{{Short description|Chemical compound}} {{Drugbox | verifiedrevid = 447763951 | IUPAC_name = (''RS'')-''N'',''N''-dimethyl-4,4-dithiophen-2-yl-but-3-en-2-amine | image = Dimethylthiambutene structure.svg | image_class = skin-invert-image | width = 150 | image2 = DMTB_3D.png | image_class2 = bg-transparent | width2 = 150
<!--Clinical data--> | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_BR = A1 | 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 I | legal_US = Schedule I | legal_DE = Anlage I | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 524-84-5 | ATC_prefix = none | ATC_suffix = | PubChem = 10668 | ChEMBL = 2106265 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01444 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10218 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 915D88LM9O | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 59781 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D12665
<!--Chemical data--> | C=14 | H=17 | N=1 | S=2 | smiles = CC(C=C(C1=CC=CS1)C2=CC=CS2)N(C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C14H17NS2/c1-11(15(2)3)10-12(13-6-4-8-16-13)14-7-5-9-17-14/h4-11H,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CANBGVXYBPOLRR-UHFFFAOYSA-N | melting_point = 169 | melting_high = 170 }}
'''Dimethylthiambutene''' (''N'',''N''-Dimethyl-1-methyl-3,3-di-2-thienylallylamine, '''DMTB''', trade names '''Ohton, Aminobutene, Dimethibutin, Kobaton, Takaton, Dimethibutin''') is an opioid analgesic drug, most often used in veterinary medicine in Japan and to a lesser extent in other countries in the region and around the world. It is the most prominent and widely used of the thiambutenes, a series of open-chain opioids structurally related to methadone which are also called the thienyl derivative opioids which also includes diethylthiambutene and ethylmethylthiambutene, as well as the non-opioid cough suppressant tipepidine.
Dimethylthiambutene was developed in the United Kingdom in the late 1940s and introduced to the market by Burroughs-Wellcome in 1951. Dimethylthiambutene is now under international control under the UN Single Convention on Narcotic Drugs 1961, the laws governing habit-forming substances in virtually all countries and Schedule I of the US Controlled Substances Act of 1970 due to high abuse potential and never being introduced clinically in the United States; other countries regulate it much as morphine or diamorphine. Its DEA ACSCN is 9619 and it had a zero manufacturing quota in 2013. ==Synthesis== class=skin-invert-image|thumb|500px|center|Synthesis:<ref>{{cite journal | vauthors = Adamson DW | title = 180. Aminoalkyl tertiary carbinols and derived products. Part II. 3-Amino-1: 1-di-2′-thienyl-alkan-1-ols and-alk-1-enes. | journal = Journal of the Chemical Society (Resumed) | date = 1950 | pages = 885–890 | doi = 10.1039/JR9500000885 }}</ref> Patent:<ref>{{cite patent | inventor = Wallace AD | country = US | number = 2561899 | gdate = 1951 | assign1 = Burroughs Wellcome Co | postscript = . }}</ref>
The conjugate addition between Ethyl crotonate [623-70-1][10544-63-5] ('''1''') and dimethylamine gives Ethyl 3-(Dimethylamino)Butanoate [85118-28-1] ('''2'''). Grignard reaction with 2-Bromothiophene [1003-09-4] ('''3''') gives ('''4'''). Dehydration in acid completed the synthesis ('''5''').
==See also== *Diethylthiambutene *Tipepidine
==References== {{Reflist|2}}
{{Analgesics}} {{Opioidergics}}
Category:Synthetic opioids Category:Thiophenes Category:Dimethylamino compounds Category:Mu-opioid receptor agonists