ethyl 1-methyl-4-phenylpiperidine-4-carboxylate

• ChemBase ID: 337
• Molecular Formular: C15H21NO2
• Molecular Mass: 247.33274
• Monoisotopic Mass: 247.15722892
• SMILES: O(C(=O)C1(CCN(CC1)C)c1ccccc1)CC
• Canonical SMILES: CCOC(=O)C1(CCN(CC1)C)c1ccccc1
• InChI: InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
• InChIKey: XADCESSVHJOZHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
• IUPAC Traditional name: meperidine
• Brand Name: Centralgin; Demarol; Demerol; Dispadol; Dolantin; Dolcontral; Dolosal; Dolsin; Isonipecaine; Lidol; Lydol; Meperidine Hcl; Meperidol; Methyl phenylpiperidine carbonic acid ethyl ester; Nemerol; Operidine; Petantin; Pethanol; Pethidin; Pethidine; Pethidineter; Petydyna; Phetidine; Piperosal; Pipersal; Piridosal
• Synonyms: Meperidine; Meperidine solution; 哌替啶 溶液

Database IDs

• CAS Number: 57-42-1
• MDL Number: MFCD00057376
• PubChem SID: 160963800; 24882043; 46506899
• PubChem CID: 4058

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.14636338
• LogD (pH = 7.4): 1.627321
• Log P: 2.4558003
• Molar Refractivity: 72.4837 cm^3
• Polarizability: 28.46522 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.9
• LOG S: -2.35
• Solubility (Water): 1.11e+00 g/l

PROPERTIES

Physical Property

• Solubility: 3220 mg/L
• Flash Point: 11 °C; 51.8 °F
• Hydrophobicity(logP): 2.6

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301 + H311 + H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• RID/ADR: UN 1230 3/PG 2
• Drug Control: kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)rat ... Oprm1(25601), Slc6a3(24898), Slc6a4(25553)

Product Information

• Concentration: 1 mg/mL in methanol
• Grade: drug standard
• Empirical Formula (Hill Notation): C15H21NO2

DETAILS

DrugBank - DB00454

• Drug Groups: approved
• Description: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration. [PubChem]
• Indication: Used to control moderate to severe pain.
• Pharmacology: Meperidine is a synthetic opiate agonist belonging to the phenylpiperidine class. Meperidine may produce less smooth muscle spasm, constipation, and depression of the cough reflex than equivalent doses of morphine. The onset of action is lightly more rapid than with morphine, and the duration of action is slightly shorter. The chemical structure of meperidine is similar to local anesthetics. Meperidine is recommended for relief of moderate to severe acute pain and has the unique ability to interrupt postoperative shivering and shaking chills induced by amphotericin B. Meperidine has also been used for intravenous regional anesthesia, peripheral nerve blocks and intraarticular, epidural and spinal analgesia. Meperidine is considered a second-line agent for the treatment of acute pain.
• Affected Organisms: Humans and other mammals
• Biotransformation: Meperidine is metabolized in the liver by hydrolysis to meperidinic acid followed by partial conjugation with glucuronic acid. Meperidine also undergoes N-demethylation to normeperidine, which then undergoes hydrolysis and partial conjugation. Normeperidine is about half as potent as meperidine, but it has twice the CNS stimulation effects.
• Absorption: The oral bioavailability of meperidine in patients with normal hepatic function is 50-60% due to extensive first-pass metabolism. Bioavailability increases to 80-90% in patients with hepatic impairment (e.g. liver cirrhosis). Meperidine is less than half as effective when administered orally compared to parenteral administration. One study reported that 80-85% of the drug administered intramuscularly was absorbed within 6 hours of intragluteal injection in health adults; however, inter-individual variation and patient-specific variable appear to cause considerable variations in absorption upon IM injection.
• Half Life: Initial distribution phase (t_{1/2 α}) = 2-11 minutes; terminal elimination phase (t_{1/2 β}) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t_{1/2 β} is prolonged to 7-11 hours.
• Protein Binding: 60-80% bound to plasma proteins, primarily albumin and α₁-acid glycoprotein. The presence of cirrhosis or active viral hepatitis does not appear to affect the extent of protein binding.
• Elimination: Excreted in the urine. The proportion of drug that is excreted unchanged or as metabolites is dependent on pH. When urine pH is uncontrolled, 5-30% of the meperidine dose is excreted as normeperidine and approximately 5% is excreted unchanged. Meperidine and normeperidine are found in acidic urine, while the free and conjugated forms of meperidinic and normperidinic acids are found in alkaline urine.
• Distribution: Meperidine crosses the placenta and is distributed into breast milk.
• External Links: Wikipedia; RxList; Drugs.com