Dehydroemetine
Title: Dehydroemetine
CAS Registry Number: 4914-30-1
CAS Name: 2,3-Didehydro-6¢,7¢,10,11-tetramethoxyemetan
Additional Names: 2,3-dehydroemetine; 2-dehydroemetine
Molecular Formula: C29H38N2O4
Molecular Weight: 478.62
Percent Composition: C 72.77%, H 8.00%, N 5.85%, O 13.37%
Literature 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¢b)-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°. [a]D -183°.
Melting point: mp 94-96°
Optical Rotation: [a]D -183°
 
Derivative Type: (-)-Form dihydrobromide
Molecular Formula: C29H38N2O4.2HBr
Molecular Weight: 640.45
Percent Composition: C 54.39%, H 6.30%, N 4.37%, O 9.99%, Br 24.95%
Properties: Crystals, mp 243-245°. [a]D -97° (methanol). uv max (alc): 282 nm (e 7300).
Melting point: mp 243-245°
Optical Rotation: [a]D -97° (methanol)
Absorption maximum: uv max (alc): 282 nm (e 7300)
 
Derivative Type: (+)-Form dihydrobromide
Properties: Crystals, mp 241-243°. [a]D +95° (methanol). uv max (alc): 282 nm (e 7350).
Melting point: mp 241-243°
Optical Rotation: [a]D +95° (methanol)
Absorption maximum: uv max (alc): 282 nm (e 7350)
 
Derivative Type: (±)-Form dihydrochloride
CAS Registry Number: 14358-43-1
Trademarks: Mebadin (Glaxo)
Molecular Formula: C29H38N2O4.2HCl
Molecular Weight: 551.54
Percent Composition: C 63.15%, H 7.31%, N 5.08%, O 11.60%, Cl 12.86%
Properties: Crystals from ethanol + ether, mp 235°.
Melting point: mp 235°
 
Derivative Type: (±)-2,3-Dehydroisoemetine hydrochloride
Properties: Crystals from ethanol + ether, mp 220-225°.
Melting point: mp 220-225°
 
Derivative Type: (-)-2,3-Dehydroisoemetine dihydrobromide
Molecular Formula: C29H38N2O4.2HBr
Molecular Weight: 640.45
Percent Composition: C 54.39%, H 6.30%, N 4.37%, O 9.99%, Br 24.95%
Properties: Crystals, mp 257-260°. [a]D -107° (methanol). uv max (alc): 285 nm (e 7400).
Melting point: mp 257-260°
Optical Rotation: [a]D -107° (methanol)
Absorption maximum: uv max (alc): 285 nm (e 7400)
 
Derivative Type: (+)-2,3-Dehydroisoemetine dihydrobromide
Properties: Crystals, mp 257-258°. [a]D +109° (methanol). uv max (alc): 285 nm (e 7450).
Melting point: mp 257-258°
Optical Rotation: [a]D +109° (methanol)
Absorption maximum: uv max (alc): 285 nm (e 7450)
 
Therap-Cat: Antiamebic.
Keywords: Antiamebic.

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