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NE-100

NE-100
Identifiers
  • 4-Methoxy-3-(2-phenylethoxy)-N,N-dipropylbenzeneethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H33NO2
Molar mass355.522 g·mol−1
3D model (JSmol)
  • CCCN(CCC)CCC1=CC(=C(C=C1)OC)OCCC2=CC=CC=C2
  • InChI=1S/C23H33NO2/c1-4-15-24(16-5-2)17-13-21-11-12-22(25-3)23(19-21)26-18-14-20-9-7-6-8-10-20/h6-12,19H,4-5,13-18H2,1-3H3
  • Key:YBLIQJGXRLZBCZ-UHFFFAOYSA-N

NE-100 or 4-methoxy-3-(2-phenylethoxy)-N,N-dipropylbenzeneethanamine is a selective sigma-1 receptor antagonist, with a reported binding affinity of Ki = 1.03 ± 0.01 nM, and more than 205 times selectivity over the sigma-2 receptor.[1][2]

NE-100 was one of the earliest selective sigma-1 receptor ligands reported and has been widely used as a pharmacological tool. The original, eight step synthesis of NE-100 was reported by Atsuro Nakazato and colleagues of Taisho Pharmaceutical Company in 1999.[3] More recently, Michael Kassiou and co-workers have reported a more expedient synthesis of NE-100 that proceeds in 56% unoptimized yield over 4 steps.[4]

References

  1. ^ Okuyama S, Nakazato A (1999). "NE-100: A novel sigma receptor antagonist". CNS Drug Rev. 2 (2): 226–237. doi:10.1111/j.1527-3458.1996.tb00299.x.
  2. ^ Berardi F, Ferorelli S, Colabufo NA, Leopoldo M, Perrone R, Tortorella V (2001). "A multireceptorial binding reinvestigation on an extended class of sigma ligands: N-[omega-(indan-1-yl and tetralin-1-yl)alkyl] derivatives of 3,3-dimethylpiperidine reveal high affinities towards sigma1 and EBP sites". Bioorg. Med. Chem. 9 (5): 1325–35. doi:10.1016/s0968-0896(01)00011-6. PMID 11377189.
  3. ^ Nakazato A, Ohta K, Sekiguchi Y, Okuyama S, Chaki S, Kawashima Y, Hatayama K (1999). "Design, Synthesis, Structure-Activity Relationships, and Biological Characterization of Novel Arylalkoxyphenylalkylamine s Ligands as Potential Antipsychotic Drugs". Journal of Medicinal Chemistry. 42 (6): 1076–1087. doi:10.1021/jm980212v. PMID 10090790.
  4. ^ Banister SD, Moussa IA, Jorgensen WT, Chua SW, Kassiou M (2011). "Molecular hybridization of 4-azahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane-3-ol with sigma (s) receptor ligands modulates off-target activity and subtype selectivity". Bioorg. Med. Chem. Lett. 21 (12): 3622–3626. doi:10.1016/j.bmcl.2011.04.098. PMID 21555222.
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