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Chemical Compound Review

NE-100     N,N-diethyl-2-(4-methoxy-3- phenethyloxy...

Synonyms: SureCN2729151, AC1L3OPK, CID119381, DCL000893, NE 100, ...
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Disease relevance of N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine


Psychiatry related information on N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine

  • A selective and potent sigma receptor "antagonist" NE-100 (N, N-dipropyl-2- [4-methoxy-3-(2-phenylethoxy)-phenyl]-ethylamine monohydrochloride), which did not per se affect spontaneous locomotor activity, did not prevent the locomotor stimulatory effects of (+)MK-801 [3].
  • NE-100 did not affect dopamine agonists-induced stereotyped behavior and/or hyperactivity [2].

High impact information on N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine

  • These responses were blocked by sigma-receptor antagonists NE-100 or BD1063, but not by pretreatments with antisense oligodeoxynucleotide for sigma1 binding protein [4].
  • Moreover, MAP-induced anticipation was blocked by coadministration of the N-methyl-D-aspartate receptor antagonist MK-801 or sigma ligands rimcazol and NE-100 [5].
  • A significant correlation was observed between activities of NE-100 metabolism and dextromethorphan O-demethylation (a specific activity for CYP2D6) or testosterone 6beta-hydroxylation (a specific activity for CYP3A4) in HLM [6].
  • During absorption, NE-100 is mainly metabolized by CYP3A4 in the intestine and thereafter by CYP2D6 in the liver in the presence of therapeutic doses [6].
  • Differences in cytochrome P450 forms involved in the metabolism of N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine monohydrochloride (NE-100), a novel sigma ligand, in human liver and intestine [6].

Biological context of N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine


Anatomical context of N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine

  • We examined the characteristics of binding of radiolabeled N,N-dipropyl-2-[4-methoxy-3-(2-phenyl-ethoxy)phenyl]- ethylamine monohydrochloride ([3H] NE-100), a highly potent and selective sigma-receptor ligand, to guinea-pig brain membranes [8].
  • 2. In PM-HLM, NE-100 is predicted to be metabolized to N-despropyl-NE-100 (NE-098), p-hydroxy-NE-100 (NE-152) and m-hydroxyl-NE-100 (NE-163), but not to O-demethy-NE-100 (NE-125), which is a major metabolite in pooled human liver microsomes (EM-HLM) [9].
  • In the present study, the contribution of CYP forms involved in the formation of the major metabolites of NE-100 in human liver lacking CYP2D6 activity (PM-HLM) has been predicted by use of in vitro kinetic data on recombinant CYPs microsomes (rCYPs) [9].
  • These findings indicate that subchronic treatment with NE-100 may regulate the in vivo binding characteristics of 5-HT2A receptors in the cerebral cortex of rat brain [10].
  • Seven days after the last injection of NE-100 or vehicle, there were no significant differences between the NE-100 and vehicle treated groups in [3H]RP 62203 binding in all the regions examined except for the hippocampus [10].

Associations of N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine with other chemical compounds

  • Intrinsic clearances (CLint-HLM-total) for the metabolism of NE-100, metoprolol, clarithromycin (CAM), lornoxicam and tenoxicam were predicted from in vitro data with recombinant cytochorme P450s (CYPs) using relative activity factor (RAF) and then compared with CLint-HLM observed in human liver microsomes (HLM) [11].
  • These observations suggest that NE-100 indirectly modulates the N-methyl-D-aspartate (NMDA)/phencyclidine (PCP) receptor ion channel complex (NMDA receptor-ion channel), presumably through sigma-1 sites [12].
  • With the coinjected carrier NE-100 or haloperidol, the uptake of [N-propyl-11C]NE-100 by the liver, pancreas and spleen was significantly decreased at 15 min after injection, whereas the effect was not significant for [O-methyl-11C]NE-100 [13].
  • N, N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]-ethylamine monohydrochloride (NE-100) is a novel compound with high affinity for the sigma receptor (IC50 = 4.16 nM), but low affinity (IC50 > 10,000 nM) for D1, D2, 5-HT1A, 5-HT2 and phencyclidine (PCP) receptors [2].
  • MAIN OUTCOME MEASURES: The effects of DHEA, T, and NE-100, a selective sigma 1 receptor antagonist, on copulatory behavior following social stress were examined [14].

Gene context of N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine

  • 1. It has previously been reported that N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]-ethylamine monohydrochloride (NE-100) was predominantly metabolized by cytochrome P450 (CYP) 2D6 in human liver microsomes (HLM) [9].
  • In both cases, NE-100 dose-dependently attenuated the delayed cognitive dysfunction induced by PCP [15].
  • NE-100, a representative antagonist, showed no effect at concentrations not more than 100 nM, while it did stimulate GTPase activity at 1 and 10 microM [16].
  • In contrast, the other selective sigma1-ligand, NE-100, did not affect any of the PCP-induced behaviour patterns in this study [17].
  • For the highly sensitive and selective determination of NE-100, a novel sigma ligand, at levels of low picogram per milliliter of human plasma, a method with excellent reliability employing liquid chromatography (LC)-electrospray ionization (ESI) tandem mass spectrometry (MS-MS) combined with a column-switching technique has been developed [18].

Analytical, diagnostic and therapeutic context of N,N-diethyl-2-(4-methoxy-3-phenethyloxy-phenyl)ethanamine


  1. NE-100, a novel sigma receptor ligand: effect on phencyclidine-induced behaviors in rats, dogs and monkeys. Okuyama, S., Imagawa, Y., Sakagawa, T., Nakazato, A., Yamaguchi, K., Katoh, M., Yamada, S., Araki, H., Otomo, S. Life Sci. (1994) [Pubmed]
  2. NE-100, a novel sigma receptor ligand: in vivo tests. Okuyama, S., Imagawa, Y., Ogawa, S., Araki, H., Ajima, A., Tanaka, M., Muramatsu, M., Nakazato, A., Yamaguchi, K., Yoshida, M. Life Sci. (1993) [Pubmed]
  3. Behavioral evidence for modulation by sigma ligands of (+)MK-801-induced hyperlocomotion in monoamine-depleted mice. Okuyama, S., Imagawa, Y., Tomisawa, K. Neuropharmacology (1996) [Pubmed]
  4. Metabotropic neurosteroid/sigma-receptor involved in stimulation of nociceptor endings of mice. Ueda, H., Inoue, M., Yoshida, A., Mizuno, K., Yamamoto, H., Maruo, J., Matsuno, K., Mita, S. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  5. Involvement of dopamine, N-methyl-D-aspartate and sigma receptor mechanisms in methamphetamine-induced anticipatory activity rhythm in rats. Shibata, S., Ono, M., Fukuhara, N., Watanabe, S. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  6. Differences in cytochrome P450 forms involved in the metabolism of N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine monohydrochloride (NE-100), a novel sigma ligand, in human liver and intestine. Yamamoto, T., Hagima, N., Nakamura, M., Kohno, Y., Nagata, K., Yamazoe, Y. Drug Metab. Dispos. (2003) [Pubmed]
  7. NE-100, a novel potent sigma ligand, preferentially binds to sigma 1 binding sites in guinea pig brain. Chaki, S., Tanaka, M., Muramatsu, M., Otomo, S. Eur. J. Pharmacol. (1994) [Pubmed]
  8. Characteristics of binding of [3H]NE-100, a novel sigma-receptor ligand, to guinea-pig brain membranes. Tanaka, M., Shirasaki, T., Kaku, S., Muramatsu, M., Otomo, S. Naunyn Schmiedebergs Arch. Pharmacol. (1995) [Pubmed]
  9. Prediction of differences in in vivo oral clearance of N,N-dipropyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl] ethylamine monohydrochloride (NE-100) between extensive and poor metabolizers from in vitro metabolic data in human liver microsomes lacking CYP2D6 activity and recombinant CYPs. Yamamoto, T., Hagima, N., Nakamura, M., Kohno, Y., Nagata, K., Yamazoe, Y. Xenobiotica (2004) [Pubmed]
  10. In vivo regulation of serotonin 5-HT2A receptors in rat brain by subchronic administration of sigma receptor ligand NE-100. Hashimoto, K., Narita, N., Tomitaka, S., Iyo, M., Minabe, Y. Life Sci. (1997) [Pubmed]
  11. Prediction of oral clearance from in vitro metabolic data using recombinant CYPs: comparison among well-stirred, parallel-tube, distributed and dispersion models. Yamamoto, T., Itoga, H., Kohno, Y., Nagata, K., Yamazoe, Y. Xenobiotica (2005) [Pubmed]
  12. NE-100, a novel sigma ligand: effects on [3H]TCP binding to intact primary cultured neuronal cells. Yamamoto, H., Yamamoto, T., Sagi, N., Okuyama, S., Kawai, N., Baba, A., Moroji, T. Life Sci. (1995) [Pubmed]
  13. Synthesis and preliminary evaluation of [11C]NE-100 labeled in two different positions as a PET sigma receptor ligand. Ishiwata, K., Noguchi, J., Ishii, S., Hatano, K., Ito, K., Nabeshima, T., Senda, M. Nucl. Med. Biol. (1998) [Pubmed]
  14. Dehydroepiandrosterone alleviates copulatory disorder induced by social stress in male rats. Mizuno, T., Yotsuyanagi, S., Nagasaka, Y., Namiki, M. The journal of sexual medicine. (2006) [Pubmed]
  15. Effect of NE-100, a novel sigma receptor ligand, on phencyclidine- induced delayed cognitive dysfunction in rats. Okuyama, S., Ogawa, S., Nakazato, A., Tomizawa, K. Neurosci. Lett. (1995) [Pubmed]
  16. Sigma ligands stimulate GTPase activity in mouse prefrontal membranes: evidence for the existence of metabotropic sigma receptor. Tokuyama, S., Hirata, K., Ide, A., Ueda, H. Neurosci. Lett. (1997) [Pubmed]
  17. Effects of a novel, selective, sigma1-ligand, MS-377, on phencyclidine-induced behaviour. Takahashi, S., Takagi, K., Horikomi, K. Naunyn Schmiedebergs Arch. Pharmacol. (2001) [Pubmed]
  18. Ultrasensitive determination of NE-100, a novel sigma ligand, in human plasma by liquid chromatography and electrospray ionization tandem mass spectrometry combined with a column-switching technique. Yamaguchi, J., Watanabe, Y., Ohmichi, M., Jingu, S., Ogawa, N., Kokatsu, J., Fukushima, K., Goto, J. J. Chromatogr. B Biomed. Sci. Appl. (1999) [Pubmed]
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