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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015691

Secondary Accession Numbers

HMDB15691

Metabolite Identification

Common Name

Dimethindene

Description

Dimethindene, also known as fenistil or forhistal, belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring). As with other antihistaminic drugs, overdosage can produce the following symptoms: CNS depression accompanied by drowsiness (especially in adults), CNS stimulation and antimuscarinic effects (especially in children) including the following: excitation, ataxia, hallucinations, tonic or clonic spasms, mydriasis, dryness of the mouth, redness of the face, urine retention, fever and tachycardia. Dimethindene is a very strong basic compound (based on its pKa). In humans, dimethindene is involved in dimetindene h1-antihistamine action. Dimethindene is only found in individuals that have used or taken this drug. Dimethindene is a selective histamine H1 antagonist and binds to the histamine H1 receptor. Blood hypotension is also possible (R)-(-)-enantiomer is the eutomer (responsible for bioactivity) for histamine H1 receptor binding.

Structure

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

HMDB0015691
     RDKit          3D
Dimethindene
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.5251   -0.9656   -2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9475   -0.9137   -0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.4642   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7277    0.7712    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -0.1592    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.1960   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533   -0.6804   -0.2862 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6827   -0.4216    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319   -2.0566   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006    2.2528    0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    2.7398   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0397    4.0332   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    4.1932   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1140    3.1321   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036    1.8645   -0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979    1.6696   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432   -1.5578    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -1.5530    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8241   -2.1750    1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459   -2.8331    2.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -2.8283    2.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0821   -2.2166    1.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3904    0.0450   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989   -1.6599   -2.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999   -1.1666   -2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -1.4932   -0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852    0.0754    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742   -1.2006    0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577    1.2212   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.0994   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3577   -1.1955    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3477    0.5622    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883   -0.4012    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -2.2088   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5763   -2.4855   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -2.6695    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    2.5161    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674    2.6257   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4173    4.8489    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7519    5.1974   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1362    3.2593   -1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503    0.9948   -1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6727   -1.0680   -0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9074   -2.1515    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6744   -3.3409    3.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2422   -3.3598    3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  3  1  0
 22 17  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

 
  Mrv0541 02241214202D          

 22 24  0  0  0  0            999 V2000
   11.6738  -11.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6738  -11.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750  -12.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750  -10.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1175  -11.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1175  -11.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9013  -12.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3550  -11.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9013  -10.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1800  -11.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5925  -12.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4175  -12.1687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8300  -12.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8300  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9013   -9.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6025   -9.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1588   -9.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038   -9.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0050   -9.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0050   -8.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3038   -8.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6025   -8.7037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0  0  0  0
  2  3  1  0  0  0  0
  9 15  1  0  0  0  0
  3  6  2  0  0  0  0
 15 16  1  0  0  0  0
  5  6  1  0  0  0  0
 15 17  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  5  1  0  0  0  0
  5  4  2  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 16  1  0  0  0  0
  8 10  1  0  0  0  0
  4  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1  2  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015691

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C1=C(CCN(C)C)CC2=CC=CC=C12)C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3

> <INCHI_KEY>
MVMQESMQSYOVGV-UHFFFAOYSA-N

> <FORMULA>
C20H24N2

> <MOLECULAR_WEIGHT>
292.418

> <EXACT_MASS>
292.193948778

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.904645388861354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl(2-{3-[1-(pyridin-2-yl)ethyl]-1H-inden-2-yl}ethyl)amine

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
3.738704610333334

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.931058799151767

> <JCHEM_PKA_STRONGEST_BASIC>
9.704140922937079

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
93.5661

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethindene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015691
     RDKit          3D
Dimethindene
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.5251   -0.9656   -2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9475   -0.9137   -0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.4642   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7277    0.7712    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -0.1592    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.1960   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533   -0.6804   -0.2862 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6827   -0.4216    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319   -2.0566   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006    2.2528    0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    2.7398   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0397    4.0332   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    4.1932   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1140    3.1321   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036    1.8645   -0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979    1.6696   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432   -1.5578    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -1.5530    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8241   -2.1750    1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459   -2.8331    2.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -2.8283    2.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0821   -2.2166    1.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3904    0.0450   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989   -1.6599   -2.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999   -1.1666   -2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -1.4932   -0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852    0.0754    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742   -1.2006    0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577    1.2212   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.0994   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3577   -1.1955    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3477    0.5622    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883   -0.4012    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -2.2088   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5763   -2.4855   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -2.6695    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    2.5161    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674    2.6257   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4173    4.8489    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7519    5.1974   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1362    3.2593   -1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503    0.9948   -1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6727   -1.0680   -0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9074   -2.1515    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6744   -3.3409    3.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2422   -3.3598    3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  3  1  0
 22 17  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.791 -20.559   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.791 -22.099   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.100 -22.869   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.100 -19.789   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.486 -20.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.486 -22.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.949 -22.638   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.796 -21.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.949 -20.097   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.336 -21.329   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.106 -22.715   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      30.646 -22.715   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      31.416 -24.024   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.416 -21.406   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.949 -18.557   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.258 -17.787   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.563 -17.787   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.567 -18.557   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.876 -17.787   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.876 -16.247   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.567 -15.477   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      27.258 -16.247   0.000  0.00  0.00           N+0
CONECT    1    4    2                                                       
CONECT    2    3    1                                                       
CONECT    3    2    6                                                       
CONECT    4    5    1                                                       
CONECT    5    6    9    4                                                  
CONECT    6    3    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9   15    8    5                                                  
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15   18   22                                                  
CONECT   17   15                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0015691
HETATM    1  C1  UNL     1      -1.525  -0.966  -2.134  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.948  -0.914  -0.744  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.471   0.464  -0.427  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.728   0.771   0.036  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.860  -0.159   0.344  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.043   0.196  -0.555  1.00  0.00           C  
HETATM    7  N1  UNL     1       4.153  -0.680  -0.286  1.00  0.00           N  
HETATM    8  C7  UNL     1       4.683  -0.422   1.024  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.832  -2.057  -0.514  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.801   2.253   0.238  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.525   2.740  -0.139  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.040   4.033  -0.139  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.334   4.193  -0.568  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.114   3.132  -0.986  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.604   1.864  -0.983  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.298   1.670  -0.555  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.743  -1.558   0.272  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.094  -1.553   0.324  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.824  -2.175   1.332  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.146  -2.833   2.334  1.00  0.00           C  
HETATM   21  C20 UNL     1      -1.763  -2.828   2.265  1.00  0.00           C  
HETATM   22  N2  UNL     1      -1.082  -2.217   1.275  1.00  0.00           N  
HETATM   23  H1  UNL     1      -1.390   0.045  -2.617  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.999  -1.660  -2.821  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.600  -1.167  -2.152  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.047  -1.493  -0.869  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.185   0.075   1.409  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.574  -1.201   0.251  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.358   1.221  -0.289  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.692   0.099  -1.586  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.358  -1.195   1.760  1.00  0.00           H  
HETATM   32  H10 UNL     1       4.348   0.562   1.431  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.788  -0.401   0.948  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.842  -2.209  -0.993  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.576  -2.485  -1.237  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.933  -2.670   0.427  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.083   2.516   1.281  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.567   2.626  -0.486  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.417   4.849   0.190  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.752   5.197  -0.574  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.136   3.259  -1.324  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.150   0.995  -1.303  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.673  -1.068  -0.431  1.00  0.00           H  
HETATM   44  H22 UNL     1      -4.907  -2.152   1.343  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.674  -3.341   3.154  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.242  -3.360   3.076  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   17   26
CONECT    3    4    4   16
CONECT    4    5   10
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8    9
CONECT    8   31   32   33
CONECT    9   34   35   36
CONECT   10   11   37   38
CONECT   11   12   12   16
CONECT   12   13   39
CONECT   13   14   14   40
CONECT   14   15   41
CONECT   15   16   16   42
CONECT   17   18   18   22
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   45
CONECT   21   22   22   46
END

HMDB0015691
     RDKit          3D
Dimethindene
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.5251   -0.9656   -2.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9475   -0.9137   -0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.4642   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7277    0.7712    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -0.1592    0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.1960   -0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533   -0.6804   -0.2862 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6827   -0.4216    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319   -2.0566   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006    2.2528    0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250    2.7398   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0397    4.0332   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    4.1932   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1140    3.1321   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036    1.8645   -0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979    1.6696   -0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432   -1.5578    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -1.5530    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8241   -2.1750    1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459   -2.8331    2.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -2.8283    2.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0821   -2.2166    1.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3904    0.0450   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989   -1.6599   -2.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999   -1.1666   -2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -1.4932   -0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852    0.0754    1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5742   -1.2006    0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577    1.2212   -0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.0994   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3577   -1.1955    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3477    0.5622    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883   -0.4012    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -2.2088   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5763   -2.4855   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -2.6695    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    2.5161    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674    2.6257   -0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4173    4.8489    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7519    5.1974   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1362    3.2593   -1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503    0.9948   -1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6727   -1.0680   -0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9074   -2.1515    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6744   -3.3409    3.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2422   -3.3598    3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  3  1  0
 22 17  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+/-)-dimetahindene	HMDB
Dimethylpyrindene	HMDB
Dimethindene maleate	HMDB
Dimetindene	HMDB
Maleate, dimethindene	HMDB
Dimethpyrindene	HMDB
Fenistil	HMDB
Forhistal	HMDB
Novartis brand OF dimethindene maleate	HMDB

Chemical Formula

C₂₀H₂₄N₂

Average Molecular Weight

292.418

Monoisotopic Molecular Weight

292.193948778

IUPAC Name

dimethyl(2-{3-[1-(pyridin-2-yl)ethyl]-1H-inden-2-yl}ethyl)amine

Traditional Name

dimethindene

CAS Registry Number

5636-83-9

SMILES

CC(C1=C(CCN(C)C)CC2=CC=CC=C12)C1=CC=CC=N1

InChI Identifier

InChI=1S/C20H24N2/c1-15(19-10-6-7-12-21-19)20-17(11-13-22(2)3)14-16-8-4-5-9-18(16)20/h4-10,12,15H,11,13-14H2,1-3H3

InChI Key

MVMQESMQSYOVGV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indenes and isoindenes

Sub Class

Not Available

Direct Parent

Indenes and isoindenes

Alternative Parents

Substituents

Indene
Pyridine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015691)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Dimetindene H1-Antihistamine Action (PathBank: SMP0057582)

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.038 g/L	ALOGPS
logP	4.03	ALOGPS
logP	3.74	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	18.93	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.57 m³·mol⁻¹	ChemAxon
Polarizability	34.9 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]+	170.082	31661259
DarkChem	[M-H]-	167.413	31661259
DeepCCS	[M-2H]-	202.37	30932474
DeepCCS	[M+Na]+	177.935	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	167.5	32859911
AllCCS	[M+NH4]+	174.4	32859911
AllCCS	[M+Na]+	175.3	32859911
AllCCS	[M-H]-	181.3	32859911
AllCCS	[M+Na-2H]-	181.1	32859911
AllCCS	[M+HCOO]-	181.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dimethindene	CC(C1=C(CCN(C)C)CC2=CC=CC=C12)C1=CC=CC=N1	3064.1	Standard polar	33892256
Dimethindene	CC(C1=C(CCN(C)C)CC2=CC=CC=C12)C1=CC=CC=N1	2328.9	Standard non polar	33892256
Dimethindene	CC(C1=C(CCN(C)C)CC2=CC=CC=C12)C1=CC=CC=N1	2247.1	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 - Dimethindene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9580000000-d988cb2b7d041f1d29b4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dimethindene 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 - Dimethindene 10V, Negative-QTOF	splash10-0006-0090000000-9d54a7a45b59604fbf5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 20V, Negative-QTOF	splash10-0006-1090000000-b5c54114bd9f8ab5e29c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 40V, Negative-QTOF	splash10-056u-9370000000-c008c6758091f141fe25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 10V, Negative-QTOF	splash10-000x-0090000000-b23b853c492b4d851fdd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 20V, Negative-QTOF	splash10-000x-0590000000-f07ef0659fb9298c7d4f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 40V, Negative-QTOF	splash10-002o-1920000000-b4c8104237666425929f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 10V, Positive-QTOF	splash10-0006-0090000000-6f0b397decf52bcf1a59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 20V, Positive-QTOF	splash10-006y-2390000000-b930ccee7688ed4a0324	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 40V, Positive-QTOF	splash10-00bl-3940000000-b9bc4d1c64f0cee0fdf0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 10V, Positive-QTOF	splash10-0006-0190000000-411f16ef1c889ea21fe6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 20V, Positive-QTOF	splash10-0a4m-2690000000-797dffad8f6d13889761	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethindene 40V, Positive-QTOF	splash10-0a4i-7910000000-bf84eccff5bbaaa30cb0	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Dimetindene H1-Antihistamine Action		Not Available

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 DB08801	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08801	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08801

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dimetindene

METLIN ID

Not Available

PubChem Compound

21855

PDB ID

Not Available

ChEBI ID

126443

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

Lambrecht G, Gross J, Mutschler E: Neuronal soma-dendritic and prejunctional M1-M4 receptors in gastrointestinal and genitourinary smooth muscle. Life Sci. 1999;64(6-7):403-10. [PubMed:10069503 ]
Novartis Pamphlet [Link]

Enzymes

Enzyme Details

1. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Moree WJ, Li BF, Zamani-Kord S, Yu J, Coon T, Huang C, Marinkovic D, Tucci FC, Malany S, Bradbury MJ, Hernandez LM, Wen J, Wang H, Hoare SR, Petroski RE, Jalali K, Yang C, Sacaan A, Madan A, Crowe PD, Beaton G: Identification of a novel selective H1-antihistamine with optimized pharmacokinetic properties for clinical evaluation in the treatment of insomnia. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5874-8. doi: 10.1016/j.bmcl.2010.07.117. Epub 2010 Aug 3. [PubMed:20800486 ]
Pfaff O, Hildebrandt C, Waelbroeck M, Hou X, Moser U, Mutschler E, Lambrecht G: The (S)-(+)-enantiomer of dimethindene: a novel M2-selective muscarinic receptor antagonist. Eur J Pharmacol. 1995 Nov 24;286(3):229-40. [PubMed:8608784 ]

Enzyme Details

2. Muscarinic acetylcholine receptor M2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular weight:: 51714.6

References

Pfaff O, Hildebrandt C, Waelbroeck M, Hou X, Moser U, Mutschler E, Lambrecht G: The (S)-(+)-enantiomer of dimethindene: a novel M2-selective muscarinic receptor antagonist. Eur J Pharmacol. 1995 Nov 24;286(3):229-40. [PubMed:8608784 ]

Showing metabocard for Dimethindene (HMDB0015691)

MOL for HMDB0015691 (Dimethindene)

3D MOL for HMDB0015691 (Dimethindene)

3D SDF for HMDB0015691 (Dimethindene)

3D-SDF for HMDB0015691 (Dimethindene)

PDB for HMDB0015691 (Dimethindene)

3D PDB for HMDB0015691 (Dimethindene)

SMILES for HMDB0015691 (Dimethindene)

INCHI for HMDB0015691 (Dimethindene)

Structure for HMDB0015691 (Dimethindene)

3D Structure for HMDB0015691 (Dimethindene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References