N-Methylnorcarfentanil (R-32395) is an opioid analgesic drug related to the highly potent animal tranquilizer carfentanil, but several thousand times weaker, being only slightly stronger than morphine. It was first synthesised by a team of chemists at Janssen Pharmaceutica led by Paul Janssen, who were investigating the structure-activity relationships of the fentanyl family of drugs. They found that replacing the phenethyl group attached to the piperidine nitrogen of fentanyl with a smaller methyl group, made it so much weaker that it was inactive as an analgesic in animals. However the same change made to the more potent analogue carfentanil retained reasonable opioid receptor activity, reflecting the higher binding affinity produced by the 4-carbomethoxy group.[1][2][3]
 | |
 | |
| Legal status | |
|---|---|
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C17H24N2O3 |
| Molar mass | 304.390 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[4]
References
edit- ^ Cometta-Morini C, Maguire PA, Loew GH (January 1992). "Molecular determinants of mu receptor recognition for the fentanyl class of compounds". Molecular Pharmacology. 41 (1): 185–196. PMID 1310142.
- ^ Maguire P, Tsai N, Kamal J, Cometta-Morini C, Upton C, Loew G (March 1992). "Pharmacological profiles of fentanyl analogs at mu, delta and kappa opiate receptors". European Journal of Pharmacology. 213 (2): 219–225. doi:10.1016/0014-2999(92)90685-W. PMID 1355735.
- ^ Dukhovich FS, Darkhovskii MB, Gorbatova EN, Kurochkin VK. Molecular recognition: pharmacological aspects. 2004, Nova Science Publishers, New York. p 81. ISBN 1-59033-887-1
- ^ Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.