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BDPC
Systematic (IUPAC) name
trans-4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol
Identifiers
CAS number 77239-98-6
70895-01-1 (hydrochloride)
ATC code  ?
PubChem 9887338
Chemical data
Formula C 22H28BrNO 
Mol. mass 402.367 g/mol
SMILES eMolecules & PubChem
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, Bromadol) is a potent narcotic analgesic with a distinctive chemical structure. Considered 10,000 times the strength of morphine,[1] it was first reported The Upjohn Company in 1979. BDPC is a cyclohexanol derivative bearing some chemical similarity to tramadol and venlafaxine.[2]

Contents

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.

SAR

Several related analogues such as the p-methyl and ring-unsubstituted compounds have also been investigated.[3] Bromadol is the lead compound in this series that attracted so much interest in it initially. A large number of analogs have been prepared,[4][5] and the SAR is very well established. Lednicer constructed Dreiding models to show the similarity of bromadol to fentanyl.

NMDA Connection

For example, a positional isomer of ketamine is an idea that has been pursued. 2-Hydroxy-PCP[6] and 2-methoxyphencyclidine[7] 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.[8]

Grünenthal Ex 6 U.S. Patent 7,183,436 U.S. Patent 7,211,694 U.S. Patent 4,366,172

Legal

While structurally different from other opioid drugs, BDPC would likely be considered a Schedule II controlled substance in the United States under the Federal Analog Act since it "has a stimulant, depressant, or hallucinogenic effect on the central nervous system that is substantially similar to or greater than the stimulant, depressant, or hallucinogenic effect on the central nervous system of a controlled substance in schedule I or II."

See also

References

  1. ^ Lednicer, D; Vonvoigtlander (1979). "4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent respresentative of a new analgesic series". Journal of medicinal chemistry 22 (10): 1157–8. doi:10.1021/jm00196a001. PMID 513062.   edit
  2. ^ Yardley, JP; Husbands; Stack; Butch; Bicksler; Moyer; Muth; Andree et al. (1990). "2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: synthesis and antidepressant activity". Journal of medicinal chemistry 33 (10): 2899–905. doi:10.1021/jm00172a035. PMID 1976813.   edit
  3. ^ Report 1985, 21 pages, from Foersvarets Forskningsanstalt, Umea, Sweden. (Report in Swedish)
  4. ^ Lednicer, D; Vonvoigtlander; Emmert (1981). "4-amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function". Journal of medicinal chemistry 24 (4): 404–8. doi:10.1021/jm00136a010. PMID 7265128.   edit
  5. ^ Lednicer, D; Von Voigtlander; Emmert (1981). "4-aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. M-Hydroxyphenyl derivates". Journal of medicinal chemistry 24 (3): 341–6. doi:10.1021/jm00135a019. PMID 7265120.   edit
  6. ^ Ahmadi, A; Shafiezadeh; Fathollahi; Darvich; Mahmoudi; Bahmani; Rahmati (2005). "Synthesis with improved yield and study on the analgesic effect of 2-hydroxyphencyclidine". Arzneimittel-Forschung 55 (3): 172–6. PMID 15819390.   edit
  7. ^ Ahmadi, A; Mahmoudi (2006). "Synthesis with improved yield and study on the analgesic effect of 2-methoxyphencyclidine". Arzneimittel-Forschung 56 (5): 346–50. PMID 16821645.   edit
  8. ^ Organic Branch, Chemistry Division, Naval Weapons Center, China Lake, California. Organic Syntheses, Coll. Vol. 5, p.288 (1973); Vol. 45, p.25 (1965).
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