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{{Drugbox {{Drugbox
⚫ | verifiedrevid = 447764085
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⚫ | 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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| 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


Revision as of 18:19, 3 September 2011

Pharmaceutical compound
Ethylmethylthiambutene
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • N-ethyl-N-methyl-4,4-dithiophen-2-yl-but-3-en-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.006.482 Edit this at Wikidata
Chemical and physical data
FormulaC15H19NS2
Molar mass277.45 g/mol g·mol
3D model (JSmol)
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.

References

  1. Adamson, DW; Green, AF (1950). "A new series of analgesics". Nature. 165 (4186): 122–122. doi:10.1038/165122a0. PMID 15409854.
  2. Adamson, DW; Duffin, WM; Green, AF (1951). "Dithienylbutylamines as analgesics". Nature. 167 (4239): 153–4. doi:10.1038/167153b0. PMID 14806409.
  3. Green, AF (1953). "Analgesic and other properties of 3: 3-dithienylalkenylamines". British journal of pharmacology and chemotherapy. 8 (1): 2–9. PMC 1509239. PMID 13066683.
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