BDPC

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Not to be confused with bromidol or bromadoline.
BDPC
Bromadol Skeletal.png
Systematic (IUPAC) name
4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol
Identifiers
CAS Number 77239-98-6 YesY
70895-01-1 (HCl)
ATC code None
PubChem CID: 9887338
ChemSpider 26001358 YesY
Chemical data
Formula C22H28BrNO
Molecular mass 402.37 g/mol
  • BrC1=CC=C(C=C1)[C@]2(N(C)C)CC[C@@](CC2)(O)CCC3=CC=CC=C3
  • InChI=1S/C22H28BrNO/c1-24(2)22(19-8-10-20(23)11-9-19)16-14-21(25,15-17-22)13-12-18-6-4-3-5-7-18/h3-11,25H,12-17H2,1-2H3/t21-,22- YesY
  • Key:PRSUTWWKYIVBEU-HZCBDIJESA-N YesY
Physical data
Melting point 208 to 210 °C (406 to 410 °F)
  (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 arylcyclohexylamine 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

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.

4-(4-methylphenyl)-4-(dimethylamino)cyclohexan-1-one.png
4-(4-methylphenyl)-4-(dimethylamino)cyclohexan-1-one		 4-(4-bromophenyl)-4-(dimethylamino)cyclohexan-1-one.png
4-(4-bromophenyl)-4-(dimethylamino)cyclohexan-1-one		 Lednicer's two parent compounds for BDPC. They are equipotent, which is an unusual case for a simple cyclohexanone to display interchangeable equal potency with either a methyl or bromine in the same substitution, both having the same potency as pethidine.[8] The p-Methyl was never tested as an analogue of BDPC because 'We forgot'.[9] Although Lednicer stated that he felt that the p-Me would be equipotent.

See also

References

  1. ↑ U.S. Patent 4,366,172 - 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Report 1985, 21 pages, from Foersvarets Forskningsanstalt, Umea, Sweden. (Report in Swedish)
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ US Patent 4460604
  9. ↑ personal communication of Danial Lednicer
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