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4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol
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| Systematic (IUPAC) name | |
| trans-4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol | |
| Identifiers | |
| CAS number | ? |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C22H28BrNO |
| Mol. mass | 402.367 g/mol |
| SMILES | & |
| Physical data | |
| Melt. point | 208–210 °C (406–410 °F) |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
Legal |
| Routes | ? |
4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol (BDPC) is a potent μ-opioid agonist with a distinctive chemical structure which is not closely related to other established families of opioid drugs.1 It was invented by the chemists Daniel Lednicer and Philip VonVoigtlander in 1979.23
This compound was found to be around 10,000x more potent than morphine in animal studies (although newer data suggest it is much less potent than this, perhaps only ~600x morphine)4, however due to its structural differences from other opioid drugs it would be difficult to represent as being "substantially similar in chemical structure" to any controlled drugs, although it does retain the high-affinity opioid pharmacophore.5 Its structural distinctiveness from controlled opioid drugs makes it likely that BDPC would be legal throughout the world.
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.
See also
References
- ^ Lednicer D, VonVoigtlander PF, Emmert DE. 4-amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function. Journal of Medicinal Chemistry. 1981 Apr;24(4):404-8. PMID 7265128
- ^ Lednicer D, VonVoigtlander PF. 4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent representative of a new analgesic series. Journal of Medicinal Chemistry 1979; 22(10):1157-1158. PMID 513062
- ^ Daniel Lednicer. 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use. US Patent 4366172
- ^ Liu ZH, Jin WQ, Dai QY, Chen XJ, Zhang HP, Chi ZQ. Opioid activity of C8813, a novel and potent opioid analgesic. Life Sciences. 2003 May 30;73(2):233-41. PMID 12738037
- ^ Martin J, Andrews P. Conformation-activity relationships of opiate analgesics. Journal of Computer-Aided Molecular Design. 1987 Apr;1(1):53-72.
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