Query Query Cl H HO
Results
Date
1 substances in Reaxys
2017-11-08 16h:59m:52s (EST)
H
NH 2 H
1. Query
Search as: As drawn, No salts, No mixtures, No isotopes, No charges, No radicals
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Reaxys ID 3914295 View in Reaxys
H 2N Cl
H
1/1 CAS Registry Number: 2153-98-2 Chemical Name: (+)-Norpseudoephedrine hydrochloride; (-)Norpseudoephedrine hydrochloride; (1S,2S)-2-amino-1-phenyl-1-propanol hydrochloride; (1S,2S)-(+)-norpseudoephedrine hydrochloride; (1S,2S)-norpseudoephedrine hydrochloride; (S,S)-norpseudoephedrine hydrochloride; (+)-pseudonorephedrine hydrochloride Linear Structure Formula: C9H13NO*ClH Molecular Formula: C9H13NO*ClH Molecular Weight: 187.669 Type of Substance: isocyclic InChI Key: DYWNLSQWJMTVGJ-DKXTVVGFSA-N Note:
H OH
H
Substance Label (5) Label References (1S,2S)-6*HCl
Colman, Bob; De Sousa, Simon E.; O'Brien, Peter; Towers, Timothy D.; Watson, Will; Tetrahedron Asymmetry; vol. 10; nb. 21; (1999); p. 4175 - 4182, View in Reaxys
4
Yu, Gu-Sheng; Che, Diping; Freedman, Teresa B.; Nafie, Laurence A.; Tetrahedron: Asymmetry; vol. 4; nb. 3; (1993); p. 511 - 516, View in Reaxys
9
Boerner, Armin; Krause, Hanswalter; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 307 - 312, View in Reaxys
4*HCl
Grue-Sorensen; Spenser; Canadian Journal of Chemistry; vol. 67; nb. 6; (1989); p. 998 - 1009, View in Reaxys
9*HCl
Grunewald; Ye; Journal of Medicinal Chemistry; vol. 31; nb. 10; (1988); p. 1984 - 1986, View in Reaxys
Druglikeness (1) 1 of 1
LogP
1.51
H Bond Donors
2
H Bond Acceptors
2
Rotatable Bonds
2
TPSA
46.25
Lipinski Number
4
Veber Number
2
Melting Point (4) 1 of 4
Melting Point [°C]
181
Wolfes; Archiv der Pharmazie (Weinheim, Germany); (1930); p. 82, View in Reaxys 2 of 4
Melting Point [°C]
180 - 181
Kanao; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 241, View in Reaxys; Nagai; Kanao; Justus Liebigs Annalen der Chemie; vol. 470; (1929); p. 174; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 2553, View in Reaxys 3 of 4
Melting Point [°C]
178 - 179
Solvent (Melting Point)
ethanol
Smith; Journal of the Chemical Society; (1928); p. 51,52, View in Reaxys 4 of 4
Melting Point [°C]
178 - 179
Solvent (Melting Point)
ethanol; diethyl ether
Smith; Journal of the Chemical Society; (1928); p. 51,52, View in Reaxys Crystal Property Description (2) Colour & Other References Properties Prismen
Smith; Journal of the Chemical Society; (1928); p. 51,52, View in Reaxys
Tafeln
Smith; Journal of the Chemical Society; (1928); p. 51,52, View in Reaxys
Mutarotation (2)
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1 of 2
Type (Mutarotation)
[alpha]
Concentration (Mutarotation)
p=7
Solvent (Mutarotation)
H2O
Mutarotation [deg]
42.5
Wavelength (Mutarotation) [nm]
589
Temperature (Mutarotation) [°C]
20
Nagai; Kanao; Justus Liebigs Annalen der Chemie; vol. 470; (1929); p. 174; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 2553, View in Reaxys; Wolfes; Archiv der Pharmazie (Weinheim, Germany); (1930); p. 82, View in Reaxys 2 of 2
Type (Mutarotation)
[alpha]
Mutarotation [deg]
46.2
Wavelength (Mutarotation) [nm]
546.1
Temperature (Mutarotation) [°C]
20
Chen; Wu; Henriksen; Journal of Pharmacology and Experimental Therapeutics; vol. 36; (1929); p. 364, View in Reaxys Optical Rotatory Power (2) 1 of 2
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
1.0 g/100ml
Solvent (Optical Rotatory Power)
H2O
Optical Rotatory Power [deg]
38
Wavelength (Optical Ro- 589 tatory Power) [nm] Colman, Bob; De Sousa, Simon E.; O'Brien, Peter; Towers, Timothy D.; Watson, Will; Tetrahedron Asymmetry; vol. 10; nb. 21; (1999); p. 4175 - 4182, View in Reaxys 2 of 2
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
4.9 g/100ml
Solvent (Optical Rotatory Power)
H2O
Optical Rotatory Power [deg]
42.7
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
20
Grunewald; Ye; Journal of Medicinal Chemistry; vol. 31; nb. 10; (1988); p. 1984 - 1986, View in Reaxys NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
270
Colman, Bob; De Sousa, Simon E.; O'Brien, Peter; Towers, Timothy D.; Watson, Will; Tetrahedron Asymmetry; vol. 10; nb. 21; (1999); p. 4175 - 4182, View in Reaxys 2 of 4
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
270
Colman, Bob; De Sousa, Simon E.; O'Brien, Peter; Towers, Timothy D.; Watson, Will; Tetrahedron Asymmetry; vol. 10; nb. 21; (1999); p. 4175 - 4182, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
67.9
Colman, Bob; De Sousa, Simon E.; O'Brien, Peter; Towers, Timothy D.; Watson, Will; Tetrahedron Asymmetry; vol. 10; nb. 21; (1999); p. 4175 - 4182, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- D2O scopy) Grue-Sorensen; Spenser; Canadian Journal of Chemistry; vol. 67; nb. 6; (1989); p. 998 - 1009, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
CDCl3
Colman, Bob; De Sousa, Simon E.; O'Brien, Peter; Towers, Timothy D.; Watson, Will; Tetrahedron Asymmetry; vol. 10; nb. 21; (1999); p. 4175 - 4182, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
H2O
Wolfes; Archiv der Pharmazie (Weinheim, Germany); (1930); p. 82, View in Reaxys Raman Spectroscopy (1) Description (Ram- Comment (Raman Spectroscopy) an Spectroscopy) Spectrum
H2O
References Yu, Gu-Sheng; Che, Diping; Freedman, Teresa B.; Nafie, Laurence A.; Tetrahedron: Asymmetry; vol. 4; nb. 3; (1993); p. 511 - 516, View in Reaxys
Medchem (5) 1 of 5
Bioassay Category
In Vitro (Efficacy)
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Bioassay Name
In Vitro (others)
Bioassay Details
Effect : |transport Bioassay : Ki,cl,NMeN=contraluminal apparent Ki against N1-methylnicotinamide (NMEN), Ki,l,choline=luminal apparent Ki against choline, Ki,l,MPP=luminal apparent Ki against MPP, 3H-NMeN and 14C-inulin (0.01 mM) used as volume and/or space in vitro; kidney capsules (proximal tubule) from rats (180-200 g); luminal stop flow tubular microperfusion method; 37 degC; title comp. and 3H-methyl-4-phenylpyridinium (MPP) (0.01 mM) or 3H-choline+ (0.01 mM) applied in HCO3- Ringer's
Biological Species/NCBI Rattus norvegicus ID Substance RN
3914295View in Reaxys
Substance Name
1485906
Qualitative Results
Ki,cl,NmeN=2.3 mM; Ki,l,MPP=8.7 mM; Ki,l,choline=14.8 mM
Measurement Parameter
Qualitative
Somogyi, Andrew A.; Rumrich, Gerhard; Fritzsch, Guenter; Ullrich, Karl J.; Journal of Pharmacology and Experimental Therapeutics; vol. 278; nb. 1; (1996); p. 31 - 36, View in Reaxys 2 of 5
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
Substance Action on Target
Stimulator
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Organ contraction
Biological Species/NCBI Rattus norvegicus; Rattus norvegicus ID
3 of 5
Organs/Tissues
Vas deferens
Substance RN
3914295View in Reaxys
Substance Name
L(+)-Norpseudoephedrine
Measurement Parameter
pEC50
Qualitative value
NA
Measurement pX
1
Concomitants: Compound RN
102014
Concomitants: Compound name
Reserpine
Concomitants: Compound role
APR
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]
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Target Mutant/Chimera Details
sodium-dependent dopamine transporter [rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Target Transfection
Non Transfected
Substance Action on Target
Stimulator
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Organ contraction
Biological Species/NCBI Rattus norvegicus; Rattus norvegicus ID
4 of 5
Organs/Tissues
Vas deferens
Substance RN
3914295View in Reaxys
Substance Name
L(+)-Norpseudoephedrine
Measurement Parameter
% Max
Unit
%
Measurement Object
Maximal Effect
Quantitative value
3
Concomitants: Compound RN
102014
Concomitants: Compound name
Reserpine
Concomitants: Compound role
APR
Target Name
adrenergic receptor [Rattus norvegicus]
Target Synonyms
adrenergic receptor
Target, Subunit, Species adrenergic receptor [Rattus norvegicus] Target Mutant/Chimera Details
adrenergic receptor [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Target Transfection
Non Transfected
Substance Action on Target
Agonist
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Organ contraction
Biological Species/NCBI Rattus norvegicus ID
5 of 5
Organs/Tissues
Vas deferens
Substance RN
3914295View in Reaxys
Substance Name
14
Measurement Parameter
%
Unit
%
Measurement Object
of control max effect
Quantitative value
30
Target Name
adrenergic receptor [Rattus norvegicus]
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Target Synonyms
adrenergic receptor
Target, Subunit, Species adrenergic receptor [Rattus norvegicus] Target Mutant/Chimera Details
adrenergic receptor [Rattus norvegicus]:Wild
Target Species (Bioactivity)
Rattus norvegicus
Target Transfection
Non Transfected
Substance Action on Target
Agonist
Bioassay Category
In Vitro (Efficacy)
Bioassay Name
Organ contraction
Biological Species/NCBI Rattus norvegicus ID Organs/Tissues
Vas deferens
Substance RN
3914295View in Reaxys
Substance Name
14
Measurement Parameter
Time
Unit
second
Measurement Object
onset of action
Quantitative value
90
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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