Diethylthiambutene

Diethylthiambutene

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I UN: Psychotropic Schedule I
Identifiers
IUPAC name N,N-diethyl-4,4-dithiophen-2-yl-but-3-en-2-amine
CAS Number	86-14-6 N
PubChem CID	6833
DrugBank	DB01533 Y
ChemSpider	6572 Y
UNII	2Z91X9052O
ChEMBL	ChEMBL2106573 N
Chemical and physical data
Formula	C16H21NS2
Molar mass	291.47 g·mol−1
3D model (JSmol)	Interactive image
Melting point	152 to 153 °C (306 to 307 °F)
SMILES CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2
InChI 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 Y Key:CBYWMRHUUVRIAF-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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: Japan patents:

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').