Structure via PubChem · Public domain (PubChem)
dimethylthiambutene
Sign in to saveAlso known as Dimethibutin, Ohton, N,N-dimethyl-4,4-di(2-thienyl)-3-buten-2-amine, N,N,1-trimethyl-3,3-di(2-thienyl)-2-propenylamine, 3-dimethylamino-1,1-di-(2'-thienyl)-1-butene, N,N,1-trimethyl-3,3-di-2-thienylallylamine, 3-dimethylamino-1,1-bis(2-thienyl)-1-butene
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 a lesser extent in other countries in the region and around the world. It is the most prominent and widely used of the thiambutenes, a series of open-chain opioids structurally related to methadone which are also called the thienyl derivative opioids which also includes diethylthiambutene and ethylmethylthiambutene, as well as the non-opioid cough suppressant
Chemical data
- Formula
- C14H17NS2
- Molecular weight
- 263.4 g/mol
- IUPAC name
- N,N-dimethyl-4,4-dithiophen-2-ylbut-3-en-2-amine
- SMILES
- CC(C=C(C1=CC=CS1)C2=CC=CS2)N(C)C
- InChIKey
- CANBGVXYBPOLRR-UHFFFAOYSA-N
- XLogP
- 4.1
- 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
- 263.080242
Show 4 more facts
- chemical formula
- C₁₄H₁₇NS₂
- canonical SMILES
- CC(C=C(C1=CC=CS1)C2=CC=CS2)N(C)C
- World Health Organisation international non-proprietary name
- dimethylthiambutene
- Commons category
- Dimethylthiambutene
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
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 a lesser extent in other countries in the region and around the world. It is the most prominent and widely used of the thiambutenes, a series of open-chain opioids structurally related to methadone which are also called the thienyl derivative opioids which also includes diethylthiambutene and ethylmethylthiambutene, as well as the non-opioid cough suppressant tipepidine.
Dimethylthiambutene was developed in the United Kingdom in the late 1940s and introduced to the market by Burroughs-Wellcome in 1951. Dimethylthiambutene is now under international control under the UN Single Convention on Narcotic Drugs 1961, the laws governing habit-forming substances in virtually all countries and Schedule I of the US Controlled Substances Act of 1970 due to high abuse potential and never being introduced clinically in the United States; other countries regulate it much as morphine or diamorphine. Its DEA ACSCN is 9619 and it had a zero manufacturing quota in 2013. ==Synthesis== class=skin-invert-image|thumb|500px|center|Synthesis: Patent:
Excerpted from Wikipedia’s “dimethylthiambutene” article, available under the CC BY-SA 4.0 licence.