14-Methoxymetopon

Chemical compound changed changed 477209012 3-Hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one 14-Methoxymetopon.svg skin-invert-image changed ?? 131575-03-6 correct EBI 326684 5486940 correct drugbank correct chemspider 4589140 19 23 1 4 C[C@]12C(=O)CC[C@@]3([C@]14CCN([C@@H]3CC5=C4C(=C(C=C5)O)O2)C)OC correct chemspider 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 correct chemspider DENICFHULARDRG-WEZQJLTASA-N 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.US 5886001 Agonist compounds. 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.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 459 2–3 203–9 January 2003 12524147 10.1016/S0014-2999(02)02821-2 It binds strongly to the μ-opioid receptor and activates it to a greater extent than most similar opioid drugs.Mahurter L, Garceau C, Marino J, Schmidhammer H, Tóth G, Pasternak GW 26268795 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 October 2006 16801454 10.1124/jpet.106.105395 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.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 90 6 1359–64 June 2000 10825321 32240231 10.1097/00000539-200006000-00018 free See also 14-Methoxydihydromorphinone References 30em Category:4,5-Epoxymorphinans Category:Ethers Category:Hydroxyarenes Category:Ketones Category:Mu-opioid receptor agonists Category:Opioids Category:Semisynthetic opioids