14-Methoxymetopon

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14-Methoxymetopon
Systematic (IUPAC) name
3-hydroxy-14-methoxy-5,17-dimethyl-7,8-dihydro-4,5α-epoxy-morphinan-6-one
Identifiers
CAS number	131575-03-6
ATC code	?
PubChem	5486940
Chemical data
Formula	C19H23NO4
Mol. mass	329.39 g/mol
SMILES	eMolecules & PubChem
Synonyms	14-Methoxymetopon
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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, it is up to 1 million times the potency of morphine.^[1] It binds strongly to the μ-opioid receptor and activates it to a greater extent than most similar opioid drugs.^[2] 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.^[3]

[edit] References

1. ^ 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
2. ^ 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
3. ^ 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

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