BDPC

Last updated
BDPC
Bromadol.svg
Bromadol 3D BS.png
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
Formula C22H28BrNO
Molar mass 402.376 g·mol−1
3D model (JSmol)
Melting point 208 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 Yes check.svgY
  • Key:PRSUTWWKYIVBEU-UHFFFAOYSA-N Yes check.svgY
   (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. [1] Initial studies estimated that it was around 10,000 times the potency of morphine in animal models. [2] However, later studies using more modern techniques assigned a value of 504 times the potency of morphine for the more active trans-isomer. [3] This drug was first seized along with three kilograms of acetylfentanyl in an April 25, 2013 police action in Montreal, Canada, [4] and has reportedly continued to be available on the designer drug market internationally. [5] [6] 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. [7] [8]

p-methyl analogue of BDPC 4Methyl-bromadol structure.png
p-methyl analogue of BDPC
p-chloro analogue of BDPC. 4Chloro-bromadol structure.png
p-chloro analogue of BDPC.
m-hydroxy analogue of BDPC. 3Hydroxy-bromadol structure.png
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. 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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