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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 447764085
| Verifiedfields = changed
| Watchedfields = changed
⚫ | verifiedrevid = 399924353
| IUPAC_name = ''N''-ethyl-''N''-methyl-4,4-dithiophen-2-yl-but-3-en-2-amine | IUPAC_name = ''N''-ethyl-''N''-methyl-4,4-dithiophen-2-yl-but-3-en-2-amine
| image = Ethylmethylthiambutene structure.svg | image = Ethylmethylthiambutene structure.svg
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| pregnancy_category = | pregnancy_category =
| legal_AU = | legal_AU =
| legal_CA = | 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=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I
| legal_US = Schedule I | legal_US = Schedule I
| legal_status = | legal_DE = Anlage I
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
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| ATC_suffix = | ATC_suffix =
| PubChem = 46424 | PubChem = 46424
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01468 | DrugBank = DB01468
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 42256 | ChemSpiderID = 42256
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 722BFZ899Q | UNII = 722BFZ899Q
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D12663


<!--Chemical data--> <!--Chemical data-->
| C=15 | H=19 | N=1 | S=2 | C=15 | H=19 | N=1 | S=2
| molecular_weight = 277.45 g/mol
| smiles = CCN(C)C(C)C=C(C1=CC=CS1)C2=CC=CS2 | smiles = CCN(C)C(C)C=C(C1=CC=CS1)C2=CC=CS2
| InChI = 1/C15H19NS2/c1-4-16(3)12(2)11-13(14-7-5-9-17-14)15-8-6-10-18-15/h5-12H,4H2,1-3H3
| InChIKey = MORSAEFGQPDBKM-UHFFFAOYAM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C15H19NS2/c1-4-16(3)12(2)11-13(14-7-5-9-17-14)15-8-6-10-18-15/h5-12H,4H2,1-3H3 | StdInChI = 1S/C15H19NS2/c1-4-16(3)12(2)11-13(14-7-5-9-17-14)15-8-6-10-18-15/h5-12H,4H2,1-3H3
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}} }}


'''Ethylmethylthiambutene''' (''N''-ethyl-''N''-methyl-1-methyl-3,3-di-2-thienylallylamine, Emethibutin) is an ] ] drug from the ] family, around 1.3x the potency of ].<ref>{{cite journal | last1 = Adamson | first1 = DW | last2 = Green | first2 = AF | title = A new series of analgesics | journal = Nature | volume = 165 | issue = 4186 | pages = 122–122 | year = 1950 | pmid = 15409854 | doi = 10.1038/165122a0 }}</ref><ref>{{cite journal | last1 = Adamson | first1 = DW | last2 = Duffin | first2 = WM | last3 = Green | first3 = AF | title = Dithienylbutylamines as analgesics | journal = Nature | volume = 167 | issue = 4239 | pages = 153–4 | year = 1951 | pmid = 14806409 | doi = 10.1038/167153b0 }}</ref><ref>{{cite journal | last1 = Green | first1 = AF | title = Analgesic and other properties of 3: 3-dithienylalkenylamines | journal = British journal of pharmacology and chemotherapy | volume = 8 | issue = 1 | pages = 2–9 | year = 1953 | pmid = 13066683 | pmc = 1509239 }}</ref> It is under international control under Schedule I of the UN Single Convention On Narcotic Drugs 1961, presumably due to high abuse potential. '''Ethylmethylthiambutene''' ({{not a typo|''N''-ethyl-''N''-methyl-1-methyl-3,3-di-2-thienylallylamine}}; '''Emethibutin''') is an ] ] drug from the ] family, around 1.3x the potency of ].<ref>{{cite journal | vauthors = Adamson DW, Green AF | s2cid = 4190157 | title = A new series of analgesics | journal = Nature | volume = 165 | issue = 4186 | pages = 122 | date = January 1950 | pmid = 15409854 | doi = 10.1038/165122a0 | bibcode = 1950Natur.165..122A | doi-access = free }}</ref><ref>{{cite journal | vauthors = Adamson DW, Duffin WM, Green AF | s2cid = 4280042 | title = Dithienylbutylamines as analgesics | journal = Nature | volume = 167 | issue = 4239 | pages = 153–4 | date = January 1951 | pmid = 14806409 | doi = 10.1038/167153b0 | bibcode = 1951Natur.167..153A }}</ref><ref>{{cite journal | vauthors = Green AF | title = Analgesic and other properties of 3: 3-dithienylalkenylamines | journal = British Journal of Pharmacology and Chemotherapy | volume = 8 | issue = 1 | pages = 2–9 | date = March 1953 | pmid = 13066683 | pmc = 1509239 | doi = 10.1111/j.1476-5381.1953.tb00739.x }}</ref> It is under international control under Schedule I of the UN Single Convention On Narcotic Drugs 1961, presumably due to high abuse potential.
It is a Schedule I controlled substance in the United States with a DEA ACSCN of 9623 and zero annual manufacturing quota as of 2013.{{citation needed|date=June 2014}}


==References== == References ==
{{Reflist}} {{Reflist}}

{{Analgesics}}
{{Opioidergics}}


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