N-Phenethylnormorphine
Encyclopedia
N-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 substantially less active, or act as antagonists
. Binding studies have helped to explain the increased potency of N-phenethylnormorphine, showing that the phenethyl group extends out to reach an additional binding point deeper inside the mu opioid receptor
cleft, analogous to the binding of the phenethyl group on fentanyl.
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,...
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 derived from 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...
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 substantially less active, or act as antagonists
Receptor antagonist
A receptor antagonist is a type of receptor ligand or drug that does not provoke a biological response itself upon binding to a receptor, but blocks or dampens agonist-mediated responses...
. Binding studies have helped to explain the increased potency of N-phenethylnormorphine, showing that the phenethyl group extends out to reach an additional binding point deeper inside the mu opioid receptor
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...
cleft, analogous to the binding of the phenethyl group on fentanyl.
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...
- 14-Phenylpropoxymetopon14-Phenylpropoxymetopon14-Phenylpropoxymetopon 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...
- 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-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....
- N-PhenethylnordesomorphineN-PhenethylnordesomorphineN-Phenethylnordesomorphine is an opiate analgesic drug derived from desomorphine by replacing the N-methyl group with β-phenethyl. Since desomorphine is already around eight times more potent than morphine, the additional boost in binding affinity produced by using the larger phenethyl group makes...
- 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...