Embutramide

Source: Wikipedia, the free encyclopedia.

Embutramide
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		intravenous
ATC code
  • none
Legal status
Legal status
Identifiers
  • N-[2-ethyl-2-(3-methoxyphenyl)butyl]-4-hydroxybutanamide
JSmol)
  • O=C(NCC(c1cc(OC)ccc1)(CC)CC)CCCO
  • InChI=1S/C17H27NO3/c1-4-17(5-2,13-18-16(20)10-7-11-19)14-8-6-9-15(12-14)21-3/h6,8-9,12,19H,4-5,7,10-11,13H2,1-3H3,(H,18,20) checkY
  • Key:LMBMDLOSPKIWAP-UHFFFAOYSA-N checkY
  (verify)

Embutramide (

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.[citation needed
]

Embutramide is formulated as a

Tributame, which also contains chloroquine and lidocaine.[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,

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.[10]

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

Patents:[11][12] Synthesis:[13]

Alkylation of (3-Methoxyphenyl)acetonitrile [19924-43-7] (1) with

gamma-butyrolactone
completed the synthesis of embutramide (4).

References

  1. ISBN 978-1-4757-2085-3
    .
  2. ISBN 978-0-7514-0499-9
    .
  3. ISBN 978-0-323-24198-4
    .
  4. ^ US 3045043, Schmitt K, Henning I, Lindner E, Ott H, "New gamma-hydroxy-carboxylic acid amides and process for their manufacture", issued 17 July 1962, assigned to Hoechst AG 
  5. ^ "TRIBUTAME Euthanasia Solution" (PDF). Freedom of Information Summary NADA 141-245. U.S. Food and Drug Administration. Archived from the original (PDF) on 4 March 2017.
  6. PMID 2371711
    .
  7. ^ "DEA lists embutramide as schedule III controlled substance". Archived from the original on 8 March 2012.
  8. PMID 2815545
    .
  9. PMID 12423012
    .
  10. PMID 17139797. Archived
    from the original on 29 November 2021. Retrieved 7 August 2020.
  11. ^ Schmitt Karl, et al. U.S. patent 3,045,043 (1962 to Hoechst Ag).
  12. ^ Karl Schmitt, et al. GB1002436 (1965 to Hoechst AG).
  13. ^ "science24.com - Synthesis of embutramide in mild conditions". science24.com. Archived from the original on 19 May 2023. Retrieved 19 May 2023.


Stub icon

This analgesic-related article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Embutramide&oldid=1204967263"