Ethylmethylthiambutene

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.[1][2][3] It is under international control under Schedule I of the UN Single Convention On Narcotic Drugs 1961, presumably due to high abuse potential.

Ethylmethylthiambutene
Clinical data
ATC code
  • none
Legal status
Legal status
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
ECHA InfoCard100.006.482
Chemical and physical data
FormulaC15H19NS2
Molar mass277.44 g·mol−1
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 Y
  • Key:MORSAEFGQPDBKM-UHFFFAOYSA-N Y
  (verify)

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
  1. 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.
  2. 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.
  3. 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.
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