McN-5908

Last updated

McN-5908
McN-5908 structure.png
Identifiers
  • 4-[(6S,10bR)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-6-yl]aniline
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H20N2
Molar mass 264.372 g·mol−1
3D model (JSmol)
  • C1C[C@@H]2C3=CC=CC=C3[C@@H](CN2C1)C4=CC=C(C=C4)N
  • InChI=1S/C18H20N2/c19-14-9-7-13(8-10-14)17-12-20-11-3-6-18(20)16-5-2-1-4-15(16)17/h1-2,4-5,7-10,17-18H,3,6,11-12,19H2/t17-,18+/m0/s1
  • Key:YFRXDBYFLJJYEW-ZWKOTPCHSA-N

McN-5908 is a stimulant drug which acts as a dopamine reuptake inhibitor, with similar inhibition of noradrenaline reuptake but much weaker activity at serotonin reuptake. [1] [2]

In the SAR citation, Cmp 52 has the following Ki values (nM): DA = 0.86, NE = 0.20, SER = 44. McN-5908 is one of the most powerful psychostimulants ever discovered and the most potent in this series of agents. However it does have some toxicity to be contended with.

In terms of the SAR, McN-5908 can probably be best compared to a Hoechst agent appearing in the chemical literature PC3033738 [88823-35-2]. [3] [4] SAR analogy between this agent and nomifensine (Alival) was also performed. In terms of the SAR, it is noteworthy to mention that the para-amino analog of venlafaxine (PC13520329) was also known to be have been invented. [5] Finally, Louis Lafon invented some Clenbuterol alpha-methyl cathinone analogs with some of the compounds lacking the chlorine halogen atoms. [6] These compounds were all explored in the context of their antidepressant activity. {Louis Lafron is the same chemist who invented modafinil, flerobuterol, etc.}

See also

References

  1. Mayer RA, Kindt MV, Heikkila RE (October 1986). "Prevention of the nigrostriatal toxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by inhibitors of 3,4-dihydroxyphenylethylamine transport". Journal of Neurochemistry. 47 (4): 1073–1079. doi:10.1111/j.1471-4159.1986.tb00722.x. PMID   3489072.
  2. Maryanoff BE, McComsey DF, Gardocki JF, Shank RP, Costanzo MJ, Nortey SO, et al. (August 1987). "Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships". Journal of Medicinal Chemistry. 30 (8): 1433–1454. doi:10.1021/jm00391a028. PMID   3039136.
  3. Kunstmann, R., Gerhards, H., Kruse, H., Leven, M., Paulus, E. F., Schacht, U., et al. (May 1987). "Resolution, absolute stereochemistry, and enantioselective activity of nomifensine and hexahydro-1H-indeno[1,2-b]pyridines". Journal of Medicinal Chemistry. 30 (5): 798–804. doi:10.1021/jm00388a009. PMID   3572969 . Retrieved 9 December 2025.
  4. Kunstmann, Rudolf; Lerch, Ulrich; Gerhards, Hermann; Leven, Margret; Schacht, Ulrich (1984). "2,3,4,4a,5,9b-Hexahydro-1H-indeno[1,2-b]pyridines: potential antidepressants". Journal of Medicinal Chemistry. 27 (4): 432–439. doi:10.1021/jm00370a004.
  5. Yardley, J. P., Husbands, G. E. M., Stack, G., Butch, J., Bicksler, J., Moyer, J. A., et al. (October 1990). "2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: synthesis and antidepressant activity". Journal of Medicinal Chemistry. 33 (10): 2899–2905. doi:10.1021/jm00172a035. PMID   1976813 . Retrieved 9 December 2025.
  6. Louis Lafon, U.S. patent 5,236,922 (1993 to Cephalon France SAS).