13-03539. Ectylurea [Archived]

Nomenclature

CAS number: 95-04-5
(Z)-N-(Aminocarbonyl)-2-ethyl-2-butenamide; (2-ethylcrotonoyl)urea; (α-ethylcrotonyl)urea; (α-ethylcrotonyl)carbamide; Astyn; Ektyl; Levanil (Upjohn); Nostal (Ames); Nostyn (Ames); Cronil (Farmigea); Neuroprocin; Pacetyn.
C7H12N2O2; mol wt 156.18.
C 53.83%, H 7.74%, N 17.94%, O 20.49%.

Description and references

Prepd by treating (2-bromo-2-ethylbutyryl)urea with dil boiling NaOH: Newbery, J. Chem. Soc. 127, 295 (1925). Prepn from carbromal and isopropanol by refluxing with silver oxide: Fancher, US 2854379, US 2931832 (1958, 1960 to Miles Labs.). Pharmacology and toxicity: M. H. Pindell et al., Fed. Proc. 12, 357 (1953).

Chemical structure

Properties

Needles from benzene, mp 198°, also reported as mp 191-193° (lower melting form, mp 158°). Very slightly sol in ether, hot alcohol, other organic solvents. Sol in concd aq solns of alkalies and acids. LD50 in rats (mg/kg): 2500 orally; 900 i.p. (Pindell).

Therapeutic Category

Sedative; hypnotic.

Keywords

Sedative/Hypnotic; Acylic Ureides

Status

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