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Substance Name: Meperidine hydrochloride [USAN:USP]
RN: 50-13-5
UNII: N8E7F7Q170
InChIKey: WCNLCIJMFAJCPX-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.Cl-H

Molecular Weight

  • 283.7968
 

Classification Codes

  • Analgesic (Narcotic)
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Meperidine hydrochloride [USAN:USP]
  • Pethidine hydrochloride [JAN]

MeSH Heading

  • Meperidin

Synonyms

  • (+-)-Pethidine hydrochloride
  • 1-Methyl-4-carbethoxy-4-phenylpiperidine hydrochloride
  • 1-Methyl-4-phenyl-4-carboethoxypiperidine hydrochloride
  • 1-Methyl-4-phenylisonipecotic acid ethyl ester hydrochloride
  • 4-Piperidinecarboxylic acid, 1-methyl-4-phenyl-, ethyl ester, hydrochloride
  • Algil
  • Alodan (gerot)
  • Antiduol
  • Antidurol
  • Centralgin
  • Chlorbicyclene
  • Chlorbicyclene [French]
  • Chlorbycyclen
  • Demerol
  • Demerol hydrochloride
  • Dispadol
  • Dolantal
  • Dolantin
  • Dolaren
  • Dolargan
  • Dolcontral
  • Dolenal
  • Dolenol
  • Dolestine
  • Dolin
  • Doloneurine
  • Dolopethin
  • Dolosal
  • EINECS 200-013-3
  • Endolat
  • Ethyl 1-methyl-4-phenylisonipecotate hydrochloride
  • Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate hydrochloride
  • Ethyl 1-methyl-4-phenylpiperidyl-4-carboxylate hydrochloride
  • Ethyl-1-methyl-4-phenylisonipecotate hydrochloride
  • Isonipecaine hydrochloride
  • Lidol
  • Mefedina
  • Mepadin
  • Meperidine
  • Meperidine HCl
  • Meperidine hydrochloride
  • Meperidine hydrochloride preservative free
  • Meperitab
  • Mephedine
  • Mialgin
  • N-Methyl-4-phenyl-4-carbethoxypiperidine hydrochloride
  • NIH 10522
  • NSC 400479
  • Operidine
  • Pantalgine
  • Petantin
  • Petantin hydrochloride
  • Pethidine chloride
  • Pethidine hydrochloride
  • Petidin
  • Piridosal
  • S 140
  • Sauteralgyl
  • Spasmedal
  • Spasmodolin
  • Synelaudine
  • UNII-N8E7F7Q170
  • WY 554

Systematic Names

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

Mixture Name

  • Mepergan

Registry Numbers

CAS Registry Number

  • 50-13-5

FDA UNII

  • N8E7F7Q170

Other Registry Numbers

  • 2793-00-2
  • 55989-09-8

Related Registry Number

  • 57-42-1 (Parent)

System Generated Number

  • 0000050135

Molecular Formulas

Molecular Formula

  • C15-H21-N-O2.Cl-H

Molecular Formula Fragments

  • C15-H21-N-O2
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C15H21NO2.ClH/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;1H

InChIKey

WCNLCIJMFAJCPX-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous 100mg/kg (100mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: ANALGESIA

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Journal of Pharmacology and Experimental Therapeutics. Vol. 103, Pg. 147, 1951.
cat LDLo oral 100mg/kg (100mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 103, Pg. 147, 1951.
chicken LD50 intraperitoneal 52mg/kg (52mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Toxicology and Applied Pharmacology. Vol. 2, Pg. 558, 1960.
chicken LD50 intravenous 42mg/kg (42mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Toxicology and Applied Pharmacology. Vol. 2, Pg. 558, 1960.
dog LD50 intravenous 68mg/kg (68mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
frog LD50 parenteral 515mg/kg (515mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 103, Pg. 147, 1951.
guinea pig LD50 intramuscular 111mg/kg (111mg/kg)   Canadian Anaesthetists' Society Journal. Vol. 5, Pg. 161, 1958.
guinea pig LDLo subcutaneous 100mg/kg (100mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse LD50 intraperitoneal 104mg/kg (104mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmaceutical Sciences. Vol. 63, Pg. 451, 1974.
mouse LD50 intraperitoneal 130mg/kg (130mg/kg)   Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 12, Pg. 39, 1974.
mouse LD50 intraperitoneal 130mg/kg (130mg/kg) BEHAVIORAL: EXCITEMENT Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 12, Pg. 39, 1974.
mouse LD50 intravenous 32mg/kg (32mg/kg)   Toxicology and Applied Pharmacology. Vol. 6, Pg. 334, 1964.
mouse LD50 oral 178mg/kg (178mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 164, 1978.
mouse LD50 subcutaneous 150mg/kg (150mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 164, 1978.
rabbit LD50 intravenous 20mg/kg (20mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ANALGESIA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 216, Pg. 48, 1952.
rabbit LD50 oral 500mg/kg (500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 103, Pg. 147, 1951.
rabbit LDLo subcutaneous 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ANALGESIA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 216, Pg. 48, 1952.
rat LD50 intraperitoneal 65mg/kg (65mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: REGIDITY

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology. Vol. 14, Pg. 217, 1979.
rat LD50 intravenous 30mg/kg (30mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 115, Pg. 213, 1958.
rat LD50 oral 170mg/kg (170mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 103, Pg. 147, 1951.
rat LD50 subcutaneous 175mg/kg (175mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 238, 1953.
rat LD50 unreported 280mg/kg (280mg/kg) BEHAVIORAL: ANALGESIA Pharmacological Research Communications. Vol. 5, Pg. 175, 1973.
women TDLo intramuscular 13500ug/kg/3D (13.5mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" American Journal of Psychiatry. Vol. 144, Pg. 1062, 1987.
women TDLo intramuscular 43mg/kg/2D-I (43mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Annals of Emergency Medicine. Vol. 14, Pg. 1007, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 187.5 deg C   EXP
log P (octanol-water) 3.030 (none)   EST
Water Solubility 6550 mg/L 25 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.