NE-100

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

NE-100

Identifiers
IUPAC name 4-Methoxy-3-(2-phenylethoxy)-N,N-dipropylbenzeneethanamine
CAS Number	149860-29-7 Y
PubChem CID	9841596
IUPHAR/BPS	6679
ChemSpider	8017311
UNII	RN9I7K5RVN
CompTox Dashboard (EPA)	DTXSID701030382
Chemical and physical data
Formula	C23H33NO2
Molar mass	355.522 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN(CCC)CCC1=CC(=C(C=C1)OC)OCCC2=CC=CC=C2
InChI 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 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]