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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:07:44 UTC

Update Date

2021-09-26 23:12:23 UTC

HMDB ID

HMDB0256605

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pirlindole

Description

Pirlindole, also known as pyrazidol, belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Pirlindole is a drug which is used for the treatment of major depression. it is being studied in the treatment of fibromyalgia pain syndrome. one study determined that the effect of pirlindole on sensorimotor performance while driving a motor vehicle shows many similarities to that of placebo. the drug appears to stimulate the central nervous system, rather than exhibit a sedative effect, like many antidepressants. because of its selective, reversible inhibition of monoamine oxidase (mao-a) and short half-life, unpleasant "cheese effects" are avoided. this refers to the effects of consuming tyramine-rich foods, such as cheese while medicated with monoamine oxidase inhibitors, leading to severe headaches and hypertension [l1395]. of the available evidence supports pirlindole as a safe and effective treatment option for the management of depression and fibromyalgia syndrome [l1394]. . Based on a literature review a significant number of articles have been published on Pirlindole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pirlindole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pirlindole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256605
     RDKit          3D
Pirlindole
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.8580    0.8458   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4894    0.2455   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3097   -1.0931   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473   -1.6581   -0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237   -0.8868   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    0.4633   -0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535    1.0023   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049    0.9453    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501   -0.0919   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3617   -1.2191   -0.4314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873   -2.3893   -0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231   -2.3805    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -1.2792    0.2887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5189   -0.0450   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042    1.1412    0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042    2.3438    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    2.2982    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5634    0.1395    0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.7468    0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2621    1.0486   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1942   -1.6843   -0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -2.7162   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    2.0665    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -3.3299   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2182   -1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273   -3.3219    0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704   -2.3818    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8164   -1.2087    1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748    0.1897   -1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4474    1.0363    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    1.3104    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    3.2629    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    2.2367   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640    2.5065    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521    3.0746   -0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  2  1  0
 17  8  1  0
 10  5  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
M  END

  Mrv1572010231518132D          

 17 20  0  0  0  0            999 V2000
   -1.6089    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089   -0.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776   -0.6807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776    0.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977   -0.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313    1.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3103    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8564    1.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -1.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8564   -1.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690   -0.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  1 11  1  0  0  0  0
 12  9  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256605

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C2N3CCNC4CCCC(=C34)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18N2/c1-10-5-6-14-12(9-10)11-3-2-4-13-15(11)17(14)8-7-16-13/h5-6,9,13,16H,2-4,7-8H2,1H3

> <INCHI_KEY>
IWVRVEIKCBFZNF-UHFFFAOYSA-N

> <FORMULA>
C15H18N2

> <MOLECULAR_WEIGHT>
226.323

> <EXACT_MASS>
226.146998588

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.265314363900888

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-methyl-1,4-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraene

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
3.104723180333333

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.379546750924018

> <JCHEM_POLAR_SURFACE_AREA>
16.96

> <JCHEM_REFRACTIVITY>
70.4207

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pirlindole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0256605
     RDKit          3D
Pirlindole
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.8580    0.8458   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4894    0.2455   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3097   -1.0931   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473   -1.6581   -0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237   -0.8868   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    0.4633   -0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535    1.0023   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049    0.9453    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501   -0.0919   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3617   -1.2191   -0.4314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873   -2.3893   -0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231   -2.3805    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -1.2792    0.2887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5189   -0.0450   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042    1.1412    0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042    2.3438    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    2.2982    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5634    0.1395    0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.7468    0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2621    1.0486   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1942   -1.6843   -0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -2.7162   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    2.0665    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -3.3299   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2182   -1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273   -3.3219    0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704   -2.3818    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8164   -1.2087    1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748    0.1897   -1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4474    1.0363    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    1.3104    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    3.2629    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    2.2367   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640    2.5065    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521    3.0746   -0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  2  1  0
 17  8  1  0
 10  5  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 23-OCT-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-OCT-15         0                                  
HETATM    1  C   UNK     0      -3.003   0.731   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.003  -0.809   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.694  -1.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.385  -0.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.385   0.731   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.694   1.502   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.078  -1.271   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.002  -0.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.078   1.194   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.542  -0.038   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.313   1.502   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.925   2.657   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.313   1.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.465   2.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.925  -2.657   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.465  -2.657   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.235  -1.348   0.000  0.00  0.00           N+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5   12                                                  
CONECT   10    8   13   17                                                  
CONECT   11    1                                                            
CONECT   12    9   14                                                       
CONECT   13   10   14                                                       
CONECT   14   13   12                                                       
CONECT   15    7   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   40    0
END

COMPND    HMDB0256605
HETATM    1  C1  UNL     1       4.858   0.846  -0.105  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.489   0.245  -0.204  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.310  -1.093  -0.504  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.047  -1.658  -0.598  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.924  -0.887  -0.391  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.080   0.463  -0.088  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.354   1.002  -0.000  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.205   0.945   0.057  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.050  -0.092  -0.156  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.362  -1.219  -0.431  1.00  0.00           N  
HETATM   11  C10 UNL     1      -1.187  -2.389  -0.672  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.223  -2.380   0.459  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.113  -1.279   0.289  1.00  0.00           N  
HETATM   14  C12 UNL     1      -2.519  -0.045  -0.106  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.904   1.141   0.753  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.204   2.344   0.105  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.721   2.298   0.382  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.563   0.139   0.409  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.825   1.747   0.546  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.262   1.049  -1.100  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.194  -1.684  -0.663  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.924  -2.716  -0.836  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.457   2.066   0.239  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.616  -3.330  -0.668  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.737  -2.218  -1.625  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.827  -3.322   0.407  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.670  -2.382   1.414  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.816  -1.209   1.030  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.875   0.190  -1.134  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.447   1.036   1.758  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.989   1.310   0.782  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.679   3.263   0.454  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.324   2.237  -1.004  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.564   2.507   1.461  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.252   3.075  -0.260  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    7
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   10
CONECT    6    7    7    8
CONECT    7   23
CONECT    8    9    9   17
CONECT    9   10   14
CONECT   10   11
CONECT   11   12   24   25
CONECT   12   13   26   27
CONECT   13   14   28
CONECT   14   15   29
CONECT   15   16   30   31
CONECT   16   17   32   33
CONECT   17   34   35
END

HMDB0256605
     RDKit          3D
Pirlindole
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.8580    0.8458   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4894    0.2455   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3097   -1.0931   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473   -1.6581   -0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237   -0.8868   -0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    0.4633   -0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535    1.0023   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049    0.9453    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501   -0.0919   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3617   -1.2191   -0.4314 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873   -2.3893   -0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231   -2.3805    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1134   -1.2792    0.2887 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5189   -0.0450   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042    1.1412    0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042    2.3438    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    2.2982    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5634    0.1395    0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.7468    0.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2621    1.0486   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1942   -1.6843   -0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -2.7162   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    2.0665    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -3.3299   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.2182   -1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273   -3.3219    0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704   -2.3818    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8164   -1.2087    1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748    0.1897   -1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4474    1.0363    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    1.3104    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    3.2629    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241    2.2367   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640    2.5065    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521    3.0746   -0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  2  1  0
 17  8  1  0
 10  5  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pyrazidol	Kegg
Pirlindole hydrochloride	MeSH
Pyrlindole	MeSH
1,10-Trimethylene-8-methyl-1,2,3,4-tetrahydropyrazino(1,2-a)indole	MeSH
Pirlindol	MeSH

Chemical Formula

C₁₅H₁₈N₂

Average Molecular Weight

226.323

Monoisotopic Molecular Weight

226.146998588

IUPAC Name

12-methyl-1,4-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraene

Traditional Name

pirlindole

CAS Registry Number

Not Available

SMILES

CC1=CC=C2N3CCNC4CCCC(=C34)C2=C1

InChI Identifier

InChI=1S/C15H18N2/c1-10-5-6-14-12(9-10)11-3-2-4-13-15(11)17(14)8-7-16-13/h5-6,9,13,16H,2-4,7-8H2,1H3

InChI Key

IWVRVEIKCBFZNF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
3-alkylindole
Indole
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256605)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.1	ALOGPS
logP	3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	16.96 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.42 m³·mol⁻¹	ChemAxon
Polarizability	27.27 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	190.786	30932474
DeepCCS	[M+Na]+	165.806	30932474
AllCCS	[M+H]+	152.9	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	156.6	32859911
AllCCS	[M+Na]+	157.7	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pirlindole	CC1=CC=C2N3CCNC4CCCC(=C34)C2=C1	3098.8	Standard polar	33892256
Pirlindole	CC1=CC=C2N3CCNC4CCCC(=C34)C2=C1	2081.0	Standard non polar	33892256
Pirlindole	CC1=CC=C2N3CCNC4CCCC(=C34)C2=C1	2331.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pirlindole,1TMS,isomer #1	CC1=CC=C2C(=C1)C1=C3C(CCC1)N([Si](C)(C)C)CCN32	2321.3	Semi standard non polar	33892256
Pirlindole,1TMS,isomer #1	CC1=CC=C2C(=C1)C1=C3C(CCC1)N([Si](C)(C)C)CCN32	2312.3	Standard non polar	33892256
Pirlindole,1TMS,isomer #1	CC1=CC=C2C(=C1)C1=C3C(CCC1)N([Si](C)(C)C)CCN32	2847.2	Standard polar	33892256
Pirlindole,1TBDMS,isomer #1	CC1=CC=C2C(=C1)C1=C3C(CCC1)N([Si](C)(C)C(C)(C)C)CCN32	2516.6	Semi standard non polar	33892256
Pirlindole,1TBDMS,isomer #1	CC1=CC=C2C(=C1)C1=C3C(CCC1)N([Si](C)(C)C(C)(C)C)CCN32	2554.1	Standard non polar	33892256
Pirlindole,1TBDMS,isomer #1	CC1=CC=C2C(=C1)C1=C3C(CCC1)N([Si](C)(C)C(C)(C)C)CCN32	3018.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pirlindole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0940000000-2e2791b7eaea7b8d12f0	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirlindole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirlindole 10V, Positive-QTOF	splash10-004i-0090000000-b47c80f056435c73c9cf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirlindole 20V, Positive-QTOF	splash10-004i-0390000000-d3c7a69c768a0fa430d2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirlindole 40V, Positive-QTOF	splash10-053r-1900000000-2ee84e540a8a6ef1b275	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirlindole 10V, Negative-QTOF	splash10-004i-0090000000-a1e53c7eb3ab23d5e49c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirlindole 20V, Negative-QTOF	splash10-004i-0190000000-9b586959512f17b33c06	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirlindole 40V, Negative-QTOF	splash10-0a4j-1940000000-a26d90ae81736b362045	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09244

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

62039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pirlindole

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Pirlindole (HMDB0256605)

MOL for HMDB0256605 (Pirlindole)

3D MOL for HMDB0256605 (Pirlindole)

3D SDF for HMDB0256605 (Pirlindole)

3D-SDF for HMDB0256605 (Pirlindole)

PDB for HMDB0256605 (Pirlindole)

3D PDB for HMDB0256605 (Pirlindole)

SMILES for HMDB0256605 (Pirlindole)

INCHI for HMDB0256605 (Pirlindole)

Structure for HMDB0256605 (Pirlindole)

3D Structure for HMDB0256605 (Pirlindole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra