Norpropoxyphene

Source: Wikipedia, the free encyclopedia.
Norpropoxyphene
Names
Preferred IUPAC name
(2S,3R)-3-Methyl-4-(methylamino)-1,2-diphenylbutan-2-yl propanoate
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C21H27NO2/c1-4-20(23)24-21(17(2)16-22-3,19-13-9-6-10-14-19)15-18-11-7-5-8-12-18/h5-14,17,22H,4,15-16H2,1-3H3/t17-,21+/m1/s1 checkY
    Key: IKACRWYHQXOSGM-UTKZUKDTSA-N checkY
  • InChI=1/C21H27NO2/c1-4-20(23)24-21(17(2)16-22-3,19-13-9-6-10-14-19)15-18-11-7-5-8-12-18/h5-14,17,22H,4,15-16H2,1-3H3/t17-,21+/m1/s1
    Key: IKACRWYHQXOSGM-UTKZUKDTBF
  • O=C(O[C@@](c1ccccc1)(Cc2ccccc2)[C@H](C)CNC)CC
Properties
C21H27NO2
Molar mass 325.445
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Norpropoxyphene is a major metabolite of the

overdose.[2][3][4] It has weaker analgesic effects than dextropropoxyphene itself, but is a relatively potent pro-convulsant and blocker of sodium and potassium channels,[5] particularly in heart tissue,[6][7] which produces prolonged intracardiac conduction time and can lead to heart failure following even relatively minor overdoses.[8][9][10][11] The toxicity of this metabolite makes dextropropoxyphene up to 10 times more likely to cause death following overdose compared to other similar mild opioid analgesics,[12] and has led to dextropropoxyphene being withdrawn from the market in some countries.[13]

Because norpropoxyphene has a long half-life in the body of up to 36 hours (compared to around 6–12 hours for dextropropoxyphene), it can accumulate in tissues during chronic use of dextropropoxyphene-containing medications, especially in people whose excretion of drugs is slower than normal such as young children, the elderly, and individuals with reduced kidney or liver function, and so side effects including serious adverse events are more common in these groups and use of dextropropoxyphene should be avoided where possible.[14][15][16]

References

  1. S2CID 7680532
    .
  2. PMID 983792
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  3. PMID 949842
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  4. S2CID 1333582
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  5. PMID 13200
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  6. PMID 580345
    .
  7. PMID 10690289
    .
  8. S2CID 46978533
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  9. S2CID 13452948
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  10. S2CID 36817890
    .
  11. PMID 15728397
    .
  12. PMID 16187978
    .
  13. PMID 18489609
    .
  14. S2CID 24099122
    .
  15. S2CID 38421623
    .
  16. PMID 2590604
    .