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.
General structure of a Bentley compound with an ethano-bridge (single bond)
General structure of a Bentley compound with an etheno-bridge (double bond)
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.
- Oripavine#Bridged derivatives
.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}body.skin-vector-2022 .mw-parser-output .reflist-columns-2{column-width:27em}body.skin-vector-2022 .mw-parser-output .reflist-columns-3{column-width:22.5em}.mw-parser-output .references[data-mw-group=upper-alpha]{list-style-type:upper-alpha}.mw-parser-output .references[data-mw-group=upper-roman]{list-style-type:upper-roman}.mw-parser-output .references[data-mw-group=lower-alpha]{list-style-type:lower-alpha}.mw-parser-output .references[data-mw-group=lower-greek]{list-style-type:lower-greek}.mw-parser-output .references[data-mw-group=lower-roman]{list-style-type:lower-roman}.mw-parser-output div.reflist-liststyle-upper-alpha .references{list-style-type:upper-alpha}.mw-parser-output div.reflist-liststyle-upper-roman .references{list-style-type:upper-roman}.mw-parser-output div.reflist-liststyle-lower-alpha .references{list-style-type:lower-alpha}.mw-parser-output div.reflist-liststyle-lower-greek .references{list-style-type:lower-greek}.mw-parser-output div.reflist-liststyle-lower-roman .references{list-style-type:lower-roman}
.mw-parser-output .asbox{position:relative;overflow:hidden}.mw-parser-output .asbox table{background:transparent}.mw-parser-output .asbox p{margin:0}.mw-parser-output .asbox p+p{margin-top:0.25em}.mw-parser-output .asbox-body{font-style:italic}.mw-parser-output .asbox-note{font-size:smaller}.mw-parser-output .asbox .navbar{position:absolute;top:-0.75em;right:1em;display:none}.mw-parser-output :not(p):not(.asbox)+style+.asbox,.mw-parser-output :not(p):not(.asbox)+link+.asbox{margin-top:3em}