Ethinamate: Difference between revisions

{{Short description|Pharmaceutical drug}}

| verifiedrevid = 443740995

| image = Ethinamate structure.svg

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|CONS|ethinamate}}

| pregnancy_category =

| legal_BR = B1

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>

| legal_CA = Schedule IV

| legal_US = Schedule IV

| legal_DE = Anlage II

| legal_UK = Class C

| legal_status = Rx-only

| routes_of_administration = Oral

<!--Pharmacokinetic data-->

| bioavailability =

| metabolism =

| elimination_half-life =

<!--Identifiers-->

| IUPHAR_ligand = 7325

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

| CAS_number = 126-52-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 3284

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

| DrugBank = DB01031

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

| KEGG = D00703

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 4884

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1576

<!--Chemical data-->

| C=9 | H=13 | N=1 | O=2

'''Ethinamate''' ('''Valamin''', '''Valmid''') is a short-acting [[carbamate]]-derivative [[sedative-hypnotic]] [[medication]] used to treat [[insomnia]]. Regular use leads to [[drug tolerance]], and it is usually not effective for more than 7 days. Prolonged use can lead to [[Substance dependence|dependence]].{{fact|date=December 2018}}

Ethinamate has been replaced by other medicines (particularly [[benzodiazepine]]s), and it is not available in the [[Netherlands]], the [[United States]] or [[Canada]].{{fact|date=December 2018}}

It is a [[Controlled_Substances_Act#Schedule_IV_controlled_substances|schedule IV]] substance in the United States.<ref>{{cite book | vauthors = Lowry WT, Garriot JC | chapter = Ethinamate | chapter-url = https://books.google.com/books?id=szDnBwAAQBAJ&dq=Ethinamate&pg=PA215 |title=Forensic Toxicology: Controlled Substances and Dangerous Drugs |date=1979 |publisher=Springer US |location=Boston, MA |isbn=978-1-4684-3444-6 | page = 215 }}</ref>

==Synthesis==

Ethinamate (1-ethynylcyclohexanone carbamate) is synthesized by combining [[acetylene]] with [[cyclohexanone]] to make [[1-ethynylcyclohexanol]], and then transforming this into a [[carbamate]] by the subsequent reaction with [[phosgene]], and later with [[ammonia]]. Some lithium metal or similar is used to make the acetylene react with the cyclohexanone in the first step.<ref>{{cite patent | country = US | number = 2816910 | title = Esters of carbamic acid and a method of making same | gdate = 17 December 1957 | inventor = Pfeiffer H, Junkman K | assign1 = Schering AG }}</ref><ref>{{cite patent| country = DE | number = 1021843 | title = Verfahren zur Herstellung des Allophanats des 1-AEthinylcyclohexanols-(1) | gdate = 2 January 1958 | inventor = Emde H, Grimme W | assign1 = Rheinpreussen AG }}</ref>

:[[File:Ethinamate synthesis.png|500px]]

{{GABAAR PAMs}}

[[Category:Ethynyl compounds]]

[[Category:GABAA receptor positive allosteric modulators]]