Thebacon

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Thebacon
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
Identifiers
  • 6,7-Didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-ol acetate
JSmol)
  • CC(=O)OC1=CC[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)OC)CCN3C
  • InChI=1S/C20H23NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6-7,13-14,19H,5,8-10H2,1-3H3/t13-,14+,19-,20-/m0/s1 ☒N
  • Key:RRJQTGHQFYTZOW-ILWKUFEGSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Thebacon (

semisynthetic opioid 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.

Medical uses

Thebacon is an

antitussive, primarily used in Europe, although it is no longer in common use.[citation needed] Currently, dihydrocodeine and nicocodeine are used as second-line codeine 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 chain methadone relatives and thiambutenes
).

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 mg q6h. For both pain and coughing, thebacon can be made more effective along with

chlorpheniramine.[medical citation needed
]

Pharmacokinetics

Thebacon is most commonly taken orally as an elixir, tablet, or capsule, although rectal and

3,14-diacetyloxymorphone
.

Thebacon's

dihydrodiacetylmorphine
.

Production

Thebacon is generated by the

diacetylmorphine is produced. It is also a product of the metabolism of hydrocodone by Pseudomonas putida M10, the bacterium used for oil spill remediation. This also produces a morphinone reductase, which can turn morphine into hydromorphone in a process which produces other active opioids, such as oxymorphone, oxymorphol, or hydromorphinol
as intermediates.

Legal status

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]

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ISBN 978-0-85369-840-1
    .
  3. OCLC 1628783
    .
  4. ^ US 1731152, Schopf C, "Process for the manufacture of derivatives of dihydrocodeinone or its substitution products", assigned to Boehringer 
  5. ^ "Controlled Substance Schedules". US Department of Justice. Archived from the original on 7 February 2011.
  6. ^ "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). Diversion Control Division. U.S. Drug Enforcement Administration. pp. 59, 75, 89.
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