Bentley compounds

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]}

General structure of a Bentley compound with an ethano-bridge (single bond)

General structure of a Bentley compound with an etheno-bridge (double bond)

See also

• Oripavine#Bridged derivatives

References

1. Bentley, K. W.; Boura, A. L.; Fitzgerald, A. E.; Hardy, D. G.; McCoubrey, A.; Aikman, M. L.; Lister, R. E. (1965). "Compounds Possessing Morphine-Antagonising or Powerful Analgesic Properties". Nature. 206 (4979): 102–103. Bibcode:1965Natur.206..102B. doi:10.1038/206102a0. PMID 14334338. S2CID 4296776.
2. Bentley, K. W.; Hardy, D. G. (1967). "Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine group. I. Ketones Derived from 6,14-endo-Ethenotetrahydrothebaine". Journal of the American Chemical Society. 89 (13): 3267–3273. doi:10.1021/ja00989a030.
3. Bentley, K. W.; Hardy, D. G.; Meek, B. (1967). "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. 89 (13): 3273–3280. doi:10.1021/ja00989a031. PMID 6042763.
4. Bentley, K. W.; Hardy, D. G. (1967). "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. 89 (13): 3281–3292. doi:10.1021/ja00989a032. PMID 6042764.
5. Bentley, K. W.; Hardy, D. G.; Meek, B. (1967). "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. 89 (13): 3293–3303. doi:10.1021/ja00989a033. PMID 6042765.