Chemistry:McN-5558
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McN-5558 is a drug which acts as a selective noradrenaline reuptake inhibitor. It was investigated for potential application as an antidepressant, but was never developed for clinical use.[1][2]
Pharmacology
McN-5558 is described as a serotonin–norepinephrine reuptake inhibitor (SNRI) with equilibrium constants (Kis) for various neurotransmitter transporters:[2]
| Compound 37b | norepinephrine transporter (NE) |
dopamine transporter (DAT) |
serotonin transporter (SERT) |
|---|---|---|---|
| racemic | 1.0 | 54.3 | 23.0 |
| (+) | 1.5 | 25.7 | 9.1 |
| (-) | 2570 | 7690 | 2920 |
These data show that virtually all of the binding affinities resides in a single enantiomer. Consequently, the compound displays a very high eudysmic ratio.
SAR
In terms of the SAR, the meta-trifluorophenyl group was seen for fenfluramine, Benfluorex, and Ethyltrifluoromethylaminoindane.[3][4][5] These are anorexigenic agents for the treatment of obesity and eating disorders.
See also
References
- ↑ "Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships". Journal of Medicinal Chemistry 30 (8): 1433–1454. August 1987. doi:10.1021/jm00391a028. PMID 3039136.
- ↑ 2.0 2.1 Chapter 4. Antidepressants. Annual Reports in Medicinal Chemistry. 20. Elsevier. 1985. pp. 31–40. doi:10.1016/S0065-7743(08)61030-1. ISBN 978-0-12-040520-6.
- ↑ "Indan analogs of fenfluramine and norfenfluramine have reduced neurotoxic potential". Pharmacology, Biochemistry, and Behavior 59 (3): 709–715. March 1998. doi:10.1016/s0091-3057(97)00557-1. PMID 9512076.
- ↑ "2-[1-Methyl-4-[3-(trifluoromethyl)phenylpiperidin-4-yl]propan-2-ol"]. PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/13363402.
- ↑ Ciganek E, "4-Aryl-4-piperidinecarbinols", US patent 4485109, issued 27 November 1984
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