dimethylthiambutene

Dimethylthiambutene
Systematic (IUPAC) name
	(RS)-N,N-dimethyl-4,4-dithiophen-2-yl-but-3-en-2-amine
Clinical data
Legal status	Schedule I (US)
Identifiers
CAS number	524-84-5
ATC code	None
PubChem	CID 10668
DrugBank	DB01444
ChemSpider	10218
UNII	915D88LM9O
ChEBI	CHEBI:59781
ChEMBL	CHEMBL2106265
Chemical data
Formula	C14H17NS2
Mol. mass	263.424 g/mol
	SMILES CC(C=C(C1=CC=CS1)C2=CC=CS2)N(C)C;
	InChI InChI=1S/C14H17NS2/c1-11(15(2)3)10-12(13-6-4-8-16-13)14-7-5-9-17-14/h4-11H,1-3H3 ; Key:CANBGVXYBPOLRR-UHFFFAOYSA-N ;
Physical data
Melt. point	169–170 °C (336–338 °F)
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ジメチルチアムブテン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/06/30 23:10:27」(JST)

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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 cough suppressant tipepidine, which is weaker and not a controlled substance in most of the world.

Dimethylthiambutene was developed in the United Kingdom in the late 1940s^[1] 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

Although not show on the scheme, it is presumed that the precursor is made by the Michael addition of ethyl methacrylate with dimethylamine.

Preparation of Dimethylthiambutene.^[2]

^ U.S. Patent 2,561,899 - Dithienyl Allyl Amines
^ 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". Journal of the Chemical Society (Resumed): 885. doi:10.1039/JR9500000885. edit

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English Journal

Comparative effects of analgesics on pain threshold, respiratory frequency and gastrointestinal propulsion.

GREEN AF.
British journal of pharmacology and chemotherapy.Br J Pharmacol Chemother.1959 Mar;14(1):26-34.
In the rat, the ratio of the analgesic to the respiratory depressant potency was the same for morphine, codeine, diamorphine, methadone, dipipanone, piperidylisomethadone, phenadoxone, dextromoramide, and propoxyphene. The relative respiratory depressant activity of pethidine tended to be less, but
PMID 13651575

Related Pictures

Pharmacology Of Dimethylthiambutene 11 kb dimethylthiambutene st 9 kb 28 kb Dimethylthiambutene. Preparation of Dimethylthiambutene. [ 2 ] Description Dimethylthiambutene structure

[1] U.S. Patent 2,561,899 - Dithienyl Allyl Amines

[2] 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". Journal of the Chemical Society (Resumed): 885. doi:10.1039/JR9500000885. edit

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