14-Methoxymetopon

14-Methoxymetopon
Systematic (IUPAC) name
3-hydroxy- 14-methoxy- 5,17-dimethyl- 7,8-dihydro- 4,5α- epoxy- morphinan- 6-one
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 131575-03-6 N
ATC code  ?
PubChem CID 5486940
ChemSpider 4589140 Y
ChEMBL CHEMBL326684 Y
Synonyms 14-Methoxymetopon
Chemical data
Formula C19H23NO4 
Mol. mass 329.39 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

14-Methoxymetopon is an opiate analogue that is a 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 exhibits analgesic activity up to a million fold greater than 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

  1. ^ King, MA; Su, W; Nielan, CL; Chang, AH; Schütz, J; Schmidhammer, H; Pasternak, GW (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. 
  2. ^ Mahurter, L; Garceau, C; Marino, J; Schmidhammer, H; Tóth, G; Pasternak, GW (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. 
  3. ^ Freye, E; Schmidhammer, H; Latasch, L (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.