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.
Dehydroepiandrosterone Dehydroergosterol Delapril Delavirdine Delmadinone Acetate

Dehydroemetine
Dehydroemetine.png
Systematic (IUPAC) name
(11bS)-2-[[(1R)-6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-4,6,7,11b-tetrahydro-1H-pyrido[2,1-a]isoquinoline
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 4914-30-1 YesY
ATC code P01AX09
PubChem CID 21022
ChemSpider 19773 N
UNII 7S79QT1T91 N
KEGG D00828 YesY
ChEMBL CHEMBL547470 N
Chemical data
Formula C29H38N2O4 
Mol. mass 478.62 g/mol
 N (what is this?)  (verify)

Dehydroemetine is a synthetically produced antiprotozoal agent similar to emetine in its anti-amoebic properties and structure (they differ only in a double bond next to the ethyl substituent), but it produces fewer side effects. In the United States, it is manufactured by Roche.