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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014466

Secondary Accession Numbers

HMDB14466

Metabolite Identification

Common Name

Amitriptyline

Description

Amitriptyline hydrochloride 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, amitriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, amitriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline. 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. Amitriptyline 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

HMDB0014466
     RDKit          3D
Amitriptyline
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.1989    0.1577    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380   -0.4317   -0.5538 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0103   -1.7971   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478    0.3315   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336   -0.0791   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5831    0.7550   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5746    0.4890   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    1.5968    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8528    2.7484    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211    3.8633    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    3.8469    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6468    2.6820    0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144    1.5196    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.4050   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288   -0.7697   -0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1892   -1.4948   -0.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732   -2.8358   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -3.5997    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -2.9870    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -1.6564    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684   -0.8914    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6115    1.0111   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.5063    1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9770   -0.6018    0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -2.4639   -0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -1.8129    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9884   -2.1985   -0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7357    0.2779    0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324    1.4252   -0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5590   -1.1371   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    0.2168   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650    1.8484   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    2.7545    0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176    4.7865    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    4.7098    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7231    2.6215    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687    0.0566    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.8050   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583   -1.5174   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098   -0.4151   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082   -3.2990   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -4.6674    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880   -3.5901    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -1.1690    0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

321
  Mrv0541 02231214362D          

 21 23  0  0  0  0            999 V2000
    2.5995   -1.7286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6160    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285    0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9554    1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2852    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7718    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2844    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7725    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3926    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4070    1.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412    0.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157    0.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5995   -2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5  7  1  0  0  0  0
  5 11  2  0  0  0  0
  6  8  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  2  0  0  0  0
  8 14  2  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014466

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3

> <INCHI_KEY>
KRMDCWKBEZIMAB-UHFFFAOYSA-N

> <FORMULA>
C20H23N

> <MOLECULAR_WEIGHT>
277.4033

> <EXACT_MASS>
277.183049741

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
33.73941640344825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.10

> <JCHEM_LOGP>
4.8095349149999995

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.76073872870795

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
101.50720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amitriptyline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014466
     RDKit          3D
Amitriptyline
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.1989    0.1577    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380   -0.4317   -0.5538 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0103   -1.7971   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478    0.3315   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336   -0.0791   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5831    0.7550   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5746    0.4890   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    1.5968    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8528    2.7484    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211    3.8633    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    3.8469    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6468    2.6820    0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144    1.5196    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.4050   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288   -0.7697   -0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1892   -1.4948   -0.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732   -2.8358   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -3.5997    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -2.9870    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -1.6564    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684   -0.8914    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6115    1.0111   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.5063    1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9770   -0.6018    0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -2.4639   -0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -1.8129    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9884   -2.1985   -0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7357    0.2779    0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324    1.4252   -0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5590   -1.1371   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    0.2168   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650    1.8484   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    2.7545    0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176    4.7865    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    4.7098    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7231    2.6215    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687    0.0566    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.8050   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583   -1.5174   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098   -0.4151   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082   -3.2990   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -4.6674    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880   -3.5901    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -1.1690    0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 321                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       4.852  -3.227   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.750   4.767   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.290   4.767   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.520   1.393   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.790   3.563   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.250   3.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.132   2.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.907   2.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.520  -0.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.186  -0.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.264   4.059   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.775   4.059   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      10.066   0.952   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.186  -2.457   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      11.960   2.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.437   1.413   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.603   1.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.852  -4.767   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.519  -2.457   0.000  0.00  0.00           C+0
CONECT    1   15   20   21                                                  
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4    7    8    9                                                  
CONECT    5    2    7   11                                                  
CONECT    6    3    8   12                                                  
CONECT    7    4    5   13                                                  
CONECT    8    4    6   14                                                  
CONECT    9    4   10                                                       
CONECT   10    9   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6   17                                                       
CONECT   13    7   18                                                       
CONECT   14    8   19                                                       
CONECT   15    1   10                                                       
CONECT   16   11   18                                                       
CONECT   17   12   19                                                       
CONECT   18   13   16                                                       
CONECT   19   14   17                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014466
HETATM    1  C1  UNL     1       5.199   0.158   0.287  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.138  -0.432  -0.554  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.010  -1.797  -0.053  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.948   0.332  -0.237  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.734  -0.079  -1.017  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.583   0.755  -0.603  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.575   0.489  -0.135  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.511   1.597   0.174  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.853   2.748   0.484  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.621   3.863   0.752  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.991   3.847   0.718  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.647   2.682   0.408  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.914   1.520   0.127  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.841   0.405  -0.117  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.329  -0.770  -0.858  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.189  -1.495  -0.260  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.373  -2.836  -0.011  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.383  -3.600   0.554  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.176  -2.987   0.878  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.007  -1.656   0.633  1.00  0.00           C  
HETATM   21  C20 UNL     1      -0.968  -0.891   0.069  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.611   1.011  -0.258  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.788   0.506   1.255  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.977  -0.602   0.511  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.749  -2.464  -0.531  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.201  -1.813   1.061  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.988  -2.198  -0.169  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.736   0.278   0.843  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.132   1.425  -0.478  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.559  -1.137  -1.119  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.991   0.217  -2.123  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.765   1.848  -0.750  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.224   2.754   0.542  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.118   4.787   0.998  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.621   4.710   0.924  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.723   2.622   0.370  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.269   0.057   0.886  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.736   0.805  -0.662  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.158  -1.517  -0.995  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.010  -0.415  -1.870  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.308  -3.299  -0.263  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.538  -4.667   0.748  1.00  0.00           H  
HETATM   43  H22 UNL     1       0.588  -3.590   1.314  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.922  -1.169   0.925  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   32
CONECT    7    8   21
CONECT    8    9    9   13
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17   17   21
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   43
CONECT   20   21   21   44
END

HMDB0014466
     RDKit          3D
Amitriptyline
 44 46  0  0  0  0  0  0  0  0999 V2000
    5.1989    0.1577    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380   -0.4317   -0.5538 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0103   -1.7971   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478    0.3315   -0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336   -0.0791   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5831    0.7550   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5746    0.4890   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    1.5968    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8528    2.7484    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211    3.8633    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    3.8469    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6468    2.6820    0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144    1.5196    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    0.4050   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288   -0.7697   -0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1892   -1.4948   -0.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732   -2.8358   -0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -3.5997    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -2.9870    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074   -1.6564    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684   -0.8914    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6115    1.0111   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.5063    1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9770   -0.6018    0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490   -2.4639   -0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -1.8129    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9884   -2.1985   -0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7357    0.2779    0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1324    1.4252   -0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5590   -1.1371   -1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    0.2168   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650    1.8484   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    2.7545    0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176    4.7865    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6212    4.7098    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7231    2.6215    0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687    0.0566    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.8050   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583   -1.5174   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098   -0.4151   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082   -3.2990   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380   -4.6674    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880   -3.5901    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -1.1690    0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  7  1  0
 13  8  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,D)cycloheptene	ChEBI
10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,D)heptalene-Delta(5),gamma-propylamine	ChEBI
3-(10,11-Dihydro-5H-dibenzo(a,D)cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine	ChEBI
3-(10,11-Dihydro-5H-dibenzo[a,D]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine	ChEBI
5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,D)cycloheptatriene	ChEBI
5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,D)cycloheptene	ChEBI
5-(gamma-Dimethylaminopropylidene)-5H-dibenzo[a,D][1,4]cycloheptadiene	ChEBI
Amitriptylin	ChEBI
Laroxyl	Kegg
10,11-Dihydro-5-(g-dimethylaminopropylidene)-5H-dibenzo(a,D)cycloheptene	Generator
10,11-Dihydro-5-(γ-dimethylaminopropylidene)-5H-dibenzo(a,D)cycloheptene	Generator
10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,D)heptalene-delta(5),g-propylamine	Generator
10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,D)heptalene-δ(5),γ-propylamine	Generator
5-(g-Dimethylaminopropylidene)-5H-dibenzo[a,D][1,4]cycloheptadiene	Generator
5-(Γ-dimethylaminopropylidene)-5H-dibenzo[a,D][1,4]cycloheptadiene	Generator
10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,D)heptalene-δ(5),g-propylamine	HMDB
Amitriprolidine	HMDB
Amitryptiline	HMDB
Amitryptyline	HMDB
Amytriptiline	HMDB
APS brand OF amitriptyline hydrochloride	HMDB
Amitriptylin beta	HMDB
Apo-amitriptyline	HMDB
Apotex brand OF amitriptyline hydrochloride	HMDB
Bayer brand OF amitriptyline hydrochloride	HMDB
Desitin, amitriptylin	HMDB
Domical	HMDB
Douglas brand OF amitriptyline hydrochloride	HMDB
Goldshield brand OF amitriptyline hydrochloride	HMDB
Merck brand OF amitriptyline hydrochloride	HMDB
Merck sharp and dohme brand OF amitriptyline embonate	HMDB
Rodleben brand OF amitriptyline hydrochloride	HMDB
Saroten	HMDB
Tryptine	HMDB
Amitriptylin RPH	HMDB
Amitrol	HMDB
Apo amitriptyline	HMDB
ApoAmitriptyline	HMDB
Cahill may roberts brand OF amitriptyline hydrochloride	HMDB
Novoprotect	HMDB
Rhône poulenc rorer brand OF amitriptyline hydrochloride	HMDB
Tryptanol	HMDB
Tryptizol	HMDB
beta, Amitriptylin	HMDB
Alphapharm brand OF amitriptyline hydrochloride	HMDB
Amitrip	HMDB
Amitriptylin-neuraxpharm	HMDB
Amitriptylinneuraxpharm	HMDB
Anapsique	HMDB
Cahill may roberts brand OF amitriptyline embonate	HMDB
Damilen	HMDB
Desitin brand OF amitriptyline hydrochloride	HMDB
Endep	HMDB
Hexal brand OF amitriptyline hydrochloride	HMDB
Krewel brand OF amitriptyline hydrochloride	HMDB
Protea brand OF amitriptyline hydrochloride	HMDB
Psicofarma brand OF amitriptyline hydrochloride	HMDB
RPH, Amitriptylin	HMDB
Rhône-poulenc rorer brand OF amitriptyline hydrochloride	HMDB
Roche brand OF amitriptyline hydrochloride	HMDB
Sarotex	HMDB
Syneudon	HMDB
Triptafen	HMDB
Amineurin	HMDB
Amitriptylin desitin	HMDB
Amitriptylin neuraxpharm	HMDB
Amitriptyline hydrochloride	HMDB
Amrad brand OF amitriptyline hydrochloride	HMDB
Betapharm brand OF amitriptyline hydrochloride	HMDB
DDSA brand OF amitriptyline hydrochloride	HMDB
Elavil	HMDB
Lentizol	HMDB
Lundbeck brand OF amitriptyline hydrochloride	HMDB
Merck sharp and dohme brand OF amitriptyline hydrochloride	HMDB
Neuro hexal brand OF amitriptyline hydrochloride	HMDB
Parke davis brand OF amitriptyline hydrochloride	HMDB
Zeneca brand OF amitriptyline hydrochloride	HMDB
Neuraxpharm brand OF amitriptyline hydrochloride	HMDB

Chemical Formula

C₂₀H₂₃N

Average Molecular Weight

277.4033

Monoisotopic Molecular Weight

277.183049741

IUPAC Name

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

Traditional Name

amitriptyline

CAS Registry Number

50-48-6

SMILES

CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3

InChI Key

KRMDCWKBEZIMAB-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
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tertiary amine (CHEBI:2666 )
organic tricyclic compound (CHEBI:2666 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014466)
Membrane (HMDB: HMDB0014466)

Source

Exogenous

Exogenous (HMDB: HMDB0014466)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0014466)

Biological role

Modulator

Adrenergic uptake inhibitor (HMDB: HMDB0014466)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	196 - 197 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0045 g/L	Not Available
LogP	4.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	167.2	30932474
[M+H]+	Not Available	166.272	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000741

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
logP	5.1	ALOGPS
logP	4.81	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.51 m³·mol⁻¹	ChemAxon
Polarizability	33.74 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]+	166.107	31661259
DarkChem	[M-H]-	166.998	31661259
DeepCCS	[M-2H]-	194.942	30932474
DeepCCS	[M+Na]+	170.507	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	172.0	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.8	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.	8.55 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8187 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.1 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1445.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	438.6 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	485.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	611.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1181.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	410.3 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	1277.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	309.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	370.0 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
Amitriptyline	CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2928.7	Standard polar	33892256
Amitriptyline	CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2202.5	Standard non polar	33892256
Amitriptyline	CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12	2201.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Amitriptyline EI-B (Non-derivatized)	splash10-0a4i-9010000000-2afae55587735e5a8ce1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Amitriptyline EI-B (Non-derivatized)	splash10-0a4i-9010000000-2afae55587735e5a8ce1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amitriptyline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9040000000-fe5eb711e5e29e99efed	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amitriptyline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9210000000-989cd234a8cdf04c5f69	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 - Amitriptyline LC-ESI-QTOF , positive-QTOF	splash10-05po-5890000000-4cce07a2d07337e4ce90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-001i-1590000000-35080e23f36a6ed30005	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-66d4e2dc0e65719c8949	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-004i-0190000000-18fad36e219aa0091dcf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-05o3-3980000000-bd3bb65e31837e45268f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-0aou-2940000000-c3c71a4ddeb15eb427b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-05mo-2930000000-f6bc4a5899aed7b3047e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-0fr6-2930000000-c348567e54820b6ddff3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-fae7f4e9cc1f20e9a2dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-004i-0190000000-42ecf4fcfbd4bd102322	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-05o3-3980000000-69e1e5d2fdd46de25ba4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-0aou-2940000000-853a0f18213b600d48ae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-05mo-2930000000-9493535ee63a9a708527	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-0fr6-2930000000-fba97ca65c4bf1940385	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-ITFT , positive-QTOF	splash10-001i-1690000000-99ea606fc86c8400c4ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-QTOF , positive-QTOF	splash10-004i-0090000000-8155764b5e04e44b4ca2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-QTOF , positive-QTOF	splash10-004i-0190000000-7e3a5d063f540759d63f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-QTOF , positive-QTOF	splash10-0apl-0960000000-e35715828f4c02816f19	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitriptyline LC-ESI-QTOF , positive-QTOF	splash10-0lfu-0940000000-a6befd2c2f6b01d0c348	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptyline 10V, Positive-QTOF	splash10-004i-0190000000-e92473ae05e0e7ecb6ed	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptyline 20V, Positive-QTOF	splash10-003r-3390000000-db46c53d9e4e8729d7f3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptyline 40V, Positive-QTOF	splash10-0006-5940000000-1c8f604ddf2e5e56560e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptyline 10V, Negative-QTOF	splash10-004i-0090000000-90c019b2f9a1e35d9e6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptyline 20V, Negative-QTOF	splash10-004i-1090000000-a8d8a7f9b985c30547f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitriptyline 40V, Negative-QTOF	splash10-0536-7290000000-3505755fe83fe73e694f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00321	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00321	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

DB00321

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00022968

Chemspider ID

2075

KEGG Compound ID

C06824

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amitriptyline

METLIN ID

Not Available

PubChem Compound

2160

PDB ID

Not Available

ChEBI ID

2666

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

Otaka M, Jin M, Odashima M, Matsuhashi T, Wada I, Horikawa Y, Komatsu K, Ohba R, Oyake J, Hatakeyama N, Watanabe S: New strategy of therapy for functional dyspepsia using famotidine, mosapride and amitriptyline. Aliment Pharmacol Ther. 2005 Jun;21 Suppl 2:42-6. [PubMed:15943846 ]

Showing metabocard for Amitriptyline (HMDB0014466)

MOL for HMDB0014466 (Amitriptyline)

3D MOL for HMDB0014466 (Amitriptyline)

3D SDF for HMDB0014466 (Amitriptyline)

3D-SDF for HMDB0014466 (Amitriptyline)

PDB for HMDB0014466 (Amitriptyline)

3D PDB for HMDB0014466 (Amitriptyline)

SMILES for HMDB0014466 (Amitriptyline)

INCHI for HMDB0014466 (Amitriptyline)

Structure for HMDB0014466 (Amitriptyline)

3D Structure for HMDB0014466 (Amitriptyline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra