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L4762

Loperamide hydrochloride

98-102% (USP), powder, Ca2+ channel blocker

Synonym(s):

4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C29H33ClN2O2 · HCl
CAS Number:
34552-83-5
Molecular Weight:
513.50
NACRES:
NA.77
PubChem Substance ID:
24278042
UNSPSC Code:
12352200
EC Number:
252-082-4
MDL number:
MFCD00058581
Quality level:
200
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Product Name

Loperamide hydrochloride,

Quality Level

200

originator

Johnson & Johnson

SMILES string

Cl.CN(C)C(=O)C(CCN1CCC(O)(CC1)c2ccc(Cl)cc2)(c3ccccc3)c4ccccc4

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

Gene Information

human ... OPRM1(4988)

Application

Loperamide hydrochloride (HCl) has been used in inflammatory pain experiments and to assess the functionality of proteins. 54

Biochem/physiol Actions

Loperamide hydrochloride (HCl) is a non-selective Ca2+ channel blocker. At nanomolar concentrations, it binds to μ-opioid receptors. Loperamide HCl does not cross the blood-brain barrier.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Slightly soluble in water and dilute acids, freely soluble in methanol and in chloroform, soluble in ethanol (95%).

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000406508
0000406508
0000340740
0000312729
0000340740

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J Church et al.
Molecular pharmacology, 45(4), 747-757 (1994-04-01)
The effects of the antidiarrheal agent loperamide on high-voltage-activated (HVA) calcium channel activity and excitatory amino acid-evoked responses in two preparations of cultured hippocampal pyramidal neurons were examined. In rat hippocampal neurons loaded with the calcium-sensitive dye fura-2, rises in
Raphaël Weibel et al.
PloS one, 8(9), e74706-e74706 (2013-09-27)
Opiates are powerful drugs to treat severe pain, and act via mu opioid receptors distributed throughout the nervous system. Their clinical use is hampered by centrally-mediated adverse effects, including nausea or respiratory depression. Here we used a genetic approach to
Olivia Benguettat et al.
PLoS pathogens, 14(9), e1007279-e1007279 (2018-09-05)
The digestive tract is the first organ affected by the ingestion of foodborne bacteria. While commensal bacteria become resident, opportunistic or virulent bacteria are eliminated from the gut by the local innate immune system. Here we characterize a new mechanism
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