Loperamide hydrochloride

Base Information

• Chemical Name: Loperamide hydrochloride
• CAS No.: 34552-83-5
• Molecular Formula: C29H33ClN2O2^.HCl
• Molecular Weight: 513.507
• Hs Code.: 29333990
• European Community (EC) Number: 252-082-4
• NSC Number: 759568,696356
• UNII: 77TI35393C
• DSSTox Substance ID: DTXSID00880006
• Wikidata: Q27107231
• NCI Thesaurus Code: C1584
• RXCUI: 82038
• Pharos Ligand ID: WXFXAH3QBV55
• ChEMBL ID: CHEMBL1707
• Mol file: 34552-83-5.mol

Synonyms:Hydrochloride, Loperamide;Imodium;Loperamide;Loperamide Hydrochloride;Loperamide Monohydrochloride;Monohydrochloride, Loperamide;R 18553;R-18553;R18553

Chemical Property of Loperamide hydrochloride

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.23E-17mmHg at 25°C
• Melting Point: 223-225 °C
• Refractive Index: 1.6100 (estimate)
• Boiling Point: 647.2 °C at 760 mmHg
• PKA: 8.66(at 25℃)
• Flash Point: 345.2 °C
• PSA: 43.78000
• Density: ==
• LogP: 5.82790
• Storage Temp.: Store at RT
• Solubility.: Slightly soluble in water, freely soluble in ethanol (96 per cent) and in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 512.1997337
• Heavy Atom Count: 35
• Complexity: 623

Purity/Quality:

99.5% ^*data from raw suppliers

Loperamide hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4.Cl
• Recent ClinicalTrials: Impact of Dietary Fiber as Prebiotics on Chemotherapy-related Diarrhea in Patients With Gastrointestinal Tumors
• Recent EU Clinical Trials: Management of diarrhoea in ulcerative colitis: multi-arm multi-stage trial of low FODMAP diet, amitriptyline, ondansetron, or loperamide: MODULATE.
• Recent NIPH Clinical Trials: Single blinded study for the evaluation of bitterness of quinine hydrochloride and loperamide hydrochloride in healthy adult female and male volunteers
• Uses: Labeled Loperamide, which is used as an antidiarrheal Loperamide hydrochloride is a Ca2+ channel protein inhibitor and MOR activator.
• Indications: Loperamide hydrochloride (Imodium) structurally resembles both haloperidol and meperidine. In equal doses, loperamide protects against diarrhea longer than does diphenoxylate. It reduces the daily fecal volume and decreases intestinal fluid and electrolyte loss. Loperamide produces rapid and sustained inhibition of the peristaltic reflex through depression of longitudinal and circular muscle activity.The drug also possesses antisecretory activity, presumably through an effect on intestinal opioid receptors.
• Therapeutic Function: Antidiarrheal
• Clinical Use: Loperamide is effective against a wide range of secretory stimuli and can be used in the control and symptomatic relief of acute diarrhea that is not secondary to bacterial infection.

Technology Process of Loperamide hydrochloride

There total 3 articles about Loperamide hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

4-(4-chlorophenyl)-4-hydroxypiperidine (39512-49-7) + N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide (37743-18-3) → loperamide hydrochloride (34552-83-5)

Guidance literature:

4-(4-chlorophenyl)-4-hydroxypiperidine; With sodium carbonate; potassium iodide; In 1,3-dioxolane-4-methanol; for 0.25h;

N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide; In 1,3-dioxolane-4-methanol; at 60 ℃; for 2h;

With hydrogenchloride; In 1,3-dioxolane-4-methanol; isopropyl alcohol; for 0.333333h;

Reference yield:

4-(4-chlorophenyl)-4-hydroxypiperidine (39512-49-7) + N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide (37743-18-3) + 4-methyl-2-pentanone (108-10-1) → loperamide hydrochloride (34552-83-5)

Guidance literature:

With potassium iodide; sodium carbonate; In hydrogenchloride; isopropyl alcohol; acetone; toluene;

Reference yield:

→ loperamide hydrochloride (34552-83-5)

Guidance literature:

4a, 4-Hydroxy-4-p-chlorphenylpiperidin;

DOI:10.1021/jm00265a009

upstream raw materials:

4-(4-chlorophenyl)-4-hydroxypiperidine

N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide

4-methyl-2-pentanone

Refernces

• 1、 -. "PREPARATION OF PHARMACEUTICAL ACTIVE INGREDIENTS USING A GLYCEROL-DERIVED SOLVENT". Page/Page column 10. . Retrieved 2008/12/07.