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Showing metabocard for Amphetamine (HMDB0014328)

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enzymes (6)transporters (2) Show 8 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:00:47 UTC
HMDB IDHMDB0014328
Secondary Accession Numbers
  • HMDB14328
Metabolite Identification
Common NameAmphetamine
DescriptionAmphetamine is a chiral compound. The racemic mixture can be divided into its optical antipodes: levo- and dextro-amphetamine. Amphetamine is the parent compound of its own structural class, comprising a broad range of psychoactive derivatives, e.g., MDMA (Ecstasy) and the N-methylated form, methamphetamine. Amphetamine is a homologue of phenethylamine.
Structure
Data?1582753165
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014328 (Amphetamine)


  Mrv0541 04191212102D          

 10 10  0  0  0  0            999 V2000
   -0.1480    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625    0.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -1.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954    0.6169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for HMDB0014328 (Amphetamine)

HMDB0014328
     RDKit          3D
Amphetamine
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.6076   -0.5692   -1.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8174   -0.5476   -0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1939   -0.2098    0.2612 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527    0.5177    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4836    0.3220    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -0.4021    1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6473   -0.5737    0.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310   -0.0025   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4071    0.7175   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    0.8866   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464   -0.6811   -1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1239   -1.4735   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.3240   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6278   -1.5540    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371   -0.1444    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3163    0.7936   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139    0.5806    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2530    1.4839    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -0.8410    2.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557   -1.1453    1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849   -0.1226   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744    1.1643   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    1.4767   -1.5110 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  0
  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 HMDB0014328 (Amphetamine)


  Mrv0541 04191212102D          

 10 10  0  0  0  0            999 V2000
   -0.1480    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625    0.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -1.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954    0.6169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014328

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(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

> <INCHI_KEY>
KWTSXDURSIMDCE-UHFFFAOYSA-N

> <FORMULA>
C9H13N

> <MOLECULAR_WEIGHT>
135.2062

> <EXACT_MASS>
135.104799421

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.174738885675872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
43.7052

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adderall

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0014328 (Amphetamine)

HMDB0014328
     RDKit          3D
Amphetamine
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.6076   -0.5692   -1.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8174   -0.5476   -0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1939   -0.2098    0.2612 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527    0.5177    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4836    0.3220    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -0.4021    1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6473   -0.5737    0.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310   -0.0025   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4071    0.7175   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    0.8866   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464   -0.6811   -1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1239   -1.4735   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.3240   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6278   -1.5540    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371   -0.1444    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3163    0.7936   -0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139    0.5806    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2530    1.4839    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -0.8410    2.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557   -1.1453    1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849   -0.1226   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744    1.1643   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    1.4767   -1.5110 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  0
  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 HMDB0014328 (Amphetamine)

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -0.276   0.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.276  -1.158   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.610   1.152   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.057   1.152   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.610  -1.928   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.944   0.382   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.391   0.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.944  -1.158   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.391  -1.158   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.725   1.152   0.000  0.00  0.00           N+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    8                                                       
CONECT    7    4    9   10                                                  
CONECT    8    5    6                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0014328 (Amphetamine)

COMPND    HMDB0014328
HETATM    1  C1  UNL     1      -1.608  -0.569  -1.573  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.817  -0.548  -0.059  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.194  -0.210   0.261  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.953   0.518   0.566  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.484   0.322   0.333  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.307  -0.402   1.172  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.647  -0.574   0.938  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.231  -0.002  -0.191  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.407   0.717  -1.022  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.060   0.887  -0.781  1.00  0.00           C  
HETATM   11  H1  UNL     1      -0.546  -0.681  -1.799  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.124  -1.474  -1.970  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.011   0.324  -2.044  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.628  -1.554   0.361  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.237  -0.144   1.308  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.316   0.794  -0.068  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.214   0.581   1.646  1.00  0.00           H  
HETATM   18  H8  UNL     1      -1.253   1.484   0.109  1.00  0.00           H  
HETATM   19  H9  UNL     1       0.839  -0.841   2.046  1.00  0.00           H  
HETATM   20  H10 UNL     1       3.256  -1.145   1.615  1.00  0.00           H  
HETATM   21  H11 UNL     1       4.285  -0.123  -0.399  1.00  0.00           H  
HETATM   22  H12 UNL     1       2.874   1.164  -1.909  1.00  0.00           H  
HETATM   23  H13 UNL     1       0.511   1.477  -1.511  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 HMDB0014328 (Amphetamine)

CC(N)CC1=CC=CC=C1
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INCHI for HMDB0014328 (Amphetamine)

InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
AmfetaminKegg
AdzenysKegg
DyanavelKegg
(+/-)-benzedrineHMDB
(+/-)-beta-phenylisopropylamineHMDB
(+/-)-desoxynorephedrineHMDB
1-Methyl-2-phenylethylamineHMDB
1-Phenyl-2-aminopropaneHMDB
3-MethoxyamphetamineHMDB
alpha-MethylbenzeneethaneamineHMDB
AmfetamineHMDB
Amphetamine sulfateHMDB
beta-AminopropylbenzeneHMDB
beta-Phenyl-isopropylamineHMDB
DL-1-Phenyl-2-aminopropaneHMDB
DL-alpha-MethylphenethylamineHMDB
DL-AmphetamineHMDB
DL-BenzedrineHMDB
Fenylo-izopropylaminylHMDB
m-MethoxyamphetamineHMDB
Methamphetamine HCLHMDB
[1-(3-Methoxyphenyl)-2-propyl]amineHMDB
DesoxynorephedrinHMDB
LevoamphetamineHMDB
Levo amphetamineHMDB
Levo-amphetamineHMDB
FenamineHMDB
Miquel brand OF amfetamine sulfateHMDB
PhenoprominHMDB
Sulfate, amphetamineHMDB
Amphetamine sulfate (2:1)HMDB
CentraminaHMDB
MydrialHMDB
PhenamineHMDB
ThyramineHMDB
L AmphetamineHMDB
L-AmphetamineHMDB
AmphetamineKEGG
Chemical FormulaC9H13N
Average Molecular Weight135.2062
Monoisotopic Molecular Weight135.104799421
IUPAC Name1-phenylpropan-2-amine
Traditional Nameadderall
CAS Registry Number300-62-9
SMILES
CC(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
InChI KeyKWTSXDURSIMDCE-UHFFFAOYSA-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 Point25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.74 g/LNot Available
LogP1.8Not Available
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
Polarizability16.17 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]+128.62131661259
DarkChem[M-H]-125.89631661259
DeepCCS[M+H]+131.31830932474
DeepCCS[M-H]-128.00630932474
DeepCCS[M-2H]-165.17930932474
DeepCCS[M+Na]+140.34730932474
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
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, 2022.2.74 minutes32390414
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
AmphetamineCC(N)CC1=CC=CC=C11615.7Standard polar33892256
AmphetamineCC(N)CC1=CC=CC=C11127.5Standard non polar33892256
AmphetamineCC(N)CC1=CC=CC=C11117.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Amphetamine,1TMS,isomer #1CC(CC1=CC=CC=C1)N[Si](C)(C)C1311.4Semi standard non polar33892256
Amphetamine,1TMS,isomer #1CC(CC1=CC=CC=C1)N[Si](C)(C)C1330.8Standard non polar33892256
Amphetamine,1TMS,isomer #1CC(CC1=CC=CC=C1)N[Si](C)(C)C1604.1Standard polar33892256
Amphetamine,2TMS,isomer #1CC(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1502.1Semi standard non polar33892256
Amphetamine,2TMS,isomer #1CC(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1519.0Standard non polar33892256
Amphetamine,2TMS,isomer #1CC(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1658.6Standard polar33892256
Amphetamine,1TBDMS,isomer #1CC(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C1548.7Semi standard non polar33892256
Amphetamine,1TBDMS,isomer #1CC(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C1548.5Standard non polar33892256
Amphetamine,1TBDMS,isomer #1CC(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C1756.5Standard polar33892256
Amphetamine,2TBDMS,isomer #1CC(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1939.1Semi standard non polar33892256
Amphetamine,2TBDMS,isomer #1CC(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1931.9Standard non polar33892256
Amphetamine,2TBDMS,isomer #1CC(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1886.5Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00182 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00182 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 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 IDDB00182
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00042226
Chemspider ID13852819
KEGG Compound IDC07514
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmphetamine
METLIN IDNot Available
PubChem Compound3007
PDB IDNot Available
ChEBI ID132233
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. ZAPPI F, MILLEFIORINI M: [Treatment of the antabuse-alcohol complication with betaphenylisopropylamine; experimental aspects]. Riv Neurol. 1955 Sep-Oct;25(5):725-32. [PubMed:13298508 ]

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. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
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
3. Cocaine- and amphetamine-regulated transcript protein
General function:
Involved in protein binding
Specific function:
Satiety factor closely associated with the actions of leptin and neuropeptide y; this anorectic peptide inhibits both normal and starvation-induced feeding and completely blocks the feeding response induced by neuropeptide Y and regulated by leptin in the hypothalamus. It promotes neuronal development and survival in vitro
Gene Name:
CARTPT
Uniprot ID:
Q16568
Molecular weight:
12829.0
References
  1. Loos RJ, Rankinen T, Tremblay A, Perusse L, Chagnon Y, Bouchard C: Melanocortin-4 receptor gene and physical activity in the Quebec Family Study. Int J Obes (Lond). 2005 Apr;29(4):420-8. [PubMed:15597110 ]
  2. McAlister ED, Van Vugt DA: Effect of leptin administration versus re-feeding on hypothalamic neuropeptide gene expression in fasted male rats. Can J Physiol Pharmacol. 2004 Dec;82(12):1128-34. [PubMed:15644956 ]
  3. Muhlhausler BS, Adam CL, Marrocco EM, Findlay PA, Roberts CT, McFarlane JR, Kauter KG, McMillen IC: Impact of glucose infusion on the structural and functional characteristics of adipose tissue and on hypothalamic gene expression for appetite regulatory neuropeptides in the sheep fetus during late gestation. J Physiol. 2005 May 15;565(Pt 1):185-95. Epub 2005 Jan 20. [PubMed:15661821 ]
  4. Scruggs P, Lai CC, Scruggs JE, Dun NJ: Cocaine- and amphetamine-regulated transcript peptide potentiates spinal glutamatergic sympathoexcitation in anesthetized rats. Regul Pept. 2005 Apr 15;127(1-3):79-85. [PubMed:15680473 ]
  5. Oliveira VX Jr, Fazio MA, Miranda MT, da Silva JM, Bittencourt JC, Elias CF, Miranda A: Leptin fragments induce Fos immunoreactivity in rat hypothalamus. Regul Pept. 2005 Apr 15;127(1-3):123-32. [PubMed:15680478 ]
  6. Vicentic A, Lakatos A, Jones D: The CART receptors: background and recent advances. Peptides. 2006 Aug;27(8):1934-7. Epub 2006 May 19. [PubMed:16713658 ]
Enzyme Details
4. 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, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613 ]
  2. 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 ]
Enzyme Details
5. 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. Lott DC, Kim SJ, Cook EH Jr, de Wit H: Dopamine transporter gene associated with diminished subjective response to amphetamine. Neuropsychopharmacology. 2005 Mar;30(3):602-9. [PubMed:15602501 ]
  2. Fone KC, Nutt DJ: Stimulants: use and abuse in the treatment of attention deficit hyperactivity disorder. Curr Opin Pharmacol. 2005 Feb;5(1):87-93. [PubMed:15661631 ]
  3. 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 ]
  4. Garcia BG, Wei Y, Moron JA, Lin RZ, Javitch JA, Galli A: Akt is essential for insulin modulation of amphetamine-induced human dopamine transporter cell-surface redistribution. Mol Pharmacol. 2005 Jul;68(1):102-9. Epub 2005 Mar 28. [PubMed:15795321 ]
  5. Madras BK, Miller GM, Fischman AJ: The dopamine transporter and attention-deficit/hyperactivity disorder. Biol Psychiatry. 2005 Jun 1;57(11):1397-409. Epub 2005 Jan 5. [PubMed:15950014 ]
  6. Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. [PubMed:15728379 ]
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. Solute carrier family 22 member 5
General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [PubMed:9618255 ]
  2. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]
Enzyme Details
2. Solute carrier family 22 member 3
General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
References
  1. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]