Reaxys
PubChem
eMolecules
Reactions (13)
Substances (2)
Structure
Citations (11)
Structure/Compound Data Chemical Name: 2,5-Dimethoxy-4-nitrophenethylamine Reaxys Registry Number: 9484151
Type of Substance: isocyclic Molecular Formula: C10H14N2O4
Linear Structure Formula: C10H14N2O4
Molecular Weight: 226.232 InChI Key: ZMUSDZGRRJGRAO-UHFFFAOYSA-N
N° of preparations All Preps | All Reactions 4 prep out of 12 reactions.
Available Data
N° of ref.
Identification Physical Data (1) Spectra (3) Bioactivity (8)
11
1
Synthesize | Hide Details Find similar Chemical Names and Synonyms 2,5-Dimethoxy-4-nitrophenethylamine, 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine, 2-(2,5-dimethoxy-4-nitrophenyl)ethylamine, 2,5-dimethoxy-4nitrophenethylamine Identification Substance Label (2) Label
Reference
2C-N
Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo
British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details
Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.
Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details
Martí-Solano, Maria; De Fabritiis, Gianni; Sanz, Ferran; Pastor, Manuel; Selent, Jana; Iglesias, Alba; Brea, José; Loza, M. Isabel
Molecular Pharmacology, 2015 , vol. 87, # 4 p. 740 - 746 Title/Abstract Full Text Show Details
Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan
Patent: EP2950104 A1, 2015 ;
4
Title/Abstract Full Text Show Details
Patent-Specific Data (1) Location in Patent
Reference
Page/Page column
Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: US2015/38366 A1, 2015 ; Title/Abstract Full Text Show Details
Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: EP2835648 A1, 2015 ; Title/Abstract Full Text Show Details
Physical Data Melting Point (1) Melting Point
Reference
64 - 66 °C
Roche Diagnostics Corporation
Patent: US6525200 B1, 2003 ; Title/Abstract Full Text Show Details
Spectra NMR Spectroscopy (2) Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Frequency (NMR Spectroscopy)
Original Text (NMR Spectroscopy)
Signals
1H
CDCl3
300 MHz
1H
7.43 ppm 6.96 ppm 3.95 ppm 3.85 ppm 3 ppm 2.85 ppm 2.06 ppm
NMR (300 MHz, CDCl3): δ7.43 (s, 1H,
H3), 6.96 (s, 1H, H6), 3.95 (s, 3H, H10), 3.85 (s, 3H, H9), 3.00 (t, J=6.9 Hz, 2H, H8), 2.85 (t, J=6.9 Hz, 2H, H7), 2.06 (s, 2H, NH2)
13C
CDCl3
75.7 MHz
13C
NMR (75.7 MHz, CDCl3): δ150.6,
147.3, 136.8, 136.5, 116.2, 107.2, 56.9, 55.8, 41.6, 34.9
150.6 ppm 147.3 ppm 136.8 ppm 136.5 ppm 116.2 ppm 107.2 ppm 56.9 ppm 55.8 ppm 41.6 ppm 34.9 ppm
Kind of signal
Comment (NMR Spectroscopy)
s, 1H, H3 s, 1H, H6 s, 3H, H10 s, 3H, H9 t, J=6.9 Hz, 2H, H8 t, J=6.9 Hz, 2H, H7 s, 2H, NH&2%
Signals given
Roche Diagnostics Corporation
Patent: US6525200 B1, 2003 ; Title/Abstract Full Text Show Details
Signals given
Mass Spectrometry (1) Peak
Comment (Mass Spectrometry)
Reference
227.3 m/z
Molecular peak
Roche Diagnostics Corporation
Patent: US6525200 B1, 2003 ; Title/Abstract Full Text Show Details
Bioactivity
Reference
Roche Diagnostics Corporation
Patent: US6525200 B1, 2003 ; Title/Abstract Full Text Show Details
Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Reference
Roche Diagnostics Corporation
Patent: US6525200 B1, 2003 ; Title/Abstract Full Text Show Details
Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo
British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details
Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.
Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details
Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: US2015/38366 A1, 2015 ; Title/Abstract Full Text Show Details
Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; McConnell, Ivan; Lowry, Philip
Patent: EP2835648 A1, 2015 ; Title/Abstract Full Text Show Details
Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan
Patent: EP2950104 A1, 2015 ; Title/Abstract Full Text Show Details
Nichols, David E.
Pharmacological Reviews, 2016 , vol. 68, # 2 p. 264 - 355 Title/Abstract Full Text View citing articles Show Details
Schifano, Fabrizio; Papanti, G. Duccio; Orsolini, Laura; Corkery, John M.
Expert Review of Clinical Pharmacology, 2016 , vol. 9, # 7 p. 943 - 954 Title/Abstract Full Text View citing articles Show Details
Martí-Solano, Maria; De Fabritiis, Gianni; Sanz, Ferran; Pastor, Manuel; Selent, Jana; Iglesias, Alba; Brea, José; Loza, M. Isabel
Molecular Pharmacology, 2015 , vol. 87, # 4 p. 740 - 746 Title/Abstract Full Text Show Details
Petersen, Ida Nymann; Villadsen, Jonas; Hansen, Hanne Demant; Jensen, Anders A.; Lehel, Szabolcs; Gillings, Nic; Herth, Matthias M.; Knudsen, Gitte M.; Kristensen, Jesper L.
Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 21 p. 5353 - 5356 Title/Abstract Full Text Show Details
Nieddu, Maria; Burrai, Lucia; Baralla, Elena; Pasciu, Valeria; Varoni, Maria Vittoria; Briguglio, Irene; Demontis, Maria Piera; Boatto, Gianpiero
Journal of Analytical Toxicology, 2016 , vol. 40, # 7 art. no. BKW060, p. 492 - 497 Title/Abstract Full Text Show Details
2 of 4
3 of 4
4 of 4
Comment (Pharmacological Data)
physiological behaviour discussed
Reference
Martí-Solano, Maria; De Fabritiis, Gianni; Sanz, Ferran; Pastor, Manuel; Selent, Jana; Iglesias, Alba; Brea, José; Loza, M. Isabel
Molecular Pharmacology, 2015 , vol. 87, # 4 p. 740 - 746 Title/Abstract Full Text Show Details
Effect (Pharmacological Data)
partial agonist
Species or TestSystem (Pharmacological Data)
CHO-1C19 cells expressing human 5-HT2C receptors
Method (Pharmacological Data)
cells in serum-free medium labeled with 1 μCi/ml myo-<3H>inositol 24 h and with 0.1 μCi/ml <3H>AA 4 h at 37 deg C; then treated 10 min with title comp.; dose-response curve for total IP accumulation and AA release calculated
Further Details (Pharmacological Data)
control: vehicle; AA: arachidonic acid; IP: inositol phosphate; CHO: Chinese hamster ovary; data expressed as percent of maximal response to 5-HT; 5-HT: serotonin; PLA2 and PLC: phospholipase A2 and phospholipase C, resp.; RE: relative efficacy
Results
title comp. behaved as weak partial agonist for both PLC-mediated IP (RE = ca. 50percent, pEC50 = 5.79) and PLA2-mediated AA (RE = ca. 50percent, pEC50 = 5.91) responses with almost similar relative efficacies (figures, table)
Reference
Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.
Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
partial agonist
Species or TestSystem (Pharmacological Data)
CHO-1C19 cells expressing human 5-HT2A receptors
Method (Pharmacological Data)
cells in serum-free medium labeled with 1 μCi/ml myo-<3H>inositol 24 h and with 0.1 μCi/ml <3H>AA 4 h at 37 deg C; then treated 10 min with title comp.; dose-response curve for total IP accumulation and AA release calculated
Further Details (Pharmacological Data)
control: vehicle; AA: arachidonic acid; IP: inositol phosphate; CHO: Chinese hamster ovary; data expressed as percent of maximal response to 5-HT; 5-HT: serotonin; PLA2 and PLC: phospholipase A2 and phospholipase C, resp.; RE: relative efficacy
Results
title comp. behaved as weak partial agonist for PLA2-mediated AA release (RE = ca. 20percent, pEC50 = 4.78) but elicited no PLCmediated IP accumulation (figures, table)
Reference
Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.
Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details
Ecotoxicology (4) 1 of 4
Effect (Ecotoxicology)
membrane current; induction of
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
Ca. 1E-06 - 0.0001 mol/l
Kind of Dosing (Ecotoxicology)
used as nitrate; 6 - 7 concentrations were applied
Method (Ecotoxicology)
oocytes expressing rat 5-HT2A receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of increasing concentrations of title comp. for 10 s; stimulation of membrane currents was determined
Further Details (Ecotoxicology)
2 of 4
Type (Ecotoxicology)
EC50
Value of Type (Ecotoxicology)
5908 nmol/l
Results
title comp. concentration-dependently induced membrane current (table, figure)
Reference
Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo
British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details
Effect (Ecotoxicology)
membrane current; inhibition of
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
1E-10 - 1E-05 mol/l
Kind of Dosing (Ecotoxicology)
used as nitrate
Method (Ecotoxicology)
oocytes expressing rat 5-HT2A receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; co-application for 10 s of title comp. and 1E-8 - 1E-5 mol/l 5-HT; 5-HT-induced membrane currents were determined
Further Details (Ecotoxicology)
3 of 4
5-HT: serotonin
5-HT: serotonin; further investigations using pre-exposure with title comp. for up to 5 min
Results
title comp. competitively antagonized stimulatory effect of 5-HT; inhibition induced by title comp. did not vary with increasing of exposure time (figure)
Reference
Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo
British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details
Effect (Ecotoxicology)
membrane current; inhibition of
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
1E-09 - 0.0001 mol/l
Kind of Dosing (Ecotoxicology)
used as nitrate
Method (Ecotoxicology)
oocytes expressing rat 5-HT2C receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; co-application for 10 s of title comp. and 1E-9 - 1E-6 mol/l 5-HT; 5-HT-induced membrane currents were determined
Further Details (Ecotoxicology)
4 of 4
5-HT: serotonin; further investigations using pre-exposure with title comp. for up to 5 min
Results
title comp. non-competitively antagonized stimulatory effect of 5-HT shifting 5-HT concentration-response curves downwards in dosedependent manner; inhibition caused by pre-application of title comp. was time-dependent (figure)
Reference
Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo
British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details
Effect (Ecotoxicology)
membrane current; induction of
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
Ca. 1E-07 - 0.0001 mol/l
Kind of Dosing (Ecotoxicology)
used as nitrate; 6 - 7 concentrations were applied
Method (Ecotoxicology)
oocytes expressing rat 5-HT2C receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of increasing concentrations of title comp. for 10 s; stimulation of membrane currents was determined
Further Details (Ecotoxicology)
5-HT: serotonin; Imax: maximal current relative to that evoked by 5-HT
Type (Ecotoxicology)
EC50
Value of Type (Ecotoxicology)
504 nmol/l
Results
title comp. concentration-dependently induced membrane current with Imax = 44 percent (table, figure)
Reference
Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo
British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details
Reaxys Registry Number: 30218571
Molecular Formula: C10H14N2O4*ClH Linear Structure Formula: ClH*C10H14N2O4
Molecular Weight: 262.693 InChI Key: HBLKZKZKVLJMNC-UHFFFAOYSA-N
2
Synthesize Find similar
0 prep out of 1 reactions.
1