Reaxys
PubChem
eMolecules
Reactions (9)
Substances (7)
Structure
Citations (16)
Structure/Compound Data Chemical Name: 2,5-Dimethoxy-4-chloroamphetamine Reaxys Registry Number: 2727016
CAS Registry Number: 123431-31-2 Type of Substance: isocyclic Molecular Formula: C11H16ClNO2
Linear Structure Formula: C11H16ClNO2
Molecular Weight: 229.707 InChI Key: ACRITBNCBMTINK-UHFFFAOYSA-N
1
N° of preparations All Preps | All Reactions
Available Data
N° of ref.
3 prep out of 3 reactions.
Identification Physical Data (1) Bioactivity (2)
12
Synthesize | Hide Details Find similar Chemical Names and Synonyms 2,5-Dimethoxy-4-chloroamphetamine, 2,5-dimethoxy-4-chloroamphetamine, 4-Chloro-2,5-dimethoxyamphetamine, 4-Chlor-2,5dimethoxyphenylisopropylamin, 4-chloro-2,5-dimethoxyamphetamine Identification Substance Label (2) Label
Reference
DOC
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
1f
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles 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
Patent-Specific Data (1) Prophetic Compound
Reference
prophetic product
Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.
Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text 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 (2) 1 of 2
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
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 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
Clare, Brian W.
Journal of Medicinal Chemistry, 1998 , vol. 41, # 20 p. 3845 - 3856 Title/Abstract Full Text View citing articles Show Details
Aldous; Barrass; Brewster; Buxton; Green; Pinder; Rich; Skeels; Tutt
Journal of Medicinal Chemistry, 1974 , vol. 17, # 10 p. 1100 - 1111 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
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
Faria-Oliveira, Fábio; Carvalho, Joana; Belmiro, Celso L.R.; Martinez-Gomariz, Montserrat; Hernaez, Maria Luisa; Pavão, Mauro; Gil, Concha; Lucas, Cândida; Ferreira, Célia
BMC Microbiology, 2014 , vol. 14, # 1 art. no. 244 Title/Abstract Full Text Show Details
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
Saz; Marina
Journal of Chromatography A, 2016 , vol. 1467, p. 79 - 94 Title/Abstract Full Text Show Details
2 of 2
Comment (Pharmacological Data) Reference
5-HT2 serotonin antagonist activity
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
Chemical Name: 2,5-Dimethoxy-4-chloroamphetamine hydrochloride
no reactions.
Identification Physical Data (2) Spectra (1)
5
Reaxys Registry Number: 4029561
CAS Registry Number: 42203-77-0 Type of Substance: isocyclic Molecular Formula: C11H16ClNO2*ClH Linear Structure Formula: C11H16ClNO2*ClH Molecular Weight: 266.167 InChI Key: UOWCUOAJVCUYGV-UHFFFAOYSA-N
2
Synthesize | Hide Details Find similar Chemical Names and Synonyms 2,5-Dimethoxy-4-chloroamphetamine hydrochloride, 1-(4-Chloro-2,5-dimethoxyphenyl)-2-aminopropan-hydrochlorid Identification Substance Label (3) Label
Reference
DOC
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
1f
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details
1f-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)
Reference
187 - 188 °C
acetone ethanol
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
193 - 194.5 °C
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) 1 of 6
Comment (Pharmacological Data)
Bioactivities present
Reference
Coutts; Malicky
Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409
Bioactivity (6)
Title/Abstract Full Text View citing articles Show Details
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 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
Glennon, Richard A.; Dukat, Malgorzata; Grella, Brian; Hong, Seoung-Soo; Costantino, Luca; Teitler, Milt; Smith, Carol; Egan, Chris; Davis, Katherine; Mattson, Mariena V.
Drug and Alcohol Dependence, 2000 , vol. 60, # 2 p. 121 - 132 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
2 of 6
3 of 6
4 of 6
5 of 6
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
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)
1.4 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)
26.8 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
6 of 6
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
2.0 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-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)
31.8 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
Chemical Name: (+)-4-Chlor-2,5-dimethoxyphenylisopropylamin Reaxys Registry Number: 6793028
Type of Substance: isocyclic Molecular Formula: C11H16ClNO2
Linear Structure Formula: C11H16ClNO2
Molecular Weight: 229.707 InChI Key: ACRITBNCBMTINK-ZETCQYMHSA-N
3 prep out of 3 reactions.
1
3 prep out of 3 reactions.
1
3
Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-4-Chlor-2,5-dimethoxyphenylisopropylamin Chemical Name: (-)-4-Chlor-2,5-dimethoxyphenylisopropylamin Reaxys Registry Number: 6793029
Type of Substance: isocyclic Molecular Formula: C11H16ClNO2
Linear Structure Formula: C11H16ClNO2
Molecular Weight: 229.707 InChI Key: ACRITBNCBMTINK-SSDOTTSWSA-N 4
Synthesize | Hide Details Find similar Chemical Names and Synonyms
(-)-4-Chlor-2,5-dimethoxyphenylisopropylamin Reaxys Registry Number: 6796105
Type of Substance: isocyclic Molecular Formula: C11H16ClNO2*ClH Linear Structure Formula: C11H16ClNO2*ClH Molecular Weight: 266.167 InChI Key: UOWCUOAJVCUYGV-FJXQXJEOSA-N
no reactions.
Physical Data (2)
1
5
Synthesize | Hide Details Find similar
Physical Data Melting Point (1) Melting Point
Reference
198 °C
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
Optical Rotatory Power (1) Type (Optical Rotatory Power)
Concentration (Optical Rotatory Power)
Solvent (Optical Rotatory Power)
Optical Rotatory Power
Wavelength (Optical Rotatory Power)
Temperature (Optical Rotatory Power)
[alpha]
4 g/100ml
H2O
16 deg
589 nm
25 °C
Reaxys Registry Number: 6796106
Type of Substance: isocyclic Molecular Formula: C11H16ClNO2*ClH Linear Structure Formula: C11H16ClNO2*ClH Molecular Weight: 266.167 InChI Key: UOWCUOAJVCUYGV-OGFXRTJISA-N
6
Synthesize | Hide Details Find similar
Physical Data Melting Point (1) Melting Point
Reference
195 °C
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
Optical Rotatory Power (1)
no reactions.
Reference Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
Physical Data (2)
1
7
Type (Optical Rotatory Power)
Concentration (Optical Rotatory Power)
Solvent (Optical Rotatory Power)
Optical Rotatory Power
Wavelength (Optical Rotatory Power)
Temperature (Optical Rotatory Power)
[alpha]
4 g/100ml
H2O
-14 deg
589 nm
25 °C
Chemical Name: paraoxon+DOC
mixture (composition partially given) :
paraoxon 2,5-Dimethoxy-4-chloroamphetamine
Reference Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
no reactions.
Bioactivity (1)
1
Reaxys Registry Number: 29748917 Type of Substance: mixture (composition partially given)
Hide Details Chemical Names and Synonyms paraoxon+DOC Composition
2,5-Dimethoxy-4-chloroamphetamine
paraoxon
Synthesize
Synthesize
Find similar
Find similar
Bioactivity Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Reference
CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE D'AIX-MAR-SEILLE; CHABRIERE, Eric; ELIAS, Mikael; HIBLOT, Julien; RAOULT, Didier
Patent: US2016/115462 A1, 2016 ; Title/Abstract Full Text Show Details