MEPERIDINE

Base Information

• Chemical Name: MEPERIDINE
• CAS No.: 57-42-1
• Molecular Formula: C15H21 N O2
• Molecular Weight: 247.337
• European Community (EC) Number: 200-329-1
• UNII: 9E338QE28F
• DSSTox Substance ID: DTXSID9023253
• Nikkaji Number: J4.578K
• Wikipedia: Pethidine
• Wikidata: Q55434
• NCI Thesaurus Code: C71632
• RXCUI: 6754
• Pharos Ligand ID: SZVHZB4KFT4M
• Metabolomics Workbench ID: 42805
• ChEMBL ID: CHEMBL607
• Mol file: 57-42-1.mol

Synonyms:Isonipecoticacid, 1-methyl-4-phenyl-, ethyl ester (8CI);1-Methyl-4-phenyl-4-piperidinecarboxylic acid ethyl ester;4-Carbethoxy-1-methyl-4-phenylpiperidine; Demerol; Ethyl1-methyl-4-phenylisonipecotate; Ethyl1-methyl-4-phenylpiperidine-4-carboxylate; Isonipecaine; Meperidine; Meperidol;Pethanol; Pethidin; Pethidine; Pethidineter; Petidina; Renaudin

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of MEPERIDINE

Chemical Property:

• Melting Point: 270°C
• Refractive Index: 1.5130 (estimate)
• Boiling Point: 328.9°Cat760mmHg
• PKA: pKa 8.7 (Uncertain)
• Flash Point: 111.6°C
• PSA: 29.54000
• Density: 1.055g/cm³
• LogP: 2.15100
• Storage Temp.: −20°C
• Water Solubility.: 6.55g/L(25 oC)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 247.157228913
• Heavy Atom Count: 18
• Complexity: 276

Purity/Quality:

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Opioids
• Canonical SMILES: CCOC(=O)C1(CCN(CC1)C)C2=CC=CC=C2
• Recent ClinicalTrials: Comparing Pediatric Dental Oral Sedation Outcomes With and Without Meperidine in Children Aged 3-7 Years
• Recent EU Clinical Trials: Oxycodone compared to meperidine in the treatment of labour pain
• Uses: Analgesic (narcotic).
• Therapeutic Function: Narcotic analgesic
• Biological Functions: Meperidine (Demerol) is a phenylpiperidine derivative of morphine that was developed in the late 1930s as a potential anticholinergic agent. It has some anticholinergic side effects that lead to tachycardia, blurred vision, and dry mouth. Meperidine is approximately onefifth as potent as morphine and is absorbed only half as well when administered orally as parenterally. It has a rapid onset and short duration of action (2 hours), that is, approximately one-fourth that of morphine. Like morphine, meperidine has an active metabolite, normeperidine, formed by N-demethylation of meperidine. Normeperidine is not analgesic but is a proconvulsant and a hallucinogenic agent. For this reason, meperidine use in patients with renal or liver insufficiency is contraindicated because of the decreased clearance of the drug and its metabolite. Convulsant activity has been documented in elderly patients given meperidine and in patients using PCA who have decreased renal function. Meperidine differs from morphine in that it has far less antitussive effect and little constipative effect. The drug is particularly useful in cancer patients and in pulmonary patients, in whom the cough reflex must remain intact. However, it does have more seizure-inducing activity than morphine. Although meperidine produces spasms of the biliary tract and colon, such spasms are of shorter duration than those produced by morphine. Meperidine readily passes the placenta into the fetus. However, respiratory depression in the newborn has not been observed, and meperidine clearance in the newborn is rapid in that it does not rely upon conjugation to glucuronides. Meperidine, unlike morphine, has not been associated with prolongation of labor; conversely, it increases uterine contractions.

Technology Process of MEPERIDINE

There total 20 articles about MEPERIDINE 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: 94.0%

→ pethidine (57-42-1)

Guidance literature:

Reference yield:

ethanol (64-17-5) + 1-methyl-4-phenyl-piperidine-4-carbonitrile (3627-62-1) → pethidine (57-42-1)

Guidance literature:

With sulfuric acid; Heating;

DOI:10.1016/j.bmcl.2006.12.042

Reference yield:

pethidinic acid (3627-48-3) → pethidine (57-42-1)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01514a047

upstream raw materials:

1-methyl-4-phenyl-piperidine-4-carbonitrile

pethidinic acid

formaldehyd

Normeperidine

Downstream raw materials:

4-phenyl-piperidine-4-carboxylic acid

pethidinic acid

Normeperidine

meperidine N-oxide

Refernces

• 1、 -. "PHENYLPIPERIDINE MODULATORS OF MU-OPIOID RECEPTOR". Page/Page column 11. . Retrieved 2011/07/08.
• 2、 Mercer, Susan L.,Hassan, Hazem E.,Cunningham, Christopher W.,Eddington, Natalie D.,Coop, Andrew. "Opioids and efflux transporters. Part 1: P-Glycoprotein substrate activity of N-substituted analogs of meperidine". . p. 1160 - 1162. Retrieved 2007/10/03.