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

• ChemBase ID: 73039
• Molecular Formular: C29H34Cl2N2O2
• Molecular Mass: 513.49846
• Monoisotopic Mass: 512.1997337
• SMILES: c1c(ccc(c1)C1(CCN(CC1)CCC(C(=O)N(C)C)(c1ccccc1)c1ccccc1)O)Cl.Cl
• Canonical SMILES: Clc1ccc(cc1)C1(O)CCN(CC1)CCC(C(=O)N(C)C)(c1ccccc1)c1ccccc1.Cl
• InChI: 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
• InChIKey: PGYPOBZJRVSMDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride
• IUPAC Traditional name: loperamide hydrochloride; imodium hydrochloride
• Synonyms: Loperamide hydrochloride; 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutanamide Hydrochloride; Arret; Blox; Brek; Dissenten; Fortasec; Imodium; Imodium A-D; Imosec; Imossel; Lopemid; Lopemin; Loperazine; Loperyl; Lopodium; Maalox Antidiarrheal; NSC 696356; PJ 185; R 18553; Suprasec; Tebloc; 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride; Loperamide hydrochloride; 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidine butanamide; LOPERAMIDE; 4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride; 4-(对-氯苯基)-4-羟基-N,N-二甲基-α,α-二苯基-1-哌啶丁酰胺 盐酸盐; 洛哌丁胺 盐酸盐

Database IDs

• CAS Number: 34552-83-5
• EC Number: 252-082-4
• MDL Number: MFCD00058581
• PubChem SID: 24278042; 162037959; 24860777
• PubChem CID: 71420

CALCULATED PROPERTIES

• Acid pKa: 13.964883
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.4130412
• LogD (pH = 7.4): 2.771404
• Log P: 4.7711906
• Molar Refractivity: 139.319 cm^3
• Polarizability: 54.263134 Å^3
• Polar Surface Area: 43.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 223-225°C
• Hydrophobicity(logP): 4.662

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: TM4960000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 25; R:25
• Safety Statements: 45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... OPRM1(4988)

Product Information

• Purity: 95%
• Grade: certified reference material; VETRANAL™, analytical standard
• Salt Data: hydrochloride
• Packaging: pkg of 1 g
• Pharmacopeia Traceability: traceable to BP 635; traceable to PhEur L0750000; traceable to USP 1370000
• Empirical Formula (Hill Notation): C29H33ClN2O2 · HCl

DETAILS

MP Biomedicals - 02153676

Hydrochloride
Calcium channel antagonist.

Selleck Chemicals - S2480

Research Area: Metabolic Disease
Biological Activity:
Loperamide is an opioid-receptor agonist with an ED50 of 0.15 mg/kg. It acts on the μ-opioid receptors in the myenteric plexus of the large intestine; by itself it does not affect the central nervous system like other opioids. It works by decreasing the activity of the myenteric plexus, which, like morphine, decreases the tone of the longitudinal smooth muscles but increases tone of circular smooth muscles of the intestinal wall. This increases the amount of time substances stay in the intestine, allowing for more water to be absorbed out of the fecal matter. Loperamide also decreases colonic mass movements and suppresses the gastrocolic reflex. [1][2]

Sigma Aldrich - L4762

Biochem/physiol Actions
Non-selective Ca2+ channel blocker. At nanomolar concentrations, binds to μ opioid receptors; does not cross blood brain barrier.

Sigma Aldrich - PHR1162

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Sigma Aldrich - 34014

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - L469450

Used as an antidiarrheal.

REFERENCES

• http://en.wikipedia.org/wiki/Loperamide
• Stokbroekx, et al.: J. Med. Chem., 1, 782 (1973)
• Carter, J.E., et al.: Anal. Profiles Drug Subs., 19, 341 (1973)