Title: Methadyl Acetate
CAS Registry Number: 509-74-0
CAS Name: b-[2-(Dimethylamino)propyl]-a-ethyl-b-phenylbenzeneethanol acetate (ester)
Additional Names: 6-(dimethylamino)-4,4-diphenyl-3-heptanol acetate (ester); O-acetyl-6-dimethylamino-4,4-diphenyl-3-heptanol; 3-acetoxy-6-dimethylamino-4,4-diphenylheptane; 5-acetoxy-2-dimethylamino-4,4-diphenylheptane; acetylmethadol; acemethadone; amidolacetate; race-acetylmethadol
Molecular Formula: C23H31NO2
Molecular Weight: 353.50
Percent Composition: C 78.15%, H 8.84%, N 3.96%, O 9.05%
Literature References: Congener of methadone, q.v. Prepn of b-dl-form: M. Bockmühl, G. Ehrhart, Ann. 561, 52 (1948); of a-dl-form: M. E. Speeter et al., J. Am. Chem. Soc. 71, 57 (1949); R. L. Clark, US 2565592; US 2668814 (1951, 1954 to Merck & Co.); M. E. Speeter, US 2649445 (1953 to Bristol); of a-d and a-l-forms: A. Pohland et al., J. Am. Chem. Soc. 71, 460 (1949). The a-dl-form is more active and less toxic than the b-dl-form. The a-l-form, levomethadyl acetate, q.v. is less active than the a-d-form but is longer acting. Metabolism of the a-dl-form: R. E. McMahon et al., J. Pharmacol. Exp. Ther. 149, 436 (1965). Analgesic, depressant activity of a-dl-form in mice, rats: N. B. Eddy et al., ibid. 98, 121 (1950); of enantiomers: N. B. Eddy et al., J. Org. Chem. 17, 321 (1952). Comparison of methadone with a-dl-form in the treatment of heroin addiction: J. H. Jaffe et al., J. Am. Med. Assoc. 211, 1834 (1970).
Derivative Type: a-dl-Form hydrochloride
Molecular Formula: C23H32ClNO2
Molecular Weight: 389.96
Percent Composition: C 70.84%, H 8.27%, Cl 9.09%, N 3.59%, O 8.21%
Properties: Crystals from ethyl acetate, mp 213-214°. Sol in water. pH 4-5. LD50 in mice (mg/kg): 61.0 s.c., 118.3 orally (Eddy, 1952).
Melting point: mp 213-214°
Toxicity data: LD50 in mice (mg/kg): 61.0 s.c., 118.3 orally (Eddy, 1952)
Derivative Type: a-dl-Form hydrobromide
Molecular Formula: C23H32BrNO2
Molecular Weight: 434.41
Percent Composition: C 63.59%, H 7.42%, Br 18.39%, N 3.22%, O 7.37%
Properties: Crystals, mp 193-194.5°. Sol in water.
Melting point: mp 193-194.5°
Derivative Type: a-d-Form
Additional Names: Alphacetylmethadol
Derivative Type: a-d-Form hydrochloride
Properties: Crystals from ethanol-ether, mp 215°. [a]D25 +61.2° (c = 0.2). Sol in water. LD50 in mice (mg/kg): 72.2 s.c., 130.4 orally (Eddy, 1952).
Melting point: mp 215°
Optical Rotation: [a]D25 +61.2° (c = 0.2)
Toxicity data: LD50 in mice (mg/kg): 72.2 s.c., 130.4 orally (Eddy, 1952)
Derivative Type: a-l-Form see Levomethadyl Acetate
Derivative Type: b-l-Form
Additional Names: Betacetylmethadol
Derivative Type: b-dl-Form hydrochloride
Properties: Crystals, mp 215-217°. Sol in water. LD50 in mice (mg/kg): 42.0 s.c., 80.2 orally (Eddy, 1952).
Melting point: mp 215-217°
Toxicity data: LD50 in mice (mg/kg): 42.0 s.c., 80.2 orally (Eddy, 1952)
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11. |