Thiambutene

Thiambutene

200px
Systematic (IUPAC) name
(RS)-4,4-dithiophen-2-yl-but-3-en-2-amine
Identifiers
ATC code	none
Chemical data
Formula	C12H13NS2
Molar mass	235.368 g/mol[[]]
Physical data
Melting point	174 to 175 °C (345 to 347 °F)

The Thiambutenes are a family of opioid analgesic drugs. The parent compound thiambutene has no analgesic effects, but several compounds from this group are analgesics with around the same potency as morphine.

Notable compounds include dimethylthiambutene, diethylthiambutene, ethylmethylthiambutene, pyrrolidinylthiambutene and piperidylthiambutene. Of these, ethylmethylthiambutene is the most potent, with 1.3x the potency of morphine, pyrrolidinylthiambutene is the least potent at 0.7x, and the rest are all around the same potency as morphine. Diethylthiambutene has been the most widely used, mainly in veterinary medicine.

All of these compounds produced anticholinergic and antihistamine side effects, except for two of the weaker compounds diallylthiambutene and morpholinylthiambutene. They also all have a chiral centre around the alpha carbon (where the R1 group is attached) and so have two stereoisomers, with the dextro isomer being the more potent in all cases, although both isomers are active.

Three of these compounds are explicitly listed as illegal drugs under UN convention, diethylthiambutene, dimethylthiambutene and ethylmethylthiambutene, and so are illegal throughout the world, but the rest will only be illegal in countries such as the USA, Australia and New Zealand that have laws equivalent to the Federal Analog Act.

160px

Drug name	R1	R2	R3	Analgesic Potency (Morphine = 1)
Ethylmethylthiambutene	methyl	ethyl	methyl	1.3
Dimethylthiambutene	methyl	methyl	methyl	1.0
Diethylthiambutene	methyl	ethyl	ethyl	1.0
Piperidylthiambutene	methyl	piperidyl	piperidyl	1.0
Pyrrolidinylthiambutene	methyl	pyrrolidinyl	pyrrolidinyl	0.7
Diallylthiambutene	methyl	allyl	allyl	0.5
Methylisopropylthiambutene	methyl	methyl	isopropyl	0.5
Morpholinylthiambutene	methyl	morpholinyl	morpholinyl	0.5
Methylpropylthiambutene	methyl	methyl	propyl	0.1
	hydrogen	ethyl	ethyl	0.2
	hydrogen	pyrrolidinyl	pyrrolidinyl	0.1
	hydrogen	piperidyl	piperidyl	0.1
	phenyl	methyl	methyl	0.1