4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol

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IUPAC_name = "trans"-4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol

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PubChem = 9887338
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C = 22 | H = 28 | Br = 1 | N = 1 | O = 1
molecular_weight = 402.367 g/mol
smiles = Brc2ccc(cc2)C(N(C)C)(CC3)CCC3(O)CCc1ccccc1
melting_point = 208
melting_high = 210
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legal_status = Legal
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4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol is a potent μ-opioid agonist with a distinctive chemical structure which is not closely related to other established families of opioid drugs. [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] It was invented by the chemists Daniel Lednicer and Philip VonVoigtlander in 1979. [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]

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) [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] , 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. This makes it likely that it would be legal throughout the world.

It 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.

ee also

*C-8813

References