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Showing metabocard for Isometheptene (HMDB0015651)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2023-02-21 17:18:33 UTC
HMDB IDHMDB0015651
Secondary Accession Numbers
  • HMDB15651
Metabolite Identification
Common NameIsometheptene
DescriptionIsometheptene is only found in individuals that have used or taken this drug. It is a sympathomimetic drug which causes vasoconstriction. It is used for treating migraines and tension headaches.Isometheptene's vasoconstricting properties arise through activation of the sympathetic nervous system via epinephrine and norepinephrine (or their molecular analogues as is the case with this drug). These compounds elicites smooth muscle activation leading to vasoconstriction. These compounds interact with cell surface adrenergic receptors. Such stimuli result in a signal transduction cascade that leads to increased intracellular calcium from the sarcoplasmic reticulum through IP3 mediated calcium release, as well as enhanced calcium entry across the sarcolemma through calcium channels. The rise in intracellular calcium complexes with calmodulin, which in turn activates myosin light chain kinase. This enzyme is responsible for phosphorylating the light chain of myosin to stimulate cross bridge cycling.Once elevated, the intracellular calcium concentration is returned to its basal level through a variety of protein pumps and calcium exchangers located on the plasma membrane and sarcoplasmic reticulum. This reduction in calcium removes the stimulus necessary for contraction allowing for a return to baseline. The drug can also cause vesicular displacement of noradrenaline from the neuron into the synapse with a similar effect as tyramine.
Structure
Data?1676999912
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015651 (Isometheptene)


  Mrv0541 02241212482D          

 10  9  0  0  0  0            999 V2000
    1.9520    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0015651 (Isometheptene)

HMDB0015651
     RDKit          3D
Isometheptene
 29 28  0  0  0  0  0  0  0  0999 V2000
    3.3533    0.3158    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3674   -0.5931    0.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190   -0.1266   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4954    0.1023   -1.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -0.9600   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.1465    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    0.1621    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506    0.4043    0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3722   -0.5982   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    1.7216    0.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141   -0.2082    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    0.6975    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5275    1.1909    0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176   -0.9512    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187    0.8946   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2832    0.8578   -1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.5269   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8583   -0.8602   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237   -0.4689   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8503   -1.9305   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -1.8274   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -1.6324    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    0.8934    1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4427   -0.2960    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2550   -0.7521   -1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2835   -1.6055    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855    2.2151    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    2.3213    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989    1.6529    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
M  END
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3D SDF for HMDB0015651 (Isometheptene)


  Mrv0541 02241212482D          

 10  9  0  0  0  0            999 V2000
    1.9520    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015651

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C9H19N/c1-8(2)6-5-7-9(3)10-4/h6,9-10H,5,7H2,1-4H3

> <INCHI_KEY>
XVQUOJBERHHONY-UHFFFAOYSA-N

> <FORMULA>
C9H19N

> <MOLECULAR_WEIGHT>
141.2539

> <EXACT_MASS>
141.151749613

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.81319459717494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl(6-methylhept-5-en-2-yl)amine

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.3181725126666666

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.665220282817

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
47.58639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isometheptene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015651 (Isometheptene)

HMDB0015651
     RDKit          3D
Isometheptene
 29 28  0  0  0  0  0  0  0  0999 V2000
    3.3533    0.3158    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3674   -0.5931    0.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190   -0.1266   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4954    0.1023   -1.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -0.9600   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5936   -1.1465    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    0.1621    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506    0.4043    0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3722   -0.5982   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    1.7216    0.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141   -0.2082    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    0.6975    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5275    1.1909    0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176   -0.9512    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187    0.8946   -0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2832    0.8578   -1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.5269   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8583   -0.8602   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237   -0.4689   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8503   -1.9305   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -1.8274   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -1.6324    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    0.8934    1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4427   -0.2960    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2550   -0.7521   -1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2835   -1.6055    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855    2.2151    1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    2.3213    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989    1.6529    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
M  END
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PDB for HMDB0015651 (Isometheptene)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.644   3.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.025   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.977   1.334   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0015651 (Isometheptene)

COMPND    HMDB0015651
HETATM    1  C1  UNL     1       3.353   0.316   1.266  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.367  -0.593   0.786  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.619  -0.127  -0.336  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.495   0.102  -1.548  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.468  -0.960  -0.736  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.594  -1.147   0.302  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.169   0.162   0.703  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.451   0.404   0.548  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.372  -0.598  -0.025  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.990   1.722   0.960  1.00  0.00           C  
HETATM   11  H1  UNL     1       4.314  -0.208   1.443  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.030   0.698   2.268  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.528   1.191   0.613  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.818  -0.951   1.567  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.219   0.895  -0.063  1.00  0.00           H  
HETATM   16  H6  UNL     1       3.283   0.858  -1.380  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.845   0.527  -2.366  1.00  0.00           H  
HETATM   18  H8  UNL     1       2.858  -0.860  -1.918  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.024  -0.469  -1.614  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.850  -1.930  -1.115  1.00  0.00           H  
HETATM   21  H11 UNL     1      -1.352  -1.827  -0.138  1.00  0.00           H  
HETATM   22  H12 UNL     1      -0.236  -1.632   1.228  1.00  0.00           H  
HETATM   23  H13 UNL     1      -0.494   0.893   1.123  1.00  0.00           H  
HETATM   24  H14 UNL     1      -4.443  -0.296   0.132  1.00  0.00           H  
HETATM   25  H15 UNL     1      -3.255  -0.752  -1.116  1.00  0.00           H  
HETATM   26  H16 UNL     1      -3.283  -1.605   0.451  1.00  0.00           H  
HETATM   27  H17 UNL     1      -2.286   2.215   1.653  1.00  0.00           H  
HETATM   28  H18 UNL     1      -3.101   2.321   0.014  1.00  0.00           H  
HETATM   29  H19 UNL     1      -3.999   1.653   1.416  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14
CONECT    3    4    5   15
CONECT    4   16   17   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24   25   26
CONECT   10   27   28   29
END
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SMILES for HMDB0015651 (Isometheptene)

CNC(C)CCC=C(C)C
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INCHI for HMDB0015651 (Isometheptene)

InChI=1S/C9H19N/c1-8(2)6-5-7-9(3)10-4/h6,9-10H,5,7H2,1-4H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
MidridHMDB
Isometheptene, monomaleateHMDB
N,1,5-Trimethyl-4-hexenylamineHMDB
Isometheptene monohydrochorideHMDB
Isometheptene, maleateHMDB
Isometheptene, maleate(+-)-isomerHMDB
Isometheptene, monotartrateHMDB
Isometheptene, mucate (2:1)HMDB
Isometheptene, (+-)-isomerHMDB
Isometheptene, monomaleate(+-)-isomerHMDB
IsomethepteneMeSH
Chemical FormulaC9H19N
Average Molecular Weight141.2539
Monoisotopic Molecular Weight141.151749613
IUPAC Namemethyl(6-methylhept-5-en-2-yl)amine
Traditional Nameisometheptene
CAS Registry Number503-01-5
SMILES
CNC(C)CCC=C(C)C
InChI Identifier
InChI=1S/C9H19N/c1-8(2)6-5-7-9(3)10-4/h6,9-10H,5,7H2,1-4H3
InChI KeyXVQUOJBERHHONY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.06 g/LALOGPS
logP2.07ALOGPS
logP2.32ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)10.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.59 m³·mol⁻¹ChemAxon
Polarizability18.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.86431661259
DarkChem[M-H]-131.93931661259
DeepCCS[M+H]+137.56730932474
DeepCCS[M-H]-134.95630932474
DeepCCS[M-2H]-171.47430932474
DeepCCS[M+Na]+146.68730932474
AllCCS[M+H]+136.132859911
AllCCS[M+H-H2O]+132.032859911
AllCCS[M+NH4]+139.832859911
AllCCS[M+Na]+140.932859911
AllCCS[M-H]-138.132859911
AllCCS[M+Na-2H]-140.632859911
AllCCS[M+HCOO]-143.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.42 minutes32390414
Predicted by Siyang on May 30, 20229.5565 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.88 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid75.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1266.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid262.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid118.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid158.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid56.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid292.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid296.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)187.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid761.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid290.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid653.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid185.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid244.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate465.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA393.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water29.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsomethepteneCNC(C)CCC=C(C)C1292.3Standard polar33892256
IsomethepteneCNC(C)CCC=C(C)C1006.2Standard non polar33892256
IsomethepteneCNC(C)CCC=C(C)C1031.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isometheptene,1TMS,isomer #1CC(C)=CCCC(C)N(C)[Si](C)(C)C1245.6Semi standard non polar33892256
Isometheptene,1TMS,isomer #1CC(C)=CCCC(C)N(C)[Si](C)(C)C1253.4Standard non polar33892256
Isometheptene,1TMS,isomer #1CC(C)=CCCC(C)N(C)[Si](C)(C)C1326.6Standard polar33892256
Isometheptene,1TBDMS,isomer #1CC(C)=CCCC(C)N(C)[Si](C)(C)C(C)(C)C1470.8Semi standard non polar33892256
Isometheptene,1TBDMS,isomer #1CC(C)=CCCC(C)N(C)[Si](C)(C)C(C)(C)C1469.2Standard non polar33892256
Isometheptene,1TBDMS,isomer #1CC(C)=CCCC(C)N(C)[Si](C)(C)C(C)(C)C1478.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isometheptene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-dd5c87491214e2bb43e82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isometheptene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 10V, Positive-QTOFsplash10-0006-1900000000-8ae373b810d3e7f6525a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 20V, Positive-QTOFsplash10-01ox-7900000000-cd3bbe24706407b30acf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 40V, Positive-QTOFsplash10-0a4i-9000000000-e4dd730e679b8290bc752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 10V, Negative-QTOFsplash10-0006-0900000000-67dbd1b1dde52037d5b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 20V, Negative-QTOFsplash10-0006-1900000000-5b510335f4c2e25df0612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 40V, Negative-QTOFsplash10-0a4m-9200000000-4b1c4bc325ac7ab4ba452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 10V, Positive-QTOFsplash10-05g3-9300000000-46e34dc61b2eca51b3c72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 20V, Positive-QTOFsplash10-05o0-9000000000-5aa8028ec0809460fac72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 40V, Positive-QTOFsplash10-0aou-9000000000-eaabea0a253c4703108a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 10V, Negative-QTOFsplash10-0006-0900000000-ea8d6522f4c42a9f73682021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 20V, Negative-QTOFsplash10-0006-0900000000-b4cf9f1c84d5eef415982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isometheptene 40V, Negative-QTOFsplash10-014j-9200000000-a56cffbe0e12f3e0949d2021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06706 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06706 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06706
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21106328
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsometheptene
METLIN IDNot Available
PubChem Compound22297
PDB IDNot Available
ChEBI ID1178590
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Synaptic vesicular amine transporter
General function:
Involved in transmembrane transport
Specific function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular weight:
55712.1
References
  1. Valdivia LF, Centurion D, Perusquia M, Arulmani U, Saxena PR, Villalon CM: Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. Life Sci. 2004 May 14;74(26):3223-34. [PubMed:15094323 ]
  2. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613 ]
  3. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [PubMed:7751968 ]
  4. Parker EM, Cubeddu LX: Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding. J Pharmacol Exp Ther. 1988 Apr;245(1):199-210. [PubMed:3129549 ]
Enzyme Details
2. Alpha-1A adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Valdivia LF, Centurion D, Perusquia M, Arulmani U, Saxena PR, Villalon CM: Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. Life Sci. 2004 May 14;74(26):3223-34. [PubMed:15094323 ]
  2. Parker EM, Cubeddu LX: Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding. J Pharmacol Exp Ther. 1988 Apr;245(1):199-210. [PubMed:3129549 ]