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Phenomorphan is an
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 ...
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 ...
. It is not currently used in medicine, but has similar side-effects to other opiates, which include
itching Itch (also known as pruritus) is a sensation that causes the desire or reflex to scratch. Itch has resisted many attempts to be classified as any one type of sensory experience. Itch has many similarities to pain, and while both are unpleasan ...
,
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of th ...
and
respiratory depression Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapni ...
. Phenomorphan is a highly potent drug due to the N-phenethyl group, which boosts affinity 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 so phenomorphan is around 10x more potent than
levorphanol Levorphanol (brand name Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. It is the levorotatory enantiomer of the compound racemorphan. Its dextrorotatory counterpart is dextrorphan. It was first described in Germa ...
, which is itself 6-8x the potency of
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 ...
. Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2- thienyl)ethyl) analogues being 60x and 45x stronger than levorphanol, respectively.


See also

*
14-Cinnamoyloxycodeinone 14-Cinnamoyloxycodeinone is the most potent example in a series of opiate analgesic drugs discovered in the 1960s, with > ×100 times the potency of morphine. It is a derivative of , being the 14- cinnamate ester. In another paper, Buckett assign ...
* 14-Phenylpropoxymetopon *
7-PET 7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight. It was discovered by K.W. Bentley and is related to the more well known oripavine derivative etorphine, which is used as a veterinary painkiller and anestheti ...
* N-Phenethylnormorphine * N-Phenethylnordesomorphine * N-Phenethyl-14-ethoxymetopon *
RAM-378 RAM-378(7,8-Dihydro-14-hydroxy-N-phenethylnormorphine) is an opioid analgesic. It is the N-phenethyl derivative of hydromorphinol. See also * 14-Cinnamoyloxycodeinone * 14-Phenylpropoxymetopon * 7-PET * N-Phenethylnormorphine * N-Phenethyl-14 ...
*
Ro4-1539 Ro4-1539 (furethylnorlevorphanol) is an opioid analgesic drug from the morphinan series that was discovered by the pharmaceutical company Hoffmann–La Roche in the 1950s. It acts as a potent μ-opioid agonist, and was found to be around 30-60 t ...


References

Synthetic opioids Morphinans Phenols Mu-opioid receptor agonists {{pharm-stub