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Thebacon (INN;[2] pronounced/ˈθiːbəkɒn/), ordihydrocodeinone enol acetate, is asemisyntheticopioid that is similar tohydrocodone and is most commonly synthesised fromthebaine. Thebacon was invented inGermany in 1924, four years after the first synthesis of hydrocodone.[3] Thebacon is a derivative ofacetyldihydrocodeine, where only the 6–7double bond is saturated. Thebacon is marketed as itshydrochloride salt under the trade nameAcedicon, and as itsbitartrate underDiacodin and other trade names. The hydrochloride salt has afree base conversion ratio of 0.846. Other salts used in research and other settings include thebacon's phosphate, hydrobromide, citrate, hydroiodide, and sulfate.
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Thebacon is anopioidagonistnarcoticanalgesic of the middle range and a strongantitussive, primarily used inEurope, although it is no longer in common use.[citation needed] Currently,dihydrocodeine andnicocodeine are used assecond-linecodeine replacements. The other dihydromorphinone used as an antitussive is hydromorphone (Dilaudid cough syrup); the other narcotic antitussives are either more directly related to codeine or not related at all (open chainmethadone relatives andthiambutenes).
Thebacon is indicated for moderate to moderately severe pain and dry painful coughing, like hydrocodone. It has a duration of action in the range of 5 to 9 hours and doses typically start at 5 mgq6h. For both pain and coughing, thebacon can be made more effective along withNSAIDs,muscle relaxants, and/orantihistamines liketripelennamine,hydroxyzine,promethazine,phenyltoloxamine andchlorpheniramine.[medical citation needed]
Thebacon is most commonly taken orally as an elixir, tablet, or capsule, although rectal andsubcutaneous administration has the same advantages[according to whom?] with hydrocodone as would taking a tablet, powder, or a liquid concentratebuccally orsublingually. 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 aprodrug for stronger and/or longer-lasting opioids, primarilyhydromorphone, which is formed in the liver by thecytochrome P450 2D6 (CYP2D6) enzyme pathway as well asacetylmorphone. 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 theliberation, 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 the6-acetylmorphone analog ofcodeine. It is also a close structural relative of3,14-diacetyloxymorphone.
Thebacon'sanalgesic and antitussive potency is slightly higher than that of its parent compoundhydrocodone, 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 intohydromorphone, and also converted by other processes intohydromorphinol,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 intodiamorphine,nicomorphine &c) in a manner not unlike to that ofdihydrodiacetylmorphine.
Thebacon is generated by theesterification product of theenoltautomer ofhydrocodone (dihydrocodeineone) withacetic anhydride.[4] Although modification of thebaine is the most common way of making thebacon, preparation by refluxing hydrocodone withacetic anhydride is not uncommon, generally similar to howdiacetylmorphine is produced. It is also a product of themetabolism of hydrocodone byPseudomonas putida M10, the bacterium used for oil spill remediation. This also produces amorphinone reductase, which can turn morphine intohydromorphone in a process which produces other active opioids, such asoxymorphone,oxymorphol, orhydromorphinol as intermediates.
Thebacon is aSchedule I controlled substance in the United States, never having been in medical use there.[5] The USDEA Administrative Controlled Substance Control Number assigned by theControlled Substances Act (1970) for thebacon and all of its salts is 9315.[6]
