Bentley compounds
{{Short description|Class of chemical compounds}}
File:Bentley compounds single bond.svg
File:Bentley compounds double bond.svg
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.{{ cite journal |author1=Bentley, K. W. |author2=Boura, A. L. |author3=Fitzgerald, A. E. |author4=Hardy, D. G. |author5=McCoubrey, A. |author6=Aikman, M. L. |author7=Lister, R. E. | title = Compounds Possessing Morphine-Antagonising or Powerful Analgesic Properties | journal = Nature | year = 1965 | volume = 206 | issue = 4979 | pages = 102–103 | pmid = 14334338 | doi = 10.1038/206102a0 |bibcode=1965Natur.206..102B |s2cid=4296776 }}{{ cite journal |author1=Bentley, K. W. |author2=Hardy, D. G. | title = Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine group. I. Ketones Derived from 6,14-endo-Ethenotetrahydrothebaine | journal = Journal of the American Chemical Society | year = 1967 | volume = 89 | issue = 13 | pages = 3267–3273 | doi = 10.1021/ja00989a030 }}{{ cite journal |author1=Bentley, K. W. |author2=Hardy, D. G. |author3=Meek, B. | title = Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. II. Alcohols Derived from 6,14-endo-Etheno- and 6,14-endo-Ethanotetrahydrothebaine | journal = Journal of the American Chemical Society | year = 1967 | volume = 89 | issue = 13 | pages = 3273–3280 | pmid = 6042763 | doi = 10.1021/ja00989a031 }}{{ cite journal |author1=Bentley, K. W. |author2=Hardy, D. G. | title = 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 = Journal of the American Chemical Society | year = 1967 | volume = 89 | issue = 13 | pages = 3281–3292 | pmid = 6042764 | doi = 10.1021/ja00989a032 }}{{ cite journal |author1=Bentley, K. W. |author2=Hardy, D. G. |author3=Meek, B. | title = Novel Analgesics and Molecular Rearrangements in the Morphine-Thebaine Group. IV. Acid-Catalyzed Rearrangements of Alcohols of the 6,14-endo-Ethenotetrahydrothebaine Series | journal = Journal of the American Chemical Society | year = 1967 | volume = 89 | issue = 13 | pages = 3293–3303 | pmid = 6042765 | doi = 10.1021/ja00989a033 }}