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Hydrocodone (Molecule of the Month for April 2009)

Vicodin, Symtan, Anexsia, Dicodid, Hycodan (or generically Hydromet), Hycomine, Hycet, Lorcet, Lortab, Norco, Novahistex, Hydrovo, Duodin, Kolikodol, Orthoxycol, Mercodinone, Synkonin, Norgan, Hydrokon

Hydrocodone or dihydrocodeinone is a semi-synthetic opioid derived from two of the naturally occurring opiates, codeine and thebaine. Hydrocodone is an orally active narcotic analgesic (pain reliever) and antitussive (cough suppressant). It is commonly available in tablet, capsule, and syrup form, and is often compounded with other analgesics like paracetamol or ibuprofen. Hydrocodone was first synthesized in Germany in 1920[1] and was approved by the Food and Drug Administration on 23 March 1943 for sale in the United States and Canada under the brand name Hycodan.

As a narcotic, hydrocodone relieves pain by binding to opioid receptors in the brain and spinal cord. It can be taken with or without food as desired. When taken with alcohol, it can intensify drowsiness. It may interact with monoamine oxidase inhibitors, as well as other drugs that cause drowsiness. Studies have shown hydrocodone as stronger than codeine but only one-tenth as potent as morphine at binding to receptors, whereas roughly half as potent as morphine in analgesic properties. However other studies have shown hydrocodone to be anywhere from half as potent to oxycodone (1.5 the potency of morphine) to only 66.6~% the potency of oxycodone (equipotent to morphine). Hydrocodone can be habit-forming, which leads to physical and psychological dependence, but the potential for addiction varies from individual to individual depending on unique biological differences. Sales and production of this drug have increased significantly in recent years, as have diversion and illicit use. In the U.S., formulations containing more than 15 mg per dosage unit are considered Schedule II drugs, as would any formulation consisting of just hydrocodone alone. Those containing less than or equal to 15 mg per dosage unit in combination with acetaminophen or another non-controlled drug are called hydrocodone compounds and are considered Schedule III drugs. Hydrocodone is typically found in combination with other drugs such as paracetamol, aspirin, ibuprofen and homatropine methylbromide.

One of the major problems today with the illicit use of hydrocodone, especially in younger populations, is that users may not be aware that hydrocodone pills contain acetaminophen. Consuming more than 4,000 milligrams of acetaminophen a day can cause liver damage, jaundice, and even liver failure if the drug is being taken in excessive dosages for an extended period of time. The presence of acetaminophen in hydrocodone-containing products allegedly deters many drug users, at least in theory, from taking excessive amounts. However, some users will get around this by using cold water extraction to extract and dispose of a portion of the acetaminophen, taking advantage of the water-soluble element of the drug.

Formal Chemical Name (IUPAC)



Picture of Hydrocodone 3D model

click on the picture of  Hydrocodone above to interact
with the 3D model of the
Hydrocodone structure
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Picture of Hydrocodone

C18 H21 N O3

Update by Karl Harrison
(Molecule of the Month for April 2009 )

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