Phenomorphan
Encyclopedia
Phenomorphan is an opioid
Opioid
An opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...

 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 ....

. It is not currently used in medicine, but has similar side effects to other opiates, which include itching, nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...

 and respiratory depression.

Phenomorphan is a highly potent drug due to the N-phenethyl group which boosts affinity to the μ-opioid receptor, and so phenomorphan is around 10x more potent than levorphanol
Levorphanol
Levorphanol is an opioid medication used to treat severe pain. It is the levorotatory stereoisomer of the synthetic morphinan and a pure opioid agonist, first described in Germany in 1948 as an orally active morphine-like analgesic...

, which is itself 6-8x the potency of 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...

. Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings.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
Furan
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans....

)ethyl) and the N-(2-(2-thienyl
Thiophene
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a flat five-membered ring, it is aromatic as indicated by its extensive substitution reactions. Related to thiophene are benzothiophene and dibenzothiophene, containing the thiophene ring fused with one and two benzene...

)ethyl) analogues being 60x and 45x stronger than levorphanol respectively.

See also

  • 14-Cinnamoyloxycodeinone
    14-Cinnamoyloxycodeinone
    14-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-Phenylpropoxymetopon
    14-Phenylpropoxymetopon
    14-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-PET
    7-PET
    7-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-Phenethylnormorphine
    N-Phenethylnormorphine
    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...

  • N-Phenethylnordesomorphine
    N-Phenethylnordesomorphine
    N-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...

  • N-Phenethyl-14-ethoxymetopon
    N-Phenethyl-14-ethoxymetopon
    N-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....

  • RAM-378
    RAM-378
    RAM-378 is an opiate analgesic drug. It is the N-phenethyl derivative of hydromorphinol.-See also:* 14-Cinnamoyloxycodeinone* 14-Phenylpropoxymetopon* 7-PET* N-Phenethylnormorphine...

  • Ro4-1539
    Ro4-1539
    Ro4-1539 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...

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