14-Methoxymetopon

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

---

width = 220
CAS_number = 131575-03-6
synonyms = 14-Methoxymetopon
ATC_prefix =
ATC_suffix =
PubChem = 5486940
DrugBank =
C = 19 | H = 23 | N = 1 | O = 4
molecular_weight = 329.39 g/mol
smiles = C [C@] 12C(=O)CC [C@@] 3( [C@] 14CCN( [C@@H] 3CC5=C4C(=C(C=C5)O)O2)C)OC
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion =
pregnancy_AU =
pregnancy_US =
pregnancy_category=
legal_AU =
legal_CA =
legal_UK =
legal_US =
legal_status =
routes_of_administration =

14-Methoxymetopon is an opiate analogue that is an derivative of metopon which has been substituted with a methoxy group at the 14-position. It is a highly potent analgesic drug that is around 500x stronger than morphine when administered systemically; however, when given spinally or supraspinally, it is more than a million times the potency of 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". 2003 Jan 17;459(2-3):203-9. PMID 12524147] 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. Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon. "Journal of Pharmacology and Experimental Therapeutics". 2006 Oct;319(1):247-53. PMID 16801454] This produces an unusual pharmacological profile, and although 14-methoxymetopon acts as a potent μ-opioid full agonist in regards to some effects such as analgesia, a ceiling effect is seen on other effects such as constipation and respiratory depression. [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". 2000 Jun;90(6):1359-64. PMID 10825321]

References