14-Methoxymetopon

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;
ChemSpider	4589140 ;
ChEMBL	ChEMBL326684 ;
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 ; Key:DENICFHULARDRG-WEZQJLTASA-N ;
	(what is this?) (verify)

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]

References

^ US 5886001, "Agonist compounds" .
^ King MA, Su W, Nielan CL, Chang AH, Schütz J, Schmidhammer H, Pasternak GW (January 2003). "14-Methoxymetopon, a very potent mu-opioid receptor-selective analgesic with an unusual pharmacological profile". European Journal of Pharmacology. 459 (2–3): 203–9. doi:10.1016/S0014-2999(02)02821-2. PMID 12524147.
^ Mahurter L, Garceau C, Marino J, Schmidhammer H, Tóth G, Pasternak GW (October 2006). "Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon". The Journal of Pharmacology and Experimental Therapeutics. 319 (1): 247–53. doi:10.1124/jpet.106.105395. PMID 16801454. S2CID 26268795.
^ Freye E, Schmidhammer H, Latasch L (June 2000). "14-methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog". Anesthesia and Analgesia. 90 (6): 1359–64. doi:10.1097/00000539-200006000-00018. PMID 10825321. S2CID 32240231.

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[1] US 5886001, "Agonist compounds" .

[2] King MA, Su W, Nielan CL, Chang AH, Schütz J, Schmidhammer H, Pasternak GW (January 2003). "14-Methoxymetopon, a very potent mu-opioid receptor-selective analgesic with an unusual pharmacological profile". European Journal of Pharmacology. 459 (2–3): 203–9. doi:10.1016/S0014-2999(02)02821-2. PMID 12524147.

[3] Mahurter L, Garceau C, Marino J, Schmidhammer H, Tóth G, Pasternak GW (October 2006). "Separation of binding affinity and intrinsic activity of the potent mu-opioid 14-methoxymetopon". The Journal of Pharmacology and Experimental Therapeutics. 319 (1): 247–53. doi:10.1124/jpet.106.105395. PMID 16801454. S2CID 26268795.

[4] Freye E, Schmidhammer H, Latasch L (June 2000). "14-methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog". Anesthesia and Analgesia. 90 (6): 1359–64. doi:10.1097/00000539-200006000-00018. PMID 10825321. S2CID 32240231.

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See also

References