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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (18)transporters (2) Show 20 proteins XML

enzymes (18)transporters (2) Show 20 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2020-02-26 21:40:07 UTC

HMDB ID

HMDB0014680

Secondary Accession Numbers

HMDB14680

Metabolite Identification

Common Name

Nortriptyline

Description

Nortriptyline hydrochloride, the N-demethylated active metabolite of amitriptyline, is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, nortriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, nortriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H₁ receptors, α₁-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Nortriptyline exerts less anticholinergic and sedative side effects compared to the tertiary amine TCAs, amitriptyline and clomipramine. Nortriptyline may be used to treat depression, chronic pain (unlabeled use), irritable bowel syndrome (unlabeled use), diabetic neuropathy (unlabeled use), post-traumatic stress disorder (unlabeled use), and for migraine prophylaxis (unlabeled use).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014680
     RDKit          3D
Nortriptyline
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.9414    1.1519   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865   -0.0159   -1.5336 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -1.0981   -1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6840   -0.9921   -1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9153    0.0083   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    0.0082   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6084    1.3251    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346    2.1016    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475    3.3644    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    3.7642    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349    2.9408    0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669    1.6886    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298    0.9254   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -0.4640    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1921   -1.4189    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464   -2.7161    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666   -3.7339    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4131   -3.5139    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -2.2655    0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -1.2229    0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3945    2.0160   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    0.9237    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229    1.4978   -0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973   -0.1667   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -2.0483   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -1.3607   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813   -1.9682   -1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -0.6428   -2.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210    1.0473   -1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    1.7018    0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605    3.9983    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    4.7606    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2549    3.2705    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    0.9567   -1.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597    1.4889    0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.9130   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148   -0.4921    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7338   -2.8270    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1158   -4.7361    1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154   -4.3228    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991   -2.0211    0.3281 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  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

540
  Mrv0541 02231214452D          

 20 22  0  0  0  0            999 V2000
    2.5991   -1.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4402    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9546    1.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010    1.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279    0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7710    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2845    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0279   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715    2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840    2.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3134   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4059    1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  2  0  0  0  0
  5  8  1  0  0  0  0
  5 11  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 12  2  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014680

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-11,20H,6,12-14H2,1H3

> <INCHI_KEY>
PHVGLTMQBUFIQQ-UHFFFAOYSA-N

> <FORMULA>
C19H21N

> <MOLECULAR_WEIGHT>
263.3767

> <EXACT_MASS>
263.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
31.87459039075684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.426486977666667

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.471608936862953

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
96.21250000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nortriptyline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014680
     RDKit          3D
Nortriptyline
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.9414    1.1519   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865   -0.0159   -1.5336 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -1.0981   -1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6840   -0.9921   -1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9153    0.0083   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    0.0082   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6084    1.3251    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346    2.1016    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475    3.3644    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    3.7642    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349    2.9408    0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669    1.6886    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298    0.9254   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -0.4640    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1921   -1.4189    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464   -2.7161    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666   -3.7339    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4131   -3.5139    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -2.2655    0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -1.2229    0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3945    2.0160   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    0.9237    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229    1.4978   -0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973   -0.1667   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -2.0483   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -1.3607   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813   -1.9682   -1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -0.6428   -2.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210    1.0473   -1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    1.7018    0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605    3.9983    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    4.7606    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2549    3.2705    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    0.9567   -1.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597    1.4889    0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.9130   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148   -0.4921    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7338   -2.8270    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1158   -4.7361    1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154   -4.3228    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991   -2.0211    0.3281 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  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 540                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       4.852  -3.226   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.288   4.766   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.749   4.766   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.249   3.562   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.789   3.562   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.519   1.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.906   2.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.131   2.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.519  -0.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.774   4.058   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.263   4.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.065   0.952   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.973   0.952   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.185  -0.917   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.958   2.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   2.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.185  -2.456   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.601   1.413   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.436   1.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.852  -4.766   0.000  0.00  0.00           C+0
CONECT    1   17   20                                                       
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7   10                                                  
CONECT    5    3    8   11                                                  
CONECT    6    7    8    9                                                  
CONECT    7    4    6   12                                                  
CONECT    8    5    6   13                                                  
CONECT    9    6   14                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    7   18                                                       
CONECT   13    8   19                                                       
CONECT   14    9   17                                                       
CONECT   15   10   18                                                       
CONECT   16   11   19                                                       
CONECT   17    1   14                                                       
CONECT   18   12   15                                                       
CONECT   19   13   16                                                       
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0014680
HETATM    1  C1  UNL     1       3.941   1.152  -0.756  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.986  -0.016  -1.534  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.130  -1.098  -1.286  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.684  -0.992  -1.607  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.915   0.008  -0.901  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.121   0.008  -0.124  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.608   1.325   0.392  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.435   2.102   0.774  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.148   3.364   1.265  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.196   3.764   1.339  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.235   2.941   0.937  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.967   1.689   0.448  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.130   0.925  -0.005  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.309  -0.464   0.402  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.192  -1.419   0.406  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.646  -2.716   0.714  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.767  -3.734   0.847  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.413  -3.514   0.686  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.065  -2.265   0.387  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.816  -1.223   0.242  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.394   2.016  -1.144  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.595   0.924   0.291  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.023   1.498  -0.553  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.797  -0.167  -2.142  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.575  -2.048  -1.753  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.252  -1.361  -0.175  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.181  -1.968  -1.766  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.722  -0.643  -2.754  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.321   1.047  -1.089  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.447   1.702   0.680  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.960   3.998   1.575  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.407   4.761   1.729  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.255   3.270   1.004  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.152   0.957  -1.135  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.060   1.489   0.297  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.150  -0.913  -0.201  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.715  -0.492   1.479  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.734  -2.827   0.830  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.116  -4.736   1.083  1.00  0.00           H  
HETATM   40  H20 UNL     1       0.315  -4.323   0.792  1.00  0.00           H  
HETATM   41  H21 UNL     1       1.099  -2.021   0.328  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6    6   29
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20   41
END

HMDB0014680
     RDKit          3D
Nortriptyline
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.9414    1.1519   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865   -0.0159   -1.5336 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1300   -1.0981   -1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6840   -0.9921   -1.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9153    0.0083   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    0.0082   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6084    1.3251    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346    2.1016    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475    3.3644    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    3.7642    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349    2.9408    0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669    1.6886    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298    0.9254   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3092   -0.4640    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1921   -1.4189    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6464   -2.7161    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666   -3.7339    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4131   -3.5139    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654   -2.2655    0.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8162   -1.2229    0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3945    2.0160   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    0.9237    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229    1.4978   -0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973   -0.1667   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -2.0483   -1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -1.3607   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813   -1.9682   -1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -0.6428   -2.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210    1.0473   -1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473    1.7018    0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605    3.9983    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    4.7606    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2549    3.2705    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    0.9567   -1.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597    1.4889    0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1499   -0.9130   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148   -0.4921    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7338   -2.8270    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1158   -4.7361    1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154   -4.3228    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0991   -2.0211    0.3281 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  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-Delta(5,gamma)-propylamine	ChEBI
3-(10,11-Dihydro-5H-dibenzo[a,D]cyclohepten-5-ylidene)-N-methyl-1-propanamine	ChEBI
Ateben	ChEBI
Avantyl	ChEBI
Aventyl	ChEBI
Demethylamitriptyline	ChEBI
Desmethylamitriptyline	ChEBI
Noritren	ChEBI
Nortriptylina	ChEBI
Nortriptylinum	ChEBI
Psychostyl	ChEBI
Sensaval	ChEBI
Nortrilen	Kegg
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-delta(5,g)-propylamine	Generator
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-δ(5,γ)-propylamine	Generator
10,11-Dihydro-N-methyl-5H-dibenzo[a,D]cycloheptene-δ(5,g)-propylamine	HMDB
Apo nortriptyline	HMDB
Desmethylamitriptylin	HMDB
Gen nortriptyline	HMDB
Lundbeck brand OF nortriptyline hydrochloride	HMDB
Novo nortriptyline	HMDB
Novopharm brand OF nortriptyline hydrochloride	HMDB
Reig jofre brand OF nortriptyline hydrochloride	HMDB
Apotex brand OF nortriptyline hydrochloride	HMDB
Genpharm brand OF nortriptyline hydrochloride	HMDB
Hydrochloride, nortriptyline	HMDB
Nortriptyline hydrochloride	HMDB
Novo-nortriptyline	HMDB
PMS-Nortriptyline	HMDB
Ratio nortriptyline	HMDB
Allegron	HMDB
Apo-nortriptyline	HMDB
Dista brand OF nortriptyline hydrochloride	HMDB
Gen-nortriptyline	HMDB
Lilly brand OF nortriptyline hydrochloride	HMDB
Nu-pharm brand OF nortriptyline hydrochloride	HMDB
PMS Nortriptyline	HMDB
Pamelor	HMDB
Pharmascience brand OF nortriptyline hydrochloride	HMDB
Desitriptyline	HMDB
Mallinckrodt brand OF nortriptyline hydrochloride	HMDB
Norfenazin	HMDB
Nu nortriptyline	HMDB
Nu pharm brand OF nortriptyline hydrochloride	HMDB
Nu-nortriptyline	HMDB
Paxtibi	HMDB
Ratiopharm brand OF nortriptyline hydrochloride	HMDB
Ratio-nortriptyline	HMDB

Chemical Formula

C₁₉H₂₁N

Average Molecular Weight

263.3767

Monoisotopic Molecular Weight

263.167399677

IUPAC Name

methyl(3-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

Traditional Name

nortriptyline

CAS Registry Number

72-69-5

SMILES

CNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-11,20H,6,12-14H2,1H3

InChI Key

PHVGLTMQBUFIQQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Dibenzocycloheptenes

Sub Class

Not Available

Direct Parent

Dibenzocycloheptenes

Alternative Parents

Substituents

Dibenzocycloheptene
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organic tricyclic compound (CHEBI:7640 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Kidney (HMDB: HMDB0014680)
Liver (HMDB: HMDB0014680)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014680)

Endogenous

Endogenous (HMDB: HMDB0014680)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0014680)

Biological role

Drug metabolite (HMDB: HMDB0014680)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213 - 215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00087 g/L	Not Available
LogP	4.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	163.081	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000745

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00087 g/L	ALOGPS
logP	4.65	ALOGPS
logP	4.43	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	10.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.21 m³·mol⁻¹	ChemAxon
Polarizability	31.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.261	31661259
DarkChem	[M-H]-	163.855	31661259
DeepCCS	[M-2H]-	191.88	30932474
DeepCCS	[M+Na]+	167.445	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	160.7	32859911
AllCCS	[M+NH4]+	167.7	32859911
AllCCS	[M+Na]+	168.7	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	170.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.95 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9879 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1732.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	479.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	474.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	310.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1253.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	490.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1295.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	295.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	256.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nortriptyline	CNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	3057.3	Standard polar	33892256
Nortriptyline	CNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2241.2	Standard non polar	33892256
Nortriptyline	CNCCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2219.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nortriptyline,1TMS,isomer #1	CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C	2529.5	Semi standard non polar	33892256
Nortriptyline,1TMS,isomer #1	CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C	2579.1	Standard non polar	33892256
Nortriptyline,1TMS,isomer #1	CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C	2942.5	Standard polar	33892256
Nortriptyline,1TBDMS,isomer #1	CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2731.5	Semi standard non polar	33892256
Nortriptyline,1TBDMS,isomer #1	CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2848.1	Standard non polar	33892256
Nortriptyline,1TBDMS,isomer #1	CN(CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3050.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Nortriptyline EI-B (Non-derivatized)	splash10-0006-9000000000-bb9eae4818c0402317ee	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Nortriptyline EI-B (Non-derivatized)	splash10-0006-9000000000-bb9eae4818c0402317ee	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nortriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9040000000-03aa30e0f3d1715d991e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nortriptyline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nortriptyline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9230000000-15f73e5232a0e230f41b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QTOF , positive-QTOF	splash10-05nf-5970000000-f92c7d23474b57a4ba50	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-03di-0090000000-4c40cb3ec4df8809981e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-06sl-2590000000-be2abd28b2b0f75dd8bb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-05mo-3940000000-6a454924ec75665c6175	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-05mo-3930000000-eb8141866b19782dd1e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-00kf-4930000000-81614e655fc32d5839ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-00kf-4930000000-f918306a99d07f887503	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-0gdl-5930000000-d876ab376d0e9885d06d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-0gb9-5930000000-e51a246750bf8ce7e4ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline LC-ESI-QFT , positive-QTOF	splash10-0gbi-5930000000-c2811578219a3a7e1ccf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline , positive-QTOF	splash10-03yi-0490000000-094e7bdb831aed030f5f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline 75V, Positive-QTOF	splash10-00kf-4930000000-fb69faeba7a357c5bc5a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline 90V, Positive-QTOF	splash10-00kf-4930000000-76afa553a0a96ca36196	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline 30V, Positive-QTOF	splash10-06sl-2590000000-8294a4644460a638747b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline 15V, Positive-QTOF	splash10-03di-0090000000-ff969015b0f97e8c78bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline 45V, Positive-QTOF	splash10-05mo-3940000000-2244b5f59802d5d17a11	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline 60V, Positive-QTOF	splash10-05mo-3930000000-ae25ca0dbf191a8decb7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nortriptyline -1V, Positive-QTOF	splash10-05nf-5970000000-279d8674cee6125e1363	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nortriptyline 10V, Positive-QTOF	splash10-03e9-1090000000-0122fb1ff7e4f061277f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nortriptyline 20V, Positive-QTOF	splash10-01qc-3290000000-820f6bab951ae7e9352d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nortriptyline 40V, Positive-QTOF	splash10-0006-6950000000-d6a7a0dcc07c2ab8c35f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nortriptyline 10V, Negative-QTOF	splash10-03di-0090000000-6586d2d06dd2491b85d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nortriptyline 20V, Negative-QTOF	splash10-03di-1090000000-3af72990a6e6a4c9e3ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nortriptyline 40V, Negative-QTOF	splash10-001l-4290000000-05af30a36ff956182b21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nortriptyline 10V, Positive-QTOF	splash10-03di-0090000000-0f92e6ab1c1e69d00ae5	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00540	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00540	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00540

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4384

KEGG Compound ID

C07274

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nortriptyline

METLIN ID

Not Available

PubChem Compound

4543

PDB ID

Not Available

ChEBI ID

7640

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Prochazka AV, Weaver MJ, Keller RT, Fryer GE, Licari PA, Lofaso D: A randomized trial of nortriptyline for smoking cessation. Arch Intern Med. 1998 Oct 12;158(18):2035-9. [PubMed:9778204 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Nortriptyline E-10-hydroxylation in vitro is mediated by human CYP2D6 (high affinity) and CYP3A4 (low affinity): implications for interactions with enzyme-inducing drugs. J Clin Pharmacol. 1999 Jun;39(6):567-77. [PubMed:10354960 ]

Enzyme Details

3. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

4. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Olesen OV, Linnet K: Hydroxylation and demethylation of the tricyclic antidepressant nortriptyline by cDNA-expressed human cytochrome P-450 isozymes. Drug Metab Dispos. 1997 Jun;25(6):740-4. [PubMed:9193876 ]

Enzyme Details

5. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Nortriptyline E-10-hydroxylation in vitro is mediated by human CYP2D6 (high affinity) and CYP3A4 (low affinity): implications for interactions with enzyme-inducing drugs. J Clin Pharmacol. 1999 Jun;39(6):567-77. [PubMed:10354960 ]
Olesen OV, Linnet K: Hydroxylation and demethylation of the tricyclic antidepressant nortriptyline by cDNA-expressed human cytochrome P-450 isozymes. Drug Metab Dispos. 1997 Jun;25(6):740-4. [PubMed:9193876 ]

Enzyme Details

7. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]

Enzyme Details

8. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wen B, Ma L, Zhu M: Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67. doi: 10.1016/j.cbi.2008.02.001. Epub 2008 Feb 14. [PubMed:18359012 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Olesen OV, Linnet K: Hydroxylation and demethylation of the tricyclic antidepressant nortriptyline by cDNA-expressed human cytochrome P-450 isozymes. Drug Metab Dispos. 1997 Jun;25(6):740-4. [PubMed:9193876 ]

Enzyme Details

9. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

10. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Roubert C, Cox PJ, Bruss M, Hamon M, Bonisch H, Giros B: Determination of residues in the norepinephrine transporter that are critical for tricyclic antidepressant affinity. J Biol Chem. 2001 Mar 16;276(11):8254-60. Epub 2000 Nov 22. [PubMed:11092898 ]
Roubert C, Sagne C, Kapsimali M, Vernier P, Bourrat F, Giros B: A Na(+)/Cl(-)-dependent transporter for catecholamines, identified as a norepinephrine transporter, is expressed in the brain of the teleost fish medaka (Oryzias latipes). Mol Pharmacol. 2001 Sep;60(3):462-73. [PubMed:11502876 ]
Vaishnavi SN, Nemeroff CB, Plott SJ, Rao SG, Kranzler J, Owens MJ: Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55(3):320-2. [PubMed:14744476 ]
Kim H, Lim SW, Kim S, Kim JW, Chang YH, Carroll BJ, Kim DK: Monoamine transporter gene polymorphisms and antidepressant response in koreans with late-life depression. JAMA. 2006 Oct 4;296(13):1609-18. [PubMed:17018806 ]
Barker EL, Blakely RD: Identification of a single amino acid, phenylalanine 586, that is responsible for high affinity interactions of tricyclic antidepressants with the human serotonin transporter. Mol Pharmacol. 1996 Oct;50(4):957-65. [PubMed:8863842 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Joyce PR, Mulder RT, Luty SE, McKenzie JM, Miller AL, Rogers GR, Kennedy MA: Age-dependent antidepressant pharmacogenomics: polymorphisms of the serotonin transporter and G protein beta3 subunit as predictors of response to fluoxetine and nortriptyline. Int J Neuropsychopharmacol. 2003 Dec;6(4):339-46. [PubMed:14604448 ]
Wisner KL, Hanusa BH, Perel JM, Peindl KS, Piontek CM, Sit DK, Findling RL, Moses-Kolko EL: Postpartum depression: a randomized trial of sertraline versus nortriptyline. J Clin Psychopharmacol. 2006 Aug;26(4):353-60. [PubMed:16855451 ]
Pollock BG, Ferrell RE, Mulsant BH, Mazumdar S, Miller M, Sweet RA, Davis S, Kirshner MA, Houck PR, Stack JA, Reynolds CF, Kupfer DJ: Allelic variation in the serotonin transporter promoter affects onset of paroxetine treatment response in late-life depression. Neuropsychopharmacology. 2000 Nov;23(5):587-90. [PubMed:11027924 ]
Vaishnavi SN, Nemeroff CB, Plott SJ, Rao SG, Kranzler J, Owens MJ: Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55(3):320-2. [PubMed:14744476 ]
Rausch JL, Moeller FG, Johnson ME: Initial platelet serotonin (5-HT) transport kinetics predict nortriptyline treatment outcome. J Clin Psychopharmacol. 2003 Apr;23(2):138-44. [PubMed:12640215 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Show all enzymes and transporters

Showing metabocard for Nortriptyline (HMDB0014680)

MOL for HMDB0014680 (Nortriptyline)

3D MOL for HMDB0014680 (Nortriptyline)

3D SDF for HMDB0014680 (Nortriptyline)

3D-SDF for HMDB0014680 (Nortriptyline)

PDB for HMDB0014680 (Nortriptyline)

3D PDB for HMDB0014680 (Nortriptyline)

SMILES for HMDB0014680 (Nortriptyline)

INCHI for HMDB0014680 (Nortriptyline)

Structure for HMDB0014680 (Nortriptyline)

3D Structure for HMDB0014680 (Nortriptyline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References

Transporters

References

References