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Showing metabocard for 2'-Hydroxynicotine (HMDB0001329)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:36 UTC
HMDB IDHMDB0001329
Secondary Accession Numbers
  • HMDB01329
Metabolite Identification
Common Name2'-Hydroxynicotine
Description2'-Hydroxynicotine is a metabolite produced from the degradation of nicotine, an alkaloid found in the nightshade family of plants (Solanaceae), predominantly in tobacco, and in lower quantities in tomato, potato, eggplant (aubergine), and green pepper. Cytochrome P450 2A6 (EC 1.14.14.1) metabolizes nicotine via 2'-hydroxylation into 4-(methylamino)-1-(3-pyridyl)-1-butanone with 2'-hydroxynicotine as an intermediate (PMID: 11050152 ). 2'-Hydroxynicotine spontaneously yields nicotine-Δ1′(2′)-iminium ion, which is in equilibrium with 4-(methylamino)-1-(3-pyridyl)-1-butanone (PMID: 15734728 ). About 10% of nicotine and its metabolites are excreted as 4-oxo-4-(3-pyridyl)butanoate (keto acid) and 4-hydroxy-4-(3-pyridyl)butanoate (hydroxy acid) in the urine of smokers (PMID: 10548320 ).
Structure
Data?1676999736
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001329 (2'-Hydroxynicotine)

            
  Mrv1652305111819132D          

 13 14  0  0  0  0            999 V2000
   -2.3390    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535    0.5363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681    0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681   -0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0536   -1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390   -0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -0.3786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683   -0.7775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160   -1.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6219   -1.1132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7287   -2.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355   -1.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6969    0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
  6 10  1  0  0  0  0
 10  7  1  6  0  0  0
  8 13  1  0  0  0  0
M  END
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3D MOL for HMDB0001329 (2'-Hydroxynicotine)

HMDB0001329
     RDKit          3D
2'-Hydroxynicotine
 27 28  0  0  0  0  0  0  0  0999 V2000
   -0.8904    1.2704    1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3262    0.0084    0.8551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5851    0.0043    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.1193   -1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -1.0809   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948   -0.7742    0.1252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3219   -2.0223    0.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507   -0.2142   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0664   -0.8262    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3415   -0.2755    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    0.8992   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088    1.4802   -0.8705 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    0.9574   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2782    2.1454    0.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774    1.4199    2.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889    1.3310    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2247    0.8691    0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033   -0.9609    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0479   -0.5422   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541    0.8798   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4643   -2.0951   -1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3198   -0.9120   -2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966   -1.7722    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9436   -1.7359    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -0.7407    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5062    1.3410   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    1.4655   -1.1496 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
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  2  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
M  END
Download

3D SDF for HMDB0001329 (2'-Hydroxynicotine)

            
  Mrv1652305111819132D          

 13 14  0  0  0  0            999 V2000
   -2.3390    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535    0.5363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681    0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681   -0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0536   -1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390   -0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -0.3786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683   -0.7775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160   -1.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6219   -1.1132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7287   -2.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355   -1.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6969    0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
  6 10  1  0  0  0  0
 10  7  1  6  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001329

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC[C@@]1(O)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O/c1-12-7-3-5-10(12,13)9-4-2-6-11-8-9/h2,4,6,8,13H,3,5,7H2,1H3/t10-/m1/s1

> <INCHI_KEY>
BOQRPPFUUSHFGW-SNVBAGLBSA-N

> <FORMULA>
C10H14N2O

> <MOLECULAR_WEIGHT>
178.235

> <EXACT_MASS>
178.110613079

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.352886462170662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-2-ol

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
0.7441491849999999

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.32230496779479

> <JCHEM_PKA_STRONGEST_BASIC>
7.1079633045067325

> <JCHEM_POLAR_SURFACE_AREA>
36.36000000000001

> <JCHEM_REFRACTIVITY>
51.23270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001329 (2'-Hydroxynicotine)

HMDB0001329
     RDKit          3D
2'-Hydroxynicotine
 27 28  0  0  0  0  0  0  0  0999 V2000
   -0.8904    1.2704    1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3262    0.0084    0.8551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5851    0.0043    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.1193   -1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -1.0809   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948   -0.7742    0.1252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3219   -2.0223    0.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507   -0.2142   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0664   -0.8262    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3415   -0.2755    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    0.8992   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088    1.4802   -0.8705 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    0.9574   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2782    2.1454    0.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774    1.4199    2.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889    1.3310    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2247    0.8691    0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033   -0.9609    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0479   -0.5422   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9541    0.8798   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4643   -2.0951   -1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3198   -0.9120   -2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966   -1.7722    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9436   -1.7359    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -0.7407    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5062    1.3410   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    1.4655   -1.1496 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
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  2  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
M  END
Download

PDB for HMDB0001329 (2'-Hydroxynicotine)

HEADER    PROTEIN                                 11-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-MAY-18         0                                  
HETATM    1  C   UNK     0      -4.366   0.231   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -5.700   1.001   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -7.034   0.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.034  -1.308   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.700  -2.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.366  -1.308   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.035  -0.707   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -1.621  -1.451   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.590  -2.596   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.027  -2.078   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.360  -3.929   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.866  -3.609   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.301   0.054   0.000  0.00  0.00           C+0
CONECT    1    6    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1   10                                                  
CONECT    7   10                                                            
CONECT    8    9   10   13                                                  
CONECT    9    8   11                                                       
CONECT   10    8   12    6    7                                             
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0001329 (2'-Hydroxynicotine)

COMPND    HMDB0001329
HETATM    1  C1  UNL     1      -0.890   1.270   1.335  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.326   0.008   0.855  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.585   0.004   0.182  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.199  -0.119  -1.295  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.044  -1.081  -1.227  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.395  -0.774   0.125  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.322  -2.022   0.789  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.951  -0.214  -0.032  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.066  -0.826   0.498  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.341  -0.276   0.336  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.506   0.899  -0.363  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.409   1.480  -0.871  1.00  0.00           N  
HETATM   13  C10 UNL     1       1.170   0.957  -0.721  1.00  0.00           C  
HETATM   14  H1  UNL     1      -1.278   2.145   0.733  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.377   1.420   2.345  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.189   1.331   1.504  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.225   0.869   0.365  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.103  -0.961   0.436  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.048  -0.542  -1.894  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.954   0.880  -1.650  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.464  -2.095  -1.272  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.320  -0.912  -2.055  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.097  -1.772   1.739  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.944  -1.736   1.039  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.230  -0.741   0.743  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.506   1.341  -0.496  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.316   1.465  -1.150  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    6
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    8
CONECT    7   23
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13
CONECT   13   27
END
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SMILES for HMDB0001329 (2'-Hydroxynicotine)

CN1CCC[C@@]1(O)C1=CC=CN=C1
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INCHI for HMDB0001329 (2'-Hydroxynicotine)

InChI=1S/C10H14N2O/c1-12-7-3-5-10(12,13)9-4-2-6-11-8-9/h2,4,6,8,13H,3,5,7H2,1H3/t10-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-HydroxynicotineHMDB
Chemical FormulaC10H14N2O
Average Molecular Weight178.235
Monoisotopic Molecular Weight178.110613079
IUPAC Name(2R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-2-ol
Traditional Name(2R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-2-ol
CAS Registry Number1824020-12-3
SMILES
CN1CCC[C@@]1(O)C1=CC=CN=C1
InChI Identifier
InChI=1S/C10H14N2O/c1-12-7-3-5-10(12,13)9-4-2-6-11-8-9/h2,4,6,8,13H,3,5,7H2,1H3/t10-/m1/s1
InChI KeyBOQRPPFUUSHFGW-SNVBAGLBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct ParentPyrrolidinylpyridines
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • N-alkylpyrrolidine
  • Heteroaromatic compound
  • Pyrrolidine
  • Azacycle
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022558
KNApSAcK IDNot Available
Chemspider ID19951246
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6164
PubChem Compound23615292
PDB IDNot Available
ChEBI ID173488
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hecht SS, Hochalter JB, Villalta PW, Murphy SE: 2'-Hydroxylation of nicotine by cytochrome P450 2A6 and human liver microsomes: formation of a lung carcinogen precursor. Proc Natl Acad Sci U S A. 2000 Nov 7;97(23):12493-7. doi: 10.1073/pnas.220207697. [PubMed:11050152 ]
  2. Hukkanen J, Jacob P 3rd, Benowitz NL: Metabolism and disposition kinetics of nicotine. Pharmacol Rev. 2005 Mar;57(1):79-115. doi: 10.1124/pr.57.1.3. [PubMed:15734728 ]
  3. Hecht SS, Carmella SG, Murphy SE: Effects of watercress consumption on urinary metabolites of nicotine in smokers. Cancer Epidemiol Biomarkers Prev. 1999 Oct;8(10):907-13. [PubMed:10548320 ]