14-Methoxymetopon

14-Methoxymetopon is an experimental opioid drug developed by a team led by Professor Helmut Schmidhammer at the University of Insbruck 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
IUPAC name
  • 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)
SMILES
  • C[C@]12C(=O)CC[C@@]3([C@]14CCN([C@@H]3CC5=C4C(=C(C=C5)O)O2)C)OC
InChI
  • 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 Y
  • Key:DENICFHULARDRG-WEZQJLTASA-N Y
 NY (what is this?)  (verify)

See also
  • 14-Methoxydihydromorphinone

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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