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name Structure Reference Source Properties Activities Metabolism

Amphetamine

AlkaPlorer ID: AK005405

Synonym: ''

IUPAC Name: (2S)-1-phenylpropan-2-amine

Structure

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

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InChI: 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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InChIKey: KWTSXDURSIMDCE-QMMMGPOBSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 135.20999999999998

TPSA？: 26.02

MolLogP？: 1.5763

Number of H-Donors: 1

Number of H-Acceptors: 1

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Monoamine oxidase B Ki 300000.0 nM 10.1021/jm00403a012
Bos taurus Phenylethanolamine N-methyltransferase Ki 422000.0 nM 10.1021/jm00118a021
Bos taurus Phenylethanolamine N-methyltransferase Ki 422000.0 nM 10.1021/jm00352a020
Bos taurus Phenylethanolamine N-methyltransferase Ki 442000.0 nM 10.1021/jm00352a031
Bos taurus Phenylethanolamine N-methyltransferase Ki 1381000.0 nM 10.1021/jm00352a020
Homo sapiens Dopamine transporter Activity nan None 10.1021/acs.jmedchem.7b01313
Homo sapiens Dopamine transporter Activity nan None 10.1021/acs.jmedchem.9b01938
Homo sapiens Dopamine transporter EC50 24.8 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Dopamine transporter IC50 288.4 nM 10.1016/j.bmcl.2013.03.066
Homo sapiens Dopamine transporter Ki 109.0 nM 10.1016/j.bmcl.2013.03.066
Homo sapiens Homo sapiens Activity 0.9 % 10.1016/j.ejmech.2009.11.034
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 0.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Monoamine oxidase A Ki 14400.0 nM 10.1016/j.bmc.2010.01.029
Homo sapiens Monoamine oxidase B Ki 280000.0 nM 10.1016/j.bmc.2010.01.029
Homo sapiens Norepinephrine transporter EC50 7.1 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Norepinephrine transporter IC50 630.96 nM 10.1016/j.bmcl.2013.03.066
Homo sapiens Norepinephrine transporter Ki 101.0 nM 10.1016/j.bmcl.2013.03.066
Homo sapiens Serotonin 2a (5-HT2a) receptor Activity nan None 10.1039/C6MD00245E
Homo sapiens Serotonin 2b (5-HT2b) receptor Activity nan None 10.1039/C6MD00245E
Homo sapiens Serotonin 2c (5-HT2c) receptor Activity nan None 10.1039/C6MD00245E
Homo sapiens Serotonin transporter EC50 1770.0 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Serotonin transporter IC50 16595.87 nM 10.1016/j.bmcl.2013.03.066
Homo sapiens Serotonin transporter Ki 5728.0 nM 10.1016/j.bmcl.2013.03.066
Homo sapiens Trace amine-associated receptor 1 EC50 140.0 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Trace amine-associated receptor 1 EC50 600.0 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Trace amine-associated receptor 1 EC50 935.0 nM 10.1016/j.bmc.2008.06.009
Homo sapiens Trace amine-associated receptor 1 EC50 990.0 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Trace amine-associated receptor 1 Emax 74.0 % 10.1016/j.bmc.2008.06.009
Macaca mulatta Trace amine-associated receptor 1 EC50 1010.0 nM 10.1016/j.bmc.2011.10.007
Mus musculus Mus musculus Activity 34.0 % 10.1021/jm00200a008
Mus musculus Mus musculus Activity 59.0 % 10.1021/jm00200a008
Mus musculus Mus musculus Activity nan None 10.1021/np50004a002
Mus musculus Mus musculus Amnesia reversal 10.0 % 10.1021/jm00371a023
Mus musculus Mus musculus Amnesia reversal 15.0 % 10.1021/jm00371a023
Mus musculus Mus musculus Amnesia reversal 40.0 % 10.1021/jm00371a023
Mus musculus Mus musculus Amnesia reversal nan None 10.1021/jm00371a023
Mus musculus Mus musculus ED50 nan mg.kg-1 10.1021/jm00123a004
Mus musculus Mus musculus MED 2.5 mg kg-1 10.1021/jm00123a004
Mus musculus Mus musculus MTA 14356.0 None 10.1021/jm00347a011
Mus musculus Mus musculus Retention 28.0 % 10.1021/jm00135a020
Mus musculus Mus musculus Retention 45.0 % 10.1021/jm00135a020
Mus musculus Mus musculus Retention 60.0 % 10.1021/jm00135a020
Mus musculus Mus musculus Retention 65.0 % 10.1021/jm00135a020
Mus musculus Mus musculus Retention 80.0 % 10.1021/jm00135a020
Mus musculus Mus musculus Retention 100.0 % 10.1021/jm00135a020
Mus musculus Trace amine-associated receptor 1 Activity nan None 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 EC50 2.0 nM 10.1016/j.bmc.2011.10.007
Mus musculus Trace amine-associated receptor 1 EC50 3.98 nM 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 EC50 84.6 nM 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 EC50 210.0 nM 10.1016/j.bmc.2011.10.007
Mus musculus Trace amine-associated receptor 1 EC50 218.8 nM 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 Emax 93.05 % 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 Emax 98.0 % 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 Emax 99.8 % 10.1021/jm401316v
Rattus norvegicus Dopamine transporter EC50 24.8 nM 10.1039/C6MD00245E
Rattus norvegicus Dopamine transporter EC50 25.0 nM 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Dopamine transporter IC50 4900.0 nM 10.1021/np50124a001
Rattus norvegicus Glutamate NMDA receptor Ki 300000.0 nM 10.1016/j.bmc.2009.03.025
Rattus norvegicus Glutamate NMDA receptor Ratio Ki 1.47 None 10.1016/j.bmc.2009.03.025
Rattus norvegicus Monoamine oxidase A Ki 12200.0 nM 10.1016/j.bmc.2010.01.029
Rattus norvegicus Monoamine oxidase B Ki 100000.0 nM 10.1016/j.bmc.2010.01.029
Rattus norvegicus Monoamine oxidase B Ki 160000.0 nM 10.1021/jm00403a012
Rattus norvegicus Monoamine oxidase B Ki 580000.0 nM 10.1021/jm00403a012
Rattus norvegicus Peripheral myelin protein 22 Potency 2.3 nM None
Rattus norvegicus Rattus norvegicus Activity 20.0 % 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/jm00194a003
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/jm00200a008
Rattus norvegicus Rattus norvegicus Activity nan None 10.1021/jm00347a011
Rattus norvegicus Rattus norvegicus EC50 800.0 nM 10.1021/jm00180a006
Rattus norvegicus Rattus norvegicus EC50 11000.0 nM 10.1021/jm00180a006
Rattus norvegicus Rattus norvegicus ED50 0.2 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 0.23 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 0.28 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 0.31 mg.kg-1 10.1021/jm00109a020
Rattus norvegicus Rattus norvegicus ED50 0.4 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 0.44 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 0.62 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 1.06 umol.kg-1 10.1021/jm9705925
Rattus norvegicus Rattus norvegicus ED50 1.69 umol.kg-1 10.1021/jm00109a020
Rattus norvegicus Rattus norvegicus IC50 200.0 nM 10.1021/jm00180a006
Rattus norvegicus Rattus norvegicus SD200 5.0 uM kg-1 10.1021/jm00347a011
Rattus norvegicus Serotonin (5-HT) receptor Kd 4466.84 nM 10.1021/jm00177a017
Rattus norvegicus Serotonin transporter EC50 1765.0 nM 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Serotonin transporter EC50 1770.0 nM 10.1039/C6MD00245E
Rattus norvegicus Trace amine-associated receptor 1 EC50 13.9 nM 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 EC50 55.6 nM 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 EC50 440.0 nM 10.1016/j.bmc.2011.10.007
Rattus norvegicus Trace amine-associated receptor 1 EC50 677.4 nM 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 EC50 810.0 nM 10.1016/j.bmc.2011.10.007
Rattus norvegicus Trace amine-associated receptor 1 EC50 1200.0 nM 10.1016/j.bmc.2011.10.007
Rattus norvegicus Trace amine-associated receptor 1 Emax 93.79 % 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 Emax 102.2 % 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 Emax 103.1 % 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 FC 1000000.0 None 10.1021/jm401316v
None ADMET T1/2 10.0 hr 10.1016/j.bmcl.2019.06.043
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None No relevant target pKa 9.94 None 10.1007/s11095-013-1232-z
None Unchecked EC50 7.0 nM 10.1021/acs.jmedchem.7b00085
None Unchecked EC50 7.1 nM 10.1039/C6MD00245E
None Unchecked EC50 1120.0 nM 10.1016/j.bmc.2011.10.007
None Unchecked Ki 1000.0 nM 10.1016/j.bmc.2011.10.007
None Unchecked Ki 46000.0 nM 10.1021/acs.jmedchem.7b00085
None Unchecked Ratio EC50 10.0 None 10.1021/jm401316v
None Unchecked Ratio EC50 71.0 None 10.1039/C6MD00245E
None Unchecked Ratio IC50 20.4 None 10.1021/np50124a001
None Unchecked Ratio Ki 0.05 None 10.1016/j.bmc.2010.01.029
None Unchecked Ratio Ki 0.12 None 10.1016/j.bmc.2010.01.029

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT012700 C[C@@H](Cc1ccccc1)NC(=O)[C@@H](N)CCCCN>>C[C@H](N)Cc1ccccc1 RXN-19388
AKRT013681 C[C@H](N)Cc1ccccc1>>C[C@H](N)[C@H](O)c1ccccc1 RXN-19390