BDPC
| File:Bromadol.png | |
| Systematic (IUPAC) name | |
|---|---|
|
4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol | |
| Identifiers | |
| CAS Number |
77239-98-6 70895-01-1 (HCl) |
| ATC code | None |
| PubChem | CID 9887338 |
| ChemSpider | 8063011 |
| Chemical data | |
| Formula | C22H28BrNO |
| Molar mass | 402.37 g/mol[[Script error: No such module "String".]] |
| Script error: No such module "collapsible list". | |
| Physical data | |
| Melting point | 208 to 210 °C (406 to 410 °F) |
4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol (BDPC, Bromadol) is a potent narcotic analgesic with a distinctive chemical structure. Considered 10,000 times the strength of morphine,[1] it was first reported by The Upjohn Company in 1979. BDPC is an arylcyclohexylamine derivative also bearing some chemical similarity to tramadol and venlafaxine.[2]
Contents
Opioid pharmacology
BDPC has never been used in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence would be expected to develop rapidly based on the potency of the drug, as it is of a similar strength to carfentanil and so would most likely cause pronounced tachyphylaxis following repeated dosing, as is seen with the potent fentanyl analogues.
Structure-activity relationships
Several related analogues such as the p-methyl and ring-unsubstituted compounds have also been investigated.[3] Bromadol is the lead compound in this series that attracted so much interest in it initially. A large number of analogs have been prepared,[4][5] and the SAR is very well established. Lednicer constructed Dreiding models to show that the model of bromadol will give an exact overlay on a model of fentanyl.
NMDA receptor connection
For example, a positional isomer of ketamine is an idea that has been pursued. 2-Hydroxy-PCP[6] and 2-methoxyphencyclidine[7] were both recently reported. The 4-positional isomers would seem like a logical extension of this work. However, it is more common for the 4-keto group to be kept in the form of its corresponding ethylene ketal.
Chemistry
It is made from 1,4-cyclohexadione. Details for this are outlined in Organic Syntheses.[8]
Grünenthal Ex 6 U.S. Patent 7,183,436 U.S. Patent 7,211,694 U.S. Patent 4,366,172
See also
References
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- ↑ Lednicer, D; Vonvoigtlander, PF (1979). "4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent respresentative of a new analgesic series". Journal of Medicinal Chemistry. 22 (10): 1157–8. doi:10.1021/jm00196a001. PMID 513062.
- ↑ Yardley, JP; Husbands, GE; Stack, G; Butch, J; Bicksler, J; Moyer, JA; Muth, EA; Andree, T; Fletcher H, 3rd (1990). "2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: synthesis and antidepressant activity". Journal of Medicinal Chemistry. 33 (10): 2899–905. doi:10.1021/jm00172a035. PMID 1976813.
- ↑ Report 1985, 21 pages, from Foersvarets Forskningsanstalt, Umea, Sweden. (Report in Swedish)
- ↑ Lednicer, D; Vonvoigtlander, PF; Emmert, DE (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 (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.
- ↑ Ahmadi, A; Shafiezadeh, M; Fathollahi, Y; Darvich, MR; Mahmoudi, A; Bahmani, M; Rahmati, B (2005). "Synthesis with improved yield and study on the analgesic effect of 2-hydroxyphencyclidine". Arzneimittel-Forschung. 55 (3): 172–6. PMID 15819390.
- ↑ Ahmadi, A; Mahmoudi, A (2006). "Synthesis with improved yield and study on the analgesic effect of 2-methoxyphencyclidine". Arzneimittel-Forschung. 56 (5): 346–50. PMID 16821645.
- ↑ Organic Branch, Chemistry Division, Naval Weapons Center, China Lake, California. Organic Syntheses, Coll. Vol. 5, p.288 (1973); Vol. 45, p.25 (1965).
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