14-Methoxymetopon

14-Methoxymetopon
Clinical data
Synonyms	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;
PubChem CID	5486940;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C19H23NO4
Molar mass	329.39 g/mol
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;

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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]

References

↑ 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
↑ 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
↑ 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

Template:Opioids

Template:WikiDoc Sources

[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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14-Methoxymetopon

Overview

References

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