14-Methoxymetopon

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14-Methoxymetopon
14-methoxymetopon.svg
Clinical data
Synonyms14-Methoxymetopon
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC19H23NO4
Molar mass329.39 g/mol
3D model (JSmol)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Overview

14-Methoxymetopon is an opiate analogue that is an 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, it is up to 1 million times the potency of 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]

References

  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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