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Name |
Codeine phosphate |
EINECS | 200-137-8 |
CAS No. | 52-28-8 | Density | N/A |
PSA | 98.27000 | LogP | 1.55600 |
Solubility | Soluble in water | Melting Point |
238-240 °C |
Formula | C18H21NO3•H3O4P | Boiling Point | 462 °C at 760 mmHg |
Molecular Weight | 397.365 | Flash Point | 233.2 °C |
Transport Information | N/A | Appearance | White to off-white solid |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
Codeine phosphate anhydrous;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-,(5R,6R)-,phosphate (1:1) (salt);Tricodein;Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-, phosphate (1:1) (salt);UNII-GSL05Y1MN6; |
Article Data | 2 |
1、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.
2、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.
3、Numerous codeine salts have been prepared since the drug was discovered.
The Codeine phosphate with CAS registry number of 52-28-8 is also known as Codeine phosphate anhydrous. The systematic name is (5α,6α)-3-Methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol phosphate (salt). It belongs to product categories of Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 200-137-8. In addition, the formula is C18H21NO3•H3O4P and the molecular weight is 397.36. This chemical is a white to off-white solid that soluble in water. What's more, it can be used as weak narcotic analgesic, potent antitussive and controlled substance.
Physical properties about Codeine phosphate are:
(1)ACD/LogP: 1.20; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.41; (4)ACD/LogD (pH 7.4): 0.27; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 12.48; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 30.93Å2; (13)Flash Point: 233.2 °C; (14)Enthalpy of Vaporization: 76.18 kJ/mol; (15)Boiling Point: 462 °C at 760 mmHg; (16)Vapour Pressure: 2.47E-09 mmHg at 25 °C.
Uses of Codeine phosphate:
It is used to produce 1-bromo-4,5a-epoxy-3-methoxy-17-methyl-morphin-7-en-6a-ol. The reaction occurs with reagent Br2 and solvent acetic acid. The yield is about 62%.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O.OP(=O)(O)O
2. Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O.OP(=O)(O)O
3. 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
4. InChIKey: WUXLCJZUUHIXFY-FFHNEAJVSA-N
The toxicity data of Codeine phosphate is as follows:
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: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA 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) | 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. |
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) | SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: SLEEP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Clinical Pharmacy. Vol. 5, Pg. 15, 1986. |