Bentley compounds


Bentley compounds

Bentley compounds are a class of semi-synthetic opioids that were first synthesized from thebaine by K. W. Bentley. The compounds include: oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine. They represent the first series of more potent μ-opioid agonists, with some compounds in the series being over 1000 times the potency of morphine as an analgesic. The latter was then used in veterinarian medicine as a narcotic for elephants and other large animals.[1][2][3]

The true "bentley compounds" are properly known as the orvinols, and include a series of bridged oripavine derivatives which can be manufactured with thebaine or oripavine itself. The trademark of these compounds is the presence of a 6,14 endoetheno bridge and their substitution at carbon position 7.

Oxycodone, oxymorphone, naloxone, or nalbuphine do not possess either of these characteristics and were not discovered by K. W. Bentley or Reckitt Research Group; Oxymorphone and oxycodone are in the codeinone/morphinone class, while naloxone is a non-bridged thebaine derivative. Nalbuphine is a morphinan class mixed agonist/antagonist.

References

  1. ^ Bentley KW, Boura AL, Fitzgerald AE, Hardy DG, McCoubrey A, Aikman ML, Lister RE. Compounds Possessing Morphine-Antagonising or Powerful Analgesic Properties. Nature. 1965 Apr 3;206:102-3. PMID 14334338
  2. ^ Bentley KW, Hardy DG, 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 Jun 21;89(13):3273-80. PMID 6042763
  3. ^ Bentley KW, Hardy DG, 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 Jun 21;89(13):3293-303. PMID 6042765