BDPC — Mediated Wiki

{{Short description|Synthetic opioid}} {{Distinguish|bromperidol|bromadoline}} {{Drugbox | Watchedfields = changed | verifiedrevid = 451567905 | IUPAC_name = 4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol | image = Bromadol.svg | image_class = skin-invert-image | width= 200px | image2 = Bromadol 3D BS.png | image_class2 = bg-transparent | width2 = 200px

| tradename = | pregnancy_category = | legal_status = | routes_of_administration =

| bioavailability = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 77239-98-6 | CAS_supplemental = <br />70895-01-1 (HCl) | ATC_prefix = None | ATC_suffix = | PubChem = 9887338 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8063011 | ChEMBL = 3303774 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = G8HCJ9R4VZ

| C=22 | H=28 | Br=1 | N=1 | O=1 | smiles = CN(C)C1(CCC(CC1)(CCC2=CC=CC=C2)O)C3=CC=C(C=C3)Br | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = PRSUTWWKYIVBEU-UHFFFAOYSA-N | melting_point = 208 | melting_high = 210 }}

'''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.<ref>{{cite patent | country = US | number = 4366172 | title = 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use | inventor1-first=Daniel|inventor1-last = Lednicer | assign = Upjohn Company | gdate = 1982-12-28 }}</ref> Initial studies estimated that it was around 10,000 times the potency of morphine in animal models.<ref>{{cite journal | vauthors = Lednicer D, VonVoigtlander PF | title = 4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent representative of a new analgesic series | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 10 | pages = 1157–8 | date = October 1979 | pmid = 513062 | doi = 10.1021/jm00196a001 }}</ref> However, later studies using more modern techniques assigned a value of 504 times the potency of morphine for the more active ''trans''-isomer.<ref>{{cite journal | vauthors = Liu ZH, Jin WQ, Dai QY, Chen XJ, Zhang HP, Chi ZQ | title = Opioid activity of C8813, a novel and potent opioid analgesic | journal = Life Sciences | volume = 73 | issue = 2 | pages = 233–41 | date = May 2003 | pmid = 12738037 | doi = 10.1016/S0024-3205(03)00263-7 }}</ref> This drug was first seized along with three kilograms of acetylfentanyl in an April 25, 2013 police action in Montreal, Canada,<ref>{{cite news | url = https://www.cbc.ca/news/canada/montreal/extremely-potent-painkiller-hits-montreal-black-market-1.1340808 | title = Extremely potent painkiller hits Montreal black market | publisher = CBC News | date = May 13, 2013}}</ref> and has reportedly continued to be available on the designer drug market internationally.<ref>{{cite journal | vauthors = Sharma KK, Hales TG, Rao VJ, NicDaeid N, McKenzie C | title = The search for the "next" euphoric non-fentanil novel synthetic opioids on the illicit drugs market: current status and horizon scanning | journal = Forensic Toxicology | volume = 37 | issue = 1 | pages = 1–16 | date = January 2019 | pmid = 30636980 | doi = 10.1007/s11419-018-0454-5 | pmc = 6314991 }}</ref><ref name="pmid32734307">{{cite journal | vauthors = Vandeputte MM, Cannaert A, Stove CP | title = In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances | journal = Archives of Toxicology | volume = 94 | issue = 11 | pages = 3819–3830 | date = November 2020 | pmid = 32734307 | doi = 10.1007/s00204-020-02855-7 | bibcode = 2020ArTox..94.3819V | s2cid = 220881657 | url = https://biblio.ugent.be/publication/8687070 | hdl = 1854/LU-8687070 | hdl-access = free }}</ref> 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.<ref name="pmid7265128">{{cite journal | vauthors = Lednicer D, VonVoigtlander PF, Emmert DE | title = 4-amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function | journal = Journal of Medicinal Chemistry | volume = 24 | issue = 4 | pages = 404–8 | date = April 1981 | pmid = 7265128 | doi = 10.1021/jm00136a010 }}</ref><ref name="pmid7265120">{{cite journal | vauthors = Lednicer D, Von Voigtlander PF, Emmert DE | title = 4-aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. m-Hydroxyphenyl derivates | journal = Journal of Medicinal Chemistry | volume = 24 | issue = 3 | pages = 341–6 | date = March 1981 | pmid = 7265120 | doi = 10.1021/jm00135a019 }}</ref> class=skin-invert-image|160px|thumb|left|p-methyl analogue of BDPC{{clear-left}} [[File:4Chloro-bromadol_structure.png|class=skin-invert-image|160px|thumb|left|p-chloro analogue of BDPC. [https://pubchem.ncbi.nlm.nih.gov/compound/10135240]]]{{clear-left}} [[File:3Hydroxy-bromadol_structure.png|class=skin-invert-image|160px|thumb|left|m-hydroxy analogue of BDPC. [https://pubchem.ncbi.nlm.nih.gov/compound/12681771]]]{{clear-left}}

== See also == * 3-HO-PCP * 4-Keto-PCP * C-8813 * Cebranopadol * Ciramadol * Dimetamine * Faxeladol * Profadol * Tapentadol * Tramadol

== References == {{Reflist}}

Category:Arylcyclohexylamines Category:Dimethylamino compounds Category:Mu-opioid receptor agonists Category:4-Bromophenyl compounds Category:Synthetic opioids