Reaxys
PubChem
eMolecules
Reactions (17)
Substances (5)
Structure
Citations (23)
Structure/Compound Data Chemical Name: 1-(2,5-dimethoxy-4-nitrophenyl) propan-2-amine Reaxys Registry Number: 3550428
CAS Registry Number: 67460-68-8 Type of Substance: isocyclic Molecular Formula: C11H16N2O4
Linear Structure Formula: C11H16N2O4
Molecular Weight: 240.259
InChI Key: JQJRESSXOVAECC-UHFFFAOYSA-N
1
N° of preparations All Preps | All Reactions
Available Data
N° of ref.
6 prep out of 15 reactions.
Identification Physical Data (1) Bioactivity (10)
20
Synthesize | Hide Details Find similar Chemical Names and Synonyms 1-(2,5-dimethoxy-4-nitrophenyl) propan-2-amine, 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine, 2,5-dimethoxy-4-nitroamphetamine, 4-Nitro-2,5dimethoxyamphetamine, (+/-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane Identification Substance Label (5) Label
Reference
DON
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
Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel
Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 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
Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero
Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details
1d
Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon
Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details
3
Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt
Journal of Medicinal Chemistry, 1988 , vol. 31, # 1 p. 5 - 7 Title/Abstract Full Text View citing articles Show Details
(+/-)DON
Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos
European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details
1h
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
Patent-Specific Data (2) Prophetic Compound
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
Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.
Patent: US2007/27208 A1, 2007 ;
prophetic product
Title/Abstract Full Text Show Details
Derivative (1) Derivative
Reference
(+/-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane hydrochloride
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Physical Data Chromatographic Data (1) Chromatographic data
Reference
CE (Capillar electrophoresis)
Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero
Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (8) 1 of 8
Comment (Pharmacological Data)
Bioactivities present
Reference
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.
Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details
Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon
Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details
Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos
European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details
Glennon, Richard A.; Seggel, Mark R.; Soine, William H.; Herrick-Davis, Katherine; Lyon, Robert A.; Titeler, Milt
Journal of Medicinal Chemistry, 1988 , vol. 31, # 1 p. 5 - 7 Title/Abstract Full Text View citing articles Show Details
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Clare, Brian W.
Journal of Medicinal Chemistry, 1998 , vol. 41, # 20 p. 3845 - 3856 Title/Abstract Full Text View citing articles 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
Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel
Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 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
Gomez-Jeria; Cassels; Saavedra-Aguilar
European Journal of Medicinal Chemistry, 1987 , vol. 22, # 5 p. 433 - 437 Title/Abstract Full Text Show Details
Glennon
Journal of Medicinal Chemistry, 1987 , vol. 30, # 1 p. 1 - 12 Title/Abstract Full Text Show Details
Shannon; Battaglia; Glennon; Titeler
European journal of pharmacology, 1984 , vol. 102, # 1 p. 23 - 29 Title/Abstract Full Text Show Details
Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero
Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details
SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL
Chemical reviews, 1983 , vol. 83, # 6 p. 633 - 649 Title/Abstract Full Text 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
Saz; Marina
Journal of Chromatography A, 2016 , vol. 1467, p. 79 - 94 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 8
3 of 8
Effect (Pharmacological Data)
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. had similar relative efficacies for PLC-mediated IP accumulation (RE = ca. 50percent, pEC50 = 5.74) and for PLA2-mediated AA release (RE = ca. 40percent, pEC50 = 6.01) (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)
agonist
Species or Test-
CHO-1C19 cells expressing human 5-HT2C receptors
System (Pharmacological Data)
4 of 8
5 of 8
Concentration (Pharmacological Data)
1E-08 - 0.0005 mol/l
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. preferentially stimulated PLC-mediated IP response (RE = ca. 85percent, pEC50 = 5.62); RE for PLA2-mediated AA release was ca. 60percent, pEC50 = 5.63 (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)
enzyme; inhib. of
Species or TestSystem (Pharmacological Data)
IIBCE rat brain mitochondrial monoamine oxidase B
Sex
male
Concentration (Pharmacological Data)
0.01 - 100 μmol/l
Kind of Dosing (Pharmacological Data)
in distilled water; used as nitrate salt
Method (Pharmacological Data)
MAO-B activity determined by HPLC with electrochemical detection after incubation with selective substrate of DMAPEA in presence of title comp. at 37 deg C for 5 min, pH 7.4; DMAPEA and its MAO-B metabolite DMAPAA used to calculate MAO-B activity
Further Details (Pharmacological Data)
MAO-B = monoamine oxidase B; DMAPEA = 4-dimethylaminophenethylamine, 5 μmol/l; DMAPAA = 4-dimethylaminophenylacetic acid
Comment (Pharmacological Data)
No effect
Reference
Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel
Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
enzyme; inhib. of
Species or TestSystem (Pharmacological Data)
IIBCE rat brain mitochondrial monoamine oxidase A
Sex
male
Concentration (Pharmacological Data)
0.01 - 100 μmol/l
Kind of Dosing (Pharmacological Data)
in distilled water; used as nitrate salt
Method (Pharmacological Data)
MAO-A activity determined by HPLC with electrochemical detection after incubation with selective substrate of 5-HT in presence of title comp. at 37 deg C for 10 min, pH 7.4; 5-HT and its MAO-A metabolite 5-HIAA used to calculate MAO-A activity
Further Details (Pharmacological Data)
MAO-A = monoamine oxidase A; 5-HT = serotonin, 2.5 μmol/l; 5-HIAA = 5-hydroxyindoleacetic acid
Comment (Pharmacological
No effect
Data) Reference
6 of 8
7 of 8
8 of 8
Comment (Pharmacological Data)
Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel
Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details
5-HT2 serotonin antagonist activity
Reference
Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon
Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details
Comment (Pharmacological Data)
serotonin binding affinity in the rat stomach fundus
Reference
Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos
European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details
Comment (Pharmacological Data)
the serotonin (5-HT) receptor affinities, ED50= 0.76 mg/kg
Reference
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Ecotoxicology (2) 1 of 2
Effect (Ecotoxicology)
membrane current; induction of
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
Ca. 1E-07 - 1E-05 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 2
5-HT: serotonin; Imax: maximal current relative to that evoked by 5-HT
Type (Ecotoxicology)
EC50
Value of Type (Ecotoxicology)
1848 nmol/l
Results
title comp. concentration-dependently induced membrane current with Imax = 22 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
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
6055 nmol/l
(Ecotoxicology) Results
title comp. concentration-dependently induced membrane current with Imax = 35 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
Chemical Name: (R)-(-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane Reaxys Registry Number: 5746403
CAS Registry Number: 64778-74-1 Type of Substance: isocyclic Molecular Formula: C11H16N2O4
Linear Structure Formula: C11H16N2O4
Molecular Weight: 240.259
InChI Key: JQJRESSXOVAECC-SSDOTTSWSA-N
2
1 prep out of 1 reactions.
Identification Bioactivity (2)
Synthesize | Hide Details Find similar Chemical Names and Synonyms (R)-(-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane, (R)-(-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropan Identification Substance Label (2) Label
Reference
(R)-(-)-DON
Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos
European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details
(-)-9
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Derivative (1) Derivative
Reference
(R)-(-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropan hydrochloride
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (2) 1 of 2
2 of 2
Comment (Pharmacological Data)
Bioactivities present
Reference
Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos
European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Deeb, Omar; Clare, Brian W.
Chemical Biology and Drug Design, 2008 , vol. 71, # 4 p. 352 - 362 Title/Abstract Full Text View citing articles Show Details
Gomez-Jeria; Cassels; Saavedra-Aguilar
European Journal of Medicinal Chemistry, 1987 , vol. 22, # 5 p. 433 - 437 Title/Abstract Full Text Show Details
Shannon; Battaglia; Glennon; Titeler
European journal of pharmacology, 1984 , vol. 102, # 1 p. 23 - 29 Title/Abstract Full Text Show Details
Comment
serotonin binding affinity in the rat stomach fundus
5
(Pharmacological Data) Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos
European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details
Reference
Chemical Name: (+/-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane hydrochloride Reaxys Registry Number: 4036029
CAS Registry Number: 42203-79-2 Type of Substance: isocyclic Molecular Formula: C11H16N2O4*ClH Linear Structure Formula: C11H16N2O4*ClH Molecular Weight: 276.72
InChI Key: OUWUAAJFFCYVBE-UHFFFAOYSA-N
3
0 prep out of 1 reactions.
Synthesize | Hide Details Find similar Chemical Names and Synonyms (+/-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane hydrochloride, 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine hydrochloride, 1-(2,5Dimethoxy-4-nitrophenyl)-2-aminopropan-hydrochlorid Identification Substance Label (3) Label
Reference
DON
Nelson; Lucaites; Wainscott; Glennon
Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
1h
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
1h-HCl
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
Physical Data Melting Point (2) Melting Point
Solvent (Melting Point)
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
207 - 209 °C
203 - 204 °C
Reference
ethanol diethyl ether
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
Spectra IR Spectroscopy (1) Description (IR Spectroscopy)
Reference
Bands
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (6)
Identification Physical Data (2) Spectra (1) Bioactivity (6)
3
1 of 6
2 of 6
3 of 6
4 of 6
Comment (Pharmacological Data)
Bioactivities present
Reference
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Nelson; Lucaites; Wainscott; Glennon
Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
receptor; binding activity
Species or TestSystem (Pharmacological Data)
membrane preparation of human 5-HT2A receptors
Method (Pharmacological Data)
suspension-grown AV12 cells stably transformed with human 5-HT2A receptors; receptors labeled with <125I>1-(4-iodo-2,5dimethoxyphenyl)propan-2-amine; determination of non-specific binding
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
5.5 mmol/l
Reference
Nelson; Lucaites; Wainscott; Glennon
Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
receptor; binding activity
Species or TestSystem (Pharmacological Data)
membrane preparation of rat 5-HT2B receptors
Method (Pharmacological Data)
suspension-grown AV12 cells stably transformed with rat 5-HT2B receptors; receptors labeled with <3H>serotonin; determination of nonspecific binding
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
248 nmol/l
Reference
Nelson; Lucaites; Wainscott; Glennon
Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
receptor; binding activity
Species or TestSystem (Pharmacological Data)
membrane preparation of human 5-HT2C receptors
Method (Pharmacological Data)
suspension-grown AV12 cells stably transformed with human 5-HT2C receptors; receptors labeled with <125I>1-(4-iodo-2,5dimethoxyphenyl)propan-2-amine; determination of non-specific binding
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
22.4 nmol/l
Reference
Nelson; Lucaites; Wainscott; Glennon
Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
5 of 6
6 of 6
Effect (Pharmacological Data)
receptor; binding activity
Species or TestSystem (Pharmacological Data)
membrane preparation of human 5-HT2B receptors
Method (Pharmacological Data)
suspension-grown AV12 cells stably transformed with human 5-HT2B receptors; receptors labeled with <3H>serotonin; determination of non-specific binding
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
166 nmol/l
Reference
Nelson; Lucaites; Wainscott; Glennon
Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
Comment (Pharmacological Data)
the serotonin (5-HT) receptor affinities, ED50= 0.76 mg/kg
Reference
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Chemical Name: (R)-(-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropan hydrochloride
no reactions.
Physical Data (2) Bioactivity (2)
1
Reaxys Registry Number: 6493256
Type of Substance: isocyclic Molecular Formula: C11H16N2O4*ClH Linear Structure Formula: C11H16N2O4*ClH Molecular Weight: 276.72
InChI Key: OUWUAAJFFCYVBE-OGFXRTJISA-N 4
Synthesize | Hide Details Find similar Chemical Names and Synonyms (R)-(-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropan hydrochloride Physical Data Melting Point (1) Melting Point
Solvent (Melting Point)
Reference
231 - 232 °C
ethanol diethyl ether
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Optical Rotatory Power (1) Type (Optical Rotatory Power)
Solvent (Optical Rotatory Power)
Optical Rotatory Power
Wavelength (Optical Rotatory Power)
Temperature (Optical Rotatory Power)
[alpha]
H2O
-12.5 deg
589 nm
23 °C
Reference Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (2) 1 of 2
2 of 2
Comment (Pharmacological Data)
Bioactivities present
Reference
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Comment (Pharmacological Data)
the serotonin (5-HT) receptor affinities, ED50= 0.57 mg/kg
Reference
Glennon; Young; Benington; Morin
Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details
Chemical Name: (+/-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane nitrate Reaxys Registry Number: 5369553
CAS Registry Number: 145518-38-3 Type of Substance: isocyclic Molecular Formula: C11H16N2O4*HNO3
Linear Structure Formula: C11H16N2O4*HNO3
Molecular Weight: 303.272
InChI Key: VQVUPLZUQVLNQP-UHFFFAOYSA-N
5
no reactions.
Identification Physical Data (1) Spectra (2)
1
Synthesize | Hide Details Find similar Chemical Names and Synonyms (+/-)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane nitrate Identification Substance Label (1) Label
Reference
DON nitrate
Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.
Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details
Physical Data Melting Point (1) Melting Point
Solvent (Melting Point)
Reference
154 - 155.5 °C
propan-2-ol diethyl ether
Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.
Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details
Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Chemical shifts
1H
D2O
Comment (NMR Spectroscopy)
Reference Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.
Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details
Spin-spin coupling constants
D2O
1H-1H
Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.
Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details