Hydrocodone
Title: Hydrocodone
CAS Registry Number: 125-29-1
CAS Name: 4,5-Epoxy-3-methoxy-17-methylmorphinan-6-one
Additional Names: dihydrocodeinone
Trademarks: Bekadid; Dicodid (Knoll)
Molecular Formula: C18H21NO3
Molecular Weight: 299.36
Percent Composition: C 72.22%, H 7.07%, N 4.68%, O 16.03%
Literature References: Prepn by hydrogenation of codeinone: Mannich, Löwenheim, Arch. Pharm. 258, 295 (1920); by oxidation of dihydrocodeine, DE 415097 (1925 to E. Merck), Frdl. 15, 1518 (1925-1927); by catalytic rearrangement of codeine: DE 623821. Industrial prepn from dihydrocodeine: K. Pfister, M. Tishler, US 2715626 (1955 to Merck & Co.). Pharmacology and toxicity data: N. B. Eddy, J. G. Reid, J. Pharmacol. Exp. Ther. 52, 468 (1934). Brief description: A. Stein, Pharmazie 10, 180 (1955). Review: Small, Lutz, "Chemistry of the Opium Alkaloids" in U.S. Public Health Reports Suppl. No. 103 (Washington, 1932).
Properties: Prisms from alcohol, mp 198°. Sol in alcohol, dil acids. Insol in water. uv max: 280 nm (e 1310). LD50 s.c. in mice: 85.7 mg/kg (Eddy, Reid).
Melting point: mp 198°
Absorption maximum: uv max: 280 nm (e 1310)
Toxicity data: LD50 s.c. in mice: 85.7 mg/kg (Eddy, Reid)
 
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C18H21NO3.HCl.H2O
Molecular Weight: 353.84
Percent Composition: C 61.10%, H 6.84%, N 3.96%, O 18.09%, Cl 10.02%
Properties: Crystals, mp 185-186° dec. [a]D27 -130° (c = 2.877). Very sol in water.
Melting point: mp 185-186° dec
Optical Rotation: [a]D27 -130° (c = 2.877)
 
Derivative Type: Bitartrate hemipentahydrate
CAS Registry Number: 34195-34-1
Trademarks: Calmodid; Codinovo; Duodin; Kolikodal; Orthoxycol; Mercodinone; Synkonin; Norgan; Hydrokon
Molecular Formula: C18H21NO3.C4H6O6.2½H2O
Molecular Weight: 494.49
Percent Composition: C 53.44%, H 6.52%, N 2.83%, O 37.21%
Properties: Needles, mp 118-128°. One gram dissolves in 16 ml water, in 150 g 95% ethanol. Almost insol in ether, chloroform. pH of a 2% aq soln about 3.6.
Melting point: mp 118-128°
 
Derivative Type: Hydriodide
Molecular Formula: C18H21NO3.HI
Molecular Weight: 427.28
Percent Composition: C 50.60%, H 5.19%, N 3.28%, O 11.23%, I 29.70%
Properties: mp 219-220°.
Melting point: mp 219-220°
 
Derivative Type: Methiodide
Molecular Formula: C18H21NO3.CH3I
Molecular Weight: 441.30
Percent Composition: C 51.71%, H 5.48%, N 3.17%, O 10.88%, I 28.76%
Properties: mp 250-255°.
Melting point: mp 250-255°
 
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic); antitussive.
Keywords: Analgesic (Narcotic); Antitussive.

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