Dehydroemetine
Basic information
- CAS
1986-67-0- Standard SMILES
CCC1=C(C[C@H]2NCCc3cc(OC)c(OC)cc32)C[C@H]2c3cc(OC)c(OC)cc3CCN2C1- InChIKey
XXLZPUYGHQWHRN-RPBOFIJWSA-N- Molecular formula
- C29H38N2O4
- Average molar mass
- 478.6 g/mol
- Monoisotopic mass
- 478.2831577
Overview
Dehydroemetine is a pyridoisoquinoline which was developed in response to the cardiovascular toxicity associated with emetine and results from the dehydrogenation of the heterotricylic ring of emetine. It is an antiprotozoal agent and displays antimalarial, antiamoebic, and antileishmanial properties. It has a role as an antiprotozoal drug, an antimalarial and an antileishmanial agent. It is a member of isoquinolines, an aromatic ether and a pyridoisoquinoline. It derives from a hydride of an emetan.
Names & identifiers
- Preferred name
- Dehydroemetine
- IUPAC
- (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-benzo[a]quinolizine
- English name
- dehydroemetine
- Molecular formula
- C29H38N2O4
- Molecular weight
- 478.62
Names & synonyms
Dehydroemetine4914-30-1Mebadin2-DehydroemetineDehidroemetinaDehydroemetinum(-)-2,3-DehydroemetineBT 4362,3-DidehydroemetineRo 1-9334/19(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-benzo[a]quinolizineNSC-131546
Show more names
Dametin2,3-DEHYDROEMETINEdehydroemetine USP/EP/BPDehydroemetine hydrochlorideDehydroemetine, 10 mM in DMSO4H-Benzo[a]quinolizine, 3-ethyl-1,6,7,11b-tetrahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-, (11bS)-
2,3-Didehydro-6',7',10,11-tetramethoxyemetan7S79QT1T91DTXSID901023600Ro-19334193-Ethyl-9,10-dimethoxy-1,6,7,11b-tetrahydro-2-((1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl)-4H-benzo(a)quinolizineCHEBI:149634RO-1-9334/19NSC131546
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 52.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 744
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 94 · 94-96°
- alpha
- -183 ° · D -183°
- Boiling point
- 604.7 · 604.7±55.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- pka
- 8.86 · 8.86±0.40(Predicted)
- form
- Solid
- color
- Off-white to light yellow
- FDA UNII
- 7 S79QT1T91 · 7S79QT1T91
- ATC code
- 1 AX09 · P01AX09
Chemistry & industry
Pharmacology
ATC CodeP - Antiparasitic products, insecticides and repellents
Applications
UsesDehydroemetine is an orally active antiparasitic agent. Dehydroemetine can inhibit parasites such as Entamoeba histolytica, and it can also be used in the research of parasitic diseases like visceral leishmaniasis[1][2][3].
Additional notes
DefinitionChEBI: Dehydroemetine is a pyridoisoquinoline which was developed in response to the cardiovascular toxicity associated with emetine and results from the dehydrogenation of the heterotricylic ring of emetine. It is an antiprotozoal agent and displays antimalarial, antiamoebic, and antileishmanial properties. It has a role as an antiprotozoal drug, an antimalarial and an antileishmanial agent. It is a member of isoquinolines, an aromatic ether and a pyridoisoquinoline. It derives from a hydride of an emetan.
Related reactions
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Compound notes
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