BDPC

From Wikipedia, the free encyclopedia
  (Redirected from Bromadol)
Jump to: navigation, search
Not to be confused with bromidol or bromadoline.
BDPC
Bromadol Skeletal.png
Systematic (IUPAC) name
4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol
Clinical data
Identifiers
77239-98-6 YesY
70895-01-1 (HCl)
None
PubChem CID 9887338
ChemSpider 26001358 YesY
Chemical data
Formula C22H28BrNO
402.37 g/mol
Physical data
Melting point 208 to 210 °C (406 to 410 °F)
 YesY (what is this?)  (verify)

BDPC (systematic name 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol; also known as bromadol) is a potent narcotic analgesic with a distinctive benzenoid chemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s.[1] Initial studies estimated that it was around 10,000 times the strength of morphine in animal models.[2] However, later studies assigned a value of 504 times the potency of morphine for the more active trans-isomer.[3] To date, it is unknown if this drug has been used by humans, however, it was seized along with three kilograms of acetylfentanyl in an April 25, 2013 police action in Montreal, Canada. Despite taking precautions, at least two officers became intoxicated due to handling the drugs.[4]

Structure-activity relationships[edit]

Several related analogs such as the p-methyl and ring-unsubstituted compounds have also been investigated.[5] BDPC is the lead compound in this series that attracted so much interest in it initially. A large number of analogs have been prepared,[6][7] and the SAR is very well established. Lednicer constructed Dreiding models to show that the model of BDPC will give an exact overlay on a model of fentanyl.

See also[edit]

References[edit]

  1. ^ U.S. Patent 4,366,172 - 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use
  2. ^ Lednicer, D.; Vonvoigtlander, P. F. (1979). "4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent representative of a new analgesic series". Journal of Medicinal Chemistry 22 (10): 1157–1158. doi:10.1021/jm00196a001. PMID 513062.  edit
  3. ^ Liu, Z. H.; Jin, W. Q.; Dai, Q. Y.; Chen, X. J.; Zhang, H. P.; Chi, Z. Q. (2003). "Opioid activity of C8813, a novel and potent opioid analgesic". Life Sciences 73 (2): 233–241. doi:10.1016/S0024-3205(03)00263-7. PMID 12738037.  edit
  4. ^ "Extremely potent painkiller hits Montreal black market". CBC News. May 13, 2013. 
  5. ^ Report 1985, 21 pages, from Foersvarets Forskningsanstalt, Umea, Sweden. (Report in Swedish)
  6. ^ Lednicer, D.; Vonvoigtlander, P. F.; Emmert, D. E. (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): 404–408. doi:10.1021/jm00136a010. PMID 7265128.  edit
  7. ^ Lednicer, D.; Von Voigtlander, P. F.; Emmert, D. E. (1981). "4-aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. M-Hydroxyphenyl derivates". Journal of Medicinal Chemistry 24 (3): 341–346. doi:10.1021/jm00135a019. PMID 7265120.  edit