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Codeine phosphate

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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 Molecular Structure of 52-28-8 (Codeine phosphate) 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

Codeine phosphate History

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.

 

Codeine phosphate Consensus Reports

EPA Genetic Toxicology Program.

Codeine phosphate Specification

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%.

Codeine phosphate is used to produce 1-bromo-4,5a-epoxy-3-methoxy-17-methyl-morphin-7-en-6a-ol.

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.