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

Identifiers
IUPAC name 3-Hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one
CAS Number	131575-03-6 N
PubChem CID	5486940
ChemSpider	4589140 Y
ChEMBL	ChEMBL326684 Y
CompTox Dashboard (EPA)	DTXSID50927273
Chemical and physical data
Formula	C19H23NO4
Molar mass	329.396 g·mol−1
3D model (JSmol)	Interactive image
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