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Substance Name: Meperidine
RN: 57-42-1
UNII: 9E338QE28F
InChIKey: XADCESSVHJOZHK-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C15-H21-N-O2

Molecular Weight

  • 247.3359
 

Classification Codes

Classification Codes

  • Adjuvants, Anesthesia
  • Analgesics
  • Analgesics, Opioid
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Narcotics
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule II

Names and Synonyms

Results Name

  • Meperidine

Name of Substance

  • Meperidine
  • Pethidine [INN:BAN]

MeSH Heading

  • Meperidine

Synonyms

  • 1-Methyl-4-phenyl-piperidin-4-carbon-saeure-aethylester
  • 1-Methyl-4-phenyl-piperidin-4-carbon-saeure-aethylester [German]
  • 1-Methyl-4-phenylisonipecotic acid, ethyl ester
  • 1-Methyl-4-phenylpiperidine-4-carboxylic acid ethyl ester
  • Demerol
  • EINECS 200-329-1
  • Ethyl 1-methyl-4-phenylisonipecotate
  • Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
  • HSDB 3116
  • Isonipecaine
  • Isonipecotic acid, 1-methyl-4-phenyl-, ethyl ester
  • Meperidine
  • Meperidol
  • Methyl phenylpiperidine carbonic acid ethyl ester
  • N-Methyl-4-phenyl-4-carbethoxypiperidine
  • Nemerol
  • Pethanol
  • Pethidin
  • Pethidine
  • Pethidineter
  • Pethidinum
  • Pethidinum [INN-Latin]
  • Petidina
  • Petidina [INN-Spanish]
  • Petydyna
  • Petydyna [Polish]
  • Phetidine
  • Pipersal
  • UNII-9E338QE28F

Systematic Names

  • 4-Piperidinecarboxylic acid, 1-methyl-4-phenyl-, ethyl ester
  • Isonipecotic acid, 1-methyl-4-phenyl-, ethyl ester
  • Pethidine

Superlist Names

  • DEA No. 9230
  • Meperidine
  • Pethidine

Registry Numbers

CAS Registry Number

  • 57-42-1

FDA UNII

  • 9E338QE28F

Related Registry Number

  • 50-13-5 (hydrochloride)

System Generated Number

  • 0000057421

Structure Descriptors

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

Smiles

CCOC(=O)C1(CCN(CC1)C)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 intraperitoneal 130mg/kg (130mg/kg)   United States Patent Document. Vol. #4205173,
man LDLo unreported 15mg/kg (15mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo unreported 57mg/kg (57mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: MUSCLE WEAKNESS
New England Journal of Medicine. Vol. 312, Pg. 509, 1985.
mouse LD50 intraperitoneal 135mg/kg (135mg/kg)   Strahlentherapie. Vol. 127, Pg. 245, 1965.
mouse LD50 intravenous 34700ug/kg (34.7mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
mouse LD50 oral 200mg/kg (200mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
mouse LD50 parenteral 178mg/kg (178mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Medicinal Chemistry. Vol. 11, Pg. 889, 1968.
mouse LD50 subcutaneous 112mg/kg (112mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 47, Pg. 323, 1958.
rabbit LD50 intravenous 40mg/kg (40mg/kg)   Journal of New Drugs. Vol. 2, Pg. 43, 1962.
rat LD50 intraperitoneal 87mg/kg (87mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 47, Pg. 323, 1958.
rat LD50 intravenous 22500ug/kg (22.5mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 7, Pg. 196, 1952.
rat LD50 oral 162mg/kg (162mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969.
rat LD50 subcutaneous 113mg/kg (113mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
rat LDLo intraspinal 4mg/kg (4mg/kg) BEHAVIORAL: ANALGESIA Acta Pharmacologica et Toxicologica. Vol. 56, Pg. 50, 1985.
women TDLo intramuscular 2mg/kg (2mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Allergy. Vol. 55, Pg. 305, 2000.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 270 deg C   EXP
pKa Dissociation Constant 8.59 (none)   EXP
log P (octanol-water) 2.72 (none)   EXP
Water Solubility 3220 mg/L 30 EXP
Vapor Pressure 6.89E-05 mm Hg 25 EST
Henry's Law Constant 9.61E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.74E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.