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thiambutenes

n. (plural of thiambutene English)

Wikipedia
Thiambutenes

The Thiambutenes are a family of opioid analgesic drugs developed at the British research laboratory of Burroughs-Wellcome in the late 1940s. 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 on 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.

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