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Showing NP-Card for Pseudoephedrine (NP0000736)

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Record Information
Version1.0
Created at2006-05-18 09:17:15 UTC
Updated at2021-10-07 20:41:29 UTC
NP-MRD IDNP0000736
Secondary Accession NumbersNone
Natural Product Identification
Common NamePseudoephedrine
DescriptionPseudoephedrine is a member of the class of phenylethanolamines that is (1S)-2-(methylamino)-1-phenylethan-1-ol in which the pro-S hydrogen at position 2 is replaced by a methyl group. It has a role as a sympathomimetic agent, an anti-asthmatic drug, a bronchodilator agent, a vasoconstrictor agent, a central nervous system drug, a nasal decongestant, a xenobiotic and a plant metabolite. It is a secondary alcohol, a secondary amino compound and a member of phenylethanolamines. It is a conjugate base of a pseudoephedrine(1+). Pseudoephedrine is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as a stimulant, or as a wakefulness-promoting agent in higher doses. It was first characterized in 1889, by the German chemists Ladenburg and Oelschlägel, who used a sample that had been isolated from Ephedra vulgaris by the Merck pharmaceutical corporation of Darmstadt, Germany. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations, either as a single ingredient or (more commonly) in a fixed-dose combination with one or more additional active ingredients such as antihistamines, guaifenesin, dextromethorphan, paracetamol (acetaminophen) or an NSAID (such as aspirin or ibuprofen). At first, pseudoephedrine was known as a natural substance that occurs in shrubs of the Ephedra genus, which grow worldwide. Almost all commercial pseudoephedrine, however, is produced by fermenting dextrose in the presence of benzaldehyde. The primary product, (R)-phenylacetylcarbinol, is aminated to make pseudoephedrine. Pseudoephedrine acts on α- and β2-adrenergic receptors, to cause vasoconstriction and relaxation of smooth muscle in the bronchi, respectively. α-Adrenergic receptors are located on the muscles lining the walls of blood vessels. When these receptors are activated, the muscles contract, causing the blood vessels to constrict (vasoconstriction). The constricted blood vessels now allow less fluid to leave the blood vessels and enter the nose, throat and sinus linings, which results in decreased inflammation of nasal membranes, as well as decreased mucus production. Thus, by constriction of blood vessels, mainly those located in the nasal passages, pseudoephedrine causes a decrease in the symptoms of nasal congestion. Activation of β2-adrenergic receptors produces relaxation of smooth muscle of the bronchi, causing bronchial dilation and in turn decreasing congestion (although not fluid) and difficulty breathing.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000736 (Pseudoephedrine)

852
  Mrv1652305271900272D          

 12 12  0  0  1  0            999 V2000
    1.6500    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  6  0  0  0
  3  2  1  1  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000736 (Pseudoephedrine)

HMDB0001943
     RDKit          3D
Pseudoephedrine
 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.8217    0.4854   -1.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6066   -0.0554   -0.6635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2120    0.3935    0.6333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2286    0.0017    1.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -0.2818    1.0001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1797   -1.6693    0.9919 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718   -0.0520    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    0.9587   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884    1.0979   -1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456    0.2413   -1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3129   -0.7743   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2438   -0.9255    0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888    0.7246   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413   -0.2527   -1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080    1.4472   -1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4001   -1.0285   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674    1.4825    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    0.8283    2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.3240    1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644   -0.8647    2.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.0458    2.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536   -2.0954    0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    1.6347   -0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2380    1.9347   -2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766    0.3423   -2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742   -1.4511   -0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -1.7523    0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  6
  4 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  1
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
M  END
Download

3D SDF for NP0000736 (Pseudoephedrine)

852
  Mrv1652305271900272D          

 12 12  0  0  1  0            999 V2000
    1.6500    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  6  0  0  0
  3  2  1  1  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H](C)[C@@H](O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1

> <INCHI_KEY>
KWGRBVOPPLSCSI-WCBMZHEXSA-N

> <FORMULA>
C10H15NO

> <MOLECULAR_WEIGHT>
165.2322

> <EXACT_MASS>
165.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.826538197427055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
1.3178347283333334

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.889531450472283

> <JCHEM_PKA_STRONGEST_BASIC>
9.524908674853327

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
49.68730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pseudoephedrine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000736 (Pseudoephedrine)

HMDB0001943
     RDKit          3D
Pseudoephedrine
 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.8217    0.4854   -1.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6066   -0.0554   -0.6635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2120    0.3935    0.6333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2286    0.0017    1.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -0.2818    1.0001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1797   -1.6693    0.9919 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718   -0.0520    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    0.9587   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884    1.0979   -1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456    0.2413   -1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3129   -0.7743   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2438   -0.9255    0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888    0.7246   -0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413   -0.2527   -1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6080    1.4472   -1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4001   -1.0285   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674    1.4825    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    0.8283    2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869   -0.3240    1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644   -0.8647    2.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413   -0.0458    2.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536   -2.0954    0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    1.6347   -0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2380    1.9347   -2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766    0.3423   -2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1742   -1.4511   -0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -1.7523    0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  6
  4 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  1
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
M  END
Download

PDB for NP0000736 (Pseudoephedrine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 852                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       3.080   1.540   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    3    9                                                       
CONECT    3    2    4    6                                                  
CONECT    4    1    3    5                                                  
CONECT    5    4    7    8                                                  
CONECT    6    3                                                            
CONECT    7    5   10                                                       
CONECT    8    5   11                                                       
CONECT    9    2                                                            
CONECT   10    7   12                                                       
CONECT   11    8   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000736 (Pseudoephedrine)

COMPND    HMDB0001943
HETATM    1  C1  UNL     1      -2.822   0.485  -1.170  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.607  -0.055  -0.664  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.212   0.393   0.633  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.229   0.002   1.710  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.076  -0.282   1.000  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.180  -1.669   0.992  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.172  -0.052   0.051  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.214   0.959  -0.879  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.288   1.098  -1.734  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.346   0.241  -1.691  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.313  -0.774  -0.764  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.244  -0.926   0.099  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.589   0.725  -0.430  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.241  -0.253  -1.902  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.608   1.447  -1.722  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.400  -1.028  -0.895  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.167   1.482   0.637  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.423   0.828   2.414  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.187  -0.324   1.271  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.864  -0.865   2.318  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.441  -0.046   2.020  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.154  -2.095   0.163  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.392   1.635  -0.920  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.238   1.935  -2.446  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.177   0.342  -2.346  1.00  0.00           H  
HETATM   26  H14 UNL     1       4.174  -1.451  -0.749  1.00  0.00           H  
HETATM   27  H15 UNL     1       2.301  -1.752   0.794  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16
CONECT    3    4    5   17
CONECT    4   18   19   20
CONECT    5    6    7   21
CONECT    6   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   27
END
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SMILES for NP0000736 (Pseudoephedrine)

CN[C@@H](C)[C@@H](O)C1=CC=CC=C1
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INCHI for NP0000736 (Pseudoephedrine)

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
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Synonyms
ValueSource
(+) Threo-2-(methylamino)-1-phenyl-1-propanolChEBI
(+)-(1S,2S)-PseudoephedrineChEBI
(+)-PseudoephedrineChEBI
(+)-Psi-ephedrineChEBI
(+)-Threo-ephedrineChEBI
(1S,2S)-(+)-PseudoephedrineChEBI
(1S,2S)-PseudoephedrineChEBI
2-(Methylamino)-1-phenyl-1-propanolChEBI
D-IsoephedrineChEBI
D-PseudoephedrineChEBI
D-Psi-2-methylamino-1-phenyl-1-propanolChEBI
D-Psi-ephedrineChEBI
IsoephedrineChEBI
L(+)-Psi-ephedrineChEBI
L-(+)-PseudoephedrineChEBI
PseudoefedrinaChEBI
Pseudoephedrine D-formChEBI
PseudoephedrinumChEBI
Psi-ephedrinChEBI
Psi-ephedrineChEBI
trans-EphedrineChEBI
(1S,2S)-2-(Methylamino)-1-phenylpropan-1-olKegg
NeodurasinaKegg
AcunasoKegg
1-EphedrineHMDB
BesanHMDB
D-Pseudoephedrine baseHMDB
NovafedHMDB
Pseudoephedrine ephedrineHMDB
SudafedHMDB
Ephedrine threo isomerHMDB
Pseudoephedrine HCLHMDB
Threo isomer OF ephedrineHMDB
Pseudoephedrine hydrochlorideHMDB
Chemical FormulaC10H15NO
Average Mass165.2322 Da
Monoisotopic Mass165.11536 Da
IUPAC Name(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
Traditional Namepseudoephedrine
CAS Registry Number90-82-4
SMILES
CN[C@@H](C)[C@@H](O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
InChI KeyKWGRBVOPPLSCSI-WCBMZHEXSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ephedra californicaLOTUS Database
Ephedra ciliata SAM.KNApSAcK Database
Ephedra distachyaPlant
Ephedra distachya L.KNApSAcK Database
Ephedra equisetinaPlant
Ephedra equisetina Bge.KNApSAcK Database
Ephedra foliataLOTUS Database
Ephedra gerardianaKNApSAcK Database
Ephedra helveticaPlant
Ephedra intermediaKNApSAcK Database
Ephedra L. NULL
    • Ueber das "Pseudo-Ephedrin" [On pseudo-ephedrine]. Berichte der Deutschen Chemischen Gesellschaft...
Ephedra majorPlant
Ephedra nebrodensisKNApSAcK Database
Ephedra pachycladaLOTUS Database
Ephedra pachyclada BoissPlant
Ephedra procera var.chrysocarpa.KNApSAcK Database
Ephedra przewalskiiLOTUS Database
Ephedra sincaKNApSAcK Database
Ephedra sinicaKNApSAcK Database
Ephedra spp.KNApSAcK Database
Ephedra vulgarisPlant
Hamelia patensPlant
Roemeria refractaKNApSAcK Database
Sida rhombifoliaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.89Kril, M. B., & Fung, H. L. (1990). Influence of hydrophobicity on the ion exchange selectivity coefficients for aromatic amines. Journal of pharmaceutical sciences, 79(5), 440-443.
Predicted Properties
PropertyValueSource
Water Solubility8.26 g/LALOGPS
logP1ALOGPS
logP1.32ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.69 m³·mol⁻¹ChemAxon
Polarizability18.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001943
DrugBank IDDB00852
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022758
KNApSAcK IDC00031097
Chemspider ID6761
KEGG Compound IDC02765
BioCyc IDCPD-9954
BiGG IDNot Available
Wikipedia LinkPseudoephedrine
METLIN ID2189
PubChem Compound7028
PDB IDNot Available
ChEBI ID51209
Good Scents IDNot Available
References
General References
  1. Strindelius LC, Nation RL, Evans AM, Cabot JL, Corbett KM: Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat. Clin Exp Pharmacol Physiol. 2001 Jan-Feb;28(1-2):43-7. doi: 10.1046/j.1440-1681.2001.03393.x. [PubMed:11153535 ]
  2. Gonzalo-Garijo MA, Perez-Calderon R, de Argila D, Rodriguez-Nevado I: Erythrodermia to pseudoephedrine in a patient with contact allergy to phenylephrine. Allergol Immunopathol (Madr). 2002 Jul-Aug;30(4):239-42. doi: 10.1016/s0301-0546(02)79127-1. [PubMed:12199969 ]
  3. Authors unspecified: Gastroschisis and pseudoephedrine during pregnancy. Prescrire Int. 2004 Aug;13(72):141-3. [PubMed:15532139 ]
  4. Kendirli T, Kismet E, Atay AA, Akin R, Kurekci AE, Koseoglu V: Stroke associated with pseudoephedrine in a child with rhabdomyosarcoma. J Clin Neurosci. 2006 Jan;13(1):109-11. doi: 10.1016/j.jocn.2004.11.024. [PubMed:16410207 ]
  5. Hodges K, Hancock S, Currell K, Hamilton B, Jeukendrup AE: Pseudoephedrine enhances performance in 1500-m runners. Med Sci Sports Exerc. 2006 Feb;38(2):329-33. doi: 10.1249/01.mss.0000183201.79330.9c. [PubMed:16531903 ]