Proxorphan

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Proxorphan
Clinical data
ATC code
  • None
Identifiers
  • 17-(Cyclopropylmethyl)-6-oxamorphinan-3-ol
    or
    (1S,9R,10R)-17-(cyclopropylmethyl)-13-oxa-17-azatetracyclo[7.5.3.0~1,10~.0~2,7~]heptadeca-2,4,6-trien-4-ol
JSmol)
  • c1cc2c(cc1O)C34CCN(C(C2)C3CCOC4)CC5CC5

Proxorphan (

μ-opioid receptor partial agonist.[2][3][4][5][6]

Synthesis

T. A. Montzka, J. D. Matiskella and R. A. Partyka, U.S. patent 4,246,413; Chem. Abstr. 95, 43442z (1981).

Starting material for this preparation is ketoester 1, available by one of the classical benzomorphan syntheses.

BrCN (or ethyl chloroformate) followed by saponification of the intermediate leads to the 2° amine (6). This is converted to the cyclopropylmethyl derivative 8 by acylation with cyclopropylcarbonyl chloride[8][9] followed by reduction of the thus formed amide (7) with LiAlH4. Cleaving off the O-methyl ether with sodium ethanethiol
affords proxorphan (9).

See also

References

  1. ISBN 978-1-4757-2085-3
    .
  2. PMID 6137557
    .
  3. S2CID 54433737
    .
  4. PMID 2566680
    .
  5. PMID 1331411
    .
  6. ISBN 978-1-4832-8798-0
    .
  7. PMID 20240573
    .
  8. ^ Zhang K, Lu M, Li Y (18 October 2018). "Synthesis of cyclopropanecarbonyl chloride". Chemical Industry Times. 17 (7): 36–38.
  9. ^ U.S. patent 5,504,245


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