Chemistry:BDPC
 | |
 | |
| Clinical data | |
|---|---|
| ATC code |
|
| Identifiers | |
| |
| 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) |
| |
| |
| (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 strength 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]
See also
References
- ↑ Lednicer, Daniel, "4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use", US patent 4366172, issued 1982-12-28
- ↑ "4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent representative of a new analgesic series". Journal of Medicinal Chemistry 22 (10): 1157–8. October 1979. doi:10.1021/jm00196a001. PMID 513062.
- ↑ "Opioid activity of C8813, a novel and potent opioid analgesic". Life Sciences 73 (2): 233–41. May 2003. doi:10.1016/S0024-3205(03)00263-7. PMID 12738037.
- ↑ "Extremely potent painkiller hits Montreal black market". CBC News. May 13, 2013. https://www.cbc.ca/news/canada/montreal/extremely-potent-painkiller-hits-montreal-black-market-1.1340808.
- ↑ "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. January 2019. doi:10.1007/s11419-018-0454-5. PMID 30636980.
- ↑ "In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances". Archives of Toxicology 94 (11): 3819–3830. November 2020. doi:10.1007/s00204-020-02855-7. PMID 32734307. https://biblio.ugent.be/publication/8687070.
- ↑ "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. April 1981. doi:10.1021/jm00136a010. PMID 7265128.
- ↑ "4-aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. m-Hydroxyphenyl derivates". Journal of Medicinal Chemistry 24 (3): 341–6. March 1981. doi:10.1021/jm00135a019. PMID 7265120.
 |  |
