and inhibitory neuromuscular function in the human colon. Neurogastroenterol Motil. 2022 Nov;34(11):e14442. doi: 10.1111/nmo.14442. Epub 2022 Aug 21. PMID: 36054796. 15: Geno KA, Badea A, Lynch KL, Jannetto P, Hubbard JA, Nerenz RD, Cervinski MA. An Opioid Hiding in Plain Sight: Loperamide-Induced False-Positive Fentanyl and Buprenorphine Immunoassay Results. J Appl Lab Med. 2022 Oct 29;7(6):1318-1328. doi: 10.1093/jalm/jfac065. PMID: 36036092. 16: Lin Q, Liu M, Erhunmwunsee F, Li B, Mou Y, Wang S, Zhang G, Tian J. Chinese patent medicine shouhui tongbian capsule attenuated loperamide-induced constipation through modulating the gut microbiota in rat. J Ethnopharmacol. 2022 Nov 15;298:115575. doi: 10.1016/j.jep.2022.115575. Epub 2022 Aug 4. PMID: 35934189. 17: Lei Z, Rong H, Yang Y, Yu S, Zhang T, Chen L, Nie Y, Song Q, Hu Q, Guo J. Loperamide induces excessive accumulation of bile acids in the liver of mice with different diets. Toxicology. 2022 Jul;477:153278. doi: 10.1016/j.tox.2022.153278. Epub 2022 Aug 1. PMID: 35926757. 18: Kim HR, Park IS, Park SB, Yang HJ, Jeong DY, Kim SY. Comparison of laxative effects of fermented soybeans (Cheonggukjang) containing toxins and biogenic amines against loperamide-induced constipation mouse model. Nutr Res Pract. 2022 Aug;16(4):435-449. doi: 10.4162/nrp.2022.16.4.435. Epub 2021 Nov 29. PMID: 35919294; PMCID: PMC9314190. 19: Tang T, Wang J, Jiang Y, Zhu X, Zhang Z, Wang Y, Shu X, Deng Y, Zhang F. Bifidobacterium lactis TY-S01 Prevents Loperamide-Induced Constipation by Modulating Gut Microbiota and Its Metabolites in Mice. Front Nutr. 2022 Jun 29;9:890314. doi: 10.3389/fnut.2022.890314. PMID: 35845767; PMCID: PMC9277448. 20: Giesing W, Koester C, Al-Akchar M, Kulkarni A, Labedi M. Loperamide-Induced Ventricular Tachycardia Storm. Avicenna J Med. 2022 Jun 22;12(2):93-96. doi: 10.1055/s-0042-1749628. PMID: 35833161; PMCID: PMC9272451.