Query Query
Results
Date
4 substances in Reaxys
2017-10-28 15h:48m:02s (EST)
NH
1. Query N
Search as: As drawn
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1/18
2017-10-28 15:52:54
Reaxys ID 173122 View in Reaxys
1/4 CAS Registry Number: 61-52-9 Chemical Name: Dipropyltryptamine; DPT; (2-indol-3-yl-ethyl)dipropyl-amine; (2-Indol-3-yl-aethyl)-dipropyl-amin Linear Structure Formula: C16H24N2 Molecular Formula: C16H24N2 Molecular Weight: 244.38 Type of Substance: heterocyclic InChI Key: BOOQTIHIKDDPRW-UHFFFAOYSA-N Note:
NH
N
Substance Label (2) Label References QH-15
Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; TianjinChase Sun Pharmaceutical Co., Ltd; Zhu, Dayuan; Zuo, Jianping; Tan, Changheng; Qu, Shijin; Duan, Wenhu; Wang, Guifeng; Sun, Changhai; Yao, Xiaoqing; (44 pag.); CN103601683; (2016); (B) Chinese, View in Reaxys
DPT
Thiagaraj, Harish V.; Russo, Ethan B.; Burnett, Andrea; Goldstein, Eric; Thompson, Charles M.; Parker, Keith K.; Pharmacology; vol. 74; nb. 4; (2005); p. 193 - 199, View in Reaxys; Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys
Patent-Specific Data (1) References Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; TianjinChase Sun Pharmaceutical Co., Ltd; Zhu, Dayuan; Zuo, Jianping; Tan, Changheng; Qu, Shijin; Duan, Wenhu; Wang, Guifeng; Sun, Changhai; Yao, Xiaoqing; (44 pag.); CN103601683; (2016); (B) Chinese, View in Reaxys Druglikeness (1) 1 of 1
LogP
3.601
H Bond Donors
1
H Bond Acceptors
2
Rotatable Bonds
7
TPSA
19.03
Lipinski Number
4
Veber Number
2
Derivative (1) Comment (Derivative)
References
HCl: F: 169-171grad
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Crystal Property Description (1) Colour & Other References Properties colourless
Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, Da-Yuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys
Dissociation Exponent (1) 1 of 1
Dissociation Exponent (pK)
8.6
Solvent (Dissociation Exponent)
H2O
Method (Dissociation Exponent)
potentiometric
Type (Dissociation Exponent)
a/apparent
Vane; British Journal of Pharmacology and Chemotherapy; vol. 14; (1959); p. 87,91, View in Reaxys NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy)
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2/18
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Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
Paragraph 0109; 0112
Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; TianjinChase Sun Pharmaceutical Co., Ltd; Zhu, Dayuan; Zuo, Jianping; Tan, Changheng; Qu, Shijin; Duan, Wenhu; Wang, Guifeng; Sun, Changhai; Yao, Xiaoqing; (44 pag.); CN103601683; (2016); (B) Chinese, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, DaYuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys 3 of 3
Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, DaYuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum
Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, Da-Yuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys
ESI (Electrospray Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, ionisation); HRMS Da-Yuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys (High resolution mass spectrometry); Spectrum Medchem (27) 1 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : |agonist Target : CHO cell membranes expressing H5-HT1aRBioassay : H5HT1aR: human 5-HT1a receptor; vehicle control; further investigations in the presence of 5-HT; reference compound: 5-HT; LSC: liquid scintillation counting membranes incubated with title comp. and 0.1 nmol/l <35S>γ-S-GTP in Hepes buffer (pH 7.4) for 30 min at 30 deg C; nonspecific binding determined in the presence of γ-S-GTP; <35S>γ-S-GTP incorporation into membranes measured by LSC
Substance RN
173122View in Reaxys
Substance Name
DPT
Substance Dose
0.100000 µM
Copyright © 2017 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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2017-10-28 15:52:54
Qualitative Results
title comp. showed dose-dependent incorporation of <35S>γ-S-GTP (76 percent above control at dose 0.1 μmol/l); suggested that tittle comp. acted as H5-HT1aR partial agonist (diagram)
Measurement Parameter
Qualitative
Thiagaraj, Harish V.; Russo, Ethan B.; Burnett, Andrea; Goldstein, Eric; Thompson, Charles M.; Parker, Keith K.; Pharmacology; vol. 74; nb. 4; (2005); p. 193 - 199, View in Reaxys 2 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : |agonist Target : CHO cells expressing H5-HT1aRBioassay : H5-HT1aR: human 5HT1a receptor; further investigations in the presence of 5-HT; reference compounds: 5-HT and 8-OH-DPAT (8-hydroxy-2(di-n-propylamino)tetralin) cells incubated with 30 μmol/l forskolin and title comp. in medium for 20 min at 37 deg C; intracellular cAMP measured by colorimetric enzyme immunoassay
Substance RN
173122View in Reaxys
Substance Name
DPT
Substance Dose
0.100000 µM
Qualitative Results
title comp. dose-dependently reduced forskolin-stimulated cAMP conc.; suggested that title comp. acted as H5-HT1aR partial agonist (diagram)
Measurement Parameter
Qualitative
Thiagaraj, Harish V.; Russo, Ethan B.; Burnett, Andrea; Goldstein, Eric; Thompson, Charles M.; Parker, Keith K.; Pharmacology; vol. 74; nb. 4; (2005); p. 193 - 199, View in Reaxys 3 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : |receptor; binding activity Target : CHO cell membranes expressing H5-HT1aRBioassay : H5-HT1aR: human 5-HT1a receptor; 8-OH-DPAT: 8-hydroxy-2(di-n-propylamino)tetralin radioligand binding assay; 0.2-1.0 nmol/l <3H>8-OH-DPAT used as radioligand; membranes incubated with title comp. and radioligand for 30 min at 30 deg C; nonspecific binding determined in the presence of 10 μmol/l 5-HT; liquid scintillation counting
Substance RN
173122View in Reaxys
Substance Name
DPT
Substance Dose
1.00000E-10 M
Measurement Parameter
IC50
Unit
µM
Quantitative value
0.1
Measurement pX
7
Thiagaraj, Harish V.; Russo, Ethan B.; Burnett, Andrea; Goldstein, Eric; Thompson, Charles M.; Parker, Keith K.; Pharmacology; vol. 74; nb. 4; (2005); p. 193 - 199, View in Reaxys 4 of 27
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [guinea pig]:Wild
Target Species (Bioactivity)
guinea pig
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [guinea pig]
Target Transfection
Transfected
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Binding
Biological Species/NCBI Escherichia coli BL21 (DE3) ID
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Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
Ki
Unit
nM
Quantitative value
1600
Measurement pX
5.8
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [guinea pig]
5 of 27
Target Subunit Synonyms
sigma non-opioid intracellular receptor 1
Compound RN
5481796
Compound name
[3H]-(+)-Pentazocine
Compound role
RAD
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
NCI-H460
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
6 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Copyright © 2017 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.
5/18
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Cells/Cell Lines
SKOV3
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
7 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
DU 145
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
8 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Copyright © 2017 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.
6/18
2017-10-28 15:52:54
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
MCF-7
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
9 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
SF268
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
10 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Copyright © 2017 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.
7/18
2017-10-28 15:52:54
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
A 549
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
11 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
MDA-MB-231
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
12 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
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8/18
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Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
HT 29
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
13 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
HCT 15
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
14 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Copyright © 2017 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.
9/18
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Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
MCF-10A
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
15 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
Sigma non-opioid intracellular receptor 1 [human]:Wild
Substance Action on Target
Antagonist
Target Species (Bioactivity)
human
Target Subunit Proteins
Sigma non-opioid intracellular receptor 1 [human]
Target Transfection
Non Transfected
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Name
Cell/tumor cell: proliferation/viability/growth
Cells/Cell Lines
NCI-H1299
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Target, Subunit, Species Sigma non-opioid intracellular receptor 1 [human]
16 of 27
Target Subunit Synonyms
aag8; aging-associated gene 8 protein; hsigmar1; oprs1; sig-1r; sigma 1-type opioid receptor; sigma non-opioid intracellular receptor 1; sigma1-receptor; sigma1r; sigmar1; srbp; sr31747-binding protein; srbp
Target Uniprot ID
q99720
Target Mutant/Chimera Details
5-hydroxytryptamine receptor 1E [human]:Wild
Target Species (Bioactivity)
human
Target Subunit Proteins
5-hydroxytryptamine receptor 1E [human]
Copyright © 2017 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.
10/18
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Target Transfection
Transfected
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Binding
Cells/Cell Lines
HEK 293
Cell Fraction
Membrane
Substance RN
173122View in Reaxys
Substance Name
22
Measurement Parameter
Ki
Unit
nM
Quantitative value
3030
Deviation
840
Measurement pX
5.52
Target, Subunit, Species 5-hydroxytryptamine receptor 1E [human] Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2545 - 2552, View in Reaxys
17 of 27
Target Subunit Synonyms
5-ht-1e; 5-ht1e; 5-hydroxytryptamine receptor 1e; htr1e; s31; serotonin receptor 1e
Target Uniprot ID
p28566
Compound RN
626221; 8144579; 1716295
Compound name
Methiothepin; [3H]-5-HT; EDTA
Compound role
NSB; RAD; COM
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : monoamine re-uptake; inhibition ofTarget : brain cortex synaptosomes of SpragueDawley ratBioassay : non-specific uptake obtained at 0 deg C; positive control: cocaine (IC50 = 3.4E-7 M) and methamphetamine (IC50 = 2.0E-7 M) synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>norepinephrine addition; 5 min at 37 deg C; scintillation counted
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
M
Quantitative value
9.1E-06
Measurement pX
5.04
Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 18 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : monoamine re-uptake; inhibition ofTarget : brain cortex synaptosomes of SpragueDawley ratBioassay : non-specific uptake obtained in the presence of citalopram; positive control: cocaine (IC50 = 2.1E-6 M) and methamphetamine (IC50 = 4.0E-6 M); 5-HT: serotonin synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>5-HT addition; 5 min at 37 deg C; scintillation counted
Substance RN
173122View in Reaxys
Substance Name
DPT
Copyright © 2017 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.
11/18
2017-10-28 15:52:54
Measurement Parameter
IC50
Unit
M
Quantitative value
2.9E-06
Measurement pX
5.54
Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 19 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : monoamine re-uptake; inhibition ofTarget : brain crude striatum synaptosomes of Sprague-Dawley ratBioassay : non-specific uptake obtained in the presence of GBR12909; positive control: cocaine (IC50 = 8.5E-7 M) and methamphetamine (IC50 = 3.7E-7 M) synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>dopamine addition; 5 min at 37 deg C; scintillation counted
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
IC50
Unit
M
Quantitative value
2.3E-05
Measurement pX
4.64
Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 20 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : |transmitter releasing Target : brain cortex synaptosomes of Sprague-Dawley ratBioassay : non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 1.1E-8 M); cocaine: no effect synaptosomes pre-loaded with <3H>norepinephrine added to plate containing title comp.; 30 min at 25 deg C; scintillation counted
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
EC50
Unit
M
Quantitative value
0.0001
Measurement pX
4
Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 21 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : |transmitter releasing Target : brain cortex synaptosomes of Sprague-Dawley ratBioassay : non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 7.9E-7 M); cocaine: no effect; 5-HT: serotonin synaptosomes pre-loaded with <3H>5-HT added to plate containing title comp.; 30 min at 25 deg C; scintillation counted
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
EC50
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Unit
M
Quantitative value
0.0001
Measurement pX
4
Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 22 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
In Vitro (others)
Bioassay Details
Effect : |transmitter releasing Target : brain crude striatum synaptosomes of SpragueDawley ratBioassay : non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 2.80E-8 M); cocaine: no effect synaptosomes pre-loaded with <3H>dopamine added to plate containing title comp.; 5 min at 25 deg C; scintillation counted
Substance RN
173122View in Reaxys
Substance Name
DPT
Measurement Parameter
EC50
Unit
M
Quantitative value
0.0001
Measurement pX
4
Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 23 of 27
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
In vitro inhibitory concentration of the compound against Hepatitis B virus DNA replication in HepG2.2.15 cells; n=3
Biological Species/NCBI Hepatitis B virus ID Substance RN
173122View in Reaxys
Measurement Parameter
IC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, DaYuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys
24 of 27
Measurement Object
DNA REPLICATION
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Cytotoxic concentration of the compound against HepG2.2.15 cells upon incubation for 8 days by MTT assay; n=3
Substance RN
173122View in Reaxys
Measurement Parameter
CC50
Unit
µM
Qualitative value
>
Quantitative value
100
Measurement pX
1
Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, DaYuan; Bioorganic and Medicinal Chemistry; vol. 19; nb. 10; (2011); p. 3120 - 3127, View in Reaxys
Copyright © 2017 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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25 of 27
Measurement Object
cell death
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
The maximal percent increase in [35S]GTPg S binding to rat cortical membranes upon incubation HEPES buffer, pH 7.6 at 30 degree C for 90 min
Biological Species/NCBI Rattus norvegicus ID Substance RN
173122View in Reaxys
Measurement Parameter
Emax(%)
Unit
%
Qualitative value
=
Quantitative value
23.7
Nonaka, Ryouichi; Nagai, Fumiko; Ogata, Akio; Satoh, Kanako; Biological and Pharmaceutical Bulletin; vol. 30; nb. 12; (2007); p. 2328 - 2333, View in Reaxys
26 of 27
Measurement Object
The maximal percent increase in [35S]GTPg S binding to rat cortical membranes
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective concentration of compound required to elicit G protein activation equal to half of the maximum effect in rat cortical membranes using [35S]GTPS as radioligand upon incubation HEPES buffer, pH 7.6 at 30 degree C for 90 min; ND= Not determined because binding was not maximum at10-4 M.
Biological Species/NCBI Rattus norvegicus ID Substance RN
173122View in Reaxys
Qualitative Results
ND
Measurement Parameter
Qualitative
Nonaka, Ryouichi; Nagai, Fumiko; Ogata, Akio; Satoh, Kanako; Biological and Pharmaceutical Bulletin; vol. 30; nb. 12; (2007); p. 2328 - 2333, View in Reaxys
27 of 27
Measurement Object
EC50
Compound name
[35S]GTPgammaS
Compound role
RAD
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
The maximal percent increase in [35S]GTPg S binding in rat cortical membranes expressed as a percentage of the maximal 5-HT response upon incubation HEPES buffer, pH 7.6 at 30 degree C for 90 min
Biological Species/NCBI Rattus norvegicus ID Substance RN
173122View in Reaxys
Measurement Parameter
Activity
Unit
%
Qualitative value
=
Quantitative value
46
Nonaka, Ryouichi; Nagai, Fumiko; Ogata, Akio; Satoh, Kanako; Biological and Pharmaceutical Bulletin; vol. 30; nb. 12; (2007); p. 2328 - 2333, View in Reaxys Measurement Object
The maximal percent increase in [35S]GTPg S binding in rat cortical membranes
Copyright © 2017 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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Reaxys ID 18865485 View in Reaxys
2H
2H
2/4 CAS Registry Number: 1174656-39-3 Chemical Name: N,N-di-n-propyl-[α,α,β,β-d4]-tryptamine Linear Structure Formula: C16H20 (2)H4N2 Molecular Formula: C16H24N2 Molecular Weight: 248.348 InChI Key: BOOQTIHIKDDPRW-ZXSHKXLLSA-N Note:
N 2H
2H
NH
Druglikeness (1) 1 of 1
LogP
3.601
H Bond Donors
1
H Bond Acceptors
2
Rotatable Bonds
7
TPSA
19.03
Lipinski Number
4
Veber Number
2
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300.1
Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
75.5
Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray mol peak ionisation); HRMS (High resolution mass spectrometry)
References Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 429, View in Reaxys
Reaxys ID 11196837 View in Reaxys
Copyright © 2017 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.
3/4
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2H
2H
Chemical Name: [2-(1H-indol-3-yl)-ethyl]-[2H6]-dipropylamine Linear Structure Formula: C16H18 (2)H6N2 Molecular Formula: C16H24N2 Molecular Weight: 250.332 InChI Key: BOOQTIHIKDDPRW-WFGJKAKNSA-N Note:
2H
2H
2H 2H
N
NH
Substance Label (1) Label References 6, DPT
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 1368, View in Reaxys
Druglikeness (1) 1 of 1
LogP
3.601
H Bond Donors
1
H Bond Acceptors
2
Rotatable Bonds
7
TPSA
19.03
Lipinski Number
4
Veber Number
2
Crystal Property Description (1) Colour & Other References Properties brown
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 1368, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
75.5
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
film
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys Mass Spectrometry (1)
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Description (Mass References Spectrometry) spectrum; electron impact (EI)
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 1368, View in Reaxys
Reaxys ID 3724506 View in Reaxys
4/4 CAS Registry Number: 16382-06-2 Chemical Name: (2-indol-3-yl-ethyl)-dipropyl-amine; hydrochloride; (2-Indol-3-yl-aethyl)-dipropyl-amin; Hydrochlorid Linear Structure Formula: C16H24N2*ClH Molecular Formula: C16H24N2*ClH Molecular Weight: 280.841 Type of Substance: heterocyclic InChI Key: AIAASKTUEVUIQM-UHFFFAOYSA-N Note:
NH
N
Cl
H
Substance Label (1) Label References 22
Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2545 - 2552, View in Reaxys
Druglikeness (1) 1 of 1
LogP
4.113
H Bond Donors
1
H Bond Acceptors
2
Rotatable Bonds
7
TPSA
19.03
Lipinski Number
4
Veber Number
2
Melting Point (2) 1 of 2
Melting Point [°C]
176 - 178
Solvent (Melting Point)
ethanol; butan-2-one; diethyl ether
Barlow; Khan; British Journal of Pharmacology and Chemotherapy; vol. 14; (1959); p. 99,101, View in Reaxys 2 of 2
Melting Point [°C]
174.5 - 176
Solvent (Melting Point)
ethanol; diethyl ether
Vitali; Mossini; Bollettino Scientifico della Facolta di Chimica Industriale di Bologna; vol. 17; (1959); p. 84,86, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
ethanol
Absorption Maxima (UV/ 221; 281; 289 VIS) [nm] Vitali; Mossini; Bollettino Scientifico della Facolta di Chimica Industriale di Bologna; vol. 17; (1959); p. 84,86, View in Reaxys Medchem (1) 1 of 1
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
receptor; binding activityHEK cell membranesHEK cells stably expressing human 5-HT1E receptor; methiothepin (10 μmol/l) used to define nonspecific binding; 5-HT, serotonin
Substance RN
3724506View in Reaxys
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Measurement Parameter
Ki
Unit
nM
Quantitative value
3030
Measurement pX
5.52
Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 10; (2004); p. 2545 - 2552, View in Reaxys
Copyright © 2017 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.
18/18
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