Viminol (marketed under the

brandname A brand is a name, term, design, symbol or any other feature that distinguishes one seller's good or service from those of other sellers. Brands are used in business, marketing, and advertising for recognition and, importantly, to create a ...

Dividol) is an

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 use ...

analgesic developed by a team at the drug company

Zambon Zambon is an Italian company that has been operating in the pharmaceutical and fine chemical industry since 1906. The company is currently run by Elena Zambon who is the daughter of the founder.{{Cite news, url=http://www.repubblica.it/economia/a ...

in the 1960s. Viminol is based on the α-pyrryl-2-aminoethanol structure, unlike any other class of opioids. Viminol has both

antitussive Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including ...

(cough suppressing) and analgesic (pain reducing) effects. Viminol has additional effects similar to other opioids including sedation and euphoria. It has six different

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 which have varying properties. Four are inactive, but the 1''S''-(''R'',''R'')-disecbutyl isomer is a μ-opioid full agonist around 5.5 times more potent than

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 pain medication, and is also commonly used recreationally, or to make other illicit opioids. T ...

and the 1''S''-(''S'',''S'')-disecbutyl isomer is an antagonist. Since viminol is supplied as a

racemic In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

mixture of isomers, the overall effect is a mixed agonist–antagonist profile similar to that of opioids such as

pentazocine Pentazocine, sold under the brand name Talwin among others, is a painkiller used to treat moderate to severe pain. It is believed to work by activating (agonizing) κ-opioid receptors (KOR) and μ-opioid receptors (MOR). As such it is called an ...

, although with somewhat fewer side effects.

Side effects

Side effects are similar to other opioids, and can include: *

Itching Itch (also known as pruritus) is a Wikt:sensation, sensation that causes the desire or reflex to scratch. Itch has resisted many attempts to be classified as any one type of Sensory system, sensory experience. Itch has many similarities to pain, ...

Nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...

* Sedation * Respiratory depression - can be potentially life-threatening However, since viminol is supplied as a racemic mixture of agonist and antagonist isomers, the

abuse potential Substance abuse, also known as drug abuse, is the use of a drug in amounts or by methods which are harmful to the individual or others. It is a form of substance-related disorder. Differing definitions of drug abuse are used in public health, ...

and respiratory depression tends to be less than that of μ-opioid full agonist drugs. Drug dependence may occur.

Related compounds

Later work showed that replacing the chlorine atom with an fluorine atom ( 2F-Viminol) or with a

trifluoromethyl The trifluoromethyl group is a functional group that has the formula -CF3. The naming of is group is derived from the methyl group (which has the formula -CH3), by replacing each hydrogen atom by a fluorine atom. Some common examples are trifluoro ...

group produced a compound with twice the potency and half the acute toxicity. A later team at Zambon found that one isomer of a pyrrolidone

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

is 318 times as potent as morphine in its analgesic activity in animal studies. A number of related compounds were also found to be active, allowing a QSAR model to be constructed.

References

{{Opioidergics Opioids Pyrroles Secondary alcohols Chloroarenes Mu-opioid receptor agonists