Dimethylthiambutene

Clinical data
ATC code	none
Legal status
Legal status	BR: Class A1 (Narcotic drugs)[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name (RS)-N,N-dimethyl-4,4-dithiophen-2-yl-but-3-en-2-amine
CAS Number	524-84-5 Y
PubChem CID	10668
DrugBank	DB01444 Y
ChemSpider	10218 Y
UNII	915D88LM9O
KEGG	D12665 Y
ChEBI	CHEBI:59781 Y
ChEMBL	ChEMBL2106265
Chemical and physical data
Formula	C14H17NS2
Molar mass	263.42 g·mol−1
3D model (JSmol)	Interactive image
Melting point	169 to 170 °C (336 to 338 °F)
SMILES CC(C=C(C1=CC=CS1)C2=CC=CS2)N(C)C
InChI InChI=1S/C14H17NS2/c1-11(15(2)3)10-12(13-6-4-8-16-13)14-7-5-9-17-14/h4-11H,1-3H3 Y Key:CANBGVXYBPOLRR-UHFFFAOYSA-N Y
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Dimethylthiambutene (N,N-Dimethyl-1-methyl-3,3-di-2-thienylallylamine, DMTB, trade names Ohton, Aminobutene, Dimethibutin, Kobaton, Takaton, Dimethibutin) is an opioid analgesic drug, most often used in veterinary medicine in Japan and to a lesser extent in other countries in the region and around the world. It is the most prominent and widely used of the thiambutenes, a series of open-chain opioids structurally related to methadone which are also called the thienyl derivative opioids which also includes diethylthiambutene and ethylmethylthiambutene, as well as the non-opioid cough suppressant tipepidine.

Dimethylthiambutene was developed in the United Kingdom in the late 1940s and introduced to the market by Burroughs-Wellcome in 1951. Dimethylthiambutene is now under international control under the UN Single Convention on Narcotic Drugs 1961, the laws governing habit-forming substances in virtually all countries and Schedule I of the US Controlled Substances Act of 1970 due to high abuse potential and never being introduced clinically in the United States; other countries regulate it much as morphine or diamorphine. Its DEA ACSCN is 9619 and it had a zero manufacturing quota in 2013.

Synthesis

The conjugate addition between Ethyl crotonate [623-70-1][10544-63-5] (1) and dimethylamine gives Ethyl 3-(Dimethylamino)Butanoate [85118-28-1] (2). Grignard reaction with 2-Bromothiophene [1003-09-4] (3) gives (4). Dehydration in acid completed the synthesis (5).