2870. Dehydroemetine
Nomenclature
Description and references
Synthetic analog of emetine, q.v.; the (-)-form is therapeutically active. Synthesis of racemic 2,3-dehydroemetine: Brossi et al., Helv. Chim. Acta 42, 772 (1959). Stereospecific synthesis of (±)-form and (±)-2,3-dehydroisoemetine, the (1′β)-isomer: Clark et al., J. Chem. Soc. 1962, 2479. Separation of the four possible isomers: Brossi, Burkhardt, Experientia 18, 211 (1962). Absolute configuration and bioactivity of isomers: A. Brossi et al., Helv. Chim. Acta 45, 2219 (1962). Prepn of pure (-)-form: A. Brossi, BE 629898; eidem, US 3311633 (1963, 1967 both to Hoffmann-La Roche); N. Whittaker J. Chem. Soc. C 1969, 94. Antiprotozoal activity in vitro: G. H. Al-Khateeb et al., Chemotherapy (Basel) 23, 267 (1977). Review of use in amebiasis: G. Woolfe, Prog. Drug Res. 8, 12 (1965).
Properties
Crystals from isopropyl ether, mp 94-96°. [α]D -183°.Derivative
(-)-Form dihydrobromide.Properties
Crystals, mp 243-245°. [α]D -97° (methanol). uv max (alc): 282 nm (ε 7300).Derivative
(+)-Form dihydrobromide.Properties
Crystals, mp 241-243°. [α]D +95° (methanol). uv max (alc): 282 nm (ε 7350).Derivative
(±)-Form dihydrochloride.Nomenclature
Properties
Crystals from ethanol + ether, mp 235°.Derivative
(±)-2,3-Dehydroisoemetine hydrochloride.Properties
Crystals from ethanol + ether, mp 220-225°.Derivative
(-)-2,3-Dehydroisoemetine dihydrobromide.Properties
Crystals, mp 257-260°. [α]D -107° (methanol). uv max (alc): 285 nm (ε 7400).Derivative
(+)-2,3-Dehydroisoemetine dihydrobromide.Properties
Crystals, mp 257-258°. [α]D +109° (methanol). uv max (alc): 285 nm (ε 7450).Therapeutic Category
Antiamebic.
Keywords
Antiamebic