Bentley compounds explained

The Bentley compounds are a class of semi-synthetic opioids that were first synthesized by K. W. Bentley by Diels-Alder reaction of thebaine with various dienophiles. The compounds are also known as thevinols, orvinols, or bridged oripavine derivatives, due to the characteristic 6,14-endo-ethano- or etheno-bridge and substitution at the 7α position. Buprenorphine and etorphine are perhaps the best known of the family, which was the first series of extremely potent μ-opioid agonists, with some compounds in the series having over many thousands of times the analgesic potency of morphine.^{[1] [2] [3] [4] [5]}

See also

• Oripavine#Bridged derivatives

Notes and References

1. Bentley, K. W. . Boura, A. L. . Fitzgerald, A. E. . Hardy, D. G. . McCoubrey, A. . Aikman, M. L. . Lister, R. E. . Compounds Possessing Morphine-Antagonising or Powerful Analgesic Properties . Nature . 1965 . 206 . 4979 . 102–103 . 14334338 . 10.1038/206102a0 . 1965Natur.206..102B . 4296776 .
2. Bentley, K. W. . Hardy, D. G. . Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine group. I. Ketones Derived from 6,14-endo-Ethenotetrahydrothebaine . Journal of the American Chemical Society . 1967 . 89 . 13 . 3267–3273 . 10.1021/ja00989a030 .
3. Bentley, K. W. . Hardy, D. G. . Meek, B. . Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. II. Alcohols Derived from 6,14-endo-Etheno- and 6,14-endo-Ethanotetrahydrothebaine . Journal of the American Chemical Society . 1967 . 89 . 13 . 3273–3280 . 6042763 . 10.1021/ja00989a031 .
4. Bentley, K. W. . Hardy, D. G. . Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. III. Alcohols of the 6,14-endo-ethenotetrahydrooripavine Series and Derived Analogs of N-Allylnormorphine and -norcodeine . Journal of the American Chemical Society . 1967 . 89 . 13 . 3281–3292 . 6042764 . 10.1021/ja00989a032 .
5. Bentley, K. W. . Hardy, D. G. . Meek, B. . Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. IV. Acid-Catalyzed Rearrangements of Alcohols of the 6,14-endo-Ethenotetrahydrothebaine Series . Journal of the American Chemical Society . 1967 . 89 . 13 . 3293–3303 . 6042765 . 10.1021/ja00989a033 .