Diethylthiambutene (Thiambutene, Themalon, Diethibutin, ''N'',''N''-Diethyl-1-methyl-3,3-di-2-thienylallylamine) is an

opioid Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioi ...

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

drug developed in the 1950s which was mainly used as an

anesthetic An anesthetic (American English) or anaesthetic (British English; see spelling differences) is a drug used to induce anesthesia ⁠— ⁠in other words, to result in a temporary loss of sensation or awareness. They may be divided into tw ...

veterinary Veterinary medicine is the branch of medicine that deals with the prevention, management, diagnosis, and treatment of disease, disorder, and injury in animals. Along with this, it deals with animal rearing, husbandry, breeding, research on nutri ...

medicine and continues, along with the other two thiambutenes

dimethylthiambutene 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 ...

and ethylmethylthiambutene to be used for this purpose, particularly in Japan. It is now under international control under Schedule I of the UN Single Convention On Narcotic Drugs 1961, presumably due to high abuse potential, although little more information is available. It is listed under Schedule I of the US Controlled Substances Act as a Narcotic and has an ACSCN of 9616 with zero annual manufacturing quota as of 2013.

Synthesis

The conjugate addition of diethylamine 09-89-7to ethyl crotonate 23-70-1 0544-63-5(1) gives ethyl 3-(diethylamino)butanoate
CID:10679145
(2). Addition of two equivalents of 2-thienyllithium to the ester gives the tertiary alcohol

4094-46-9 4 (four) is a number, numeral and digit. It is the natural number following 3 and preceding 5. It is the smallest semiprime and composite number, and is considered unlucky in many East Asian cultures. In mathematics Four is the smalles ...

(4'). The dehydration of this then completes the synthesis of diethylthiambutene (5').

References

Synthetic opioids Thiophenes Diethylamino compounds Mu-opioid receptor agonists {{analgesic-stub