5184. Isomethadone
Nomenclature
CAS number: 466-40-0
6-(Dimethylamino)-5-methyl-4,4-diphenyl-3-hexanone; 6-dimethylamino-4,4-diphenyl-5-methyl-3-hexanone; 1-dimethylamino-2-methyl-3,3-diphenyl-4-hexanone; isoamidone. C21H27NO; mol wt 309.45.
C 81.51%, H 8.79%, N 4.53%, O 5.17%.
Description and references
Synthetic opioid analgesic. 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
dl-Form.Nomenclature
CAS number: 116836-09-0
Properties
Slightly yellow, very viscous liq, bp12 215°.Derivative
dl-Form hydrobromide.C21H27NO.HBr; mol wt 390.36.
C 64.61%, H 7.23%, N 3.59%, O 4.10%, Br 20.47%.
Properties
Crystals from water, mp 149-150°.Derivative
d-Form.Nomenclature
CAS number: 26594-41-2
Properties
Oil, [α]D25 +20.8°.Derivative
d-Form hydrochloride.Nomenclature
CAS number: 63814-06-2
C21H27NO.HCl; mol wt 345.91.
C 72.92%, H 8.16%, N 4.05%, O 4.63%, Cl 10.25%.
Properties
mp 231-232°. [α]D25 +70°.Derivative
d-Form hydrochloride monohydrate.C21H27NO.HCl.H2O; mol wt 363.92.
C 69.31%, H 8.31%, N 3.85%, O 8.79%, Cl 9.74%.
Properties
mp 176-177°. [α]D25 +66°.Derivative
l-Form.Nomenclature
CAS number: 561-10-4
Properties
Oily liq, bp0.6 162-165°. [α]D25 20° (c = 1.5 in 95% ethanol).Derivative
l-Form hydrobromide.Properties
Crystals, mp 217-218°. [α]D25 59° (c = 1.5).Derivative
l-Form hydrochloride.Nomenclature
CAS number: 7487-81-2