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Diethylthiambutene

Chemical compound

Diethylthiambutene

Chemical compound

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Diethylthiambutene (Thiambutene, Themalon, Diethibutin, N,N-Diethyl-1-methyl-3,3-di-2-thienylallylamine) is an opioid analgesic drug developed in the 1950s which was mainly used as an anesthetic in veterinary medicine and continues, along with the other two thiambutenes dimethylthiambutene 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

Synthesis:<ref>Adamson, D. W. (1950). &quot;180. Aminoalkyl tertiary carbinols and derived products. Part II. 3-Amino-1 : 1-di-2′-thienyl-alkan-1-ols and -alk-1-enes&quot;. J. Chem. Soc. 0 (0): 885–890. doi:10.1039/JR9500000885.</ref> Japan patents:<ref>JP,43-006621,B (1968) JP,0528324,B</ref>

The conjugate addition of diethylamine [109-89-7] to ethyl crotonate [623-70-1] [10544-63-5] (1) gives ethyl 3-(diethylamino)butanoate, CID:10679145 (2). Addition of two equivalents of 2-thienyllithium to the ester gives the tertiary alcohol [94094-46-9] (**4''''). The dehydration of this then completes the synthesis of diethylthiambutene (**5'''').

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. (November 1956). "Analgesics and their antagonists: some steric and chemical considerations. II. The influence of the basic group on physico-chemical properties and the activity of methadone and thiambutene-type compounds". The Journal of Pharmacy and Pharmacology.
  3. (November 1968). "The use of thiambutene hydrochloride". The Veterinary Record.
  4. (December 1974). "Thiambutene and acepromazine as analgesic and preanaesthetic agents in horses and sheep". Australian Veterinary Journal.
  5. 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". J. Chem. Soc. 0 (0): 885–890. doi:10.1039/JR9500000885.
  6. JP,43-006621,B (1968) JP,0528324,B
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synthetic-opioids thiophenes diethylamino-compounds mu-opioid-receptor-agonists
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