Dihydrocodeinone enol acetate
Encyclopedia
Thebacon or dihydrocodeinone enol acetate is a semisynthetic
opioid
that is similar to hydrocodone
and manufactured from Thebaine
. It is marketed as its hydrochloride salt
under the trade name Acedicon and as the bitartrate as Diacodin and possibly other trade names. Other salts used in medicine include the hydroiodide and sulphate.
It is a narcotic analgesic of the middle range and an antitussive, primarily in Europe, although it is no longer in common use. It was invented in Germany in 1924.
It is the esterification product of the enol
tautomer
of hydrocodone
(dihydrocodeineone) with acetic acid
.
Dihydrocodeinone enol acetate's analgesic
and antitussive potency is slightly higher than that of its parent compound hydrocodone
.
Like all of its chemical relatives in this therapeutic class (codeine-based narcotic antitussives and midrange analgesics), Dihydrocodeinone enol acetate exerts some of its effect by being a prodrug
for a stronger opioid, namely hydromorphone
, which is formed in the liver by the Cytochrome P450 2D6 (CYP2D6
) enzyme pathway, meaning that effectiveness of a given dose will vary amongst patients and other drugs taken at the same time can antagonise or cause potentiation.
Dihydrocodeinone enol acetate is a Schedule I controlled substance in the US.
Semisynthetic
"Semisynthesis" or partial chemical synthesis is a type of chemical synthesis that uses compounds isolated from natural sources as starting materials. These natural biomolecules are usually large and complex molecules...
opioid
Opioid
An opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...
that is similar to hydrocodone
Hydrocodone
Hydrocodone or dihydrocodeinone is a semi-synthetic opioid derived from either of two naturally occurring opiates: codeine and thebaine. It is an orally active narcotic analgesic and antitussive...
and manufactured from Thebaine
Thebaine
Thebaine , its name coming from the Greek Θῆβαι, Thēbai, an ancient city in Upper Egypt, is an opiate alkaloid. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects, causing convulsions similar to strychnine...
. It is marketed as its hydrochloride salt
Hydrochloride
In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....
under the trade name Acedicon and as the bitartrate as Diacodin and possibly other trade names. Other salts used in medicine include the hydroiodide and sulphate.
It is a narcotic analgesic of the middle range and an antitussive, primarily in Europe, although it is no longer in common use. It was invented in Germany in 1924.
It is the esterification product of the enol
Enol
Enols are alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. Alkenes with a hydroxyl group on both sides of the double bond are called enediols. Deprotonated anions of enols are called enolates...
tautomer
Tautomer
Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. This reaction commonly results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond...
of hydrocodone
Hydrocodone
Hydrocodone or dihydrocodeinone is a semi-synthetic opioid derived from either of two naturally occurring opiates: codeine and thebaine. It is an orally active narcotic analgesic and antitussive...
(dihydrocodeineone) with acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...
.
Dihydrocodeinone enol acetate's analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
and antitussive potency is slightly higher than that of its parent compound hydrocodone
Hydrocodone
Hydrocodone or dihydrocodeinone is a semi-synthetic opioid derived from either of two naturally occurring opiates: codeine and thebaine. It is an orally active narcotic analgesic and antitussive...
.
Like all of its chemical relatives in this therapeutic class (codeine-based narcotic antitussives and midrange analgesics), Dihydrocodeinone enol acetate exerts some of its effect by being a prodrug
Prodrug
A prodrug is a pharmacological substance administered in an inactive form. Once administered, the prodrug is metabolised in vivo into an active metabolite, a process termed bioactivation. The rationale behind the use of a prodrug is generally for absorption, distribution, metabolism, and...
for a stronger opioid, namely hydromorphone
Hydromorphone
Hydromorphone, a more common synonym for dihydromorphinone, commonly a hydrochloride is a very potent centrally-acting analgesic drug of the opioid class. It is a derivative of morphine, to be specific, a hydrogenated ketone thereof and, therefore, a semi-synthetic drug...
, which is formed in the liver by the Cytochrome P450 2D6 (CYP2D6
CYP2D6
Cytochrome P450 2D6 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. Also, many substances are bioactivated by CYP2D6 to form their active compounds...
) enzyme pathway, meaning that effectiveness of a given dose will vary amongst patients and other drugs taken at the same time can antagonise or cause potentiation.
Dihydrocodeinone enol acetate is a Schedule I controlled substance in the US.