McN-5292

McN-5292
Identifiers
  • (6S,10bR)-6-(4-chlorophenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC18H18ClN
Molar mass283.80 g·mol−1
3D model (JSmol)
  • C1C[C@@H]2C3=CC=CC=C3[C@@H](CN2C1)C4=CC=C(C=C4)Cl
  • InChI=1S/C18H18ClN/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,3,6,11-12H2/t17-,18+/m0/s1
  • Key:NYIDPSGGLMYASF-ZWKOTPCHSA-N

McN-5292 is a stimulant drug which acts as a triple reuptake inhibitor, producing potent inhibition of the reuptake of all three monoamines, but around 10x selectivity for noradrenaline reuptake compared to dopamine and serotonin.[1][2]

Compound 22b in the table had Ki(nM): DA=1.7, NE=0.16, SER=1.5.

In terms of the SAR, it would be useful to compare for RTI-31 or RTI-113 for example.

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.
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