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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:52:53 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254524

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methapyrilene

Description

Methapyrilene, also known as lullamin or restryl, belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. Methapyrilene is a very strong basic compound (based on its pKa). In humans, methapyrilene is involved in methapyrilene h1-antihistamine action. It has relatively strong sedative effects, to the extent that its primary use was as a medication for insomnia rather than for its antihistamine action. All of these products were reformulated in the late 1970s when methapyrilene was demonstrated to cause liver cancer in rats when given chronically. Together with scopolamine, it was the main ingredient in Sominex, Nytol, and Sleep-Eze. It was sold under the trade names Co-Pyronil and Histadyl EC. Methapyrilene is an antihistamine and anticholinergic of the pyridine chemical class which was developed in the early 1950s. The thionyl halides should not be confused with "thionylan" and include thionyl fluoride, thionyl chloride, and thionyl bromide. "Thionylan" redirects here. It also provided the sedative component of Excedrin PM. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methapyrilene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methapyrilene 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

HMDB0254524
     RDKit          3D
methapyrilene
 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.9029   -0.7463   -1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953   -0.0283   -0.2323 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -0.2532    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702   -0.3612    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3037    0.2118   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.0905   -0.3130 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.4544   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856   -1.5644    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140   -1.3094   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912   -1.4649    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668   -1.8724    1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942   -2.0213    1.6821 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    0.9673    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335    1.6227   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703    2.6759   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990    3.0311    0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7261    2.3640    1.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    1.3363    1.3733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477   -1.6061   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9716   -0.9560   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6970   -0.0124   -2.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1979    0.0429    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5046    0.3136    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8581   -1.3367    0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.4285    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    0.1529    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    1.3027   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5241   -0.2503   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940   -1.9424   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -2.0417    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480   -0.9801   -1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802   -1.2852   -0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0244   -2.0554    2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6137    1.3424   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    3.1662   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1561    3.8543    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    2.6768    2.8149 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  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  8  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

4819
  Mrv1652309181718452D          

 18 19  0  0  1  0            999 V2000
    1.7282    2.0975    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    2.9180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9579    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724    2.9180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    2.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9579    1.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5289    3.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9579    3.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145    2.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434    0.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724    0.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9579    4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    3.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087    2.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724    4.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9212    1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    3.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 16  1  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  6  1  0  0  0  0
  3 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4  8  1  0  0  0  0
  4 17  2  0  0  0  0
  5  6  1  0  0  0  0
  7  9  1  0  0  0  0
  8 12  2  0  0  0  0
  9 13  2  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  2  0  0  0  0
 15 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254524

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3

> <INCHI_KEY>
HNJJXZKZRAWDPF-UHFFFAOYSA-N

> <FORMULA>
C14H19N3S

> <MOLECULAR_WEIGHT>
261.39

> <EXACT_MASS>
261.129968798

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.495487807612527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(dimethylamino)ethyl]-N-[(thiophen-2-yl)methyl]pyridin-2-amine

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.114073790333332

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.763872009855984

> <JCHEM_POLAR_SURFACE_AREA>
19.37

> <JCHEM_REFRACTIVITY>
78.16480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rest-on

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254524
     RDKit          3D
methapyrilene
 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.9029   -0.7463   -1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953   -0.0283   -0.2323 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -0.2532    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702   -0.3612    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3037    0.2118   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.0905   -0.3130 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.4544   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856   -1.5644    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140   -1.3094   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912   -1.4649    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668   -1.8724    1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942   -2.0213    1.6821 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    0.9673    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335    1.6227   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703    2.6759   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990    3.0311    0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7261    2.3640    1.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    1.3363    1.3733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477   -1.6061   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9716   -0.9560   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6970   -0.0124   -2.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1979    0.0429    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5046    0.3136    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8581   -1.3367    0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.4285    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    0.1529    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    1.3027   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5241   -0.2503   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940   -1.9424   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -2.0417    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480   -0.9801   -1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802   -1.2852   -0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0244   -2.0554    2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6137    1.3424   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    3.1662   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1561    3.8543    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    2.6768    2.8149 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  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  8  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 18-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4819                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-17         0                                  
HETATM    1  S   UNK     0       3.226   3.915   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       6.054   5.447   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       7.388   1.597   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.722   5.447   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.054   3.907   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.388   3.137   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.721   6.217   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.388   6.217   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.387   5.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.054   0.827   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.722   0.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.388   7.757   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.980   6.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.950   4.929   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.722   8.527   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.720   3.595   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.056   6.217   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.056   7.757   0.000  0.00  0.00           C+0
CONECT    1    9   16                                                       
CONECT    2    5    7    8                                                  
CONECT    3    6   10   11                                                  
CONECT    4    8   17                                                       
CONECT    5    2    6                                                       
CONECT    6    3    5                                                       
CONECT    7    2    9                                                       
CONECT    8    2    4   12                                                  
CONECT    9    1    7   13                                                  
CONECT   10    3                                                            
CONECT   11    3                                                            
CONECT   12    8   15                                                       
CONECT   13    9   14                                                       
CONECT   14   13   16                                                       
CONECT   15   12   18                                                       
CONECT   16    1   14                                                       
CONECT   17    4   18                                                       
CONECT   18   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0254524
HETATM    1  C1  UNL     1      -3.903  -0.746  -1.456  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.595  -0.028  -0.232  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.611  -0.253   0.781  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.270  -0.361   0.256  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.304   0.212  -0.743  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.045  -0.091  -0.313  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.471  -1.454  -0.337  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.886  -1.564   0.155  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.014  -1.309  -0.557  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.191  -1.465   0.056  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.167  -1.872   1.364  1.00  0.00           C  
HETATM   12  S1  UNL     1       2.494  -2.021   1.682  1.00  0.00           S  
HETATM   13  C10 UNL     1       0.871   0.967   0.099  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.633   1.623  -0.827  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.470   2.676  -0.470  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.499   3.031   0.851  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.726   2.364   1.779  1.00  0.00           C  
HETATM   18  N3  UNL     1       0.922   1.336   1.373  1.00  0.00           N  
HETATM   19  H1  UNL     1      -3.248  -1.606  -1.630  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.972  -0.956  -1.485  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.697  -0.012  -2.286  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.198   0.043   1.761  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.505   0.314   0.496  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.858  -1.337   0.868  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.100  -1.428   0.368  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.138   0.153   1.237  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.462   1.303  -0.891  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.524  -0.250  -1.746  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.394  -1.942  -1.318  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.158  -2.042   0.365  1.00  0.00           H  
HETATM   31  H13 UNL     1       2.948  -0.980  -1.619  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.180  -1.285  -0.426  1.00  0.00           H  
HETATM   33  H15 UNL     1       5.024  -2.055   2.036  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.614   1.342  -1.892  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.055   3.166  -1.231  1.00  0.00           H  
HETATM   36  H18 UNL     1       3.156   3.854   1.117  1.00  0.00           H  
HETATM   37  H19 UNL     1       1.780   2.677   2.815  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   13
CONECT    7    8   29   30
CONECT    8    9    9   12
CONECT    9   10   31
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   13   14   14   18
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   18   37
END

HMDB0254524
     RDKit          3D
methapyrilene
 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.9029   -0.7463   -1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953   -0.0283   -0.2323 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -0.2532    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702   -0.3612    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3037    0.2118   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0452   -0.0905   -0.3130 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.4544   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856   -1.5644    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0140   -1.3094   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912   -1.4649    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668   -1.8724    1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942   -2.0213    1.6821 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    0.9673    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6335    1.6227   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703    2.6759   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990    3.0311    0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7261    2.3640    1.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    1.3363    1.3733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477   -1.6061   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9716   -0.9560   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6970   -0.0124   -2.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1979    0.0429    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5046    0.3136    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8581   -1.3367    0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.4285    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    0.1529    1.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    1.3027   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5241   -0.2503   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940   -1.9424   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581   -2.0417    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480   -0.9801   -1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802   -1.2852   -0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0244   -2.0554    2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6137    1.3424   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555    3.1662   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1561    3.8543    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    2.6768    2.8149 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  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  8  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[[2-(Dimethylamino)ethyl]-2-thenylamino]pyridine	ChEBI
Histadyl	ChEBI
Lullamin	ChEBI
Methypyrilene	ChEBI
N,N-Dimethyl-n'-pyrid-2-yl-n'-2-thenylethylenediamine	ChEBI
N,N-Dimethyl-n'-pyridin-2-yl-n'-(2-thienylmethyl)ethane-1,2-diamine	ChEBI
N-(alpha-Pyridyl)-N-(alpha-thenyl)-n',n'-dimethylethylenediamine	ChEBI
Paradormalene	ChEBI
Pyrathyn	ChEBI
Pyrinistab	ChEBI
Pyrinistol	ChEBI
Rest-ON	ChEBI
Restryl	ChEBI
Semikon	ChEBI
Sleepwell	ChEBI
Thenylene	ChEBI
Thenylpyramine	ChEBI
Thionylan	ChEBI
N-(a-Pyridyl)-N-(a-thenyl)-n',n'-dimethylethylenediamine	Generator
N-(Α-pyridyl)-N-(α-thenyl)-n',n'-dimethylethylenediamine	Generator
Tenalin	MeSH
N,N-Dimethyl-n'-2-pyridinyl-n'-(2-thienylmethyl)-1,2-ethanediamine	MeSH
Methapyrilene	MeSH

Chemical Formula

C₁₄H₁₉N₃S

Average Molecular Weight

261.39

Monoisotopic Molecular Weight

261.129968798

IUPAC Name

N-[2-(dimethylamino)ethyl]-N-[(thiophen-2-yl)methyl]pyridin-2-amine

Traditional Name

rest-on

CAS Registry Number

Not Available

SMILES

CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1

InChI Identifier

InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3

InChI Key

HNJJXZKZRAWDPF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylarylamines

Alternative Parents

Substituents

Dialkylarylamine
Aminopyridine
Imidolactam
Pyridine
Heteroaromatic compound
Thiophene
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethylenediamine derivative (CHEBI:6820 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	2.71	ALOGPS
logP	3.11	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	19.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.16 m³·mol⁻¹	ChemAxon
Polarizability	29.5 Å³	ChemAxon
Number of Rings	2	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+H]+	152.75	30932474
DeepCCS	[M-H]-	150.392	30932474
DeepCCS	[M-2H]-	184.42	30932474
DeepCCS	[M+Na]+	159.772	30932474
AllCCS	[M+H]+	158.5	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	161.9	32859911
AllCCS	[M+Na]+	162.9	32859911
AllCCS	[M-H]-	163.3	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
methapyrilene	CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1	2683.8	Standard polar	33892256
methapyrilene	CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1	1981.9	Standard non polar	33892256
methapyrilene	CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1	1960.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methapyrilene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9110000000-4181872f47d3a02dd809	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methapyrilene 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 - Methapyrilene 10V, Positive-QTOF	splash10-03di-2090000000-6a82f3fa59dfcb3d5cbb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Positive-QTOF	splash10-00xr-9580000000-66df093facc7da7ba9a4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Positive-QTOF	splash10-05fr-7900000000-187b0a5cc21b2289ac2c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 10V, Negative-QTOF	splash10-03di-1190000000-3839376e1dbdc67717b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Negative-QTOF	splash10-03dr-2790000000-8d6a8b1bba5b77d67199	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Negative-QTOF	splash10-0a4i-9300000000-8fb70107ed819654b063	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 10V, Positive-QTOF	splash10-03di-0090000000-459dc8d4959d8ddcb7af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Positive-QTOF	splash10-03xs-4090000000-00c2ba1773b22af75a4f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Positive-QTOF	splash10-0592-9400000000-3b73e8d3f5c2ab2ffa05	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 10V, Negative-QTOF	splash10-03di-0090000000-76de687c6f5596a5f70c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Negative-QTOF	splash10-0bu9-5930000000-d00db17d32d33f7ae619	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Negative-QTOF	splash10-001i-8900000000-32c1bdff1e8fd5d287f1	2021-10-12	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11114

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methapyrilene

METLIN ID

Not Available

PubChem Compound

4098

PDB ID

Not Available

ChEBI ID

6820

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 Methapyrilene (HMDB0254524)

MOL for HMDB0254524 (Methapyrilene)

3D MOL for HMDB0254524 (Methapyrilene)

3D SDF for HMDB0254524 (Methapyrilene)

3D-SDF for HMDB0254524 (Methapyrilene)

PDB for HMDB0254524 (Methapyrilene)

3D PDB for HMDB0254524 (Methapyrilene)

SMILES for HMDB0254524 (Methapyrilene)

INCHI for HMDB0254524 (Methapyrilene)

Structure for HMDB0254524 (Methapyrilene)

3D Structure for HMDB0254524 (Methapyrilene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra