Dimethylthiambutene

Title: Dimethylthiambutene
CAS Registry Number: 524-84-5
CAS Name: N,N-Dimethyl-4,4-di-2-thienyl-3-buten-2-amine
Additional Names: N,N,1-trimethyl-3,3-di-2-thienylallylamine; 3-dimethylamino-1,1-bis(2-thienyl)-1-butene; 3-dimethylamino-1,1-di(2¢-thienyl)but-1-ene
Manufacturers' Codes: 338C48; NIH-4542
Trademarks: Ohton; Aminobutene; Dimethibutin; Kobaton; Takaton
Molecular Formula: C14H17NS2
Molecular Weight: 263.42
Percent Composition: C 63.83%, H 6.50%, N 5.32%, S 24.35%
Literature References: Prepn: Grignard reaction of ethyl b-dimethylaminobutyrate with 2-thienyllithium and dehydration of the resulting 3-dimethylamino-1,1-di-2-thienylbutanol with HCl: Adamson, J. Chem. Soc. 1950, 885; US 2561899 (1951 to Burroughs Wellcome); GB 657301 (1951 to Wellcome Foundation). Toxicity data: Y. Kase et al., Chem. Pharm. Bull. 7, 372 (1959).
Properties: Viscous, dark brown or yellow oil, bp0.05 123-125°; bp3 157-158°. Sol in chloroform, ether. LD50 in mice (mg/10 kg): 1.21 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase).
Boiling point: bp0.05 123-125°; bp3 157-158°
Toxicity data: LD50 in mice (mg/10 kg): 1.21 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase)
Derivative Type: Hydrochloride
Molecular Formula: C14H18ClNS2
Molecular Weight: 299.88
Percent Composition: C 56.07%, H 6.05%, Cl 11.82%, N 4.67%, S 21.39%
Properties: May be recrystallized from mixt of ethyl acetate and ethanol, mp 168-169°. Sol in water, chloroform. LD50 in mice (mg/10 kg): 1.37 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase).
Melting point: mp 168-169°
Toxicity data: LD50 in mice (mg/10 kg): 1.37 s.c.; in dogs (mg/kg): 20.3 i.v. (Kase)
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Dimethylzinc Dimetilan Dimetofrine Dimetridazole Diminazene Aceturate

Dimethylthiambutene
Dimethylthiambutene structure.svg
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 YesY
ATC code None
PubChem CID 10668
DrugBank DB01444
ChemSpider 10218 YesY
UNII 915D88LM9O YesY
ChEBI CHEBI:59781 YesY
ChEMBL CHEMBL2106265
Chemical data
Formula C14H17NS2 
Mol. mass 263.424 g/mol
Physical data
Melt. point 169–170 °C (336–338 °F)
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Dimethylthiambutene (N,N-Dimethyl-1-methyl-3,3-di-2-thienylallylamine, 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.

  1. ^ US Patent 2561899 - Dithienyl Allyl Amines