14-Phenylpropoxymetopon
Encyclopedia
14-Phenylpropoxymetopon (PPOM) is an opiate
analogue that is an derivative of metopon
which has been substituted with a γ-phenylpropoxy group at the 14-position. It is a highly potent analgesic
drug several thousand times stronger than morphine
, with a similar in vivo potency to etorphine
. The 14-phenylpropoxy substitution appears to confer potent μ-opioid
agonist activity, even when combined with substitutions such as N-cyclopropyl or N-allyl, which normally result in μ-opioid antagonist compounds.
It has never been used in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation
, euphoria
, constipation
, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence
would be expected to develop rapidly based on the potency of the drug, as it is of a similar strength to the potent fentanyl analogues and so would most likely cause pronounced tachyphylaxis
following repeated dosing.
Opiate
In medicine, the term opiate describes any of the narcotic opioid alkaloids found as natural products in the opium poppy plant.-Overview:Opiates are so named because they are constituents or derivatives of constituents found in opium, which is processed from the latex sap of the opium poppy,...
analogue that is an derivative of metopon
Metopon
Metopon is an opiate analogue that is a methylated derivative of hydromorphone which was invented in 1948 as an analgesic....
which has been substituted with a γ-phenylpropoxy group at the 14-position. It is a highly potent analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
drug several thousand times stronger than morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
, with a similar in vivo potency to etorphine
Etorphine
Etorphine is a semi-synthetic opioid possessing an analgesic potency approximately 200 times that of morphine. It was first prepared in 1960 from oripavine, which does not generally occur in opium poppy extract but rather in "poppy straw" and in related plants, Papaver orientale and Papaver...
. The 14-phenylpropoxy substitution appears to confer potent μ-opioid
Mu Opioid receptor
The μ-opioid receptors are a class of opioid receptors with high affinity for enkephalins and beta-endorphin but low affinity for dynorphins. They are also referred to as μ opioid peptide receptors. The prototypical μ receptor agonist is the opium alkaloid morphine; μ refers to morphine...
agonist activity, even when combined with substitutions such as N-cyclopropyl or N-allyl, which normally result in μ-opioid antagonist compounds.
It has never been used in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation
Sedation
Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure...
, euphoria
Euphoria (emotion)
Euphoria is medically recognized as a mental and emotional condition in which a person experiences intense feelings of well-being, elation, happiness, ecstasy, excitement and joy...
, constipation
Constipation
Constipation refers to bowel movements that are infrequent or hard to pass. Constipation is a common cause of painful defecation...
, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence
Physical dependence
Physical dependence refers to a state resulting from chronic use of a drug that has produced tolerance and where negative physical symptoms of withdrawal result from abrupt discontinuation or dosage reduction...
would be expected to develop rapidly based on the potency of the drug, as it is of a similar strength to the potent fentanyl analogues and so would most likely cause pronounced tachyphylaxis
Tachyphylaxis
Tachyphylaxis is a medical term describing a decrease in the response to a drug due to previous exposure to that drug. Increasing the dose of the drug may be able to restore the original response. In this context tachyphylaxis is a synonym for drug tolerance...
following repeated dosing.
See also
- 14-Cinnamoyloxycodeinone14-Cinnamoyloxycodeinone14-Cinnamoyloxycodeinone is an opiate analgesic drug discovered in the 1960s, with around 100 times the potency of morphine. It is a derivative of oxycodeinone, being the 14-cinnamate ester.-See also:* 14-Phenylpropoxymetopon* 7-PET...
- 7-PET7-PET7-PET was discovered by K.W. Bentley and is a potent analgesic drug, 300 times the potency of morphine by weight. It is related to the more well-known oripavine derivative opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic medication, used primarily for the...
- N-PhenethylnormorphineN-PhenethylnormorphineN-Phenethylnormorphine is an opiate analgesic drug derived from morphine by replacing the N-methyl group with β-phenethyl. It is around eight to fourteen times more potent than morphine as a result of this modification, in contrast to most other N-substituted derivatives of morphine which are...
- N-Phenethyl-14-ethoxymetoponN-Phenethyl-14-ethoxymetoponN-Phenethyl-14-ethoxymetopon is a drug which is a derivative of metopon. It is a potent analgesic, around 60 times stronger than morphine and produces significantly less constipation....
- PhenomorphanPhenomorphanPhenomorphan is an opioid analgesic. It is not currently used in medicine, but has similar side effects to other opiates, which include itching, nausea and respiratory depression....
- RAM-378RAM-378RAM-378 is an opiate analgesic drug. It is the N-phenethyl derivative of hydromorphinol.-See also:* 14-Cinnamoyloxycodeinone* 14-Phenylpropoxymetopon* 7-PET* N-Phenethylnormorphine...
- Ro4-1539Ro4-1539Ro4-1539 is an opioid analgesic drug from the morphinan series, which was developed by the pharmaceutical company Hoffmann–La Roche in the 1950s. It acts as a potent μ-opioid agonist, and was found to be around 30-60x more potent than the related drug levorphanol in animal experiments...