Diethylthiambutene

Diethylthiambutene (Thiambutene, Themalon, Diethibutin, N,N-Diethyl-1-methyl-3,3-di-2-thienylallylamine) is an opioid analgesic drug developed in the 1950s[2] 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.[3][4] 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.

Diethylthiambutene
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • N,N-diethyl-4,4-dithiophen-2-yl-but-3-en-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC16H21NS2
Molar mass291.47 g·mol−1
3D model (JSmol)
Melting point152 to 153 °C (306 to 307 °F)
  • CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2
  • InChI=1S/C16H21NS2/c1-4-17(5-2)13(3)12-14(15-8-6-10-18-15)16-9-7-11-19-16/h6-13H,4-5H2,1-3H3 checkY
  • Key:CBYWMRHUUVRIAF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Synthesis
Synthesis:[5] Japan patents:[6]

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
  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. Beckett AH, Casy AF, Harper NJ, Phillips PM (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. 8 (11): 860–73. doi:10.1111/j.2042-7158.1956.tb12216.x. PMID 13368083. S2CID 41750428.
  3. Hayes MJ (November 1968). "The use of thiambutene hydrochloride". The Veterinary Record. 83 (20): 528. doi:10.1136/vr.83.20.528-a. PMID 5694027. S2CID 45820838.
  4. Harbison WD, Slocombe RF, Watts SJ, Stewart GA (December 1974). "Thiambutene and acepromazine as analgesic and preanaesthetic agents in horses and sheep". Australian Veterinary Journal. 50 (12): 543–6. doi:10.1111/j.1751-0813.1974.tb14073.x. PMID 4156466.
  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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