Dimethylthiambutene (''N'',''N''-Dimethyl-1-methyl-3,3-di-2-thienylallylamine, DMTB, trade names Ohton, Aminobutene, Dimethibutin, Kobaton, Takaton, Dimethibutin) is an

opioid Opioids are a class of Drug, drugs that derive from, or mimic, natural substances found in the Papaver somniferum, opium poppy plant. Opioids work on opioid receptors in the brain and other organs to produce a variety of morphine-like effects, ...

analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...

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 Methadone, sold under the brand names Dolophine and Methadose among others, is a synthetic opioid used medically to treat chronic pain and opioid use disorder. Prescribed for daily use, the medicine relieves cravings and opioid withdrawal sym ...

which are also called the thienyl derivative opioids which also includes diethylthiambutene and ethylmethylthiambutene, as well as the non-opioid

cough suppressant Cold medicines are a group of medicinal, medications taken individually or in Combination drug, combination as a Symptomatic treatment, treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The ter ...

tipepidine Tipepidine (International Nonproprietary Name, INN; also known as tipepidine hibenzate (Japanese Accepted Name, JAN); brand names Asverin, Antupex, Asvelik, Asvex, Bitiodin, Cofdenin A, Hustel, Nodal, and Sotal) is a Organic compound#Synthetic co ...

. 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 The Single Convention on Narcotic Drugs, 1961 (Single Convention, 1961 Convention, or C61) is an international treaty that controls activities (cultivation, production, supply, trade, transport) involving specific narcotic drugs and lays down a ...

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 Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are ...

diamorphine Heroin, also known as diacetylmorphine and diamorphine among other names, is a morphinan opioid substance synthesized from the Opium, dried latex of the Papaver somniferum, opium poppy; it is mainly used as a recreational drug for its eupho ...

. Its DEA ACSCN is 9619 and it had a zero manufacturing quota in 2013.

Synthesis

The conjugate addition between Ethyl crotonate 23-70-110544-63-5] (1) and dimethylamine gives Ethyl 3-(Dimethylamino)Butanoate 5118-28-1(2). Grignard reaction with 2-Bromothiophene 003-09-4(3) gives (4). Dehydration in acid completed the synthesis (5).

References

{{Opioidergics Synthetic opioids Thiophenes Dimethylamino compounds Mu-opioid receptor agonists

Synthesis

See also

References