Query Query
1. Query N
Results
Date
1 substances in Reaxys
2018-03-03 04h:52m:44s (EST)
Search as: As drawn
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Reaxys ID 1239844 View in Reaxys
1/1 CAS Registry Number: 59529-21-4 Chemical Name: 1-pentyl-1H-indole; 1-pentylindole; N-pentylindole; 1-amylindole; 1-pentyl-indole; N-Pentylindol Linear Structure Formula: C13H17N Molecular Formula: C13H17N Molecular Weight: 187.285 Type of Substance: heterocyclic InChI Key: QWLCOOAYMQWDPR-UHFFFAOYSA-N Note:
N
Substance Label (8) Label References 2f
Garayalde, David; Rusconi, Giulia; Nevado, Cristina; Helvetica Chimica Acta; vol. 100; nb. 3; (2017), View in Reaxys
5i
Jiang, Xue; Tang, Weijun; Xue, Dong; Xiao, Jianliang; Wang, Chao; ACS Catalysis; vol. 7; nb. 3; (2017); p. 1831 - 1835, View in Reaxys
1
Yao, Shun-Jiang; Ren, Zhi-Hui; Wang, Yao-Yu; Guan, Zheng-Hui; Journal of Organic Chemistry; vol. 81; nb. 10; (2016); p. 4226 - 4234, View in Reaxys
14
Banister, Samuel D.; Wilkinson, Shane M.; Longworth, Mitchell; Stuart, Jordyn; Apetz, Nadine; English, Katrina; Brooker, Lance; Goebel, Catrin; Hibbs, David E.; Glass, Michelle; Connor, Mark; McGregor, Iain S.; Kassiou, Michael; ACS Chemical Neuroscience; vol. 4; nb. 7; (2013); p. 1081 - 1092, View in Reaxys
5, R=H
Huffman, John W.; Szklennik, Paul V.; Almond, Amanda; Bushell, Kristen; Selley, Dana E.; He, Hengjun; Cassidy, Michael P.; Wiley, Jenny L.; Martin, Billy R.; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 18; (2005); p. 4110 - 4113, View in Reaxys
8b
Caddick, Stephen; Aboutayab, Karim; West, Robert I.; Journal of the Chemical Society, Chemical Communications; nb. 13; (1995); p. 1353 - 1354, View in Reaxys
10c, 14f
Katritzky, Alan R.; Lang, Hengyuan; Lan, Xiangfu; Tetrahedron; vol. 49; nb. 14; (1993); p. 2829 - 2838, View in Reaxys
3d
Barco et al.; Synthesis; (1976); p. 124, View in Reaxys
Druglikeness (1) 1 of 1
LogP
4.398
H Bond Donors
0
H Bond Acceptors
1
Rotatable Bonds
4
TPSA
4.93
Lipinski Number
4
Veber Number
2
Boiling Point (1) Boiling Point [°C] 110 - 113
Pressure (Boiling Point) [Torr]
References
2
Barco et al.; Synthesis; (1976); p. 124, View in Reaxys
Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)
Banister, Samuel D.; Wilkinson, Shane M.; Longworth, Mitchell; Stuart, Jordyn; Apetz, Nadine; English, Katrina; Brooker, Lance; Goebel, Catrin; Hibbs, David E.; Glass, Michelle; Connor, Mark; McGregor, Iain S.; Kassiou, Michael; ACS Chemical Neuroscience; vol. 4; nb. 7; (2013); p. 1081 - 1092, View in Reaxys
Crystal Property Description (2) Colour & Other References Properties yellow
Banister, Samuel D.; Wilkinson, Shane M.; Longworth, Mitchell; Stuart, Jordyn; Apetz, Nadine; English, Katrina; Brooker, Lance; Goebel, Catrin; Hibbs, David E.; Glass, Michelle; Connor, Mark; McGre-
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gor, Iain S.; Kassiou, Michael; ACS Chemical Neuroscience; vol. 4; nb. 7; (2013); p. 1081 - 1092, View in Reaxys yellow
Blaazer, Antoni R.; Lange, Jos H.M.; Van Der Neut, Martina A.W.; Mulder, Arie; Den Boon, Femke S.; Werkman, Taco R.; Kruse, Chris G.; Wadman, Wytse J.; European Journal of Medicinal Chemistry; vol. 46; nb. 10; (2011); p. 5086 - 5098, View in Reaxys
NMR Spectroscopy (6) 1 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
500
Banister, Samuel D.; Wilkinson, Shane M.; Longworth, Mitchell; Stuart, Jordyn; Apetz, Nadine; English, Katrina; Brooker, Lance; Goebel, Catrin; Hibbs, David E.; Glass, Michelle; Connor, Mark; McGregor, Iain S.; Kassiou, Michael; ACS Chemical Neuroscience; vol. 4; nb. 7; (2013); p. 1081 - 1092, View in Reaxys 2 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Blaazer, Antoni R.; Lange, Jos H.M.; Van Der Neut, Martina A.W.; Mulder, Arie; Den Boon, Femke S.; Werkman, Taco R.; Kruse, Chris G.; Wadman, Wytse J.; European Journal of Medicinal Chemistry; vol. 46; nb. 10; (2011); p. 5086 - 5098, View in Reaxys 3 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Katritzky, Alan R.; Lang, Hengyuan; Lan, Xiangfu; Tetrahedron; vol. 49; nb. 14; (1993); p. 2829 - 2838, View in Reaxys; Bogdal, Dariusz; Pielichowski, Jan; Jaskot, Krzysztof; Heterocycles; vol. 45; nb. 4; (1997); p. 715 - 722, View in Reaxys 4 of 6
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)
1H-1H
Katritzky, Alan R.; Lang, Hengyuan; Lan, Xiangfu; Tetrahedron; vol. 49; nb. 14; (1993); p. 2829 - 2838, View in Reaxys; Bogdal, Dariusz; Pielichowski, Jan; Jaskot, Krzysztof; Heterocycles; vol. 45; nb. 4; (1997); p. 715 - 722, View in Reaxys 5 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
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Solvents (NMR Spectro- CDCl3 scopy) Katritzky, Alan R.; Lang, Hengyuan; Lan, Xiangfu; Tetrahedron; vol. 49; nb. 14; (1993); p. 2829 - 2838, View in Reaxys 6 of 6
Description (NMR Spec- NMR troscopy) Barco et al.; Synthesis; (1976); p. 124, View in Reaxys
IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
neat (no solvent)
Comment (IR Spectroscopy)
3087 - 739 cm**(-1)
Bogdal, Dariusz; Pielichowski, Jan; Jaskot, Krzysztof; Heterocycles; vol. 45; nb. 4; (1997); p. 715 - 722, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Bogdal, Dariusz; Pielichowski, Jan; Jaskot, Krzysztof; Heterocycles; vol. 45; nb. 4; (1997); p. 715 - 722, View in Reaxys
Medchem (6) 1 of 6
Bioassay Category
In Vivo (Animal models)
Biological Species/NCBI Institute for Cancer Research mouse ID Substance RN
1239844View in Reaxys
Substance Name
N-pentylindole
Substance Dose
30 mg/kg
Substance Route of Adm.
intraperitoneal administration
Substance Dosing Regi- Single men Measurement Parameter
ED50
Measurement Object
% of maximum possible effect
Qualitative value
Not active
Measurement pX
1
Thomas, Brian F.; Lefever, Timothy W.; Cortes, Ricardo A.; Grabenauer, Megan; Kovach, Alexander L.; Cox, Anderson O.; Patel, Purvi R.; Pollard, Gerald T.; Marusich, Julie A.; Kevin, Richard C.; Gamage, Thomas F.; Wiley, Jenny L.; Journal of Pharmacology and Experimental Therapeutics; vol. 361; nb. 1; (2017); p. 162 - 171, View in Reaxys 2 of 6
Bioassay Category
In Vivo (Animal models)
Biological Species/NCBI Institute for Cancer Research mouse ID Substance RN
1239844View in Reaxys
Substance Name
N-pentylindole
Substance Dose
30 mg/kg
Substance Route of Adm.
intraperitoneal administration
Substance Dosing Regi- Single men
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Measurement Parameter
ID50
Measurement Object
dose which reduces 50% of spontaneous activity
Qualitative value
Not active
Measurement pX
1
Thomas, Brian F.; Lefever, Timothy W.; Cortes, Ricardo A.; Grabenauer, Megan; Kovach, Alexander L.; Cox, Anderson O.; Patel, Purvi R.; Pollard, Gerald T.; Marusich, Julie A.; Kevin, Richard C.; Gamage, Thomas F.; Wiley, Jenny L.; Journal of Pharmacology and Experimental Therapeutics; vol. 361; nb. 1; (2017); p. 162 - 171, View in Reaxys 3 of 6
Bioassay Category
In Vivo (Animal models)
Biological Species/NCBI Institute for Cancer Research mouse ID Substance RN
1239844View in Reaxys
Substance Name
N-pentylindole
Substance Dose
30 mg/kg
Substance Route of Adm.
intraperitoneal administration
Substance Dosing Regi- Single men Measurement Parameter
ED50
Measurement Object
change in rectal temperature in °C
Qualitative value
Not active
Measurement pX
1
Thomas, Brian F.; Lefever, Timothy W.; Cortes, Ricardo A.; Grabenauer, Megan; Kovach, Alexander L.; Cox, Anderson O.; Patel, Purvi R.; Pollard, Gerald T.; Marusich, Julie A.; Kevin, Richard C.; Gamage, Thomas F.; Wiley, Jenny L.; Journal of Pharmacology and Experimental Therapeutics; vol. 361; nb. 1; (2017); p. 162 - 171, View in Reaxys 4 of 6
Bioassay Category
In Vivo (Animal models)
Biological Species/NCBI Institute for Cancer Research mouse ID Substance RN
1239844View in Reaxys
Substance Name
N-pentylindole
Substance Dose
30 mg/kg
Substance Route of Adm.
intraperitoneal administration
Substance Dosing Regi- Single men Measurement Parameter
ED50
Qualitative value
Not active
Measurement pX
1
Thomas, Brian F.; Lefever, Timothy W.; Cortes, Ricardo A.; Grabenauer, Megan; Kovach, Alexander L.; Cox, Anderson O.; Patel, Purvi R.; Pollard, Gerald T.; Marusich, Julie A.; Kevin, Richard C.; Gamage, Thomas F.; Wiley, Jenny L.; Journal of Pharmacology and Experimental Therapeutics; vol. 361; nb. 1; (2017); p. 162 - 171, View in Reaxys 5 of 6
Target Name
Cannabinoid receptor 2 [human]
Target Synonyms
cannabinoid receptor 2; cb-2; cb2; cb2a; cb2b; cnr2; cx5; hcb2
Target Uniprot ID
p34972
Target, Subunit, Species Cannabinoid receptor 2 [human]
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Target Mutant/Chimera Details
Cannabinoid receptor 2 [human]:Wild
Target Species (Bioactivity)
human
Target Transfection
Transfected
Substance Action on Target
Inhibitor
Bioassay Category
In Vitro (Efficacy)
Cells/Cell Lines
HEK293
Cell Fraction
Membrane
Substance RN
1239844View in Reaxys
Substance Name
N-pentylindole
Measurement Parameter
Ki
Unit
μM
Qualitative value
>
Quantitative value
10
Measurement pX
1
Concomitants: Compound RN
6659789
Concomitants: Compound name
(-)-cis-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)cyclohexanol
Concomitants: Compound role
RAD
Thomas, Brian F.; Lefever, Timothy W.; Cortes, Ricardo A.; Grabenauer, Megan; Kovach, Alexander L.; Cox, Anderson O.; Patel, Purvi R.; Pollard, Gerald T.; Marusich, Julie A.; Kevin, Richard C.; Gamage, Thomas F.; Wiley, Jenny L.; Journal of Pharmacology and Experimental Therapeutics; vol. 361; nb. 1; (2017); p. 162 - 171, View in Reaxys 6 of 6
Target Name
Cannabinoid receptor 1 [human]
Target Synonyms
cann6; cannabinoid receptor 1; cb-r; cb1; cnr; cnr1 (cannabinoid receptor 1)
Target Uniprot ID
p21554; p21554-3
Target, Subunit, Species Cannabinoid receptor 1 [human] Target Mutant/Chimera Details
Cannabinoid receptor 1 [human]:Wild
Target Species (Bioactivity)
human
Target Transfection
Transfected
Substance Action on Target
Inhibitor
Bioassay Category
In Vitro (Efficacy)
Cells/Cell Lines
HEK293
Cell Fraction
Membrane
Substance RN
1239844View in Reaxys
Substance Name
N-pentylindole
Measurement Parameter
Ki
Unit
μM
Qualitative value
>
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Quantitative value
10
Measurement pX
1
Concomitants: Compound RN
6659789
Concomitants: Compound name
(-)-cis-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)cyclohexanol
Concomitants: Compound role
RAD
Thomas, Brian F.; Lefever, Timothy W.; Cortes, Ricardo A.; Grabenauer, Megan; Kovach, Alexander L.; Cox, Anderson O.; Patel, Purvi R.; Pollard, Gerald T.; Marusich, Julie A.; Kevin, Richard C.; Gamage, Thomas F.; Wiley, Jenny L.; Journal of Pharmacology and Experimental Therapeutics; vol. 361; nb. 1; (2017); p. 162 - 171, View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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