Reaxys
PubChem
eMolecules
Reactions (18)
Substances (2)
Structure
Citations (24)
Structure/Compound Data Chemical Name: alpha demethyl DOM Reaxys Registry Number: 2211617
CAS Registry Number: 24333-19-5 Type of Substance: isocyclic Molecular Formula: C11H17NO2
Linear Structure Formula: C11H17NO2
Molecular Weight: 195.261
InChI Key: UNQQFDCVEMVQHM-UHFFFAOYSA-N
1
N° of preparations All Preps | All Reactions 5 prep out of 9 reactions.
Available Data
N° of ref.
Identification Bioactivity (12)
22
Synthesize | Hide Details Find similar Chemical Names and Synonyms alpha demethyl DOM, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane, 2,5-Dimethoxy-4-methylphenethylamin, 2,5-dimethoxy-4methylphenethylamine, 2,5-dimethoxy-4methylphenethylamine Identification Substance Label (6) Label
Reference
2C-D
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
Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo
British Journal of Pharmacology, 2004 , vol. 141, # 7 p. 1167 - 1174 Title/Abstract Full Text View citing articles Show Details
Theobald, Denis S.; Maurer, Hans H.
Journal of Mass Spectrometry, 2006 , vol. 41, # 11 p. 1509 - 1519 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
Herth, Matthias M.; Leth-Petersen, Sebastian; Lehel, Szabolcs; Hansen, Martin; Knudsen, Gitte M.; Gillings, Nic; Madsen, Jacob; Kristensen, Jesper L.
RSC Advances, 2014 , vol. 4, # 41 p. 21347 - 21350 Title/Abstract Full Text View citing articles Show Details
36
Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella
Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 15 p. 7415 - 7423 Title/Abstract Full Text View citing articles Show Details
7c
Cheng; Castagnoli Jr.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 4 p. 513 - 520 Title/Abstract Full Text View citing articles Show Details
2g
Standridge; Howell; Gylys; et al.
Journal of Medicinal Chemistry, 1976 , vol. 19, # 12 p. 1400 - 1404 Title/Abstract Full Text View citing articles Show Details
2a
Standridge; Howell; Gylys; et al.
Journal of Medicinal Chemistry, 1976 , vol. 19, # 12 p. 1400 - 1404 Title/Abstract Full Text View citing articles Show Details
4
Ho; Tansey; Balster; An; McIsaac; Harris
Journal of medicinal chemistry, 1970 , vol. 13, # 1 p. 134 - 135 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (7) 1 of 7
Comment (Pharmacological Data)
Bioactivities present
Reference
Ho; Tansey; Balster; An; McIsaac; Harris
Journal of medicinal chemistry, 1970 , vol. 13, # 1 p. 134 - 135 Title/Abstract Full Text View citing articles Show Details
Standridge; Howell; Gylys; et al.
Journal of Medicinal Chemistry, 1976 , vol. 19, # 12 p. 1400 - 1404 Title/Abstract Full Text View citing articles Show Details
Cheng; Castagnoli Jr.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 4 p. 513 - 520 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
Altun, Ahmet; Golcuk, Kurtulus; Kumru, Mustafa; Jalbout, Abraham F.
Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 18 p. 3861 - 3868 Title/Abstract Full Text View citing articles Show Details
Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo
British Journal of Pharmacology, 2004 , vol. 141, # 7 p. 1167 - 1174 Title/Abstract Full Text View citing articles Show Details
Thakur, Mamta; Thakur, Abhilash; Khadikar, Padmakar V.
Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 4 p. 825 - 831 Title/Abstract Full Text View citing articles Show Details
Theobald, Denis S.; Maurer, Hans H.
Journal of Mass Spectrometry, 2006 , vol. 41, # 11 p. 1509 - 1519 Title/Abstract Full Text View citing articles Show Details
Theobald, Denis S.; Maurer, Hans H.
Biochemical Pharmacology, 2007 , vol. 73, # 2 p. 287 - 297 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
Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella
Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 15 p. 7415 - 7423 Title/Abstract Full Text View citing articles Show Details
Blaazer, Antoni R.; Smid, Pieter; Kruse, Chris G.
ChemMedChem, 2008 , vol. 3, # 9 p. 1299 - 1309 Title/Abstract Full Text View citing articles Show Details
Meyer, Markus R.; Maurer, Hans H.
Current Drug Metabolism, 2010 , vol. 11, # 5 p. 468 - 482 Title/Abstract Full Text View citing articles Show Details
Standridge; Howell; Gylys; Partyka; Shulgin
Journal of medicinal chemistry, 1976 , vol. 19, # 12 p. 1400 - 1404 Title/Abstract Full Text Show Details
Saez; Borges; Gonzalez; Cassels
General Pharmacology, 1994 , vol. 25, # 1 p. 211 - 216 Title/Abstract Full Text Show Details
Clare
Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 687 - 702 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
SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL
Chemical reviews, 1983 , vol. 83, # 6 p. 633 - 649 Title/Abstract Full Text Show Details
Herth, Matthias M.; Leth-Petersen, Sebastian; Lehel, Szabolcs; Hansen, Martin; Knudsen, Gitte M.; Gillings, Nic; Madsen, Jacob; Kristensen, Jesper L.
RSC Advances, 2014 , vol. 4, # 41 p. 21347 - 21350 Title/Abstract Full Text View citing articles Show Details
2 of 7
3 of 7
4 of 7
Comment (Pharmacological Data)
Bioactivities present
Reference
Glicksberg, Lindsay; Bryand, Kelsie; Kerrigan, Sarah
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 2016 , vol. 1035, p. 91 - 103 Title/Abstract Full Text Show Details
Carbonaro, Theresa M.; Gatch, Michael B.
Brain Research Bulletin, 2016 , vol. 126, p. 74 - 88 Title/Abstract Full Text Show Details
Effect (Pharmacological Data)
agonist
Species or TestSystem (Pharmacological Data)
RD-HGA16 cells expressing human TAAR 1 receptor
Method (Pharmacological Data)
hTAAR1 activation assay; title comp. incubated with test cells in presence of Calcium 3 dye as fluorescent substrate (HAM's F-12 medium, 10percent FBS, 5percent CO2/95percent air, 37 deg C, 1 h); title comp. effect on internal calcium mobilization assessed; fluorimetry
Further Details (Pharmacological Data)
hTAAR1: human trace amine receptor 1; Emax: maximal title comp. efficacy
Type (Pharmacological Data)
EC50
Value of Type (Pharmacological Data)
6478 nmol/l
Results
title comp. exhibited Emax 36percent
Reference
Lewin, Anita H.; Navarro, Hernan A.; Wayne Mascarella
Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 15 p. 7415 - 7423 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
behavioural symptoms
Species or TestSystem (Pharmacological Data)
Sprague-Dawley rat
Sex
male
Route of Application
intraperitoneal
Concentration (Pharmacological Data)
8.4 μmol/kg
Method (Pharmacological Data)
immediately after title comp. injection rats placed in dark Plexiglas box and number of head shakes was quantified for 25 min, starting 5 min after title comp. administration
Further Details (Pharmacological Data)
control: saline; 5-HT: serotonin
Comment (Pharmacological
No effect
Data)
5 of 7
6 of 7
7 of 7
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 both PLC-mediated IP (RE = ca. 20percent, pEC50 = 5.61) and PLA2-mediated AA (RE = ca. 15percent, pEC50 = 5.09) 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-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. 40percent, pEC50 = 4.85) and PLA2-mediated AA (RE = ca. 40percent, pEC50 = 4.73) 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)
biotransformation
Species or TestSystem (Pharmacological Data)
Wistar rat
Sex
male
Route of Application
peroral
Concentration (Pharmacological Data)
20 mg/kg
Kind of Dosing (Pharmacological Data)
aqueous suspension
Method (Pharmacological Data)
in vivo; urine collected separately from feces over 24 h period; metabolites identified by GC/MS
Metabolite (Pharmacological Data)
2-(2-amino-ethyl)-4-methoxy-5-methyl-phenol [Reaxys RN: 10537609] ; 5-(2-amino-ethyl)-4-methoxy-2-methyl-phenol [Reaxys RN: 10537945] ; N-[2-(2,5-dimethoxy-4-methyl-phenyl)-ethyl]-acetamide [Reaxys RN: 10545892]
Comment (Pharmacological Data)
Further metabolite(s)
Reference
Theobald, Denis S.; Maurer, Hans H.
Journal of Mass Spectrometry, 2006 , vol. 41, # 11 p. 1509 - 1519 Title/Abstract Full Text View citing articles Show Details
Ecotoxicology (5) 1 of 5
Effect (Ecotoxicology)
antagonist
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
10 - 30 nmol/l
Kind of Dosing (Ecotoxicology)
used as hydrochloride salt; dissolved in Barth's solution
Method (Ecotoxicology)
cultured cells expressing rat 5-HT2A receptors voltage-clamped at membrane potential of -70 mV; cells superfused with title comp. preapplied for 2 min prior to challenge with increasing concentrations of 5-HT; changes in 5-HT-evoked currents recorded
Further Details (Ecotoxicology)
2 of 5
Results
title comp. antagonized 5-HT2A receptors; it concentration-dependently blocked 5-HT-evoked currents (figure)
Reference
Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo
British Journal of Pharmacology, 2004 , vol. 141, # 7 p. 1167 - 1174 Title/Abstract Full Text View citing articles Show Details
Effect (Ecotoxicology)
membrane current; inhibition of
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
10 nmol/l
Kind of Dosing (Ecotoxicology)
used as hydrochloride salt; dissolved in Barth's solution
Method (Ecotoxicology)
cultured cells expressing rat 5-HT2A receptors voltage-clamped at membrane potential of -70 mV; cells superfused with title comp. preapplied for 1 - 3 min prior to challenge with 100 nmol/l of 5-HT; changes in 5-HT-evoked currents recorded
Further Details (Ecotoxicology)
3 of 5
5-HT: 5-hydroxytryptamine
5-HT: 5-hydroxytryptamine
Results
title comp. antagonized 5-HT2A receptors; it time-dependently blocked 5-HT-evoked currents (figure)
Reference
Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo
British Journal of Pharmacology, 2004 , vol. 141, # 7 p. 1167 - 1174 Title/Abstract Full Text View citing articles Show Details
Effect (Ecotoxicology)
antagonist
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Concentration (Ecotoxicology)
Ca. 1E-11 - 1E-05 mol/l
Kind of Dosing (Ecotoxicology)
used as hydrochloride salt; dissolved in Barth's solution
Method (Ecotoxicology)
cultured cells expressing rat 5-HT2A receptors voltage-clamp at membrane potential of -70 mV; cells superfused with title comp. preapplicated 2 min prior to challenge with 100 nmol/l of 5-HT; 5-HT-evoked currents recorded
Further Details (Ecotoxicology)
5-HT: 5-hydroxytryptamine
Type (Ecotoxicology)
pIC50
Value of Type (Ecotoxicology)
7.42 dimensionless
Results
title comp. behaved as 5-HT2A receptor antagonist, it reversibly and concentration-dependently blocked 5-HT-evoked currents (figure)
Reference
Villalobos, Claudio A.; Bull, Paulina; Saez, Patricio; Cassels, Bruce K.; Huidobro-Toro, J. Pablo
British Journal of Pharmacology, 2004 , vol. 141, # 7 p. 1167 - 1174 Title/Abstract Full Text View citing articles Show Details
4 of 5
Effect (Ecotoxicology)
membrane current; induction of
Species or TestSystem (Ecotoxicology)
Xenopus laevis oocyte
Kind of Dosing (Ecotoxicology)
used as hydrochloride; 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)
5 of 5
5-HT: serotonin
Type (Ecotoxicology)
EC50
Value of Type (Ecotoxicology)
586 nmol/l
Results
title comp. concentration-dependently induced membrane current (table)
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
Kind of Dosing (Ecotoxicology)
used as hydrochloride; 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)
1308 nmol/l
Results
title comp. concentration-dependently induced membrane current with Imax = 48 percent (table)
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: 2C-D Reaxys Registry Number: 7285071
Type of Substance: isocyclic Molecular Formula: C11H17NO2*ClH Linear Structure Formula: C11H17NO2*ClH Molecular Weight: 231.722
InChI Key: UIPCUUZBUOLEMM-UHFFFAOYSA-N
2
Synthesize | Hide Details Find similar Chemical Names and Synonyms 2C-D, 2,5-dimethoxy-4-methyl-β-phenethylamine hydrochloride, 2,5-dimethoxy-4-methylphenethylamine hydrochloride Identification
0 prep out of 9 reactions.
Identification Physical Data (2) Bioactivity (2)
5
Substance Label (2) Label
Reference
2C-D
Theobald, Denis S.; Maurer, Hans H.
Biochemical Pharmacology, 2007 , vol. 73, # 2 p. 287 - 297 Title/Abstract Full Text View citing articles Show Details
4*HCl
Ho; Tansey; Balster; An; McIsaac; Harris
Journal of medicinal chemistry, 1970 , vol. 13, # 1 p. 134 - 135 Title/Abstract Full Text View citing articles Show Details
Physical Data Melting Point (2) Melting Point
Solvent (Melting Point)
Reference
214 - 215.5 °C
propan-2-ol
Standridge; Howell; Gylys; et al.
Journal of Medicinal Chemistry, 1976 , vol. 19, # 12 p. 1400 - 1404 Title/Abstract Full Text View citing articles Show Details
212 - 213 °C
ethanol
Ho; Tansey; Balster; An; McIsaac; Harris
Journal of medicinal chemistry, 1970 , vol. 13, # 1 p. 134 - 135 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
Ho; Tansey; Balster; An; McIsaac; Harris
Journal of medicinal chemistry, 1970 , vol. 13, # 1 p. 134 - 135 Title/Abstract Full Text View citing articles Show Details
Standridge; Howell; Gylys; et al.
Journal of Medicinal Chemistry, 1976 , vol. 19, # 12 p. 1400 - 1404 Title/Abstract Full Text View citing articles Show Details
Theobald, Denis S.; Maurer, Hans H.
Biochemical Pharmacology, 2007 , vol. 73, # 2 p. 287 - 297 Title/Abstract Full Text View citing articles Show Details
Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.
Psychopharmacology, 2014 , vol. 231, # 5 p. 875 - 888 Title/Abstract Full Text View citing articles Show Details
Hansen, Martin; Phonekeo, Karina; Paine, James S.; Leth-Petersen, Sebastian; Begtrup, Mikael; Braeuner-Osborne, Hans; Kristensen, Jesper L.
ACS Chemical Neuroscience, 2014 , vol. 5, # 3 p. 243 - 249 Title/Abstract Full Text View citing articles Show Details
Comment (Pharmacological Data)
physiological behaviour discussed
Reference
Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.
Psychopharmacology, 2014 , vol. 231, # 5 p. 875 - 888 Title/Abstract Full Text View citing articles Show Details