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Showing NP-Card for alpha-((Methylamino)methyl)benzyl alcohol (NP0002723)

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Record Information
Version1.0
Created at2020-11-23 19:38:50 UTC
Updated at2021-08-12 19:51:58 UTC
NP-MRD IDNP0002723
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-((Methylamino)methyl)benzyl alcohol
Provided ByBMRBBMRB logo
Description(1R)-2-(methylamino)-1-phenylethan-1-ol belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on (1R)-2-(methylamino)-1-phenylethan-1-ol (PMID: 31990212).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)


     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.6616    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791    0.8721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -0.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3007   -1.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386   -2.6365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8689   -0.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403    0.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    1.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    1.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4366   -0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -1.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    2.1260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -0.8390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1441    0.4149    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    2.2703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.2366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040    0.4078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702   -2.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -4.0347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    1.2755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812    3.3765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    2.2900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8348   -0.6750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4957   -2.5534    0.0000 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  6
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  1
  3 17  1  0
  4 18  1  1
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

3D MOL for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)

NP0002723
     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.7539    0.6463   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -0.3278    0.3324 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    0.2288    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322   -0.7489    0.6123 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5923   -1.9059   -0.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411   -0.3064    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3427    0.9964    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    1.3629    0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544    0.4049    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868   -0.9165    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9526   -1.2555    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281    1.6634    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588    0.4356    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    0.5834   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -0.6891    1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379    0.4484   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601    1.1835    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477   -1.0851    1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.6181   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    1.7405    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9103    2.4004   -0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6776    0.7156    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -1.6504    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7424   -2.3062    0.6945 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  1
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

3D SDF for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)


     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.6616    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791    0.8721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -0.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3007   -1.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386   -2.6365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8689   -0.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403    0.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    1.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    1.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4366   -0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2670   -1.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    2.1260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -0.8390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1441    0.4149    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359    2.2703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.2366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040    0.4078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4702   -2.4062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -4.0347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    1.2755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812    3.3765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    2.2900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8348   -0.6750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4957   -2.5534    0.0000 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  6
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  1
  3 17  1  0
  4 18  1  1
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
> <DATABASE_ID>
NP0002723

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3/t9-/m0/s1

> <INCHI_KEY>
ZCTYHONEGJTYQV-VIFPVBQESA-N

> <FORMULA>
C9H13NO

> <MOLECULAR_WEIGHT>
151.209

> <EXACT_MASS>
151.099714043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.012686773049865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-2-(methylamino)-1-phenylethan-1-ol

> <JCHEM_LOGP>
0.9012597036666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.121327899503143

> <JCHEM_PKA_STRONGEST_BASIC>
9.434562222633247

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
45.268499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-2-(methylamino)-1-phenylethanol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)

NP0002723
     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.7539    0.6463   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -0.3278    0.3324 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    0.2288    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322   -0.7489    0.6123 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5923   -1.9059   -0.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411   -0.3064    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3427    0.9964    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643    1.3629    0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544    0.4049    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868   -0.9165    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9526   -1.2555    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281    1.6634    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588    0.4356    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    0.5834   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -0.6891    1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379    0.4484   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601    1.1835    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477   -1.0851    1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.6181   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    1.7405    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9103    2.4004   -0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6776    0.7156    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -1.6504    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7424   -2.3062    0.6945 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  1
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
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PDB for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    9   10                                                       
CONECT    8    5    6    9                                                  
CONECT    9    7    8   11                                                  
CONECT   10    1    7                                                       
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)

COMPND    NP0002723
HETATM    1  C1  UNL     1       3.754   0.646  -0.116  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.802  -0.328   0.332  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.473   0.229   0.159  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.432  -0.749   0.612  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.592  -1.906  -0.186  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.941  -0.306   0.473  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.343   0.996   0.274  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.664   1.363   0.147  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.654   0.405   0.218  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.287  -0.916   0.417  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.953  -1.256   0.541  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.428   1.663   0.117  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.759   0.436   0.300  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.797   0.583  -1.240  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.973  -0.689   1.279  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.338   0.448  -0.912  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.460   1.184   0.702  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.648  -1.085   1.649  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.366  -1.618  -1.112  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.576   1.740   0.219  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.910   2.400  -0.007  1.00  0.00           H  
HETATM   22  H11 UNL     1      -4.678   0.716   0.116  1.00  0.00           H  
HETATM   23  H12 UNL     1      -4.074  -1.650   0.470  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.742  -2.306   0.695  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15
CONECT    3    4   16   17
CONECT    4    5    6   18
CONECT    5   19
CONECT    6    7    7   11
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   24
END
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SMILES for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)

CNC[C@H](O)C1=CC=CC=C1
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INCHI for NP0002723 (alpha-((Methylamino)methyl)benzyl alcohol)

InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3/t9-/m0/s1
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SynonymsNot Available
Chemical FormulaC9H13NO
Average Mass151.2090 Da
Monoisotopic Mass151.09971 Da
IUPAC Name(1R)-2-(methylamino)-1-phenylethan-1-ol
Traditional Name(1R)-2-(methylamino)-1-phenylethanol
CAS Registry NumberNot Available
SMILES
CNC[C@H](O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3/t9-/m0/s1
InChI KeyZCTYHONEGJTYQV-VIFPVBQESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.9ChemAxon
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.27 m³·mol⁻¹ChemAxon
Polarizability17.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5323580
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Crawford C, Wang YH, Avula B, Bae JY, Khan IA, Deuster PA: The scoop on brain health dietary supplement products containing huperzine A. Clin Toxicol (Phila). 2020 Oct;58(10):991-996. doi: 10.1080/15563650.2020.1713337. Epub 2020 Jan 28. [PubMed:31990212 ]