Phenomorphan
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Phenomorphan is an
opioid Opioids are a class of Drug, drugs that derive from, or mimic, natural substances found in the Papaver somniferum, opium poppy plant. Opioids work on opioid receptors in the brain and other organs to produce a variety of morphine-like effects, ...
analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...
. It is not currently used in medicine, but has similar side-effects to other opiates, which include
itching An itch (also known as pruritus) is a sensation that causes a strong desire or reflex to scratch. Itches have resisted many attempts to be classified as any one type of sensory experience. Itches have many similarities to pain, and while both ...
,
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...
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 Ge ...
, which is itself 6-8x the potency of
morphine Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are ...
. 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 Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reacti ...
)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 over 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 * 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 Hydromorphinol (RAM-320, 14-hydroxydihydromorphine), is an opiate analogue that is a derivative of morphine, wher ...
* Ro4-1539


References

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