Query Query
Results
Date
4 substances in Reaxys
2018-05-13 23h:45m:17s (UTC)
O N
1. Query
O
NH 2
Search as: As drawn ) AND (IDE.XRN=2215967)) OR (IDE.XRN=3730437) OR (IDE.XRN=3876278) OR (IDE.XRN=3881863))
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Reaxys ID 2215967 View in Reaxys
1/4 CAS Registry Number: 94-15-5 Chemical Name: dimethocaine; Dimethocaine; 4-amino-benzoic acid-(3-diethylamino-2,2-dimethyl-propyl ester); 4-Amino-benzoesaeure-(3-diaethylamino-2,2-dimethyl-propylester); 3-Diaethylamino-1-(4-amino-benzoyloxy)-2,2-dimethyl-propan; Larocain Linear Structure Formula: C16H26N2O2 Molecular Formula: C16H26N2O2 Molecular Weight: 278.395 Type of Substance: isocyclic InChI Key: OWQIUQKMMPDHQQ-UHFFFAOYSA-N Note:
O N O
NH 2
Patent-Specific Data (1) Location in Patent References Claim
Patent; Levin, Bruce H.; US2001/4644; (2001); (A1) English, View in Reaxys; Patent; Galin; Miles A.; Salamone; Joseph C.; Israel; Stanley C.; US5972326; (1999); (A) English, View in Reaxys; Patent; Cleary, Gary W.; Mudumba, Sri; Parandoosh, Shohreh; Cleary, Colin J.; Birudaraj, Raj; Park, Pathamar; US2003/27833; (2003); (A1) English, View in Reaxys; Patent; Tsao, Fu-Pao; US2003/133986; (2003); (A1) English, View in Reaxys
Druglikeness (1) 1 of 1
LogP
2.89
H Bond Donors
1
H Bond Acceptors
4
Rotatable Bonds
8
TPSA
55.56
Lipinski Number
4
Veber Number
2
Highest Clinical Phase (1) Highest Clinical Phase Marketed Derivative (2) Comment (Derivative)
References
Hydrochlorid Dusinsky; Chemicke Zvesti; vol. 17; (1963); p. 265; Chem.Abstr.; vol. 59; nb. 12596; (1963), View in Reaxys C16H26N2O2*HCl : Kinetik der alkal. Hydrolyse (oszillopolarogr. ermittelt) 2,4,6-trinitro benzoate (mp: 110-117 degree , yellow red); Further Data see Handbook
Fischer; Reichel; Pharmazeutische Zentralhalle; vol. 85; (1944); p. 8,11, View in Reaxys
Melting Point (3) 1 of 3
Melting Point [°C]
53
Schmidt, Andrea C.; Pharmaceutical Research; vol. 22; nb. 12; (2005); p. 2121 - 2133, View in Reaxys 2 of 3
Melting Point [°C]
199
Brandstaetter-Kuhnert; Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 287,302; Chem.Abstr.; nb. 9210; (1960), View in Reaxys 3 of 3
Melting Point [°C]
54
Brandstaetter-Kuhnert; Grimm; Microchimica Acta; (1957); p. 427,434, View in Reaxys Further Information (1) Description (FurReferences ther Information) Further information Dusinsky; Chemicke Zvesti; vol. 17; (1963); p. 265; Chem.Abstr.; vol. 59; nb. 12596; (1963), View in Reaxys Liquid/Solid Systems (MCS) (1)
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1 of 1
Description (Liquid/Solid Systems (MCS))
Eutectic
Brandstaetter-Kuhnert; Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 287,302; Chem.Abstr.; nb. 9210; (1960), View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
H2O (pH 7.1)
Comment (UV/VIS Spectroscopy)
220 - 340 nm
Kalow; Journal of Pharmacology and Experimental Therapeutics; vol. 104; (1952); p. 122,124, View in Reaxys Use (10) Use Pattern
Location
References
Pharmaceuticals
Page/Page column 17-18
Patent; Becton, Dickinson and Company; Kelley, III, John J.; Valdes, Thelma I.; (19 pag.); US9248093; (2016); (B2) English, View in Reaxys
catheter locking solution
Page/Page column 17-18
Patent; Becton, Dickinson and Company; Kelley, III, John J.; Valdes, Thelma I.; (19 pag.); US9248093; (2016); (B2) English, View in Reaxys
local anesthetic
Page/Page column 17-18
Patent; Becton, Dickinson and Company; Kelley, III, John J.; Valdes, Thelma I.; (19 pag.); US9248093; (2016); (B2) English, View in Reaxys
inhibit the feeling of skin irritation
Patent; Ramirez, Jose E.; Faryniarz, Joseph; US2007/190190; (2007); (A1) English, View in Reaxys
anesthetic component of skin composition
Patent; Ramirez, Jose E.; Faryniarz, Joseph; US2007/190190; (2007); (A1) English, View in Reaxys
reducing of pain upon tissue penetration
Patent; Ramirez, Jose E.; Faryniarz, Joseph; US2007/190190; (2007); (A1) English, View in Reaxys
preparing of skin to make it more receptive to the corrective step
Patent; Ramirez, Jose E.; Faryniarz, Joseph; US2007/190190; (2007); (A1) English, View in Reaxys
acne vulgaris
Patent; Ramirez, Jose E.; Faryniarz, Joseph; US2007/190190; (2007); (A1) English, View in Reaxys
local anesthetic
Patent; Cassel, R. Douglas; US2006/29654; (2006); (A1) English, View in Reaxys
pain induced by a sports injury
Patent; Cassel, R. Douglas; US2006/29654; (2006); (A1) English, View in Reaxys
Medchem (31) 1 of 31
Target Name
Sodium-dependent dopamine transporter [Rattus norvegicus]
Target Synonyms
da transporter; dat; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target Uniprot ID
p23977
Target, Subunit, Species
Sodium-dependent dopamine transporter [Rattus norvegicus]
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Target Transfection
Non Transfected
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Binding
Biological Species/NCBI ID
Sprague Dawley rat
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Organs/Tissues
putamen
Substance RN
2215967View in Reaxys
Substance Name
19
Measurement Parameter
Ki (inhibition constant)
Unit
nM
Quantitative value
603
Measurement pX
6.22
Concomitants: Compound RN
91034; 4354534
Concomitants: Compound name
Cocaine; [3H]-WIN 35428
Concomitants: Compound role
NSB; RAD
Izenwasser; Terry; Heller; Witkin; Kats; European Journal of Pharmacology; vol. 263; nb. 3; (1994); p. 277 - 283, View in Reaxys 2 of 31
Bioassay Category
In Vivo (Animal models)
Bioassay Name
Spontaneous activity
Biological Species/NCBI ID
Swiss Webster mouse
Substance RN
2215967View in Reaxys
Substance Name
19
Substance Route of Adm.
intraperitoneal administration
Substance Dosing Regimen
Single
Measurement Parameter
ED50
Unit
mg/kg
Measurement Object
dose which induces locomotor activity in 50% mouse
Quantitative value
8.94
Izenwasser; Terry; Heller; Witkin; Kats; European Journal of Pharmacology; vol. 263; nb. 3; (1994); p. 277 - 283, View in Reaxys 3 of 31
Bioassay Category
In Vivo (Animal models)
Bioassay Name
Spontaneous activity
Biological Species/NCBI ID
Swiss Webster mouse
Substance RN
2215967View in Reaxys
Substance Name
19
Measurement Parameter
ED50
Unit
µmol/kg
Measurement Object
dose which induces locomotor activity in 50% mouse
Quantitative value
36.8
Izenwasser; Terry; Heller; Witkin; Kats; European Journal of Pharmacology; vol. 263; nb. 3; (1994); p. 277 - 283, View in Reaxys 4 of 31
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Details
Lowest lethal dose of the compound in rabbit upon subcutaneous administration
Biological Species/NCBI ID
Leporidae
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Substance RN
2215967View in Reaxys
Substance Route of Adm.
subcutaneous administration
Measurement Parameter
LDLo
Unit
mg/kg
Measurement Object
Lowest lethal dose
Quantitative value
150
Physiological reviews; vol. 12; (1932); p. 190, View in Reaxys 5 of 31
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Details
Lowest lethal dose of the compound in mouse upon intravenous administration
Biological Species/NCBI ID
Mus musculus
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
LDLo
Unit
mg/kg
Measurement Object
Lowest lethal dose
Quantitative value
40
Physiological reviews; vol. 12; (1932); p. 190, View in Reaxys 6 of 31
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Details
Lowest lethal dose of the compound in rabbit upon intravenous administration
Biological Species/NCBI ID
Leporidae
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
LDLo
Unit
mg/kg
Measurement Object
Lowest lethal dose
Quantitative value
150
Physiological reviews; vol. 12; (1932); p. 190, View in Reaxys 7 of 31
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Details
Lowest lethal dose of the compound in guinea pig upon subcutaneous administration
Biological Species/NCBI ID
guinea pig
Substance RN
2215967View in Reaxys
Substance Route of Adm.
subcutaneous administration
Measurement Parameter
LDLo
Unit
mg/kg
Measurement Object
Lowest lethal dose
Quantitative value
200
Physiological reviews; vol. 12; (1932); p. 190, View in Reaxys 8 of 31
Substance Action on Target
Inhibitor
Bioassay Category
In Vitro (Efficacy)
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Bioassay Details
In vitro inhibitory concentration of dimethocaine against dopamine uptake in monkey caudate nucleus tissue upon incubated for 10 min at 37 degree C
Substance RN
2215967View in Reaxys
Measurement Parameter
IC50
Unit
µM
Measurement Object
Dopamine uptake
Qualitative value
=
Quantitative value
11
Measurement pX
4.96
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 9 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR400) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
mg/kg
Measurement Object
Effective dose
Qualitative value
=
Quantitative value
0.29
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 10 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR400) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
µmol/kg
Measurement Object
Effective dose
Qualitative value
=
Quantitative value
0.95
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 11 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR200) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
mg/kg
Measurement Object
Effective dose
Qualitative value
=
Quantitative value
0.26
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Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 12 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR200) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
µmol/kg
Measurement Object
Effective dose
Qualitative value
=
Quantitative value
0.82
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 13 of 31
Bioassay Category
In Vivo (Animal models)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR50) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
mg/kg
Measurement Object
Effective dose
Qualitative value
=
Quantitative value
0.19
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 14 of 31
Bioassay Category
In Vivo (Animal models)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR50) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
µmol/kg
Measurement Object
Effective dose
Qualitative value
=
Quantitative value
0.6
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 15 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR100) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
mg/kg
Qualitative value
=
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Quantitative value
0.41
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 16 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effective dose required for local anesthetic effect under a progressive-ratio (PR100) procedure in rhesus monkeys upon intravenous administration
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
ED50
Unit
µmol/kg
Qualitative value
=
Quantitative value
1.3
Wilcox; Wilcox, Kristin M.; Rowlett; Rowlett, James K.; Paul; Paul, Ian A.; Ordway; Ordway, Gregory A.; Woolverton; Woolverton, William L.; Psychopharmacology; vol. 153; nb. 1; (2000); p. 139 - 147, View in Reaxys 17 of 31
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Details
Lowest lethal dose of the compound in frog upon parenteral administration
Biological Species/NCBI ID
Anura
Substance RN
2215967View in Reaxys
Substance Route of Adm.
intravenous administration
Measurement Parameter
LDLo
Unit
mg/kg
Measurement Object
Lowest lethal dose
Quantitative value
860
Naunyn-Schmiedebergs Arch. Exp. Pathol. Pharmakol.(1925-1966) ; vol. 168; (1932); p. 447, View in Reaxys 18 of 31
Bioassay Category
Toxicity/Safety Pharmacology
Bioassay Details
Lowest lethal dose of the compound in mouse upon subcutaneous administration
Biological Species/NCBI ID
Mus musculus
Substance RN
2215967View in Reaxys
Substance Route of Adm.
subcutaneous administration
Measurement Parameter
LDLo
Unit
mg/kg
Measurement Object
Lowest lethal dose
Quantitative value
380
Naunyn-Schmiedebergs Arch. Exp. Pathol. Pharmakol.(1925-1966) ; vol. 168; (1932); p. 447, View in Reaxys 19 of 31
Target Name
Sodium-dependent dopamine transporter
Target Synonyms
da transporter; dat; dat-1; dat1; fmn; protein fumin; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target, Subunit, Species
Sodium-dependent dopamine transporter
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter:Wild
Substance Action on Target
Inhibitor
Bioassay Category
In Vitro (Efficacy)
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Bioassay Details
Inhibition of 30 nM [3H]CFT binding at dopamine transporter upon incubation in 50 mM Tris-HCl, pH 7.4 for 2 h at 0 degree C
Substance RN
2215967View in Reaxys
Measurement Parameter
Ki (inhibition constant)
Unit
nM
Qualitative value
=
Quantitative value
1400
Measurement pX
5.85
Concomitants: Compound name
[3H]CFT
Concomitants: Compound role
RAD
Woodward; Compton; Balster; Martin; European Journal of Pharmacology; vol. 277; nb. 1; (1995); p. 7 - 13, View in Reaxys 20 of 31
Target Name
Sodium-dependent dopamine transporter
Target Synonyms
da transporter; dat; dat-1; dat1; fmn; protein fumin; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target, Subunit, Species
Sodium-dependent dopamine transporter
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter:Wild
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Inhibitory concentration of the compound against [3H]dopamine uptake by dopamine transporter
Substance RN
2215967View in Reaxys
Measurement Parameter
IC50
Unit
µM
Qualitative value
=
Quantitative value
1.2
Measurement pX
5.92
Woodward; Compton; Balster; Martin; European Journal of Pharmacology; vol. 277; nb. 1; (1995); p. 7 - 13, View in Reaxys 21 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Inhibition constant of the compound against 30 nM [3H]CFT binding to rat striatal homogenate upon incubation in 50 mM Tris-HCl, pH 7.4 for 2 h at 0 degree C
Biological Species/NCBI ID
Rattus norvegicus
Substance RN
2215967View in Reaxys
Measurement Parameter
Ki (inhibition constant)
Unit
µM
Qualitative value
=
Quantitative value
1.4
Measurement pX
5.85
Concomitants: Compound name
[3H]CFT
Concomitants: Compound role
RAD
Woodward; Compton; Balster; Martin; European Journal of Pharmacology; vol. 277; nb. 1; (1995); p. 7 - 13, View in Reaxys 22 of 31
Target Name
Sodium-dependent dopamine transporter
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Target Synonyms
23 of 31
da transporter; dat; dat-1; dat1; fmn; protein fumin; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target, Subunit, Species
Sodium-dependent dopamine transporter
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter:Wild
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Dopamine transporter occupancy by displacing FECNT in monkey striatum measured by neuroimaging with positron emission tomography (PET); Value range = <10-41
Substance RN
2215967View in Reaxys
Measurement Parameter
percentage
Unit
%
Measurement Object
Occupancy rate
Qualitative value
=
Quantitative value
41
Target Name
Sodium-dependent dopamine transporter
Target Synonyms
da transporter; dat; dat-1; dat1; fmn; protein fumin; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target, Subunit, Species
Sodium-dependent dopamine transporter
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter:Wild
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Inhibitory concentration against dopamine uptake by dopamine transporter
Substance RN
2215967View in Reaxys
Measurement Parameter
IC50
Unit
µM
Qualitative value
=
Quantitative value
1.2
Measurement pX
5.92
Woodward; Compton; Balster; Martin; European Journal of Pharmacology; vol. 277; nb. 1; (1995); p. 7 - 13, View in Reaxys 24 of 31
Bioassay Category
In Vivo (Animal models)
Bioassay Details
Antinociceptive response of the compound in mice upon s.c. administration; Induced dose-dependently
Biological Species/NCBI ID
Mus musculus
Substance RN
2215967View in Reaxys
Substance Route of Adm.
subcutaneous administration
Measurement Parameter
Activity
Measurement Object
Effect
Qualitative value
ND
Rigon, Adriana Regina; Takahashi, Reinaldo Naoto; General Pharmacology; vol. 27; nb. 4; (1996); p. 647 - 650, View in Reaxys 25 of 31
Bioassay Category
In Vivo (Animal models)
Bioassay Details
Effect of the compound on locomotor activity of mice upon i.p. administration; Significantly increased
Biological Species/NCBI ID
Mus musculus
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10/16
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Substance RN
2215967View in Reaxys
Substance Route of Adm.
intraperitoneal administration
Measurement Parameter
Activity
Measurement Object
Effect
Qualitative value
ND
Rigon, Adriana R.; Takahashi, Reinaldo N.; Psychopharmacology; vol. 127; nb. 4; (1996); p. 323 - 327, View in Reaxys 26 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Effect on tail-flick and paw-licking hot plate responses of mice; Significantly inhibited
Biological Species/NCBI ID
Mus musculus
Substance RN
2215967View in Reaxys
Measurement Parameter
Activity
Measurement Object
Effect
Qualitative value
ND
Rigon, Adriana Regina; Takahashi, Reinaldo Naoto; General Pharmacology; vol. 27; nb. 4; (1996); p. 647 - 650, View in Reaxys 27 of 31
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Inhibition of 50 nM [3H]dopamine uptake in rat striatal synaptosomes upon incubation in 10 mM Tris, pH 7.65 at RT
Biological Species/NCBI ID
Rattus norvegicus
Substance RN
2215967View in Reaxys
Measurement Parameter
% Inhibition
Unit
%
Qualitative value
=
Quantitative value
100
Woodward; Compton; Balster; Martin; European Journal of Pharmacology; vol. 277; nb. 1; (1995); p. 7 - 13, View in Reaxys 28 of 31
Target Name
Sodium-dependent dopamine transporter [Rattus norvegicus]
Target Synonyms
da transporter; dat; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target Uniprot ID
p23977
Target, Subunit, Species
Sodium-dependent dopamine transporter [Rattus norvegicus]
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Substance Action on Target
Inhibitor
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Inhibition of 0.15 nM [125I]RTI-55 binding to Dopamine reuptake in rat striatum
Organs/Tissues
neostriatum
Substance RN
2215967View in Reaxys
Measurement Parameter
IC50
Unit
nM
Qualitative value
=
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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29 of 31
30 of 31
31 of 31
Quantitative value
460.74
Measurement pX
6.34
Target Name
Sodium-dependent serotonin transporter [Rattus norvegicus]
Target Synonyms
5ht transporter; 5htt; sert; slc6a4; sodium-dependent serotonin transporter; solute carrier family 6 member 4
Target Uniprot ID
p31652
Target, Subunit, Species
Sodium-dependent serotonin transporter [Rattus norvegicus]
Target Mutant/Chimera Details
Sodium-dependent serotonin transporter [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Substance Action on Target
Inhibitor
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Inhibition of 0.15 nM [125I]RTI-55 binding to Serotonin reuptake in rat cerebral cortex
Organs/Tissues
brain cortex
Substance RN
2215967View in Reaxys
Measurement Parameter
IC50
Unit
nM
Qualitative value
=
Quantitative value
34572.3
Measurement pX
4.46
Target Name
Sodium-dependent dopamine transporter [Rattus norvegicus]
Target Synonyms
da transporter; dat; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target Uniprot ID
p23977
Target, Subunit, Species
Sodium-dependent dopamine transporter [Rattus norvegicus]
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Substance Action on Target
Inhibitor
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Dopamine transporter activity was determined by inhibition of [125I]RTI-55 (0.15 nM) binding in rat cerebral cortex
Organs/Tissues
brain cortex
Substance RN
2215967View in Reaxys
Measurement Parameter
IC50
Unit
nM
Qualitative value
=
Quantitative value
34572.3
Measurement pX
4.46
Target Name
Sodium-dependent dopamine transporter [Rattus norvegicus]
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Target Synonyms
da transporter; dat; slc6a3; sodium-dependent dopamine transporter; solute carrier family 6 member 3
Target Uniprot ID
p23977
Target, Subunit, Species
Sodium-dependent dopamine transporter [Rattus norvegicus]
Target Mutant/Chimera Details
Sodium-dependent dopamine transporter [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Substance Action on Target
Inhibitor
Substance Effect
inhibitory activity
Bioassay Category
In Vitro (Efficacy)
Bioassay Details
Dopamine transporter activity was determined by inhibition of [125I]RTI-55 (0.15 nM) binding in rat striatum
Organs/Tissues
neostriatum
Substance RN
2215967View in Reaxys
Measurement Parameter
IC50
Unit
nM
Qualitative value
=
Quantitative value
460.74
Measurement pX
6.34
Reaxys ID 3730437 View in Reaxys
2/4
H 2N
N
Cl
CAS Registry Number: 553-63-9 Chemical Name: dimethocaine hydrochloride; 4-amino-benzoic acid-(3-diethylamino-2,2-dimethyl-propylester); hydrochloride; 4Amino-benzoesaeure-(3-diaethylamino-2,2-dimethyl-propylester); Hydrochlorid; Larocain Linear Structure Formula: C16H26N2O2*ClH Molecular Formula: C16H26N2O2*ClH Molecular Weight: 314.856 Type of Substance: isocyclic InChI Key: WWTWKTDXBNHESE-UHFFFAOYSA-N Note:
H
O O
Druglikeness (1) 1 of 1
LogP
3.402
H Bond Donors
1
H Bond Acceptors
4
Rotatable Bonds
8
TPSA
55.56
Lipinski Number
4
Veber Number
2
Melting Point (3) 1 of 3
Melting Point [°C]
199
Schmidt, Andrea C.; Pharmaceutical Research; vol. 22; nb. 12; (2005); p. 2121 - 2133, View in Reaxys 2 of 3
Melting Point [°C]
197 - 199
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2018-05-13 23:45:48
Fischer; Reichel; Pharmazeutische Zentralhalle; vol. 85; (1944); p. 8,11, View in Reaxys; Brandstaetter-Kuhnert; Grimm; Microchimica Acta; (1957); p. 427,434, View in Reaxys 3 of 3
Melting Point [°C]
195 - 196
Solvent (Melting Point)
propan-2-ol
Lesser,B.; Diss. <Frankfurt 1930> S. 29, View in Reaxys Crystal System (1) Crystal System References rhombic
Wickstroem; Journal of Pharmacy and Pharmacology; vol. 5; (1953); p. 158,163, View in Reaxys
Medchem (2) 1 of 2
Substance Effect
Dopaminergic
Bioassay Category
In Vivo (Animal models)
Bioassay Name
In vivo Measurement
Bioassay Details
Bioassay : levels of dopamine (DA) and its metabolites 3-methoxytyramine (3-MT) and dihydroxyphenylacetic acid (DOPAC) in the striatum (STR), nucleus accumbens (NAcc) and prefrontal cortex PFC) rats weighing 185 to 310 g; food and water ad libitum; 12 h light-dark cycle; sacrificed; time course (dose of title comp.: 88 μmol/kg) and dose response study; reverse-phase HPLC with electrochemical detection and gas chromatography-mass spectrometry
Biological Species/NCBI ID
Rattus norvegicus
Substance RN
3730437View in Reaxys
Substance Name
1484799
Substance Dose
56 µmol/kg
Substance Route of Adm.
intraperitoneal administration
Qualitative Results
increase the synaptic presence of DA; numerical data and diagrams given
Measurement Parameter
qualitative
Graham III; Maher; Robinson; Journal of Pharmacology and Experimental Therapeutics; vol. 274; nb. 2; (1995); p. 707 - 717, View in Reaxys 2 of 2
Substance Effect
Anaesthesic
Bioassay Category
In Vivo (Animal models)
Bioassay Name
In vivo Measurement
Bioassay Details
Bioassay : behavior maintained by food presentation under a fixed ratio 32 schedule of reinforcement; four daily (sunday-friday) behavioral session for substitution and antagonism tests monkeys, trained to discriminate sympathomimetic stimulant cocaine from saline, injected with title comp. 10 min before the session alone in various concns. or with saline
Biological Species/NCBI ID
squirrel monkey
Substance RN
3730437View in Reaxys
Substance Name
1484799
Substance Dose
0.0100000 mg/kg
Substance Route of Adm.
intramuscular administration
Measurement Parameter
ED50
Unit
µmol/kg
Quantitative value
2.29
Mansbach; Jortani; Balster; European Journal of Pharmacology; vol. 274; nb. 1-3; (1995); p. 167 - 173, View in Reaxys
Reaxys ID 3876278 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.
3/4
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O O
Chemical Name: 4-amino-benzoic acid-(3-diethylamino-2,2-dimethyl-propylester); picrate; 4-Amino-benzoesaeure-(3-diaethylamino-2,2dimethyl-propylester); Picrat Linear Structure Formula: C16H26N2O2*C6H3N3O7 Molecular Formula: C6H3N3O7*C16H26N2O2 Molecular Weight: 507.5 Type of Substance: isocyclic InChI Key: JAVSCQSYKWVESR-UHFFFAOYSA-N Note:
N O
HO
N O
O
N O O
N O
NH 2
Druglikeness (1) 1 of 1
H Bond Donors
2
H Bond Acceptors
4
Rotatable Bonds
11
TPSA
213.25
Lipinski Number
2
Veber Number
0
Melting Point (2) 1 of 2
Melting Point [°C]
164 - 165
Fischer; Reichel; Pharmazeutische Zentralhalle; vol. 85; (1944); p. 8,11, View in Reaxys 2 of 2
Melting Point [°C]
166
Fischer; Archiv der Pharmazie (Weinheim, Germany); vol. 271; (1933); p. 466,469, View in Reaxys
Reaxys ID 3881863 View in Reaxys
4/4
O
O
N
N
O
Chemical Name: 4-amino-benzoic acid-(3-diethylamino-2,2-dimethyl-propylester); compound with 2,4,6-trinitro-resorcinol; 4-Aminobenzoesaeure-(3-diaethylamino-2,2-dimethyl-propylester); Verbindung mit 2,4,6-Trinitro-resorcin Linear Structure Formula: C16H26N2O2*C6H3N3O8 Molecular Formula: C6H3N3O8*C16H26N2O2 Molecular Weight: 523.5 Type of Substance: isocyclic InChI Key: KQELRHUHJCLXSX-UHFFFAOYSA-N Note:
O
HO
OH N O
O O
N O
NH 2
Druglikeness (1) 1 of 1
H Bond Donors
3
H Bond Acceptors
4
Rotatable Bonds
11
TPSA
233.48
Lipinski Number
2
Veber Number
0
Melting Point (2) 1 of 2
Melting Point [°C]
147 - 151
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.
15/16
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Fischer; Reichel; Pharmazeutische Zentralhalle; vol. 85; (1944); p. 8,11, View in Reaxys 2 of 2
Melting Point [°C]
149 - 150
Fischer; Archiv der Pharmazie (Weinheim, Germany); vol. 271; (1933); p. 466,469, 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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