12-05984. Metamfepramone [Archived]
Nomenclature
CAS number: 15351-09-4
2-(Dimethylamino)-1-phenylpropanone; 2-(dimethylamino)propiophenone; benzoyl-α-(dimethylamino)ethane; α-(dimethylamino)propiophenone; metamfepyramone; N-methylephedrone; dimepropion. C11H15NO; mol wt 177.24.
C 74.54%, H 8.53%, N 7.90%, O 9.03%.
Description and references
Prepn from 2-bromopropiophenone and dimethylamine: Thomson, Stevens, J. Chem. Soc. 1932, 1932; from N,N-dimethyl-2-(dimethylamino)propionamide and phenylmagnesium bromide: Eidebenz, Arch. Pharm. 280, 49 (1942); from α-acetylbenzyl alcohol and dimethylamine: Iwao et al., J. Pharm. Soc. Jpn. 74, 551 (1954). Prepn of d-form: Freudenberg, Nikolai, Ann. 510, 223 (1934). Resolution of dl-form: Takamatsu, J. Pharm. Soc. Jpn. 76, 1219 (1956).
Derivative
dl-Form.Properties
bp13 126°.Derivative
dl-Form hydrochloride.Nomenclature
Effilone.C11H15NO.HCl; mol wt 213.70.
C 61.82%, H 7.55%, N 6.55%, O 7.49%, Cl 16.59%.
Properties
Crystals, mp 202-204° (Iwao) also reported as dec 201-202° (Eidebenz).Derivative
l-Form.Properties
[α]D26 60°.Derivative
l-Form hydrochloride.Properties
Prisms, mp 197-199°. [α]D26 52.5°.Therapeutic Category
Anorexic.
Keywords
Anorexic
Status
This monograph has been retired and is no longer subject to revision or update.