Dimethylthiambutene

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Dimethylthiambutene
Dimethylthiambutene structure.svg
Systematic (IUPAC) name
(RS)-N,N-dimethyl-4,4-dithiophen-2-yl-but-3-en-2-amine
Clinical data
Legal status
Identifiers
CAS number 524-84-5 YesY
ATC code None
PubChem CID 10668
DrugBank DB01444
ChemSpider 10218 YesY
UNII 915D88LM9O YesY
ChEBI CHEBI:59781 YesY
ChEMBL CHEMBL2106265
Chemical data
Formula C14H17NS2 
Mol. mass 263.424 g/mol
Physical data
Melt. point 169–170 °C (336–338 °F)
 YesY (what is this?)  (verify)

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 cough suppressant tipepidine, which is weaker and not a controlled substance in most of the world.

Dimethylthiambutene was developed in the United Kingdom in the late 1940s[1] 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[edit]

Although not show on the scheme, it is presumed that the precursor is made by the Michael addition of ethyl methacrylate with dimethylamine.

Preparation of Dimethylthiambutene.[2]

References[edit]

  1. ^ U.S. Patent 2,561,899 - Dithienyl Allyl Amines
  2. ^ Adamson, D. W. (1950). "180. Aminoalkyl tertiary carbinols and derived products. Part II. 3-Amino-1 : 1-di-2?-thienyl-alkan-1-ols and -alk-1-enes". Journal of the Chemical Society (Resumed): 885. doi:10.1039/JR9500000885.  edit