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embutramide
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Embutramide (INN, USAN, BAN; brand name Embutane) is a potent sedative drug that is structurally related to GHB. It was developed by Hoechst A.G. in 1958 and was investigated as a general anesthetic agent, but was found to have a very narrow therapeutic window, with a 50 mg/kg dose producing effective sedation and a 75 mg/kg dose being fatal. Along with strong sedative effects, embutramide also produces respiratory depression and ventricular arrhythmia. Because of these properties, it was never adopted for medical use as an anesthetic as it was considered too dangerous for this purpo
Chemical data
- Formula
- C17H27NO3
- Molecular weight
- 293.4 g/mol
- IUPAC name
- N-[2-ethyl-2-(3-methoxyphenyl)butyl]-4-hydroxybutanamide
- SMILES
- CCC(CC)(CNC(=O)CCCO)C1=CC(=CC=C1)OC
- InChIKey
- LMBMDLOSPKIWAP-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 58.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 293.199
Show 3 more facts
- Commons category
- Embutramide
- chemical formula
- C₁₇H₂₇NO₃
- canonical SMILES
- CCC(CC)(CNC(=O)CCCO)C1=CC(=CC=C1)OC
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- Chemistry
- Synthesis
- References
Embutramide (INN, USAN, BAN; brand name Embutane) is a potent sedative drug that is structurally related to GHB. It was developed by Hoechst A.G. in 1958 and was investigated as a general anesthetic agent, but was found to have a very narrow therapeutic window, with a 50 mg/kg dose producing effective sedation and a 75 mg/kg dose being fatal. Along with strong sedative effects, embutramide also produces respiratory depression and ventricular arrhythmia. Because of these properties, it was never adopted for medical use as an anesthetic as it was considered too dangerous for this purpose. Instead it is used for euthanasia in veterinary medicine, mainly for the euthanization of dogs.
Embutramide is formulated as a combination product under the brand name Tributame, which also contains chloroquine and lidocaine.
Excerpted from Wikipedia’s “embutramide” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
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