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14-Methoxymetopon: Wikis


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Systematic (IUPAC) name
3-hydroxy- 14-methoxy- 5,17-dimethyl- 7,8-dihydro- 4,5α- epoxy- morphinan- 6-one
CAS number 131575-03-6
ATC code  ?
PubChem 5486940
Chemical data
Formula C 19H23NO4  
Mol. mass 329.39 g/mol
SMILES eMolecules & PubChem
Synonyms 14-Methoxymetopon
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

14-Methoxymetopon is an opiate analogue that is a derivative of metopon which has been substituted with a methoxy group at the 14-position. It is a highly potent analgesic drug that is around 500x stronger than morphine when administered systemically; however, when given spinally or supraspinally, it exhibits analgesic activity up to a million fold greater than morphine.[1] It binds strongly to the μ-opioid receptor and activates it to a greater extent than most similar opioid drugs.[2] This produces an unusual pharmacological profile, and although 14-methoxymetopon acts as a potent μ-opioid full agonist in regards to some effects such as analgesia, a ceiling effect is seen on other effects such as constipation and respiratory depression.[3]


  1. ^ King MA, Su W, Nielan CL, Chang AH, Schütz J, Schmidhammer H, Pasternak GW. 14-Methoxymetopon, a very potent mu-opioid receptor-selective analgesic with an unusual pharmacological profile. European Journal of Pharmacology. 2003 Jan 17;459(2-3):203-9. PMID 12524147
  2. ^ Mahurter L, Garceau C, Marino J, Schmidhammer H, Tóth G, Pasternak GW. Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon. Journal of Pharmacology and Experimental Therapeutics. 2006 Oct;319(1):247-53. PMID 16801454
  3. ^ Freye E, Schmidhammer H, Latasch L. 14-methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog. Anesthesia and Analgesia. 2000 Jun;90(6):1359-64. PMID 10825321


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