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Bromadol

CAS number:
77239-98-6
70895-01-1 (HCl)

PubChem:
CID 9887338

ChemSpider:
8063011

Formula:
C22H28BrNO

Mol. mass:
402.37 g/mol

Main:
4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol (BDPC, Bromadol) is a potent narcotic analgesic with a distinctive chemical structure. Considered 10,000 times the strength of morphine, it was first reported by The Upjohn Company in 1979. BDPC is an arylcyclohexylamine derivative also bearing some chemical similarity to tramadol and venlafaxine.

Opioid pharmacology

BDPC has never been used in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence would be expected to develop rapidly based on the potency of the drug, as it is of a similar strength to carfentanil and so would most likely cause pronounced tachyphylaxis following repeated dosing, as is seen with the potent fentanyl analogues.

Structure-activity relationships

Several related analogues such as the p-methyl and ring-unsubstituted compounds have also been investigated. 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.

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 ketal.

Chemistry

It is made from 1,4-cyclohexadione. Details for this are outlined in Organic Syntheses.
GrĂ¼nenthal Ex 6 U.S. Patent 7,183,436 U.S. Patent 7,211,694 U.S. Patent 4,366,172

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