Structure via PubChem · Public domain (PubChem)
diethylthiambutene
Sign in to saveDiethylthiambutene (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
In the Vinony graph
Within Vinony's link graph, diethylthiambutene is referenced by 15 other articles, and connects out to (+)-catechin, butorphanol and xenon.
It is catalogued under topics including Diethylamino compounds, Drugboxes which contain changes to verified fields and Drugs not assigned an ATC code.
Its subject is documented across 7 Wikipedia language editions.
Chemical data
- Formula
- C16H21NS2
- Molecular weight
- 291.5 g/mol
- IUPAC name
- N,N-diethyl-4,4-dithiophen-2-ylbut-3-en-2-amine
- SMILES
- CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2
- InChIKey
- CBYWMRHUUVRIAF-UHFFFAOYSA-N
- XLogP
- 4.9
- Polar surface area
- 59.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 291.112
Show 3 more facts
- chemical formula
- C₁₆H₂₁NS₂
- canonical SMILES
- CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2
- Commons category
- Diethylthiambutene
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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== class=skin-invert-image|thumb|center|500px|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'). == References ==
Excerpted from Wikipedia’s “diethylthiambutene” article, available under the CC BY-SA 4.0 licence.