14-Methoxymetopon is an experimental

opioid Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid use ...

drug developed by a team led by Professor Helmut Schmidhammer at the University of Insbruck in the mid 1990s. It is a derivative of

metopon Metopon (5-methylhydromorphone) is an opioid analogue that is a methylated derivative of hydromorphone which was invented in 1929 as an analgesic. Metopon is sometimes used in medicine, although longer acting than hydromorphone, Metopon is less ...

in which a

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

group has been inserted at the 14-position. It is a highly potent analgesic drug that is around 500 times stronger than

morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. T ...

when administered systemically; however, when given spinally or supraspinally, it exhibits analgesic activity up to a million fold greater than morphine. It binds strongly to the

μ-opioid receptor The μ-opioid receptors (MOR) are a class of opioid receptors with a high affinity for enkephalins and beta-endorphin, but a low affinity for dynorphins. They are also referred to as μ(''mu'')-opioid peptide (MOP) receptors. The prototypical � ...

and activates it to a greater extent than most similar opioid drugs. This produces an unusual pharmacological profile, and although 14-methoxymetopon acts as a potent μ-opioid full agonist in regard to some effects such as analgesia, a ceiling effect is seen on other effects such as

constipation Constipation is a bowel dysfunction that makes bowel movements infrequent or hard to pass. The stool is often hard and dry. Other symptoms may include abdominal pain, bloating, and feeling as if one has not completely passed the bowel movement ...

and respiratory depression which is believed to involve interaction with the

κ-opioid receptor The κ-opioid receptor or kappa opioid receptor, abbreviated KOR or KOP, is a G protein-coupled receptor that in humans is encoded by the ''OPRK1'' gene. The KOR is coupled to the G protein Gi/G0 and is one of four related receptors that bind op ...

References

4,5-Epoxymorphinans Ethers Ketones Mu-opioid receptor agonists Opioids Phenols Semisynthetic opioids {{analgesic-stub

See also

References