The Thiambutenes are a family of

opioid Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid us ...

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

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 is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a analgesic, pain medication, and is also commonly used recreational drug, recreationally, or to make ...

. Notable compounds include

dimethylthiambutene 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 ...

diethylthiambutene Diethylthiambutene (Thiambutene, Themalon, Diethibutin, ''N'',''N''-Diethyl-1-methyl-3,3-di-2-thienylallylamine) is an opioid analgesic drug developed in the 1950s which was mainly used as an anesthetic in veterinary medicine and continues, along ...

ethylmethylthiambutene Ethylmethylthiambutene (; Emethibutin) is an opioid analgesic drug from the thiambutene family, around 1.3x the potency of morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver som ...

pyrrolidinylthiambutene Pyrrolidinylthiambutene is an opioid analgesic drug from the thiambutene family with around 3/4 of the potency of morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum'' ...

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 syntheti ...

. 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, diagnosis, and treatment of disease, disorder, and injury in animals. Along with this, it deals with animal rearing, husbandry, breeding, research on nutri ...

. All of these compounds produced

anticholinergic Anticholinergics (anticholinergic agents) are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peripheral nervous system. These agents inhibit the parasympathetic nervous system ...

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 re ...

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 Controlled Substances Act#Schedule I controlled substance ...

References

{{Opioidergics Opioids Thiophenes Amines Mu-opioid receptor agonists