13-00876. Atrolactamide [Archived]

Nomenclature

CAS number: 2019-68-3
α-Hydroxy-α-methylbenzeneacetamide; α-hydroxy-α-phenylpropionamide; 2-hydroxy-2-phenylpropionamide; 2-phenyl-2-hydroxypropionamide; M-144; Themisone (Mallinckrodt).
C9H11NO2; mol wt 165.19.
C 65.44%, H 6.71%, N 8.48%, O 19.37%.

Description and references

Prepd from atrolactic acid by treatment with ammonia water: McKenzie, Smith, J. Chem. Soc. 121, 1356 (1922); from the nitrile by treatment with fuming HCl: Staudinger, Ruzicka, Ann. 380, 291 (1911).

Chemical structure

Derivative

dl-Form.

Properties

Leaflets from dichloroethylene, mp 102°. Freely sol in water.

Derivative

l-Form.

Properties

Leaflets from benzene, mp 62.5-63.5°. [α]D15 +12.8° (c = 2.2 in acetone). Freely sol in water; sol in alcohol, acetone.

Therapeutic Category

Anticonvulsant.

Keywords

Anticonvulsant

Status

This monograph has been retired and is no longer subject to revision or update.