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Substance Name: Codeine [INN:BAN]
RN: 76-57-3
UNII: UX6OWY2V7J
InChIKey: OROGSEYTTFOCAN-DNJOTXNNSA-N

Note

  • An opioid analgesic related to MORPHINE but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough.

Molecular Formula

  • C18-H21-N-O3

Molecular Weight

  • 299.3679
 

Classification Codes

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

Names and Synonyms

Results Name

  • Codeine [INN:BAN]

Name of Substance

  • Codeine
  • Codeine anhydrous
  • Codeine polistirex [USAN]
  • Codeine [INN:BAN]

MeSH Heading

  • Codeine

Synonyms

  • 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
  • CCRIS 7555
  • Codeine
  • Codeine base
  • Codeine polistirex
  • Codeinum
  • Codicept
  • Coducept
  • EINECS 200-969-1
  • HSDB 3043
  • l-Codeine
  • Methylmorphine
  • Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-
  • Morphinan-6alpha-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-
  • Morphine 3-methyl ether
  • Morphine monomethyl ether
  • Morphine-3-methyl ether
  • Norcodeine, N-methyl
  • Norcodine, N-methyl
  • O3-Methylmorphine
  • UNII-UX6OWY2V7J

Systematic Names

  • Codeine
  • Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-
  • Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha,6-alpha)- (9CI)
  • Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-

Superlist Name

  • Codeine

Registry Numbers

CAS Registry Number

  • 76-57-3

FDA UNII

  • UX6OWY2V7J

Related Registry Number

  • 41444-62-6 (PO4)

System Generated Number

  • 0000076573

Structure Descriptors

InChI

1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1

InChIKey

OROGSEYTTFOCAN-DNJOTXNNSA-N

Smiles

COc1ccc2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5Oc1c2[C@]45CCN3C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 69mg/kg (69mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 7, Pg. 372, 1959.
man LDLo unreported 12mg/kg (12mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intramuscular 290mg/kg (290mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 13, Pg. 97, 1977.
mouse LD50 intraperitoneal 60mg/kg (60mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Annales Pharmaceutiques Francaises. Vol. 8, Pg. 261, 1950.
mouse LD50 intravenous 54mg/kg (54mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 617, 1966.
mouse LD50 oral 250mg/kg (250mg/kg)   Medicinal Chemistry: A Series of Monographs. Vol. 5, Pg. 318, 1965.
mouse LD50 subcutaneous 84100ug/kg (84.1mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
rabbit LD50 intravenous 34mg/kg (34mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Experientia. Vol. 18, Pg. 446, 1962.
rat LD50 intraperitoneal 100mg/kg (100mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 551, 1976.
rat LD50 intravenous 75mg/kg (75mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 25, Pg. 929, 1973.
rat LD50 oral 427mg/kg (427mg/kg) GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION Journal of Medicinal Chemistry. Vol. 16, Pg. 782, 1973.
rat LD50 subcutaneous 229mg/kg (229mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 157.5 deg C   EXP
pKa Dissociation Constant 8.21 (none) 25 EXP
log P (octanol-water) 1.19 (none)   EXP
Water Solubility 9000 mg/L 20 EXP
Vapor Pressure 4.15E-09 mm Hg 25 EST
Henry's Law Constant 7.58E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.43E-10 cm3/molecule-sec 25 EST

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