14-Methoxymetopon

14-Methoxymetopon is an experimental opioid drug developed by a team led by Professor Helmut Schmidhammer at the University of Innsbruck in the mid-1990s.[1] It is a derivative of metopon in which a methoxy group has been inserted at the 14-position. It is a highly potent analgesic drug that is around 500 times stronger than morphine when administered systemically; however, when given spinally or supraspinally, it exhibits analgesic activity up to a million fold greater than morphine.[2] It binds strongly to the μ-opioid receptor and activates it to a greater extent than most similar opioid drugs.[3] This produces an unusual pharmacological profile, and although 14-methoxymetopon acts as a potent μ-opioid full agonist in regard to some effects such as analgesia, a ceiling effect is seen on other effects such as constipation and respiratory depression which is believed to involve interaction with the κ-opioid receptor[4]

14-Methoxymetopon
Clinical data
Other names14-Methoxymetopon
Identifiers
  • 3-Hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23NO4
Molar mass329.396 g·mol−1
3D model (JSmol)
  • C[C@]12C(=O)CC[C@@]3([C@]14CCN([C@@H]3CC5=C4C(=C(C=C5)O)O2)C)OC
  • InChI=1S/C19H23NO4/c1-17-14(22)6-7-19(23-3)13-10-11-4-5-12(21)16(24-17)15(11)18(17,19)8-9-20(13)2/h4-5,13,21H,6-10H2,1-3H3/t13-,17+,18+,19-/m1/s1 checkY
  • Key:DENICFHULARDRG-WEZQJLTASA-N checkY
 ☒NcheckY (what is this?)  (verify)

See also

References
  1. US 5886001, "Agonist compounds"
  2. King MA, Su W, Nielan CL, Chang AH, Schütz J, Schmidhammer H, Pasternak GW (January 2003). "14-Methoxymetopon, a very potent mu-opioid receptor-selective analgesic with an unusual pharmacological profile". European Journal of Pharmacology. 459 (2–3): 203–9. doi:10.1016/S0014-2999(02)02821-2. PMID 12524147.
  3. Mahurter L, Garceau C, Marino J, Schmidhammer H, Tóth G, Pasternak GW (October 2006). "Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon". The Journal of Pharmacology and Experimental Therapeutics. 319 (1): 247–53. doi:10.1124/jpet.106.105395. PMID 16801454. S2CID 26268795.
  4. Freye E, Schmidhammer H, Latasch L (June 2000). "14-methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog". Anesthesia and Analgesia. 90 (6): 1359–64. doi:10.1097/00000539-200006000-00018. PMID 10825321. S2CID 32240231.


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