Isomethadone
Title: Isomethadone
CAS Registry Number: 466-40-0
CAS Name: 6-(Dimethylamino)-5-methyl-4,4-diphenyl-3-hexanone
Additional Names: 6-dimethylamino-4,4-diphenyl-5-methyl-3-hexanone; 1-dimethylamino-2-methyl-3,3-diphenyl-4-hexanone; isoamidone
Trademarks: Isoadanone
Molecular Formula: C21H27NO
Molecular Weight: 309.45
Percent Composition: C 81.51%, H 8.79%, N 4.53%, O 5.17%
Literature References: Prepn of dl-form: Easton et al., J. Am. Chem. Soc. 70, 76 (1948); Walton et al., J. Chem. Soc. 1949, 648; Larsen, Tullar, US 2773901 (1956 to Sterling Drug). Prepn of d- and l-forms and resolution of dl-form: Larsen et al., J. Am. Chem. Soc. 70, 4194 (1948); Howe, Sletzinger, ibid. 71, 2935 (1949); Larsen, Tullar, loc. cit. Configuration of l-form, the isomer with greater analgesic activity: Beckett et al., Chem. Ind. (London) 1960, 1418. Pharmacology: Eddy et al., J. Pharmacol. Exp. Ther. 98, 121 (1950); Winter, Flataker, ibid. 305.
 
Derivative Type: dl-Form
CAS Registry Number: 116836-09-0
Properties: Slightly yellow, very viscous liq, bp12 215°.
Boiling point: bp12 215°
 
Derivative Type: dl-Form hydrobromide
Molecular Formula: C21H27NO.HBr
Molecular Weight: 390.36
Percent Composition: C 64.61%, H 7.23%, N 3.59%, O 4.10%, Br 20.47%
Properties: Crystals from water, mp 149-150°.
Melting point: mp 149-150°
 
Derivative Type: d-Form
CAS Registry Number: 26594-41-2
Properties: Oil, [a]D25 +20.8°.
Optical Rotation: [a]D25 +20.8°
 
Derivative Type: d-Form hydrochloride
CAS Registry Number: 63814-06-2
Molecular Formula: C21H27NO.HCl
Molecular Weight: 345.91
Percent Composition: C 72.92%, H 8.16%, N 4.05%, O 4.63%, Cl 10.25%
Properties: mp 231-232°. [a]D25 +70°.
Melting point: mp 231-232°
Optical Rotation: [a]D25 +70°
 
Derivative Type: d-Form hydrochloride monohydrate
Molecular Formula: C21H27NO.HCl.H2O
Molecular Weight: 363.92
Percent Composition: C 69.31%, H 8.31%, N 3.85%, O 8.79%, Cl 9.74%
Properties: mp 176-177°. [a]D25 +66°.
Melting point: mp 176-177°
Optical Rotation: [a]D25 +66°
 
Derivative Type: l-Form
CAS Registry Number: 561-10-4
Trademarks: Liden
Properties: Oily liq, bp0.6 162-165°. [a]D25 -20° (c = 1.5 in 95% ethanol).
Boiling point: bp0.6 162-165°
Optical Rotation: [a]D25 -20° (c = 1.5 in 95% ethanol)
 
Derivative Type: l-Form hydrobromide
Properties: Crystals, mp 217-218°. [a]D25 -59° (c = 1.5).
Melting point: mp 217-218°
Optical Rotation: [a]D25 -59° (c = 1.5)
 
Derivative Type: l-Form hydrochloride
CAS Registry Number: 7487-81-2
Properties: mp 231-233°. [a]D25 -70° (c = 1.5 in water), -90° (methanol). Sol in water, alcohol. pH of 1% aq soln: 5 to 6.5. Solutions and tablets are stable. LD50 s.c. in mice: 21 mg/kg (Winter, Flataker).
Melting point: mp 231-233°
Optical Rotation: [a]D25 -70° (c = 1.5 in water), -90° (methanol)
Toxicity data: LD50 s.c. in mice: 21 mg/kg (Winter, Flataker)
 
Derivative Type: l-Form hydrochloride monohydrate
Properties: mp 173-174°.
Melting point: mp 173-174°
 
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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