Reaxys
PubChem
eMolecules
Reactions (71)
Substances (7)
Citations (25)
Structure
Structure/Compound Data Chemical Name: 3-(pyrrolidin-3-yl)-1H-indole Reaxys Registry Number: 910813
CAS Registry Number: 3766-02-7 Type of Substance: heterocyclic Molecular Formula: C12H14N2
Linear Structure Formula: C12H14N2
Molecular Weight: 186.257
InChI Key: QEHMBCDTVQBATA-UHFFFAOYSA-N
1
N° of preparations All Preps | All Reactions
Available Data
6 prep out of 25 reactions.
Identification Physical Data (3) Spectra (2) Bioactivity (1)
N° of ref. 10
Synthesize | Hide Details Find similar Chemical Names and Synonyms 3-(pyrrolidin-3-yl)-1H-indole, 3-(3-indolyl)pyrrolidine, 3-pyrrolidin-3-yl-indole, 3-pyrrolidin-3-yl-1H-indol, 3-(pyrrolidin-3-yl)indole, (+-)-3-(Indol-3-yl)pyrrolidin, 3-(3-Pyrrolidinyl)-indol Identification Substance Label (4) Label
Reference
65
UNIVERSITÄT REGENSBURG; FRIEDRICH-SCHILLER-UNIVERSITÄT JENA; UNIVERSITÄTSKLINIKUM JENA; MAHBOOBI, Siavosh; SELLMER, Andreas; PONGRATZ, Herwig; LEONHARDT, Michel; KRÄMER, Oliver; BÖHMER, Frank-Dietmar; KELTER, Gerhard
Patent: WO2016/20369 A1, 2016 ; Title/Abstract Full Text Show Details
8
SHIONOGI and CO., LTD.
Patent: EP1505061 A1, 2005 ;
Title/Abstract Full Text Show Details
IV
GRUeNENTHAL GMBH
Patent: WO2005/19208 A1, 2005 ; Title/Abstract Full Text Show Details
1
Burm, Brigitte E.A; Gremmen, Christiaan; Wanner, Martin J; Koomen, Gerrit-Jan
Tetrahedron, 2001 , vol. 57, # 10 p. 2039 - 2049 Title/Abstract Full Text View citing articles Show Details
Derivative (1) Comment (Derivative)
Reference
Hydrochlorid C12H14N2*HCl: F: 164grad (aus A./Ae.)
Julia,M.; Bagot,J.
Bulletin de la Societe Chimique de France, 1964 , p. 1924 - 1938 Full Text View citing articles Show Details
Physical Data Melting Point (2) Melting Point
Solvent (Melting Point)
Reference
102 - 104.5 °C
acetonitrile
Perron,Y.G. et al.
Journal of Medicinal Chemistry, 1966 , vol. 9, p. 136 - 140 Full Text View citing articles Show Details
Bristol Myers Co.
Patent: GB893899US , 19621959 ; Chem.Abstr., 1962 , vol. 57, # 9820b Full Text Show Details
102 - 104.5 °C
Crystal Property Description (1) Colour & Other Properties red-brown
Location
Reference
Page/Page column 122
UNIVERSITÄT REGENSBURG; FRIEDRICH-SCHILLER-UNIVERSITÄT JENA; UNIVERSITÄTSKLINIKUM JENA; MAHBOOBI, Siavosh; SELLMER, Andreas; PONGRATZ, Herwig; LEONHARDT, Michel; KRÄMER, Oliver; BÖHMER, Frank-Dietmar; KELTER, Gerhard
Patent: WO2016/20369 A1, 2016 ; Title/Abstract Full Text Show Details
Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Chemical shifts
1H
dimethylsulfoxided6
Frequency (NMR Spectroscopy) 300 MHz
Original Text (NMR Spectroscopy)
Location
Reference
1H MR (300 MHz, DMSO-d6): δ 10.93 (s, 1 1H), 7.56 (d, J= 7.8 Hz, 1H), 7.36 (d, J = 8.0 Hz, 1H), 7.16 (s, 1H), 7.07 (m, 1H), 6.97 (m, 1H), 3.91 (bs, 1H), 3.45 - 3.23 (m, 2H), 3.13 - 2.89 (m, 2H), 2.87 - 2.73 (m, 1H), 2.33 - 2.07 (m, 1H), 1.95 - 1.73 (m, 1H).
Page/Page column 122
UNIVERSITÄT REGENSBURG; FRIEDRICH-SCHILLERUNIVERSITÄT JENA; UNIVERSITÄTSKLINIKUM JENA; MAHBOOBI, Siavosh; SELLMER, Andreas; PONGRATZ, Herwig; LEONHARDT, Michel; KRÄMER, Oliver; BÖHMER, Frank-Dietmar; KELTER, Gerhard
Patent: WO2016/20369 A1, 2016 ; Title/Abstract Full Text Show Details
Mass Spectrometry (1) Description (Mass Spectrometry)
Location
Reference
electron impact (EI)
Page/Page column
UNIVERSITÄT REGENSBURG; FRIEDRICH-SCHILLER-UNIVERSITÄT JENA; UNIVERSITÄTSKLINIKUM JENA; MAHBOOBI, Siavosh; SELLMER, Andreas; PONGRATZ, Herwig; LEONHARDT, Michel; KRÄMER, Oliver; BÖHMER, Frank-Dietmar; KELTER,
spectrum
122
Gerhard
Patent: WO2016/20369 A1, 2016 ; Title/Abstract Full Text Show Details
Bioactivity Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Reference
Perron,Y.G. et al.
Journal of Medicinal Chemistry, 1966 , vol. 9, p. 136 - 140 Full Text View citing articles Show Details
Julia,M.; Bagot,J.
Bulletin de la Societe Chimique de France, 1964 , p. 1924 - 1938 Full Text View citing articles Show Details
GRUeNENTHAL GMBH
Patent: WO2004/43949 A1, 2004 ; Title/Abstract Full Text Show Details
SHIONOGI and CO., LTD.
Patent: EP1505061 A1, 2005 ; Title/Abstract Full Text Show Details
Bristol Myers Co.
Patent: GB893899US , 19621959 ; Chem.Abstr., 1962 , vol. 57, # 9820b Full Text Show Details
Burm, Brigitte E.A; Gremmen, Christiaan; Wanner, Martin J; Koomen, Gerrit-Jan
Tetrahedron, 2001 , vol. 57, # 10 p. 2039 - 2049 Title/Abstract Full Text View citing articles Show Details
GRUeNENTHAL GMBH
Patent: WO2005/19208 A1, 2005 ; Title/Abstract Full Text Show Details
Valeur, Eric; Christmann-Franck, Serge; Lepifre, Franck; Carniato, Denis; Cravo, Daniel; Charon, Christine; Bozec, Sophie; Musil, Djordje; Hillertz, Per; Doare, Liliane; Schmidlin, Fabien; Lecomte, Marc; Schultz, Melanie; Roche, Didier
Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 18 p. 5909 - 5914 Title/Abstract Full Text View citing articles Show Details
Perron; Minor; Bierwagen; Ridlon; Pindell
Journal of medicinal chemistry, 1966 , vol. 9, # 1 p. 136 - 140 Title/Abstract Full Text Show Details
UNIVERSITÄT REGENSBURG; FRIEDRICH-SCHILLER-UNIVERSITÄT JENA; UNIVERSITÄTSKLINIKUM JENA; MAHBOOBI, Siavosh; SELLMER, Andreas; PONGRATZ, Herwig; LEONHARDT, Michel; KRÄMER, Oliver; BÖHMER, Frank-Dietmar; KELTER, Gerhard
Patent: WO2016/20369 A1, 2016 ; Title/Abstract Full Text Show Details
Chemical Name: 3-(1-methylpyrrolidin-3-yl)-1H-indole
2
Reaxys Registry Number: 912643
CAS Registry Number: 151272-93-4 Type of Substance: heterocyclic Molecular Formula: C13H16N2
Linear Structure Formula: C13H16N2
Molecular Weight: 200.283
InChI Key: GIUCRWSFDBHBDT-UHFFFAOYSA-N
6 prep out of 17 reactions.
Synthesize | Hide Details Find similar Chemical Names and Synonyms 3-(1-methylpyrrolidin-3-yl)-1H-indole, 3-(N-methylpyrrolidin-3-yl)indole, 3-(1-methyl-pyrrolidin-3-yl)-indole, (R,S)-3-(1-methylpyrrolidin-3-yl)-1Hindole, (+-)-3-(Indol-3-yl)-1-methyl-pyrrolidin, 3-(1-Methylpyrrolidin-3-yl)-indol, 3-(3-Indolyl)-N-methylpyrrolidin Identification Substance Label (4) Label
Reference
Identification Physical Data (5) Spectra (13) Bioactivity (1)
13
6a
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
22
Cole, Derek C.; Lennox, William J.; Stock, Joseph R.; Ellingboe, John W.; Mazandarani, Hossein; Smith, Deborah L.; Zhang, Guoming; Tawa, Gregory J.; Schechter, Lee E.
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 21 p. 4780 - 4785 Title/Abstract Full Text View citing articles Show Details
example 1
SUVEN LIFE SCIENCES
Patent: WO2005/66157 A1, 2005 ; Title/Abstract Full Text Show Details
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
4a
Patent-Specific Data (1) Related Markush Structure (RN)
Reference
19846089
SUVEN LIFE SCIENCES
Patent: WO2005/66157 A1, 2005 ; Title/Abstract Full Text Show Details
Derivative (1) Comment (Derivative)
Reference
Hydrochlorid C13H16N2*HCl: F: 142grad (aus A./Ae.; Zers.)
Julia,M.; Bagot,J.
Bulletin de la Societe Chimique de France, 1964 , p. 1924 - 1938 Full Text View citing articles Show Details
Physical Data Melting Point (5) Melting Point
Solvent (Melting Point)
Location
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
85.3 89.6 °C
85.3 89.6 °C
supporting information
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Kambhampati, Ramasastry; Bhatta, Venugopalarao; Kota, Laxman; Shinde, Anil; Badange, Rajesh; Jayarajan, Pradeep; Bhyrapuneni, Gopinadh; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 15 p. 4577 - 4580 Title/Abstract Full Text View citing articles Show Details
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
99 102 °C
111.5 113 °C
Reference
ethyl acetate
Perron,Y.G. et al.
Journal of Medicinal Chemistry, 1966 , vol. 9, p. 136 - 140 Full Text View citing articles Show Details
Bristol Myers Co.
Patent: GB893899US , 19621959 ; Chem.Abstr., 1962 , vol. 57, # 9820b Full Text Show Details
111.5 113 °C
Spectra NMR Spectroscopy (5) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Frequency (NMR Spectroscopy)
Chemical shifts
1H
chloroform-d1
400 MHz
Location
Comment (NMR Spectroscopy)
Reference Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta,
Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
1H
chloroform-d1
Chemical shifts
1H
dimethylsulfoxided6
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Chemical shifts
13C
dimethylsulfoxided6
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Spin-spin coupling constants
400 MHz
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Kambhampati, Ramasastry; Bhatta, Venugopalarao; Kota, Laxman; Shinde, Anil; Badange, Rajesh; Jayarajan, Pradeep; Bhyrapuneni, Gopinadh; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 15 p. 4577 - 4580 Title/Abstract Full Text View citing articles Show Details
Chemical shifts
supporting information
dimethylsulfoxided6
1H-1H
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
IR Spectroscopy (4) Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Bands
potassium bromide
Bands
potassium bromide
Bands
KBr
Location
Comment (IR Spectroscopy)
Reference Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Kambhampati, Ramasastry; Bhatta, Venugopalarao; Kota, Laxman; Shinde, Anil; Badange, Rajesh; Jayarajan, Pradeep; Bhyrapuneni, Gopinadh; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 15 p. 4577 - 4580 Title/Abstract Full Text View citing articles Show Details
supporting information
1620 - 1418 cm**(-1)
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Perron,Y.G. et al.
Journal of Medicinal Chemistry, 1966 , vol. 9, p. 136 - 140 Full Text View citing articles Show Details
IR
Mass Spectrometry (4) Description (Mass Spectrometry)
Location
Comment (Mass Spectrometry)
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
electrospray ionisation (ESI) spectrum ESI (Electrospray ionisation) Spectrum
ESI (Electrospray ionisation)
Reference
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Kambhampati, Ramasastry; Bhatta, Venugopalarao; Kota, Laxman; Shinde, Anil; Badange, Rajesh; Jayarajan, Pradeep; Bhyrapuneni, Gopinadh; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 15 p. 4577 - 4580 Title/Abstract Full Text View citing articles Show Details
supporting information
Molecular peak
SUVEN LIFE SCIENCES
Patent: WO2005/66157 A1, 2005 ; Title/Abstract Full Text Show Details
spectrum electron impact (EI)
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Reference
Perron,Y.G. et al.
Journal of Medicinal Chemistry, 1966 , vol. 9, p. 136 - 140 Full Text View citing articles Show Details
Julia,M.; Bagot,J.
Bulletin de la Societe Chimique de France, 1964 , p. 1924 - 1938 Full Text View citing articles Show Details
Bristol Myers Co.
Patent: GB893899US , 19621959 ; Chem.Abstr., 1962 , vol. 57, # 9820b Full Text Show Details
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Cole, Derek C.; Lennox, William J.; Stock, Joseph R.; Ellingboe, John W.; Mazandarani, Hossein; Smith, Deborah L.; Zhang, Guoming; Tawa, Gregory J.; Schechter, Lee E.
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 21 p. 4780 - 4785 Title/Abstract Full Text View citing articles Show Details
American Home Products Corporation
Patent: US2002/198213 A1, 2002 ; Title/Abstract Full Text Show Details
SUVEN LIFE SCIENCES
Patent: WO2005/66157 A1, 2005 ; Title/Abstract Full Text Show Details
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Kambhampati, Ramasastry; Bhatta, Venugopalarao; Kota, Laxman; Shinde, Anil; Badange, Rajesh; Jayarajan, Pradeep; Bhyrapuneni, Gopinadh; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 15 p. 4577 - 4580 Title/Abstract Full Text View citing articles Show Details
Perron; Minor; Bierwagen; Ridlon; Pindell
Journal of medicinal chemistry, 1966 , vol. 9, # 1 p. 136 - 140 Title/Abstract Full Text Show Details
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
John H. Biel
Annual reports in medicinal chemistry, 1966 , vol. 2, p. 11 - 23 Title/Abstract Full Text Show Details
Ping Zhou; Derek Cecil Cole; Michael Gerard Kelly; William Joseph Lennox
Patent: US6903112 B2, 2005 ; Title/Abstract Full Text Show Details
Zhou Ping; Cole Derek Cecil; Kelly Michal Gerard; Lennox William Joseph
Patent: EP1803720 A1, 2007 ; Title/Abstract Full Text Show Details
Chemical Name: 5-fluoro-3-pyrrolidin-3-yl-1H-indole Reaxys Registry Number: 8552080
CAS Registry Number: 198474-06-5 Type of Substance: heterocyclic Molecular Formula: C12H13FN2
Linear Structure Formula: C12H13FN2
Molecular Weight: 204.247
InChI Key: ZWQBLJKCRPTUSP-UHFFFAOYSA-N
3
Synthesize | Hide Details Find similar Chemical Names and Synonyms 5-fluoro-3-pyrrolidin-3-yl-1H-indole Identification Substance Label (1)
5 prep out of 11 reactions.
Identification Spectra (1) Bioactivity (2)
3
Label
Reference
10
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
Spectra Mass Spectrometry (1) Comment (Mass Spectrometry)
Reference
Molecular peak
SYNGENTA PARTICIPATIONS AG
Patent: WO2005/58035 A1, 2005 ; Title/Abstract Full Text Show Details
Bioactivity Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Reference
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
SYNGENTA PARTICIPATIONS AG
Patent: WO2005/58035 A1, 2005 ; Title/Abstract Full Text Show Details
Valeur, Eric; Christmann-Franck, Serge; Lepifre, Franck; Carniato, Denis; Cravo, Daniel; Charon, Christine; Bozec, Sophie; Musil, Djordje; Hillertz, Per; Doare, Liliane; Schmidlin, Fabien; Lecomte, Marc; Schultz, Melanie; Roche, Didier
Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 18 p. 5909 - 5914 Title/Abstract Full Text View citing articles Show Details
2 of 2
Effect (Pharmacological Data)
<3H>5-HT reuptake inhibition
Species or TestSystem (Pharmacological Data)
rat brain synaptosomes
Method (Pharmacological Data)
in vitro; in Krebs-Ringer buffer (pH 7.4) at 37 deg C for 4 min
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
45 nmol/l
Reference
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
Chemical Name: 3-(1-ethyl-pyrrolidin-3-yl)-indole Reaxys Registry Number: 1573287
CAS Registry Number: 3671-01-0 Type of Substance: heterocyclic Molecular Formula: C14H18N2
Linear Structure Formula: C14H18N2
Molecular Weight: 214.31
InChI Key: GINDSTSZDIENFS-UHFFFAOYSA-N
4
Synthesize | Hide Details
5 prep out of 7 reactions.
Identification Physical Data (1) Bioactivity (1)
5
Find similar Chemical Names and Synonyms 3-(1-ethyl-pyrrolidin-3-yl)-indole, (+-)-1-Ethyl-3-(indol-3-yl)-pyrrolidin, 3-(1-Ethylpyrrolidin-3-yl)-indol Identification Substance Label (1) Label
Reference
6b
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
Derivative (1) Comment (Derivative)
Reference
Hydrochlorid C14H18N2*HCl: F: 145grad (aus A./Ae., mit 1mol H2O)
Julia,M.; Bagot,J.
Bulletin de la Societe Chimique de France, 1964 , p. 1924 - 1938 Full Text View citing articles Show Details
Physical Data Melting Point (1) Melting Point
Solvent (Melting Point)
Reference
67 - 68 °C
petroleum ether
Perron,Y.G. et al.
Journal of Medicinal Chemistry, 1966 , vol. 9, p. 136 - 140 Full Text View citing articles Show Details
Bioactivity Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Reference
Perron,Y.G. et al.
Journal of Medicinal Chemistry, 1966 , vol. 9, p. 136 - 140 Full Text View citing articles Show Details
Julia,M.; Bagot,J.
Bulletin de la Societe Chimique de France, 1964 , p. 1924 - 1938 Full Text View citing articles Show Details
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Kambhampati, Ramasastry; Bhatta, Venugopalarao; Kota, Laxman; Shinde, Anil; Badange, Rajesh; Jayarajan, Pradeep; Bhyrapuneni, Gopinadh; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 15 p. 4577 - 4580 Title/Abstract Full Text View citing articles Show Details
Perron; Minor; Bierwagen; Ridlon; Pindell
Journal of medicinal chemistry, 1966 , vol. 9, # 1 p. 136 - 140 Title/Abstract Full Text Show Details
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
Chemical Name: 5-Methyl-3-(N-methylpyrrolidin-3-yl)-1H-indole Reaxys Registry Number: 7705632
Type of Substance: heterocyclic Molecular Formula: C14H18N2
Linear Structure Formula: C14H18N2
Molecular Weight: 214.31
InChI Key: CAMUACPSAPSOOW-UHFFFAOYSA-N
5
Synthesize | Hide Details Find similar
3 prep out of 3 reactions.
Physical Data (1) Spectra (5) Bioactivity (1)
2
Chemical Names and Synonyms 5-Methyl-3-(N-methylpyrrolidin-3-yl)-1H-indole, 5-methyl-3-(N-methylpyrrolidin-3-yl)indole Physical Data Melting Point (1) Melting Point
Reference
105 - 107 °C
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Spectra NMR Spectroscopy (3) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Chemical shifts
1H
dimethylsulfoxide-d6
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Chemical shifts
13C
dimethylsulfoxide-d6
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Spin-spin coupling constants
dimethylsulfoxide-d6
Comment (NMR Spectroscopy)
Reference
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
1H-1H
IR Spectroscopy (1) Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Comment (IR Spectroscopy)
Reference
Bands
KBr
1628 - 1417 cm**(-1)
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Mass Spectrometry (1) Description (Mass Spectrometry)
Reference
spectrum electron impact (EI)
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Reference
Allelix Biopharmaceuticals Inc.
Patent: US5998462 A1, 1999 ; Title/Abstract Full Text Show Details
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Chemical Name: 5-methoxy-3-(N-methylpyrrolidin-3-yl)indole Reaxys Registry Number: 7708347
3 prep out of 7 reactions.
Identification Physical Data (1) Spectra (5)
4
Type of Substance: heterocyclic Molecular Formula: C14H18N2O Linear Structure Formula: C14H18N2O Molecular Weight: 230.31
InChI Key: ISLZNKXLIRVSJS-UHFFFAOYSA-N
Bioactivity (3)
6
Synthesize | Hide Details Find similar Chemical Names and Synonyms 5-methoxy-3-(N-methylpyrrolidin-3-yl)indole Identification Substance Label (2) Label
Reference
6c
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
(R,S)-4
Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.
Journal of Medicinal Chemistry, 1999 , vol. 42, # 20 p. 4257 - 4263 Title/Abstract Full Text View citing articles Show Details
Physical Data Melting Point (1) Melting Point
Reference
73 - 74 °C
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Spectra NMR Spectroscopy (3) Description (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Solvents (NMR Spectroscopy)
Chemical shifts
1H
tetradeuteriomethanol
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Chemical shifts
13C
tetradeuteriomethanol
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Spin-spin coupling constants
tetradeuteriomethanol
Comment (NMR Spectroscopy)
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
1H-1H.
IR Spectroscopy (1) Description (IR Spectroscopy)
Solvent (IR Spectroscopy)
Comment (IR Spectroscopy)
Reference
Reference
Bands
KBr
1624 - 1451 cm**(-1)
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Mass Spectrometry (1) Description (Mass Spectrometry)
Reference
spectrum electron impact (EI)
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Bioactivity Pharmacological Data (3) 1 of 3
2 of 3
3 of 3
Comment (Pharmacological Data)
Bioactivities present
Reference
Macor, John E.; Blank, David H.; Ryan, Kevin; Post, Ronald J.
Synthesis, 1997 , # 4 p. 443 - 449 Title/Abstract Full Text View citing articles Show Details
Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.
Journal of Medicinal Chemistry, 1999 , vol. 42, # 20 p. 4257 - 4263 Title/Abstract Full Text View citing articles Show Details
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Kambhampati, Ramasastry; Bhatta, Venugopalarao; Kota, Laxman; Shinde, Anil; Badange, Rajesh; Jayarajan, Pradeep; Bhyrapuneni, Gopinadh; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 15 p. 4577 - 4580 Title/Abstract Full Text View citing articles Show Details
Nirogi, Ramakrishna; Dwarampudi, Adireddy; Bhatta, Venugopalarao; Kota, Laxman; Dubey
Asian Journal of Chemistry, 2013 , vol. 25, # 16 p. 9293 - 9298 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
drug dependence
Species or TestSystem (Pharmacological Data)
Sprague-Dawley rat
Sex
male
Route of Application
intraperitoneal
Concentration (Pharmacological Data)
0.68 - 2.72 mg/kg
Kind of Dosing (Pharmacological Data)
30 min before testing
Method (Pharmacological Data)
in vivo; two-lever drug discrimination assay; (+)-lysergic acid diethylamide (LSD)-trained rats (200-220 g) maintained at 22-24 deg C, 12-h light/dark cycle and 40-50 percent relative humidity with free access to water and rationed amount of supplemental feed
Further Details (Pharmacological Data)
percent of rats selecting LSD lever ( percent SDL) for eachdose of title comp. determined; degree of substitution determined by max. percentADL for all doses of title comp.; no substitution: <= 59 percent SDL; partial substitution: 60-79 percent SDL; complete substitution: > 80 percent SDL
Results
partial substitution
Reference
Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.
Journal of Medicinal Chemistry, 1999 , vol. 42, # 20 p. 4257 - 4263 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
drug dependence
Species or TestSystem (Pharmacological Data)
Sprague-Dawley rat
Sex
male
Route of Application
intraperitoneal
Concentration (Pharmacological Data)
0.68 - 2.72 mg/kg
Kind of Dosing (Pharmacological Data)
30 min before testing
Method (Pharmacological Data)
in vivo; two-lever drug discrimination assay; 2,5-dimethoxy-4-iodoamphetamine(DOI)-trained rats (200-220 g) maintained at 22-24 deg C, 12-h light/dark cycle and 40-50 percent relative humidity with free access to water and rationed amount of supplemental feed
Further Details (Pharmacological Data)
percent of rats selecting NOI lever ( percent SDL) for eachdose of title comp. determined; degree of substitution determined by max. percentADL for all doses of title comp.; no substitution: <= 59 percent SDL; partial substitution: 60-79 percent SDL; complete substitution: > 80 percent SDL
Results
partial substitution
Reference
Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.
Journal of Medicinal Chemistry, 1999 , vol. 42, # 20 p. 4257 - 4263 Title/Abstract Full Text View citing articles Show Details
Chemical Name: 3-(5-fluoroindol-3-yl)pyrrolidine-1-carboxylic acid [4-methoxy-3-(4methylpiperazin-1-yl)phenyl]-amide Reaxys Registry Number: 8593293
Type of Substance: heterocyclic Molecular Formula: C25H30FN5O2
Linear Structure Formula: C25H30FN5O2
Molecular Weight: 451.544
InChI Key: BMVCAMBJKNURKZ-UHFFFAOYSA-N
7
2 prep out of 2 reactions.
Identification Physical Data (1) Spectra (2) Bioactivity (5)
3
Synthesize | Hide Details Find similar Chemical Names and Synonyms 3-(5-fluoroindol-3-yl)pyrrolidine-1-carboxylic acid [4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-amide Identification Substance Label (1) Label
Reference
21e
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
Patent-Specific Data (1) Location in Patent
Reference
Claim
Merck Patentgesellschaft
Patent: US6509340 B1, 2003 ; Title/Abstract Full Text Show Details
Physical Data Melting Point (1) Melting Point
Solvent (Melting Point)
210 213 °C
ethyl acetate light petroleum
Spectra
Reference Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
NMR Spectroscopy (2) Description (NMR Spectroscopy)
Chemical shifts
Frequency (NMR Spectroscopy)
Nucleus (NMR Spectroscopy)
Coupling Nuclei
Solvents (NMR Spectroscopy)
1H
1H
dimethylsulfoxided6
300 MHz
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
dimethylsulfoxided6
300 MHz
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
1H
Reference
Bioactivity Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Reference
Merck Patentgesellschaft
Patent: US6509340 B1, 2003 ; Title/Abstract Full Text Show Details
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
Henning Boettcher; Juergen Harting; Lisa Matzen; Christoph Van Amsterdam; Hartmut Greiner; Gerd Bartoszyk; Wilfried Rautenberg
Patent: US2005/176730 A1, 2005 ; Title/Abstract Full Text Show Details
2 of 5
Effect (Pharmacological Data) Species or TestSystem (Pharmacological Data)
3 of 5
receptor; binding activity
5-HT1A receptor
Method (Pharmacological Data)
in vitro; in membranes from rat hippocampus using <3H>8-OH-DPAT
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
100 nmol/l
Reference
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
receptor; binding activity
Species or TestSystem (Pharmacological Data)
5-HT1B receptor
Method (Pharmacological Data)
in vitro; in rat frontal cortex using <125I>iodocyanopindolol
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
233 nmol/l
Reference
4 of 5
5 of 5
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
receptor; binding activity
Species or TestSystem (Pharmacological Data)
5-HT1D receptor
Method (Pharmacological Data)
in vitro; in membranes from calf striatum using <3H>serotonin in the presence of 8-OH-DPAT and mesulergine
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
233 nmol/l
Reference
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details
Effect (Pharmacological Data)
<3H>5-HT reuptake inhibition
Species or TestSystem (Pharmacological Data)
rat brain synaptosomes
Method (Pharmacological Data)
in vitro; in Krebs-Ringer buffer (pH 7.4) at 37 deg C for 4 min
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
106 nmol/l
Reference
Matzen, Lisa; Van Amsterdam, Christoph; Rautenberg, Wilfried; Greiner, Hartmut E.; Harting, Juergen; Seyfried, Christoph A.; Boettcher, Henning
Journal of Medicinal Chemistry, 2000 , vol. 43, # 6 p. 1149 - 1157 Title/Abstract Full Text View citing articles Show Details