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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

1. 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.
2. 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.
3. 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.
4. 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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