embutramide

{{Short description|Chemical compound}}

{{Use dmy dates|date=May 2023}}

{{Drugbox

| verifiedrevid = 448000423

| IUPAC_name = N-[2-ethyl-2-(3-methoxyphenyl)butyl]-4-hydroxybutanamide

| image = Embutramide2DCSD.svg

| width = 280px

| image2 = Embutramide3DanJ.gif

| width2 = 300px

| tradename = Embutane

| Drugs.com = {{drugs.com|international|embutramide}}

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Schedule III

| legal_status =

| routes_of_administration = intravenous

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 15687-14-6

| ATC_prefix = none

| ATC_suffix =

| PubChem = 27453

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01487

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 25547

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3P4TQG94T1

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03984

| C=17 | H=27 | N=1 | O=3

| smiles = O=C(NCC(c1cc(OC)ccc1)(CC)CC)CCCO

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LMBMDLOSPKIWAP-UHFFFAOYSA-N

}}

Embutramide (INN, USAN, BAN; brand name Embutane) is a potent sedative drug that is structurally related to GHB.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA482|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=482–}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=mqaOMOtk61IC&pg=PA108|date=31 October 1999|publisher=Springer Science & Business Media|isbn=978-0-7514-0499-9|pages=108–}}{{cite book| vauthors = Peterson ME, Talcott PA |title=Small Animal Toxicology|url=https://books.google.com/books?id=BLkPFlB15v0C&pg=PA315|date=7 August 2013|publisher=Elsevier Health Sciences|isbn=978-0-323-24198-4|pages=315–}} It was developed by Hoechst A.G. in 1958{{cite patent | country = US | number = 3045043 | title = New gamma-hydroxy-carboxylic acid amides and process for their manufacture | inventor = Schmitt K, Henning I, Lindner E, Ott H | assign1 = Hoechst AG | gdate = 17 July 1962 }} 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.{{cn|date=February 2022}}

Embutramide is formulated as a combination product under the brand name Tributame, which also contains chloroquine and lidocaine.{{cite web | title = TRIBUTAME Euthanasia Solution | work = Freedom of Information Summary NADA 141-245 | url = https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051493.pdf | archive-url = https://web.archive.org/web/20170304100411/https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051493.pdf | archive-date = 4 March 2017 | publisher = U.S. Food and Drug Administration }}

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,{{cite journal | vauthors = Hellebrekers LJ, Baumans V, Bertens AP, Hartman W | title = [The use of T61 for the humane killing of pets and laboratory animals] | language = nl, nl-be | journal = Tijdschrift voor Diergeneeskunde | volume = 115 | issue = 13 | pages = 625–32 | date = July 1990 | pmid = 2371711 }} 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.{{cite web | url = http://www.avma.org/onlnews/javma/nov06/061101b.asp | title = DEA lists embutramide as schedule III controlled substance | archive-url = https://web.archive.org/web/20120308062857/http://www.avma.org/onlnews/javma/nov06/061101b.asp | archive-date = 8 March 2012 }} Embutramide has however been reported to be used for suicide by people with access to the drug,{{cite journal | vauthors = Smith RA, Lewis D | title = Suicide by ingestion of T-61 | journal = Veterinary and Human Toxicology | volume = 31 | issue = 4 | pages = 319–20 | date = August 1989 | pmid = 2815545 }}{{cite journal | vauthors = Kintz P, Cirimele V, Ludes B | title = Blood investigation in a fatality involving the veterinary drug T-61 | journal = Journal of Analytical Toxicology | volume = 26 | issue = 7 | pages = 529–31 | date = October 2002 | pmid = 12423012 | doi = 10.1093/jat/26.7.529 | doi-access = free }} 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.{{cite journal | title = DEA lists embutramide as schedule III controlled substance | journal = Journal of the American Veterinary Medical Association | volume = 229 | issue = 9 | pages = 1358 | date = November 2006 | pmid = 17139797 | url = https://www.avma.org/javma-news/2006-11-01/dea-lists-embutramide-schedule-iii-controlled-substance | access-date = 7 August 2020 | archive-date = 29 November 2021 | archive-url = https://web.archive.org/web/20211129022310/https://www.avma.org/javma-news/2006-11-01/dea-lists-embutramide-schedule-iii-controlled-substance | url-status = live }}