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CAS No.: | 76-57-3 |
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Name: | CODEINE |
Article Data: | 34 |
Molecular Structure: | |
Formula: | C18H21 N O3 |
Molecular Weight: | 299.37 |
Synonyms: | Morphinan-6a-ol, 7,8-didehydro-4,5a-epoxy-3-methoxy-17-methyl-(8CI); (-)-Codeine; Codeine; Codicept; Coducept; Methylmorphine; Morphine3-methyl ether; Morphine monomethyl ether; O3-Methylmorphine; l-Codeine |
EINECS: | 200-969-1 |
Density: | 1.34g/cm3 |
Melting Point: | 154 - 156 C |
Boiling Point: | 462°C at 760 mmHg |
Flash Point: | 75 C |
Solubility: |
Stability
Toxicology
|
Appearance: | white crystalline powder |
Hazard Symbols: | Habit-forming narcotic, sale legally restricted. |
Risk Codes: | R11; R23/24/25; R39/23/24/25 |
Safety: | A human poison by an unspecified route. An experimental poison by ingestion, intraperitoneal, intravenous, intramuscular, and subcutaneous routes. Human reproductive effects. An experimental teratogen. Other experimental reproductive effects. An addictive drug. Flammable when exposed to heat or flame. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of NOx. See also (−)-MORPHINE and ETHERS. |
PSA: | 41.93000 |
LogP: | 1.43900 |
Systematic Name: (5alpha,6alpha)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
Molecular Formula: C18H21NO3
Molecular Weight: 299.36424 g/mol
EINECS: 200-969-1
Product Categories: Chiral Reagents; Intermediates & Fine Chemicals;
Pharmaceuticals
Melting Point: 2-8 °C
Index of Refraction: 1.666
Molar Refractivity: 82.85 cm3
Molar Volume: 222.6 cm3
Surface Tension: 60.5 dyne/cm
Density: 1.34 g/cm3
Flash Point: 233.2 °C
Enthalpy of Vaporization: 76.18 kJ/mol
Boiling Point: 462 °C at 760 mmHg
Vapour Pressure of Codeine (CAS NO.76-57-3): ×2.47E-09 mmHg at 25 °C
Codeine (CAS NO.76-57-3) is an alkaloid found in opium and other poppy saps like Papaver bracteatum, the Iranian poppy, in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. It was first isolated in 1832 in France by Jean-Pierre Robiquet.
The effects of the Nixon War On Drugs by 1972 or so had caused across-the-board shortages of illicit and licit opiates because of a scarcity of natural opium, poppy straw and other sources of opium alkaloids, and the geopolitical situation was getting less helpful for the United States. After a large percentage of the opium and morphine in the US National Stockpile of Strategic & Critical Materials had to be tapped in order to ease severe shortages of medicinal opiates—the codeine-based antitussives in particular—in late 1973, researchers were tasked with and quickly succeeded in finding a way to synthesize codeine and its derivatives and precursors from scratch from petroleum or coal tar using a process developed at the United States' National Institutes of Health.
Codeine (CAS NO.76-57-3) is an opiate used for its analgesic, antitussive, and antidiarrheal properties. It is useful for numbing back pain, and is frequently prescribed for this purpose and is by far the most widely used opiate in the world and probably the most commonly used drug overall according to numerous reports over the years by organizations such as the World Health Organization and its League of Nations predecessor agency and others. It is one of the most effective orally-administered opioid analgesics and has a wide safety margin.
Codeine (CAS NO.76-57-3) can be isolated from opium and morphine (also obtained from opium). To direct this alkylation to the phenolic hydroxyl and to reduce alkylation of the tertiary nitrogen, a quaternary nitrogen-alkylating agent, phenyltrimethylammonium hydroxide, is employed. This results in yields of 90 to 93 percent codeine and some recovery of unalkylated morphine. The alkylation is carried out with the morphine dissolved in absolute alcohol in the presence of potassium ethylate. The dimethyl aniline and solvents are recovered and reused.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
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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) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | 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. |
A human poison by an unspecified route. An experimental poison by ingestion, intraperitoneal, intravenous, intramuscular, and subcutaneous routes. Human reproductive effects. An experimental teratogen. Other experimental reproductive effects. An addictive drug. Flammable when exposed to heat or flame. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of NOx. See also (−)-MORPHINE and ETHERS.
Hazard Codes: F,T
Risk Statements: 11-23/24/25-39/23/24/25
R11:Highly flammable.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R39:Danger of very serious irreversible effects.
Safety Statements: 7-16-36/37-45
S7:Keep container tightly closed.
S16:Keep away from sources of ignition.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR UN 1230 3/PG 2
WGK Germany: 1
Codeine (CAS NO.76-57-3), its Synonyms are 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol ; Codicept ; Coducept ; 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 . It is colorless to white crystalline solid or white powder.