Ethylmethylthiambutene: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{Drugbox		{{Drugbox
	\| verifiedrevid = 447764085		\| verifiedrevid = 447764085
	\| 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
			\| image_class = skin-invert-image
	\| width = 140		\| width = 140

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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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	\| UNII_Ref = {{fdacite\|correct\|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}}

	]		]
	]		]
	]		]
	]		]

⚫	{{analgesic-stub}}

		⚫	{{analgesic-stub}}
	]

Latest revision as of 01:52, 11 January 2025

Chemical compound Pharmaceutical compound

Ethylmethylthiambutene
Clinical data

ATC code	none
Legal status
Legal status	BR: Class A1 (Narcotic drugs) CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name N-ethyl-N-methyl-4,4-dithiophen-2-yl-but-3-en-2-amine
CAS Number	441-61-2
PubChem CID	46424
DrugBank	DB01468
ChemSpider	42256
UNII	722BFZ899Q
KEGG	D12663
CompTox Dashboard (EPA)	DTXSID60861937
ECHA InfoCard	100.006.482
Chemical and physical data
Formula	C₁₅H₁₉NS₂
Molar mass	277.44 g·mol
3D model (JSmol)	Interactive image
SMILES CCN(C)C(C)C=C(C1=CC=CS1)C2=CC=CS2
InChI InChI=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 Key:MORSAEFGQPDBKM-UHFFFAOYSA-N
(verify)

Ethylmethylthiambutene (N-ethyl-N-methyl-1-methyl-3,3-di-2-thienylallylamine; Emethibutin) is an opioid analgesic drug from the thiambutene family, around 1.3x the potency of morphine. 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.

References

Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
Adamson DW, Green AF (January 1950). "A new series of analgesics". Nature. 165 (4186): 122. Bibcode:1950Natur.165..122A. doi:10.1038/165122a0. PMID 15409854. S2CID 4190157.
Adamson DW, Duffin WM, Green AF (January 1951). "Dithienylbutylamines as analgesics". Nature. 167 (4239): 153–4. Bibcode:1951Natur.167..153A. doi:10.1038/167153b0. PMID 14806409. S2CID 4280042.
Green AF (March 1953). "Analgesic and other properties of 3: 3-dithienylalkenylamines". British Journal of Pharmacology and Chemotherapy. 8 (1): 2–9. doi:10.1111/j.1476-5381.1953.tb00739.x. PMC 1509239. PMID 13066683.

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine +aspirin +paracetamol Morphine (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol

Paracetamol-type

NSAIDs

Propionates	Benoxaprofen Fenoprofen Flurbiprofen Ibuprofen (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib Parecoxib Rofecoxib Valdecoxib
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid) (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone