Thebacon (INN;[2] pronounced /ˈθiːbəkɒn/), or dihydrocodeinone enol acetate, is a semisyntheticopioid that is similar to hydrocodone and is most commonly synthesised from thebaine. Thebacon was invented in Germany in 1924, four years after the first synthesis of hydrocodone.[3] Thebacon is a derivative of acetyldihydrocodeine, where only the 6–7 double bond is saturated. Thebacon is marketed as its hydrochloride salt under the trade name Acedicon, and as its bitartrate under Diacodin and other trade names. The hydrochloride salt has a free base conversion ratio of 0.846. Other salts used in research and other settings include thebacon's phosphate, hydrobromide, citrate, hydroiodide, and sulfate.
Thebacon is most commonly taken orally as an elixir, tablet, or capsule, although rectal and subcutaneous administration has the same advantages [according to whom?] with hydrocodone as would taking a tablet, powder, or a liquid concentrate buccally or sublingually. Like all of its chemical relatives in this class (codeine-based semi-synthetic narcotic antitussives), thebacon exerts its analgesic effect and a large part of its antitussive and antiperistaltic action as a prodrug for stronger and/or longer-lasting opioids, primarily hydromorphone, which is formed in the liver by the cytochrome P450 2D6 (CYP2D6) enzyme pathway as well as acetylmorphone. As a result, the effectiveness of a given dose of thebacon will vary amongst patients, and some food and drugs can affect various parts of the liberation, absorption, distribution, metabolism and elimination profile, and therefore a variable proportion of the potency of thebacon. Thebacon can be said to be the 6-monoacetylmorphine analog of hydrocodone, and/or the 6-acetylmorphone analog of codeine. It is also a close structural relative of 3,14-diacetyloxymorphone.
Thebacon's analgesic and antitussive potency is slightly higher than that of its parent compound hydrocodone, which gives it approximately eight times the milligram strength of codeine. The acetylation at position 3 and the conversion into a dihydromorphinone class semisynthetic (at position 14 on the morphine carbon skeleton) allows for the drug to more rapidly enter the central nervous system in greater quantity where it is de-acetylated into hydromorphone, and also converted by other processes into hydromorphinol, morphine and various other active and inactive substances; it therefore simultaneously takes advantage of two methods of increasing the effectiveness of morphine and its derivatives, those being catalytic hydrogenation (codeine into hydrocodone) and esterification (morphine into diamorphine, nicomorphine &c) in a manner not unlike to that of dihydrodiacetylmorphine.
Thebacon is a Schedule I controlled substance in the United States, never having been in medical use there.[5] The US DEA Administrative Controlled Substance Control Number assigned by the Controlled Substances Act (1970) for thebacon and all of its salts is 9315.[6]
