Surf Wiki
Save to docs
general/anesthetics

From Surf Wiki (app.surf) — the open knowledge base

Embutramide

Potent opioid used in euthanasia

Embutramide

Potent opioid used in euthanasia

| Drugs.com =

| elimination_half-life =

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.

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, and so may be less humane than older drugs used for this purpose such as pentobarbital; 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. Embutramide has however been reported to be used for suicide by people with access to the drug, and was added to the list 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.

Chemistry

Embutramide is considered an analog of gamma-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.

Synthesis

url-status=live}}</ref>

Alkylation of (3-methoxyphenyl)acetonitrile (1) with bromoethane 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 with gamma-butyrolactone (GBL) completes the synthesis of embutramide (4).

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. (31 October 1999). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Science & Business Media.
  3. (7 August 2013). "Small Animal Toxicology". Elsevier Health Sciences.
  4. "New gamma-hydroxy-carboxylic acid amides and process for their manufacture".
  5. "TRIBUTAME Euthanasia Solution". U.S. Food and Drug Administration.
  6. (July 1990). "[The use of T61 for the humane killing of pets and laboratory animals]". Tijdschrift voor Diergeneeskunde.
  7. "DEA lists embutramide as schedule III controlled substance".
  8. (August 1989). "Suicide by ingestion of T-61". Veterinary and Human Toxicology.
  9. (October 2002). "Blood investigation in a fatality involving the veterinary drug T-61". Journal of Analytical Toxicology.
  10. (November 2006). "DEA lists embutramide as schedule III controlled substance". Journal of the American Veterinary Medical Association.
  11. Schmitt Karl, et al. {{US patent. 3045043 (1962 to Hoechst Ag).
  12. Karl Schmitt, et al. GB1002436 (1965 to Hoechst AG).
  13. "science24.com - Synthesis of embutramide in mild conditions".
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

anesthetics hypnotics sedatives 3-methoxyphenyl-compounds carboxamides primary-alcohols opioids
Want to explore this topic further?

Ask Mako anything about Embutramide — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report