Meperidine hydrochloride

Base Information

• Chemical Name: Meperidine hydrochloride
• CAS No.: 50-13-5
• Deprecated CAS: 55989-09-8,2793-00-2
• Molecular Formula: C15H21 N O2 . Cl H
• Molecular Weight: 283.798
• Hs Code.: 2933330000
• European Community (EC) Number: 200-013-3
• NSC Number: 400479
• UNII: N8E7F7Q170
• DSSTox Substance ID: DTXSID30950620
• Wikidata: Q27284706
• NCI Thesaurus Code: C635
• RXCUI: 103755
• Pharos Ligand ID: SZVHZB4KFT4M
• ChEMBL ID: CHEMBL1701
• Mol file: 50-13-5.mol

Synonyms:Demerol;Dolantin;Dolargan;Dolcontral;Dolin;Dolosal;Dolsin;Isonipecain;Lidol;Lydol;Meperidine;Meperidine Hydrochloride;Operidine EPJ I;Operidine EPJ-I;Pethidine

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Chemical Property of Meperidine hydrochloride

Chemical Property:

• Appearance/Colour: white, crystalline powder; odourless.
• Vapor Pressure: 0.000184mmHg at 25°C
• Melting Point: 186-189°
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 328.9 °C at 760 mmHg
• Flash Point: 111.6 °C
• PSA: 29.54000
• Density: g/cm³
• LogP: 2.95300
• Storage Temp.: 2-8°C
• Solubility.: Very soluble in water, freely soluble in alcohol.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 283.1339066
• Heavy Atom Count: 19
• Complexity: 276

Purity/Quality:

Safty Information:

• Pictogram(s): TF
• Hazard Codes: T,F
• Statements: 25-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37/39-45-36/37-16-7

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1(CCN(CC1)C)C2=CC=CC=C2.Cl
• Recent ClinicalTrials: Epidural Tap in Labor Analgesia FOR LABOR ANALGESIA
• Recent EU Clinical Trials: Randomized clinical trial to compare the efficacy of opioid-free versus traditional balanced anesthesia in laparoscopic colorectal surgery
• Recent NIPH Clinical Trials: Randomized controlled trial examining the usefulness and safety of midazolam continuous intravenous infusion and pethidine hydrochloride in small intestine endoscope
• Therapeutic Function: Narcotic analgesic
• Clinical Use: Meperidine is a μ agonist with approximately one-tenth the potency of morphine after intramuscular dose. Meperidine produces the analgesia, respiratory depression, and euphoria caused by other μ opioid agonists, but it causes less constipation and does not inhibit cough. When given orally, meperidine has 40 to 60% bioavailability because of significant first-pass metabolism. Because of the limited bioavailability, it is one-third as potent after an oral dose compared to a parenteral dose. Meperidine has received extensive use in obstetrics because of its rapid onset and short duration of action. When it is given intravenously in small (25-mg) doses during delivery, the respiratory depression in the newborn child is minimized. Meperidine is used as an analgesic in a variety of nonobstetric anesthetic procedures. Meperidine is extensively metabolized in the liver, with only 5% of the drug being excreted unchanged. Prolonged dosage of meperidine may cause an accumulation of the metabolite normeperidine. Normeperidine has only weak analgesic activity, but it causes CNS excitation and can initiate grand mal seizures. It is recommended that meperidine be discontinued in any patient who exhibits signs of CNS excitation. Meperidine has a strong adverse reaction when given to patients receiving a monoamine oxidase inhibitor. This drug interaction has been seen recently in patients with Parkinson's disease taking the monoamine oxidase–selective inhibitor selegiline (Eldepryl). The elimination half-life of meperidine is 3 to 4 hours, and it can double in patients with liver disease. Acidification of the urine will cause enhanced clearance of meperidine, but there is a lesser effect on the clearance of the toxic metabolite normeperidine.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: possible opioid withdrawal with buprenorphine and pentazocine. Anti-arrhythmics: delayed absorption of mexiletine. Antidepressants: possible CNS excitation or depression with MAOIs and moclobemide - avoid; possibly increased serotonergic effects with duloxetine; increased sedative effects with tricyclics. Antiepileptics: possible increased risk of pethidine toxicity with fosphenytoin and phenytoin. Antihistamines: increased sedative effects with sedating antihistamines. Antipsychotics: enhanced sedative and hypotensive effect. Antivirals: concentration reduced by ritonavir but concentration of toxic pethidine metabolite increased - avoid. Dopaminergics: risk of CNS toxicity with rasagiline - avoid; hyperpyrexia and CNS toxicity reported with selegiline - avoid. Nalmefene: avoid concomitant use. Sodium oxybate: enhanced effect of sodium oxybate - avoid.

Technology Process of Meperidine hydrochloride

There total 2 articles about Meperidine 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: 45.0%

pethidine (57-42-1) → meperidine hydrochloride (50-13-5,55989-09-8)

Guidance literature:

With hydrogenchloride; In methanol; diethyl ether; at 20 ℃; for 6h;

Reference yield:

4-phenyl-4-cyanopiperidine (40481-13-8) → meperidine hydrochloride (50-13-5,55989-09-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / water; tetrahydrofuran / 0.5 h / 20 °C

1.2: 16 h / 0 - 20 °C

2.1: water; sulfuric acid / Reflux

2.2: 24 h / 100 °C

3.1: hydrogenchloride / diethyl ether; methanol / 6 h / 20 °C

With hydrogenchloride; sulfuric acid; water; acetic acid; In tetrahydrofuran; methanol; diethyl ether; water;

Reference yield:

meperidine hydrochloride (50-13-5,55989-09-8) → Normeperidine (77-17-8)

Guidance literature:

meperidine hydrochloride; With recombinant cytochrome P₄₅₀ CYP₂B₆; In aq. phosphate buffer; dimethyl sulfoxide; acetonitrile; at 37 ℃; for 0.0833333h; pH=7.4;

In aq. phosphate buffer; dimethyl sulfoxide; acetonitrile; at 37 ℃; for 0.166667h; Reagent/catalyst; Enzymatic reaction;

DOI:10.1080/00498254.2019.1599465

upstream raw materials:

4-phenyl-4-cyanopiperidine

pethidine

Downstream raw materials:

N-Butyl-1-methyl-4-phenyl-4-piperidinecarboxamide

Normeperidine

Refernces