BDPC

BDPC
Clinical data
ATC code	None;
Identifiers
	IUPAC name 4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol;
CAS Number	77239-98-6 ; 70895-01-1 (HCl);
PubChem CID	9887338;
ChemSpider	8063011 ;
UNII	G8HCJ9R4VZ;
ChEMBL	ChEMBL3303774;
Chemical and physical data
Formula	C22H28BrNO
Molar mass	402.376 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	208 to 210 °C (406 to 410 °F)
	SMILES CN(C)C1(CCC(CC1)(CCC2=CC=CC=C2)O)C3=CC=C(C=C3)Br;
	InChI 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.^[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]

References

^ US 4366172, Lednicer, Daniel, "4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use", issued 1982-12-28, assigned to Upjohn Company
^ 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.
^ 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.
^ "Extremely potent painkiller hits Montreal black market". CBC News. May 13, 2013.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

[pmid32734307-6] 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.

[pmid7265128-7] 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.

[pmid7265120-8] 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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Clinical data


ATC code	None
Identifiers
IUPAC name 4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol
CAS Number	77239-98-6^Y 70895-01-1 (HCl)
PubChem CID	9887338
ChemSpider	8063011^Y
UNII	G8HCJ9R4VZ
ChEMBL	ChEMBL3303774
Chemical and physical data
Formula	C₂₂H₂₈BrNO
Molar mass	402.376 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	208 to 210 °C (406 to 410 °F)
SMILES CN(C)C1(CCC(CC1)(CCC2=CC=CC=C2)O)C3=CC=C(C=C3)Br
InChI 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^Y Key:PRSUTWWKYIVBEU-UHFFFAOYSA-N^Y
(verify)

See also

References