Reaxys
PubChem
eMolecules
Reactions (6)
Substances (2)
Structure
Citations (27)
Structure/Compound Data Chemical Name: 2,5-dimethoxy-4-propylphenylisopropylamine Reaxys Registry Number: 2807901
CAS Registry Number: 63779-88-4 Type of Substance: isocyclic Molecular Formula: C14H23NO2
Linear Structure Formula: C14H23NO2
Molecular Weight: 237.342 InChI Key: UEEAUFJYLUJWQJ-UHFFFAOYSA-N
1
N° of preparations All Preps | All Reactions
Available Data
N° of ref.
6 prep out of 6 reactions.
Identification Physical Data (2) Bioactivity (3)
25
Synthesize | Hide Details Find similar Chemical Names and Synonyms 2,5-dimethoxy-4-propylphenylisopropylamine, 2,5-Dimethoxy-4-propylamphetamine, 2,5-dimethoxy-4-propylamphetamine, 4-Propyl-2,5dimethoxyamphetamine, 2,5-Dimethoxy-4-propylphenylisopropylamin, 2.5-Dimethoxy-4-n-propylamphetamin Identification Substance Label (5) Label
Reference
DOPR
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
1k
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
s.Tab.
Morin et al.
Experientia, 1975 , vol. 31, p. 93 Full Text View citing articles Show Details
9 (Table I)
Barfknecht et al.
Journal of Medicinal Chemistry, 1975 , vol. 18, p. 208,209 Full Text Show Details
6d
Shulgin; Dyer
Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 Title/Abstract Full Text View citing articles Show Details
Patent-Specific Data (1) Prophetic Compound
Related Markush Structure (RN)
Reference
prophetic product
11337200
Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.
Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details
Derivative (2) Comment (Derivative)
Reference
Hydrochlorid: F: 181-182grad
Morin et al.
Experientia, 1975 , vol. 31, p. 93 Full Text View citing articles Show Details
HCl-Salz, F: 182.5-183grad
Dow Chemical Co.
Patent: GB1147739 , 1966 ; Chem.Abstr., 1969 , vol. 71, # 12781j 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
Liquid/Liquid Systems (MCS) (1) Description (Liquid/Liquid Systems (MCS))
Reference
Distribution between solvent 1 + 2
Barfknecht et al.
Journal of Medicinal Chemistry, 1975 , vol. 18, p. 208,209 Full Text Show Details
Bioactivity Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Reference
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
Shulgin; Dyer
Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 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
Barfknecht et al.
Journal of Medicinal Chemistry, 1975 , vol. 18, p. 208,209 Full Text Show Details
Dow Chemical Co.
Patent: GB1147739 , 1966 ; Chem.Abstr., 1969 , vol. 71, # 12781j Full Text Show Details
Morin et al.
Experientia, 1975 , vol. 31, p. 93 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
Clare, Brian W.
Journal of Medicinal Chemistry, 1998 , vol. 41, # 20 p. 3845 - 3856 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
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
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
Barfknecht; Nichols; Dunn III
Journal of Medicinal Chemistry, 1975 , vol. 18, # 2 p. 208 - 210 Title/Abstract Full Text 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
Kier; Hall
Journal of Medicinal Chemistry, 1977 , vol. 20, # 12 p. 1631 - 1636 Title/Abstract Full Text Show Details
Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt
Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text Show Details
Clare
Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 687 - 702 Title/Abstract Full Text Show Details
Titeler; Lyon; Glennon
Psychopharmacology, 1988 , vol. 94, # 2 p. 213 - 216 Title/Abstract Full Text Show Details
Glennon
Journal of Medicinal Chemistry, 1987 , vol. 30, # 1 p. 1 - 12 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
S.P.Gupta
Chemical reviews, 1989 , vol. 89, # 8 p. 1765 - 1800 Title/Abstract Full Text Show Details
2 of 3
3 of 3
Comment (Pharmacological Data)
Bioactivities present
Reference
SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL
Chemical reviews, 1983 , vol. 83, # 6 p. 633 - 649 Title/Abstract Full Text Show Details
Baciu, Tatiana; Botello, Igor; Borrull, Francesc; Calull, Marta; Aguilar, Carme
TrAC - Trends in Analytical Chemistry, 2015 , vol. 74, p. 89 - 108 Title/Abstract Full Text View citing articles Show Details
Saz; Marina
Journal of Chromatography A, 2016 , vol. 1467, p. 79 - 94 Title/Abstract Full Text View citing articles 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
Punia, Bhupinder Singh; Yadav, Praveen Kumar; Bumbrah, Gurvinder Singh; Sharma, Rakesh Mohan
Journal of AOAC International, 2017 , vol. 100, # 1 p. 109 - 125 Title/Abstract Full Text View citing articles Show Details
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-propylamphetamine hydrochloride Reaxys Registry Number: 6785618
Type of Substance: isocyclic Molecular Formula: C14H23NO2*ClH Linear Structure Formula: C14H23NO2*ClH Molecular Weight: 273.803 InChI Key: HDNDRDMJFFBLGO-UHFFFAOYSA-N
no reactions.
Identification Physical Data (2) Bioactivity (5)
4
2
Synthesize | Hide Details Find similar Chemical Names and Synonyms 2,5-Dimethoxy-4-propylamphetamine hydrochloride Identification Substance Label (2) Label
Reference
DOPR
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
6d
Shulgin; Dyer
Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 Title/Abstract Full Text View citing articles Show Details
Physical Data Melting Point (2) Melting Point
Solvent (Melting Point)
Reference
182 - 183 °C
acetonitrile
Shulgin; Dyer
Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 Title/Abstract Full Text View citing articles Show Details
283 - 284 °C
ethanol diethyl ether
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
Bioactivity Pharmacological Data (5) 1 of 5
2 of 5
Comment (Pharmacological Data)
Bioactivities present
Reference
Aldous,F.A.B. et al.
Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details
Shulgin; Dyer
Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 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
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
Effect (Pharmacological Data)
receptor; binding activity
3 of 5
4 of 5
5 of 5
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)
0.9 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)
115 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)
1.1 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)
54.4 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