Codeinone is 1/3 as active as

codeine Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, ''Papaver somniferum''. It is typically use ...

as an

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

but it is an important intermediate in the production of

hydrocodone Hydrocodone, also known as dihydrocodeinone, is an opioid used to treat pain and as a cough suppressant. It is taken by mouth. Typically it is dispensed as the combination acetaminophen/hydrocodone or ibuprofen/hydrocodone for pain severe en ...

, a painkiller about 3/4 the potency of morphine; as well as of

oxycodone Oxycodone, sold under various brand names such as Roxicodone and OxyContin (which is the extended release form), is a strong, semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive and a commonly ...

. The latter can also be synthesized from

thebaine Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, '' Thēbai'' (Thebes), an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar ...

, however.

Chemical structure

Codeinone can be described as the methylether of

morphinone Morphinone is an opioid that is the intermediate when morphine is being converted to hydromorphone (trade name Dilaudid). Chemical structure Morphinone can be described as the ketone of morphine. Legal status Morphinone itself is an active ...

: 3-methyl-morphinone. Codeinone can be also described as the

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

: codeine-6-one.

Apoptotic activity

Through renewed interest into possible anti-tumor activities of some of the

opium Opium (or poppy tears, scientific name: ''Lachryma papaveris'') is dried latex obtained from the seed capsules of the opium poppy ''Papaver somniferum''. Approximately 12 percent of opium is made up of the analgesic alkaloid morphine, which i ...

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

s and derivatives, unrelated to their antinociceptive properties and habit-forming effects, the oxidation product of codeine has been found to induce cell death in three different human cancer cell lines ''in vitro''.Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). ''Anticancer Res.'' 23(3B):2569-76.

References

Catechol ethers Enones 4,5-Epoxymorphinans Mu-opioid receptor agonists Semisynthetic opioids {{analgesic-stub