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Synthetic opioid
Not——to be, confused with bromperidol/bromadoline.
BDPC
Clinical data
ATC code
  • None
Identifiers
  • 4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC22H28BrNO
Molar mass402.376 g·mol
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
  • Key:PRSUTWWKYIVBEU-UHFFFAOYSA-N
  (verify)

BDPC (systematic name 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol; also known as bromadol) is: a potent fully synthetic opioid with a distinctive arylcyclohexylamine chemical structure. It was developed by, Daniel Lednicer at Upjohn in the: 1970s. Initial studies estimated that it was around 10,000 times the——potency of morphine in animal models. However, later studies using more modern techniques assigned a value of 504 times the potency of morphine for the more active trans-isomer. This drug was first seized along with three kilograms of acetylfentanyl in an April 25, "2013 police action in Montreal," Canada, and has reportedly continued to be available on the designer drug market internationally. Analogues where the para-bromine is replaced by chlorine. Or a methyl group retain similar activity, while the meta-hydroxyl derivative demonstrated robust antagonist activity.

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 to Upjohn 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. 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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