Thebacon

Thebacon: Thebacon

Systematic (IUPAC) name

6,7-didehydro- 4,5α-epoxy- 3-methoxy- 17-methylmorphinan- 6-ol acetate

Clinical data

AHFS/Drugs.com International Drug Names

Pregnancy cat. ?

Legal status Schedule I (US)

Identifiers

CAS number 466-90-0

ATC code R05DA10

PubChem CID 10075

UNII 520D430GDK^Y

KEGG D07386^Y

Chemical data

Formula C₂₀H₂₃N O₄

Mol. mass 341.401 g/mol

Y(what is this?) (verify)

Thebacon (INN^[1]) 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.^[2]

References

^ Sean C. Sweetman, ed (2009). Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. ISBN 0853698406.

^ "Controlled Substance Schedules". US Department of Justice. http://www.justice.gov/dea/pubs/scheduling.html.

v · d · eOpioids

Opium and
poppy straw
derivatives

Crude opiate extracts/
whole opium products

Compote/Kompot/Polish heroin • Diascordium • B & O Supprettes • Dover's powder • Kendal Black Drop • Laudanum • Mithridate • Opium • Paregoric • Poppy straw concentrate • Poppy tea • Smoking opium • Theriac

Natural opiates

Opium alkaloids
see also: Components of opium

Codeine • Morphine • Oripavine • Pseudomorphine • Thebaine

Alkaloid salts mixtures

Pantopon • Papaveretum (Omnopon)

Semisynthetics
including
Bentley compounds

Morphine family

2,4-Dinitrophenylmorphine • 6-Methylenedihydrodesoxymorphine • Chlornaltrexamine • Dihydrodesoxymorphine (Desomorphine) • Dihydromorphine • Hydromorphinol • Methyldesorphine • N-Phenethylnormorphine • RAM-378

3,6-diesters of morphine

Acetylpropionylmorphine • Diacetyldihydromorphine (Dihydroheroin, Acetylmorphinol) • Dibenzoylmorphine • Dipropanoylmorphine • Heroin (Diacetylmorphine) • Nicomorphine

Codeine-dionine family

6-Monoacetylcodeine • Benzylmorphine • Codeine methylbromide • Methyldihydromorphine (Dihydroheterocodeine) • Ethylmorphine (Dionine) • Heterocodeine • Morpholinylethylmorphine (Pholcodine) • Myrophine

Morphinones and morphols

14-Cinnamoyloxycodeinone • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 7-Spiroindanyloxymorphone • Acetylmorphone • Codeinone • Codorphone • Codoxime • Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) • Hydrocodone • Hydromorphone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxycodone • Oxymorphol • Oxymorphone • Pentamorphone • Semorphone

Morphides

Chloromorphide

Dihydrocodeine series

14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Nicocodeine • Nicodicodeine

Nitrogen morphine derivatives

Morphine-N-Oxide

Hydrazones

Oxymorphazone

Halogenated morphine derivatives

1-Iodomorphine

Active opiate
metabolites

Morphine-6-glucuronide • 6-Monoacetylmorphine • Norcodeine • Normorphine

Morphinans

Morphinan series

Cyclorphan • Dextrallorphan • Levorphanol • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Morphanol / Racemorphanol • Ro4-1539 • Xorphanol

Others

Butorphanol • Cyprodime • Drotebanol • Nalbuphine • Sinomenine (Cocculine)

Benzomorphans

8-Carboxamidocyclazocine • Alazocine • Bremazocine • Dezocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines
(Meperidines)

4-Fluoromeperidine • Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine

Prodines

Allylprodine • Meprodine (α-meprodine / β-meprodine) • MPPP (Desmethylprodine) • PEPAP • Prodine (α-prodine / β-prodine) • Prosidol • Trimeperidine (Promedol)

Ketobemidones

Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone

Others
Alvimopan • Loperamide • Picenadol

Open chain
opioids

Amidones

Dipipanone • Methadone • Normethadone • Phenadoxone (Heptazone)

Methadols

Dimepheptanol (Racemethadol) • Levacetylmethadol

Moramides

Dextromoramide • Levomoramide • Racemoramide

Thiambutenes

Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Piperidylthiambutene • Pyrrolidinylthiambutene • Thiambutene • Tipepidine

Phenalkoxams

Dextropropoxyphene (Propoxyphene) • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Norpropoxyphene

Ampromides

Diampromide • Phenampromide • Propiram

Others

IC-26 • Isoaminile • Lefetamine • R-4066

Anilidopiperidines

3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • 4-Phenylfentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thiofentanyl • Trefentanil

Oripavine
derivatives

7-PET • Acetorphine • BU-48 • Buprenorphine • Cyprenorphine • Dihydroetorphine • Etorphine • Norbuprenorphine

Phenazepanes

Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine

Pirinitramides

Bezitramide • Piritramide

Benzimidazoles

Clonitazene • Etonitazene

Indoles

18-MC • 7-Hydroxymitragynine • Akuammine • Eseroline • Hodgkinsine • Mitragynine • Pericine

Diphenylmethylpiperazines

BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80

Opioid peptides
see also: Opioid neuropeptides

Adrenorphin • Amidorphin • Casomorphin • DADLE • DAMGO • Dermorphin • Dynorphin • Endomorphin • Endorphins • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5

Others

AD-1211 • AH-7921 • Azaprocin • BDPC • BRL-52537 • Bromadoline • C-8813 • Ciramadol • Doxpicomine • Enadoline • Faxeladol • GR-89696 • Herkinorin • ICI-199,441 • ICI-204,448 • J-113,397 • JTC-801 • Ketamine • LPK-26 • Methopholine • MT-45 • N-Desmethylclozapine • NNC 63-0532 • Nortilidine • O-Desmethyltramadol • Phencyclidine • Prodilidine • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tifluadom • Tilidine • Tramadol • Trimebutine • U-50,488 • U-69,593 • Viminol • W-18

Opioid antagonists
&
inverse agonists

5'-Guanidinonaltrindole • Alvimopan • Chlornaltrexamine • Cyclazocine • Cyprodime • Diprenorphine (M5050) • JDTic • Levallorphan • Methylnaltrexone • Nalfurafine • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexol-d4 • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan

List of opioids

v · d · eAnalgesics (N02A, N02B)

Opioids
See also: Opioids template

Opium & alkaloids thereof

Codeine^# • Morphine^# • Opium • Laudanum • Paregoric

Semi-synthetic opium
derivatives

Acetyldihydrocodeine • Benzylmorphine • Buprenorphine • Desomorphine • Dihydrocodeine • Dihydromorphine • Ethylmorphine • Diamorphine • Hydrocodone • Hydromorphinol • Hydromorphone • Nicocodeine • Nicodicodeine • Nicomorphine • Oxycodone • Oxymorphone

Synthetic opioids

Alphaprodine • Anileridine • Butorphanol • Dextromoramide • Dextropropoxyphene • Dezocine • Fentanyl • Ketobemidone • Levorphanol • Methadone • Meptazinol • Nalbuphine • Pentazocine • Propoxyphene • Propiram • Pethidine • Phenazocine • Piminodine • Piritramide • Tapentadol • Tilidine • Tramadol

Pyrazolones
Ampyrone/Aminophenazone • Metamizole • Phenazone • Propyphenazone

Cannabinoids
Ajulemic acid • AM404 • Cannabidiol • Cannabis • Nabilone • Nabiximols • Tetrahydrocannabinol

Anilides
Paracetamol (acetaminophen)^# • Phenacetin • Propacetamol

Non-steroidal
anti-inflammatories
See also: NSAIDs template

Propionic acid class

Fenoprofen • Flurbiprofen • Ibuprofen^# • Ketoprofen • Naproxen • Oxaprozin

Oxicam class

Meloxicam • Piroxicam

Acetic acid class

Diclofenac • Indometacin • Ketorolac • Nabumetone • Sulindac • Tolmetin

COX-2 inhibitors

Celecoxib • Rofecoxib • Valdecoxib • Parecoxib • Lumiracoxib

Anthranilic acid
(fenamate) class

Meclofenamate • Mefenamic acid

Salicylates

Aspirin (Acetylsalicylic acid)^# • Benorylate • Diflunisal • Ethenzamide • Magnesium salicylate • Salicin • Salicylamide • Salsalate • Trisalate • Wintergreen (Methyl salicylate)

Atypical, adjuvant and potentiators,
Metabolic agents and miscellaneous
Amitryptiline • Befiradol • Bicifadine • Carisoprodol • Camphor • Cimetidine • Clonidine • Chlorzoxazone • Cyclobenzaprine • Duloxetine • Esreboxetine • Flupirtine • Gabapentin • Glafenine • Hydroxyzine • Ketamine • Menthol • Mephenoxalone • Methocarbamol • Nefopam • Orphenadrine • Pregabalin • Proglumide • Scopolamine • Tebanicline • Trazodone • Gabapentin enacarbil • Ziconotide

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: CNS

anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug(N1A/2AB/C/3/4/7A/B/C/D)

v · d · eCough and cold preparations (R05)

Expectorants
Althea root • Antimony pentasulfide • Creosote • Guaiacolsulfonate • Guaifenesin • Ipecacuanha (Syrup of ipecac) • Levoverbenone • Potassium iodide • Senega • Tyloxapol

Mucolytics
Acetylcysteine • Ambroxol • Bromhexine • Carbocisteine • Domiodol • Dornase alfa • Eprazinone • Erdosteine • Letosteine • Mesna • Neltenexine • Sobrerol • Stepronin • Tiopronin

Cough suppressants

Opium alkaloids,
opioids,
and derivatives

Acetyldihydrocodeine • Benzylmorphine • Codeine • Dextromethorphan • Diacetylmorphine • Dihydrocodeine • Dimemorfan • Droxypropine • Ethylmorphine • Hydrocodone • Hydromorphone • Isoaminile • Laudanum • Levomethadone • Levopropoxyphene • Methadone • Nicocodeine • Nicodicodeine • Normethadone • Noscapine • Pholcodine • Thebacon • Tipepidine • Zipeprol

Other

Benzonatate • Benproperine • Bibenzonium bromide • Butamirate • Clobutinol • Clofedanol • Cloperastine • Diphenhydramine • Dibunate • Dimethoxanate • Dropropizine • Fedrilate • Glaucine • Levodropropizine • Meprotixol • Morclofone • Nepinalone • Oxolamine • Oxeladin • Pentoxyverine • Pipazetate • Prenoxdiazine • Piperidione

M: RES

anat(n, x, l, c)/phys/devp

noco(c, p)/cong/tumr, sysi/epon, injr

proc, drug(R1/2/3/5/6/7)

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Academic Dictionaries and Encyclopedias

Thebacon

References

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Systematic (IUPAC) name
6,7-didehydro- 4,5α-epoxy- 3-methoxy- 17-methylmorphinan- 6-ol acetate
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	Schedule I (US)
Identifiers
CAS number	466-90-0
ATC code	R05DA10
PubChem	CID 10075
UNII	520D430GDK^Y
KEGG	D07386^Y
Chemical data
Formula	C₂₀H₂₃N O₄
Mol. mass	341.401 g/mol
Y(what is this?) (verify)

Academic Dictionaries and Encyclopedias

Wikipedia

Thebacon

References

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