Bentley compounds
Class of chemical compounds
![](http://upload.wikimedia.org/wikipedia/commons/thumb/7/77/Bentley_compounds_single_bond.svg/220px-Bentley_compounds_single_bond.svg.png)
![](http://upload.wikimedia.org/wikipedia/commons/thumb/3/33/Bentley_compounds_double_bond.svg/220px-Bentley_compounds_double_bond.svg.png)
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
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
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Opioid receptor modulators
(MOR)
(DOR)
(KOR)
(NOP)
Agonists |
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Antagonists |
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- Enkephalinase inhibitors: Amastatin
- BL-2401
- Candoxatril
- D -Phenylalanine
- Dexecadotril (retorphan)
- Ecadotril (sinorphan)
- Kelatorphan
- Racecadotril (acetorphan)
- RB-101
- RB-120
- RB-3007
- Opiorphan
- Selank
- Semax
- Spinorphin
- Thiorphan
- Tynorphin
- Ubenimex (bestatin)
- Propeptides: β-Lipotropin (proendorphin)
- Prodynorphin
- Proenkephalin
- Pronociceptin
- Proopiomelanocortin (POMC)
- Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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