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Showing metabocard for Dextroamphetamine (HMDB0015516)

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enzymes (6)transporters (1) Show 7 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015516
Secondary Accession Numbers
  • HMDB15516
Metabolite Identification
Common NameDextroamphetamine
DescriptionDextroamphetamine is only found in individuals that have used or taken this drug. It is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. It is a slightly polar, weak base and is lipophilic. The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect.
Structure
Data?1582753305
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015516 (Dextroamphetamine)

1576
  Mrv0541 02231215342D          

 10 10  0  0  1  0            999 V2000
    3.0790    1.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.9034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for HMDB0015516 (Dextroamphetamine)

HMDB0015516
     RDKit          3D
Dextroamphetamine
 23 23  0  0  0  0  0  0  0  0999 V2000
    3.0826    0.4340   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082    0.4612    0.1240 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7241   -0.3391    1.3024 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7272   -0.0341   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683   -0.0581   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -1.1859    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -1.2500    0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560   -0.1523    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846    0.9945   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4940    1.0442   -0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.9514   -1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154   -0.6006   -0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7597    0.9895    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4480    1.5064    0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8088   -0.5830    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547   -1.0567    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0011   -1.0440   -1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7538    0.6173   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971   -2.0526    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -2.1764    1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2647   -0.2260    0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    1.8205   -0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431    1.9396   -1.0227 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
M  END
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3D SDF for HMDB0015516 (Dextroamphetamine)

1576
  Mrv0541 02231215342D          

 10 10  0  0  1  0            999 V2000
    3.0790    1.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.9034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015516

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](N)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1

> <INCHI_KEY>
KWTSXDURSIMDCE-QMMMGPOBSA-N

> <FORMULA>
C9H13N

> <MOLECULAR_WEIGHT>
135.2062

> <EXACT_MASS>
135.104799421

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.080575367482364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-phenylpropan-2-amine

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.8042504816666665

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.01443581771614

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
43.705200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amphetamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015516 (Dextroamphetamine)

HMDB0015516
     RDKit          3D
Dextroamphetamine
 23 23  0  0  0  0  0  0  0  0999 V2000
    3.0826    0.4340   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082    0.4612    0.1240 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7241   -0.3391    1.3024 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7272   -0.0341   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683   -0.0581   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1571   -1.1859    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -1.2500    0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560   -0.1523    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846    0.9945   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4940    1.0442   -0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618    0.9514   -1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154   -0.6006   -0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7597    0.9895    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4480    1.5064    0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8088   -0.5830    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547   -1.0567    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0011   -1.0440   -1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7538    0.6173   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971   -2.0526    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -2.1764    1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2647   -0.2260    0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663    1.8205   -0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431    1.9396   -1.0227 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
M  END
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PDB for HMDB0015516 (Dextroamphetamine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1576                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.747   3.226   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.747   1.686   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.414   0.916   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414  -0.624   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   0.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -1.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080  -1.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -2.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -2.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.704   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    6    7                                                  
CONECT    5    2                                                            
CONECT    6    4    8                                                       
CONECT    7    4    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0015516 (Dextroamphetamine)

COMPND    HMDB0015516
HETATM    1  C1  UNL     1       3.083   0.434  -0.526  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.708   0.461   0.124  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.724  -0.339   1.302  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.727  -0.034  -0.917  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.668  -0.058  -0.408  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.157  -1.186   0.210  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.443  -1.250   0.695  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.256  -0.152   0.555  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.785   0.995  -0.064  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.494   1.044  -0.545  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.062   0.951  -1.497  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.415  -0.601  -0.675  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.760   0.989   0.139  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.448   1.506   0.360  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.809  -0.583   1.691  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.455  -1.057   1.352  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.001  -1.044  -1.251  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.754   0.617  -1.815  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.497  -2.053   0.314  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.772  -2.176   1.177  1.00  0.00           H  
HETATM   21  H11 UNL     1      -4.265  -0.226   0.945  1.00  0.00           H  
HETATM   22  H12 UNL     1      -3.466   1.821  -0.144  1.00  0.00           H  
HETATM   23  H13 UNL     1      -1.143   1.940  -1.023  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4   14
CONECT    3   15   16
CONECT    4    5   17   18
CONECT    5    6    6   10
CONECT    6    7   19
CONECT    7    8    8   20
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   23
END
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SMILES for HMDB0015516 (Dextroamphetamine)

C[C@H](N)CC1=CC=CC=C1
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INCHI for HMDB0015516 (Dextroamphetamine)

InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(+)-(S)-AmphetamineChEBI
(+)-alpha-MethylphenethylamineChEBI
(+)-alpha-MethylphenylethylamineChEBI
(+)-AmphetamineChEBI
(AlphaS)-alpha-methylbenzeneethanamineChEBI
(S)-(+)-AmphetamineChEBI
(S)-(+)-beta-PhenylisopropylamineChEBI
(S)-1-Phenyl-2-aminopropaneChEBI
(S)-1-Phenyl-2-propylamineChEBI
(S)-alpha-MethylbenzeneethanamineChEBI
D-AmphetamineChEBI
DexamphetamineChEBI
DexamfetamineKegg
(+)-a-MethylphenethylamineGenerator
(+)-Α-methylphenethylamineGenerator
(+)-a-MethylphenylethylamineGenerator
(+)-Α-methylphenylethylamineGenerator
(AlphaS)-a-methylbenzeneethanamineGenerator
(AlphaS)-α-methylbenzeneethanamineGenerator
(S)-(+)-b-PhenylisopropylamineGenerator
(S)-(+)-Β-phenylisopropylamineGenerator
(S)-a-MethylbenzeneethanamineGenerator
(S)-Α-methylbenzeneethanamineGenerator
(S)-AmphetamineHMDB
Celltech brand OF dextroamphetamine sulfateHMDB
OxydessHMDB
Sulfate, dextroamphetamineHMDB
D AmphetamineHMDB
CurbanHMDB
Dextro-amphetamine sulfateHMDB
GlaxoSmithKline brand OF dextroamphetamine sulfateHMDB
Dextro-amphetamineHMDB
Dextro amphetamine sulfateHMDB
DextroStatHMDB
Shire brand OF dextroamphetamine sulfateHMDB
D-Amphetamine sulfateHMDB
DexedrineHMDB
Dextroamphetamine sulfateHMDB
Mallinckrodt brand OF dextroamphetamine sulfateHMDB
Pasadena brand OF dextroamphetamineHMDB
Vortech brand OF dextroamphetamine sulfateHMDB
D Amphetamine sulfateHMDB
Dextro amphetamineHMDB
DextroamphetamineChEBI
Chemical FormulaC9H13N
Average Molecular Weight135.2062
Monoisotopic Molecular Weight135.104799421
IUPAC Name(2S)-1-phenylpropan-2-amine
Traditional Nameamphetamine
CAS Registry Number51-64-9
SMILES
C[C@H](N)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
InChI KeyKWTSXDURSIMDCE-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleIndirect biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.74 g/LNot Available
LogP1.76SANGSTER (1994); similar isomer
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.74 g/LALOGPS
logP1.85ALOGPS
logP1.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.71 m³·mol⁻¹ChemAxon
Polarizability16.08 ųChemAxon
Number of Rings1ChemAxon
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]+129.67231661259
DarkChem[M-H]-127.07131661259
DeepCCS[M+H]+133.15230932474
DeepCCS[M-H]-129.93830932474
DeepCCS[M-2H]-166.90930932474
DeepCCS[M+Na]+142.44730932474
AllCCS[M+H]+129.132859911
AllCCS[M+H-H2O]+124.532859911
AllCCS[M+NH4]+133.532859911
AllCCS[M+Na]+134.832859911
AllCCS[M-H]-131.132859911
AllCCS[M+Na-2H]-132.932859911
AllCCS[M+HCOO]-134.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202210.3939 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.71 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid72.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1049.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid346.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid124.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid200.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid93.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid309.9 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 Acid346.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)177.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid869.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid313.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid816.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid218.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid276.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate361.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA326.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water39.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DextroamphetamineC[C@H](N)CC1=CC=CC=C11645.8Standard polar33892256
DextroamphetamineC[C@H](N)CC1=CC=CC=C11128.0Standard non polar33892256
DextroamphetamineC[C@H](N)CC1=CC=CC=C11147.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dextroamphetamine,1TMS,isomer #1C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C1334.7Semi standard non polar33892256
Dextroamphetamine,1TMS,isomer #1C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C1339.0Standard non polar33892256
Dextroamphetamine,1TMS,isomer #1C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C1618.3Standard polar33892256
Dextroamphetamine,2TMS,isomer #1C[C@@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1539.5Semi standard non polar33892256
Dextroamphetamine,2TMS,isomer #1C[C@@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1524.0Standard non polar33892256
Dextroamphetamine,2TMS,isomer #1C[C@@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1644.4Standard polar33892256
Dextroamphetamine,1TBDMS,isomer #1C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C1564.4Semi standard non polar33892256
Dextroamphetamine,1TBDMS,isomer #1C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C1562.5Standard non polar33892256
Dextroamphetamine,1TBDMS,isomer #1C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C1758.8Standard polar33892256
Dextroamphetamine,2TBDMS,isomer #1C[C@@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1970.2Semi standard non polar33892256
Dextroamphetamine,2TBDMS,isomer #1C[C@@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1936.9Standard non polar33892256
Dextroamphetamine,2TBDMS,isomer #1C[C@@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1881.7Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01576 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01576 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01576
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5621
KEGG Compound IDC07884
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDextroamphetamine
METLIN IDNot Available
PubChem Compound5826
PDB IDNot Available
ChEBI ID4469
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 References
  1. Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. [PubMed:2180548 ]
  2. Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6. [PubMed:6506758 ]
  3. Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40. [PubMed:10901342 ]
  4. Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68. [PubMed:11782985 ]
  5. Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6. [PubMed:14520168 ]
  6. Greer CA, Alpern HP: Maturational changes related to dopamine in the effects of d-amphetamine, cocaine, nicotine, and strychnine on seizure susceptibility. Psychopharmacology (Berl). 1979 Sep;64(3):255-60. [PubMed:116267 ]
  7. Lile JA, Stoops WW, Durell TM, Glaser PE, Rush CR: Discriminative-stimulus, self-reported, performance, and cardiovascular effects of atomoxetine in methylphenidate-trained humans. Exp Clin Psychopharmacol. 2006 May;14(2):136-47. [PubMed:16756417 ]
  8. Patel JB, Migler B: A sensitive and selective monkey conflict test. Pharmacol Biochem Behav. 1982 Oct;17(4):645-9. [PubMed:7178177 ]
  9. Chiueh CC, Moore KE: D-amphetamine-induced release of "newly synthesized" and "stored" dopamine from the caudate nucleus in vivo. J Pharmacol Exp Ther. 1975 Mar;192(3):642-53. [PubMed:1120962 ]
  10. Glick SD, Cox RD, Greenstein S: Relationship of rats' spatial preferences to effects of d-amphetamine on timing behavior. Eur J Pharmacol. 1975 Aug;33(1):173-82. [PubMed:1236804 ]

Enzymes

Enzyme Details
1. Cytochrome P450 2D6
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
2. 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. 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 ]
  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 ]
Enzyme Details
3. Sodium-dependent dopamine transporter
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular weight:
68494.255
References
  1. Zhen J, Chen N, Reith ME: Differences in interactions with the dopamine transporter as revealed by diminishment of Na(+) gradient and membrane potential: dopamine versus other substrates. Neuropharmacology. 2005 Nov;49(6):769-79. Epub 2005 Aug 24. [PubMed:16122767 ]
  2. Kuczenski R, Segal DS, Cho AK, Melega W: Hippocampus norepinephrine, caudate dopamine and serotonin, and behavioral responses to the stereoisomers of amphetamine and methamphetamine. J Neurosci. 1995 Feb;15(2):1308-17. [PubMed:7869099 ]
  3. Rothman RB, Dersch CM, Ananthan S, Partilla JS: Studies of the biogenic amine transporters. 13. Identification of "agonist" and "antagonist" allosteric modulators of amphetamine-induced dopamine release. J Pharmacol Exp Ther. 2009 May;329(2):718-28. doi: 10.1124/jpet.108.149088. Epub 2009 Feb 24. [PubMed:19244097 ]
Enzyme Details
4. 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Enzyme Details
5. Alpha-1B 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
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Enzyme Details
6. Trace amine-associated receptor 1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for trace amines, including beta- phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase
Gene Name:
TAAR1
Uniprot ID:
Q96RJ0
Molecular weight:
39091.3
References
  1. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. [PubMed:17218486 ]
  2. Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. [PubMed:17234900 ]
  3. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. [PubMed:17212650 ]
  4. Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. [PubMed:17234899 ]
  5. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. [PubMed:15764732 ]

Transporters

Enzyme Details
1. Sodium-dependent noradrenaline transporter
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Dlugos A, Freitag C, Hohoff C, McDonald J, Cook EH, Deckert J, de Wit H: Norepinephrine transporter gene variation modulates acute response to D-amphetamine. Biol Psychiatry. 2007 Jun 1;61(11):1296-305. Epub 2007 Jan 17. [PubMed:17239355 ]
  2. Dlugos AM, Hamidovic A, Palmer AA, de Wit H: Further evidence of association between amphetamine response and SLC6A2 gene variants. Psychopharmacology (Berl). 2009 Oct;206(3):501-11. doi: 10.1007/s00213-009-1628-y. [PubMed:19727679 ]
  3. Burnette WB, Bailey MD, Kukoyi S, Blakely RD, Trowbridge CG, Justice JB Jr: Human norepinephrine transporter kinetics using rotating disk electrode voltammetry. Anal Chem. 1996 Sep 1;68(17):2932-8. [PubMed:8794928 ]