The Thiambutenes are a family of
opioid
Opioids are a class of Drug, drugs that derive from, or mimic, natural substances found in the Papaver somniferum, opium poppy plant. Opioids work on opioid receptors in the brain and other organs to produce a variety of morphine-like effects, ...
analgesic
An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...
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
Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are ...
.
Notable compounds include
dimethylthiambutene,
diethylthiambutene,
ethylmethylthiambutene,
pyrrolidinylthiambutene and
piperidylthiambutene
Piperidylthiambutene (Piperidinohton) is a synthetic opioid analgesic drug from the thiambutene family, which has around the same potency as morphine. Piperidylthiambutene is structurally distinct from fentanyl, its analogues, and other synthet ...
. 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
Veterinary medicine is the branch of medicine that deals with the prevention, management, medical diagnosis, diagnosis, and treatment of disease, disorder, and injury in non-human animals. The scope of veterinary medicine is wide, covering all a ...
.
All of these compounds produced
anticholinergic
Anticholinergics (anticholinergic agents) are substances that block the action of the acetylcholine (ACh) neurotransmitter at synapses in the central nervous system, central and peripheral nervous system.
These agents inhibit the parasympatheti ...
and
antihistamine
Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provides ...
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
stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
s, 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 US, Australia and New Zealand that have laws equivalent to the
Federal Analog Act
The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...
.
References
{{Opioidergics
Opioids
Thiophenes
Amines
Mu-opioid receptor agonists