Structural Formula Vector Image
Title: Diacetylmorphine
CAS Registry Number: 561-27-3
CAS Name: (5a,6a)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester)
Additional Names: heroin; diamorphine; acetomorphine
Molecular Formula: C21H23NO5
Molecular Weight: 369.41
Percent Composition: C 68.28%, H 6.28%, N 3.79%, O 21.66%
Literature References: Narcotic analgesic prepared from morphine and acetic anhydride: O. Hesse, Ann. 220, 203 (1883); from morphine and acetyl chloride: Small, Lutz, Chemistry of the Opium Alkaloids, Supplement No. 103, Public Health Reports, Washington (1932); K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954). Comparison with acetylmorphine: N. B. Eddy, H. A. Howes, J. Pharmacol. Exp. Ther. 53, 430 (1935). Pharmacodynamics: J. G. Umans, C. E. Inturrisi, ibid. 218, 409 (1981). Toxicity: eidem, Eur. J. Pharmacol. 85, 317 (1982). Vapor pressure studies: A. H. Lawrence et al., Can. J. Chem. 42, 1886 (1984). Comprehensive description: D. K. Wyatt, L. T. Grady, Anal. Profiles Drug Subs. 10, 357-403 (1981).
Properties: Orthorhombic plates, tablets from ethyl acetate. mp 173°. bp12 272-274°. [a]D25 -166° (c = 1.49 in methanol). One gram dissolves in 1.5 ml chloroform, 31 ml alcohol, 100 ml ether, 1700 ml water. Slightly sol in ammonia or sodium carbonate soln, sol in alkalies, dec by boiling with water. Turns pink and emits acetic odor on prolonged exposure to air. LD50 i.v. in mice: 59 mmol/kg (Umans, Inturrisi).
Melting point: mp 173°
Boiling point: bp12 272-274°
Optical Rotation: [a]D25 -166° (c = 1.49 in methanol)
Toxicity data: LD50 i.v. in mice: 59 mmol/kg (Umans, Inturrisi)
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C21H23NO5.HCl.H2O
Molecular Weight: 423.89
Percent Composition: C 59.50%, H 6.18%, N 3.30%, O 22.65%, Cl 8.36%
Properties: Fine crystals, mp 243-244°. [a]D24 -156° (c = 1.044). Sol in 2 parts water, 11 parts alcohol. Insol in ether.
Melting point: mp 243-244°
Optical Rotation: [a]D24 -156° (c = 1.044)
Derivative Type: Methyl iodide
Molecular Formula: C21H23NO5.CH3I
Molecular Weight: 511.35
Percent Composition: C 51.67%, H 5.12%, N 2.74%, O 15.64%, I 24.82%
Properties: Needles, mp 252°, [a]D15 -107° (c = 0.896).
Melting point: mp 252°
Optical Rotation: [a]D15 -107° (c = 0.896)
NOTE: "China White" has been used as a term for very pure Southeast Asian heroin. This term has also been erroneously used to refer to 3-methylfentanyl and a-methylfentanyl, q.v., which are potent derivs of fentanyl, q.v. See: S. Stinson, Chem. Eng. News 59, 71 (Jan. 19, 1981).
NOTE: This is a controlled substance (opium derivative): 21 CFR, 1308.11.

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