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| Trade names | Embutane |
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| Routes of administration | intravenous |
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| ECHA InfoCard | 100.036.149 |
| Chemical and physical data | |
| Formula | C17H27NO3 |
| Molar mass | 293.407 g·mol−1 |
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Embutramide (INN,USAN,BAN; brand nameEmbutane) is a potentsedativedrug that is structurally related toGHB.[1][2][3] It was developed byHoechst A.G. in 1958[4] and was investigated as ageneral 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 strongsedative effects, embutramide also producesrespiratory depression andventricular 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 foreuthanasia inveterinary medicine, mainly for the euthanization of dogs.[citation needed]
Embutramide is formulated as acombination product under the brand nameTributame, which also containschloroquine andlidocaine.[5]
Embutramide is used for euthanasia of a range of different animals, mainly small animals kept as pets rather than large farm animals. It may cause significant pain to the animal being euthanized,[6] and so may be less humane than older drugs used for this purpose such aspentobarbital; however, it may have less abuse potential than barbiturates especially in the Tributame combination formulation, and so is less likely to be diverted for recreational abuse.[7] Embutramide has however been reported to be used forsuicide by people with access to the drug,[8][9] and was added to thelist of Schedule III drugs in the US in 2006, as a Non-Narcotic with ACSCN 2020, which classifies it with depressants such as benzodiazepines, barbiturates, and other sedative-hypnotics.[10]
Embutramide is considered an analog ofgamma-hydroxybutyrate (GHB) due to its structural similarity to this naturally occurring neurotransmitter. GHB is known for its medical applications, such as treating narcolepsy and alcohol withdrawal symptoms. However, its recreational use has led to its classification as a controlled substance in many countries. The analog status of embutramide is significant in terms of its regulation and controlled use to prevent any potential misuse or abuse.
Alkylation of (3-methoxyphenyl)acetonitrile (1) withbromoethane gives 2-ethyl-2-(3-methoxyphenyl)butanenitrile (2).Sodium borohydride is used to reduce the nitrile group to give 2-ethyl-2-(3-methoxyphenyl)butan-1-amine (3). Amide formation via reaction withgamma-butyrolactone (GBL) completes the synthesis of embutramide (4).
