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BDPC

From WikiProjectMed
Synthetic opioid
Not to be confused withbromperidol orbromadoline.
Pharmaceutical compound
BDPC
Clinical data
ATC code
  • None
Identifiers
  • 4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC22H28BrNO
Molar mass402.376 g·mol−1
3D model (JSmol)
Melting point208 to 210 °C (406 to 410 °F)
  • CN(C)C1(CCC(CC1)(CCC2=CC=CC=C2)O)C3=CC=C(C=C3)Br
  • 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 checkY
  • Key:PRSUTWWKYIVBEU-UHFFFAOYSA-N checkY
  (verify)

BDPC (systematic name4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol; also known asbromadol) is a potent fully syntheticopioid with a distinctivearylcyclohexylaminechemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s.[1] Initial studies estimated that it was around 10,000 times the potency ofmorphine in animal models.[2] However, later studies using more modern techniques assigned a value of 504 times the potency of morphine for the more activetrans-isomer.[3] This drug was first seized along with three kilograms ofacetylfentanyl in an April 25, 2013 police action in Montreal, Canada,[4] and has reportedly continued to be available on thedesigner drug market internationally.[5][6] Analogues where thepara-bromine is replaced by chlorine or a methyl group retain similar activity, while themeta-hydroxyl derivative demonstrated robust antagonist activity.[7][8]

p-methyl analogue of BDPC
p-chloro analogue of BDPC.
m-hydroxy analogue of BDPC.

See also

References

  1. US 4366172,Lednicer, Daniel,"4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use",issued 1982-12-28, assigned toUpjohn Company 
  2. Lednicer D, VonVoigtlander PF (October 1979). "4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent representative of a new analgesic series".Journal of Medicinal Chemistry.22 (10):1157–8.doi:10.1021/jm00196a001.PMID 513062.
  3. Liu ZH, Jin WQ, Dai QY, Chen XJ, Zhang HP, Chi ZQ (May 2003). "Opioid activity of C8813, a novel and potent opioid analgesic".Life Sciences.73 (2):233–41.doi:10.1016/S0024-3205(03)00263-7.PMID 12738037.
  4. "Extremely potent painkiller hits Montreal black market". CBC News. May 13, 2013.
  5. Sharma KK, Hales TG, Rao VJ, NicDaeid N, McKenzie C (January 2019)."The search for the "next" euphoric non-fentanil novel synthetic opioids on the illicit drugs market: current status and horizon scanning".Forensic Toxicology.37 (1):1–16.doi:10.1007/s11419-018-0454-5.PMC 6314991.PMID 30636980.
  6. Vandeputte MM, Cannaert A, Stove CP (November 2020)."In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances".Archives of Toxicology.94 (11):3819–3830.Bibcode:2020ArTox..94.3819V.doi:10.1007/s00204-020-02855-7.hdl:1854/LU-8687070.PMID 32734307.S2CID 220881657.
  7. Lednicer D, VonVoigtlander PF, Emmert DE (April 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.
  8. Lednicer D, Von Voigtlander PF, Emmert DE (March 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.
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Nociceptin
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