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4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol (BDPC, Bromadol)
is a potent narcotic analgesicwith a distinctive chemical structure.
It was developed by Daniel Lednicer at Upjohn in the 1970s.
Initialstudies showed that it was around 10,000 times the strength of morphine in animal models although
later studiesassigned a value of x504 morphine for the trans (the more active) isomer.

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Opioid pharmacologyBDPC has never been used in humans,
but would be expected to produce effects similar to those of other potentopioid agonists,
including strong analgesia, sedation, euphoria,
constipation,
itching and respiratory depressionwhich could be harmful or fatal.
Tolerance and dependence would be expected to develop rapidly based on the potencyof the drug,
as it is of a similar strength to sufentanil and so would most likely cause
pronounced tachyphylaxisfollowing repeated dosing,
as is seen with the potent fentanyl analogues.
Structure-activity relationshipsSeveral related analogues
such as the p-methyl and ring-unsubstituted
compounds have also been investigated.

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Bromadol is the lead compound in this series

that attracted so much interest in it initially. A large number of

analogs have been prepared, and the SAR is very well established.

Lednicer constructed Dreiding models to

show that the model of bromadol will give an exact overlay on a model of fentanyl.

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NMDA receptor connection

For example,

a positional isomer of ketamine is an idea that has been pursued. 2-Hydroxy-PCP and 2-

methoxyphencyclidine were both recently reported.

The 4-positional isomers would seem like a logical extension

of this work. However,

it is more common for the 4-keto group to be kept in the form of its corresponding ethylene

Chemistry

It is made from 1,4-cyclohexadione. Details for this are outlined in Organic Syntheses.

 
BromadolBromadol is a novel research
opioid with a structure dissimilar to any other commercial opioid in existence.
Informations complémentaires
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