Query Query Cl
Results
Date
1 substances in Reaxys
2017-11-08 16h:51m:47s (EST)
H
HO
1. Query H 2N
Search as: As drawn, No salts, No mixtures, No isotopes, No charges, No radicals
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Reaxys ID 4299828 View in Reaxys
1/1 CAS Registry Number: 53643-20-2 Chemical Name: (1R,2R)-norephedrine hydrochloride; (1R, 2R)-2-amino-1-phenyl-propan-1-ol hydrochloride; (1R,2R)-1phenyl-2-amino-1-propanol hydrochloride; (+)-(2R:3R)-threoNorpseudoephedrinhydrochlorid; (-)-(1R,2R)-norpseudoephedrine hydrochloride; (1R,2R)-(+)-norpseudoephedrine hydrochloride; (1R,2R)-(-)-norpseudoephedrine hydrochloride Linear Structure Formula: C9H13NO*HCl Molecular Formula: C9H13NO*ClH Molecular Weight: 187.669 Type of Substance: isocyclic InChI Key: DYWNLSQWJMTVGJ-JXLXBRSFSA-N Note:
HO Cl
H
H 2N
Substance Label (9) Label References 1b-(th)
Cruz, Alejandro; Contreras, Rosalinda; Padilla-Martinez, Itzia I.; Juarez-Juarez, Minerva; Tetrahedron Asymmetry; vol. 17; nb. 10; (2006); p. 1499 - 1505, View in Reaxys; Cruz, Alejandro; Padilla-Martinez, Itzia Irene; Garcia-Baez, Efren V.; Contreras, Rosalinda; Tetrahedron Asymmetry; vol. 18; nb. 1; (2007); p. 123 - 130, View in Reaxys
6
McGhee, Andrea M.; Kizirian, Jean-Claude; Procter, David J.; Organic and Biomolecular Chemistry; vol. 5; nb. 7; (2007); p. 1021 - 1024, View in Reaxys
(1R,2R)-16k
Shirai, Ryuichi; Sato, Daisaku; Aoki, Kazumasa; Tanaka, Masahide; Kawasaki, Hisashi; Koga, Kenji; Tetrahedron; vol. 53; nb. 17; (1997); p. 5963 - 5972, View in Reaxys
6b*HCl
Pelter; Ward; Sirit; Tetrahedron Asymmetry; vol. 5; nb. 9; (1994); p. 1745 - 1762, View in Reaxys
23
Vries, Erik F. J. de; Steenwinkel, Pablo; Brussee, Johannes; Kruse, Chris G.; Gen, Arne van der; Journal of Organic Chemistry; vol. 58; nb. 16; (1993); p. 4315 - 4325, View in Reaxys
2
Egli, Martin; Dobler, Max; Helvetica Chimica Acta; vol. 72; (1989); p. 1151 - 1157, View in Reaxys
10*HCl
Grunewald; Ye; Journal of Medicinal Chemistry; vol. 31; nb. 10; (1988); p. 1984 - 1986, View in Reaxys
28*HCl
Hua, Duy H.; Chan-Yu-King, Roch; McKie, Jeffrey A.; Myer, Les; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 5026 - 5029, View in Reaxys
7
Claremon; Lumma; Phillips; Journal of the American Chemical Society; vol. 108; nb. 26; (1986); p. 8265 8266, 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
Derivative (1) Derivative (1R,2R)-norpseudoephedrine hydrothiocyanate
References Cruz, Alejandro; Contreras, Rosalinda; Padilla-Martinez, Itzia I.; Juarez-Juarez, Minerva; Tetrahedron Asymmetry; vol. 17; nb. 10; (2006); p. 1499 - 1505, View in Reaxys
Melting Point (3) 1 of 3
Melting Point [°C]
169 - 172
McGhee, Andrea M.; Kizirian, Jean-Claude; Procter, David J.; Organic and Biomolecular Chemistry; vol. 5; nb. 7; (2007); p. 1021 - 1024, View in Reaxys 2 of 3
Melting Point [°C]
180 - 181
Dopke; Schwertner; Pharmazie; vol. 45; nb. 11; (1990); p. 867 - 867, View in Reaxys 3 of 3
Melting Point [°C]
180 - 181
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Solvent (Melting Point)
ethanol
Kanao; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 2553, View in Reaxys Density (1) 1 of 1
Density [g·cm-3]
1.23
Type (Density)
crystallographic
Egli, Martin; Dobler, Max; Helvetica Chimica Acta; vol. 72; (1989); p. 1151 - 1157, View in Reaxys Crystal Phase (1) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination
β=104.6 grad, a=5.44 Angstroem, b=8.05 Angstroem, c=11.99 Angstroem, n=2.; Method of determination: X-ray Diffraction
Egli, Martin; Dobler, Max; Helvetica Chimica Acta; vol. 72; (1989); p. 1151 - 1157, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties Prismen
Kanao; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 2553, View in Reaxys
Crystal System (1) Crystal System References monoclinic
Egli, Martin; Dobler, Max; Helvetica Chimica Acta; vol. 72; (1989); p. 1151 - 1157, View in Reaxys
Interatomic Distances and Angles (1) Description References Interatomic distances and angles
Egli, Martin; Dobler, Max; Helvetica Chimica Acta; vol. 72; (1989); p. 1151 - 1157, View in Reaxys
Mutarotation (1) 1 of 1
Type (Mutarotation)
[alpha]
Concentration (Mutarotation)
p=7
Solvent (Mutarotation)
H2O
Mutarotation [deg]
-42.7
Wavelength (Mutarotation) [nm]
589
Temperature (Mutarotation) [°C]
20
Kanao; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 2553, View in Reaxys Optical Rotatory Power (4) 1 of 4
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
1.2 g/100ml
Solvent (Optical Rotatory Power)
H2O
Optical Rotatory Power [deg]
-21.6
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
20
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McGhee, Andrea M.; Kizirian, Jean-Claude; Procter, David J.; Organic and Biomolecular Chemistry; vol. 5; nb. 7; (2007); p. 1021 - 1024, View in Reaxys 2 of 4
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
7.2 g/100ml
Solvent (Optical Rotatory Power)
H2O
Optical Rotatory Power [deg]
-41.8
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
23
Grunewald; Ye; Journal of Medicinal Chemistry; vol. 31; nb. 10; (1988); p. 1984 - 1986, View in Reaxys 3 of 4
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
1.0 g/100ml
Solvent (Optical Rotatory Power)
H2O
Optical Rotatory Power [deg]
-38.9
Wavelength (Optical Ro- 589 tatory Power) [nm] Claremon; Lumma; Phillips; Journal of the American Chemical Society; vol. 108; nb. 26; (1986); p. 8265 - 8266, View in Reaxys 4 of 4
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
c=1.8
Solvent (Optical Rotatory Power)
H2O
Optical Rotatory Power [deg]
-42.9
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
30
Fles; Markovac-Prpic; Croatica Chemica Acta; vol. 29; (1957); p. 183,185, View in Reaxys Space Group (1) Space Group
References
4
Egli, Martin; Dobler, Max; Helvetica Chimica Acta; vol. 72; (1989); p. 1151 - 1157, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
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McGhee, Andrea M.; Kizirian, Jean-Claude; Procter, David J.; Organic and Biomolecular Chemistry; vol. 5; nb. 7; (2007); p. 1021 - 1024, View in Reaxys 2 of 3
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
McGhee, Andrea M.; Kizirian, Jean-Claude; Procter, David J.; Organic and Biomolecular Chemistry; vol. 5; nb. 7; (2007); p. 1021 - 1024, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
100
McGhee, Andrea M.; Kizirian, Jean-Claude; Procter, David J.; Organic and Biomolecular Chemistry; vol. 5; nb. 7; (2007); p. 1021 - 1024, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
solid
McGhee, Andrea M.; Kizirian, Jean-Claude; Procter, David J.; Organic and Biomolecular Chemistry; vol. 5; nb. 7; (2007); p. 1021 - 1024, View in Reaxys Medchem (1) 1 of 1
Bioassay Category
In Vitro (Efficacy)
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
4299828View in Reaxys
Substance Name
1499336
Qualitative Results
Ki,cl,NmeN=0.84 mM; Ki,l,MPP=3.0 mM; Ki,l,choline=17.5 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
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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