14-Methoxymetopon

{{Short description|Chemical compound}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477209012

| IUPAC_name = 3-Hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one

| image = 14-Methoxymetopon.svg

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 131575-03-6

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| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 326684

| PubChem = 5486940

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4589140

| C=19 | H=23 | N=1 | O=4

| smiles = C[C@]12C(=O)CC[C@@]3([C@]14CCN([C@@H]3CC5=C4C(=C(C=C5)O)O2)C)OC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DENICFHULARDRG-WEZQJLTASA-N

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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.{{cite patent |country=US |number=5886001 |title=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.{{cite journal |vauthors=King MA, Su W, Nielan CL, Chang AH, Schütz J, Schmidhammer H, Pasternak GW |title=14-Methoxymetopon, a very potent mu-opioid receptor-selective analgesic with an unusual pharmacological profile |journal=European Journal of Pharmacology |volume=459 |issue=2–3 |pages=203–9 |date=January 2003 |pmid=12524147 |doi=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.{{cite journal |vauthors=Mahurter L, Garceau C, Marino J, Schmidhammer H, Tóth G, Pasternak GW |s2cid=26268795 |title=Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=319 |issue=1 |pages=247–53 |date=October 2006 |pmid=16801454 |doi=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.{{cite journal |vauthors=Freye E, Schmidhammer H, Latasch L |title=14-methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog |journal=Anesthesia and Analgesia |volume=90 |issue=6 |pages=1359–64 |date=June 2000 |pmid=10825321 |s2cid=32240231 |doi=10.1097/00000539-200006000-00018 |doi-access=free}}