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Substance Name: Codeine phosphate (anhydrous)
RN: 52-28-8
UNII: 2X585M1M3T
InChIKey: WUXLCJZUUHIXFY-FFHNEAJVSA-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.H3-O4-P

Molecular Weight

  • 397.3616
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Codeine phosphate (anhydrous)

Synonyms

  • CCRIS 6003
  • Codeine phosphate
  • EINECS 200-137-8
  • Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha,6-alpha)-, phosphate
  • Tricodein
  • UNII-2X585M1M3T

Systematic Names

  • Codeine phosphate
  • Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-, phosphate (1:1)
  • Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-, phosphate (1:1) (salt)

Superlist Name

  • Codeine phosphate

Registry Numbers

CAS Registry Number

  • 52-28-8

FDA UNII

  • 2X585M1M3T

System Generated Number

  • 0000052288

Molecular Formulas

Molecular Formula

  • C18-H21-N-O3.H3-O4-P

Molecular Formula Fragments

  • C18-H21-N-O3
  • COMPONENT
  • H3-O4-P

Structure Descriptors

InChI

InChI=1S/C18H21NO3.H3O4P/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;1-5(2,3)4/h3-6,11-13,17,20H,7-9H2,1-2H3;(H3,1,2,3,4)/t11-,12+,13-,17-,18-;/m0./s1

InChIKey

WUXLCJZUUHIXFY-FFHNEAJVSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 50mg/kg (50mg/kg)   United States Patent Document. Vol. #3031377,
dog LD50 intravenous 97800ug/kg (97.8mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 961, 1970.
guinea pig LD50 intraperitoneal 352mg/kg (352mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 1450, 1977.
guinea pig LD50 oral 654mg/kg (654mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1207, 1972.
guinea pig LD50 subcutaneous 140mg/kg (140mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1207, 1972.
guinea pig LDLo intraarterial 1gm/kg (1000mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928.
guinea pig LDLo intravenous 117mg/kg (117mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 119, Pg. 205, 1959.
mammal (species unspecified) LD50 unreported 183mg/kg (183mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Chemical and Pharmaceutical Bulletin. Vol. 20, Pg. 1699, 1972.
man TDLo oral 5143ug/kg/5D- (5.143mg/kg) BEHAVIORAL: SLEEP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Clinical Pharmacy. Vol. 5, Pg. 15, 1986.
mouse LD50 intracrebral 12mg/kg (12mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacology and Experimental Therapeutics. Vol. 140, Pg. 155, 1963.
mouse LD50 intramuscular 191mg/kg (191mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 190, Pg. 124, 1971.
mouse LD50 intraperitoneal 110mg/kg (110mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1916, 1969.
mouse LD50 intravenous 62mg/kg (62mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Japanese Journal of Pharmacology. Vol. 17, Pg. 538, 1967.
mouse LD50 oral 237mg/kg (237mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 128, Pg. 384, 1960.
mouse LD50 subcutaneous 80mg/kg (80mg/kg)   United States Patent Document. Vol. #3031377,
rabbit LDLo oral 100mg/kg (100mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 72, 1955.
rabbit LDLo subcutaneous 40mg/kg (40mg/kg)   United States Patent Document. Vol. #3031377,
rat LD50 intramuscular 208mg/kg (208mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 190, Pg. 124, 1971.
rat LD50 intraperitoneal 104mg/kg (104mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 133, Pg. 117, 1961.
rat LD50 intravenous 54mg/kg (54mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 103, Pg. 200, 1955.
rat LD50 oral 85mg/kg (85mg/kg)   United States Patent Document. Vol. #3163649,
rat LD50 subcutaneous 312mg/kg (312mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacology and Experimental Therapeutics. Vol. 154, Pg. 161, 1966.
women TDLo oral 3600ug/kg/2D- (3.6mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: SLEEP

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
Clinical Pharmacy. Vol. 5, Pg. 15, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 227.5 dec deg C   EXP
pKa Dissociation Constant 8.1 (none) 25 EXP
log P (octanol-water) -1.40E+00 (none)   EXP
Water Solubility 3.10E+05 mg/L 25 EXP
Vapor Pressure 2.06E-11 mm Hg 25 EST
Henry's Law Constant 4.50E-31 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.78E-10 cm3/molecule-sec 25 EST

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