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name Structure Reference Source Properties Activities Metabolism

Methamphetamine

AlkaPlorer ID: AK008153

Synonym: '(+)-Methamphetamine', '(S)-(+)-Methamphetamine hydrochloride', 'MLS002320675', 'SMR001338821'

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

Structure

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

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InChI: InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m0/s1

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InChIKey: MYWUZJCMWCOHBA-VIFPVBQESA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 149.237

TPSA？: 12.03

MolLogP？: 1.837

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 550000.0 nM 10.1021/jm00403a012
Homo sapiens CDGSH iron-sulfur domain-containing protein 1 IC50 nan None 10.1016/j.bmcl.2016.09.009
Homo sapiens CDGSH iron-sulfur domain-containing protein 1 Ki nan None 10.1016/j.bmcl.2016.09.009
Homo sapiens Cytochrome P450 1A2 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2C19 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2C9 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 2D6 Inhibition nan % 10.1021/tx300075j
Homo sapiens Cytochrome P450 3A4 Inhibition nan % 10.1021/tx300075j
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 Liver microsomes Activity nan None 10.1021/tx300075j
Homo sapiens Liver microsomes Stability nan % 10.1021/tx300075j
Homo sapiens Sigma opioid receptor Ki 8320.0 nM 10.1021/jm00107a033
Homo sapiens Solute carrier family 22 member 5 Activity 66.0 % 10.1006/bbrc.1998.8669
Homo sapiens Trace amine-associated receptor 1 EC50 1300.0 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Trace amine-associated receptor 1 EC50 1500.0 nM 10.1016/j.bmc.2011.10.007
Homo sapiens Whole blood Retention_time 2.86 min 10.1007/s00044-012-9977-1
Macaca mulatta Trace amine-associated receptor 1 EC50 5300.0 nM 10.1016/j.bmc.2011.10.007
Mus musculus Trace amine-associated receptor 1 Activity nan None 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 EC50 17.81 nM 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 EC50 70.0 nM 10.1016/j.bmc.2011.10.007
Mus musculus Trace amine-associated receptor 1 EC50 278.9 nM 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 EC50 920.0 nM 10.1016/j.bmc.2011.10.007
Mus musculus Trace amine-associated receptor 1 EC50 1822.0 nM 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 Emax 92.22 % 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 Emax 94.04 % 10.1021/jm401316v
Mus musculus Trace amine-associated receptor 1 Emax 98.01 % 10.1021/jm401316v
Rattus norvegicus Monoamine oxidase B Ki 270000.0 nM 10.1021/jm00403a012
Rattus norvegicus Rattus norvegicus ED50 0.06 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 0.17 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus ED50 0.2 mg.kg-1 10.1021/acs.jmedchem.7b00085
Rattus norvegicus Rattus norvegicus Mean activity counts 1462.0 None 10.1021/jm00105a025
Rattus norvegicus Rattus norvegicus Mean activity counts 3728.0 None 10.1021/jm00105a025
Rattus norvegicus Solute carrier family 22 member 3 IC50 248000.0 nM 10.1074/jbc.273.49.32776
Rattus norvegicus Solute carrier family 22 member 5 Inhibition nan % None
Rattus norvegicus Synaptic vesicular amine transporter Ki 2460.0 nM 10.1016/j.bmc.2013.08.001
Rattus norvegicus Synaptic vesicular amine transporter Ki 2460.0 nM 10.1016/j.bmcl.2015.04.105
Rattus norvegicus Synaptic vesicular amine transporter Ki 80100.0 nM 10.1016/j.bmcl.2015.04.105
Rattus norvegicus Synaptic vesicular amine transporter Ratio Ki 3.0 None 10.1016/j.bmcl.2015.04.105
Rattus norvegicus Trace amine-associated receptor 1 EC50 133.3 nM 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 EC50 201.8 nM 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 EC50 890.0 nM 10.1016/j.bmc.2011.10.007
Rattus norvegicus Trace amine-associated receptor 1 EC50 2044.0 nM 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 Emax 94.31 % 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 Emax 94.33 % 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 Emax 100.9 % 10.1021/jm401316v
Rattus norvegicus Trace amine-associated receptor 1 FC 1000000.0 None 10.1021/jm401316v
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None ADMET CL 4.4 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET MRT 16.0 hr 10.1124/dmd.108.020479
None ADMET T1/2 12.0 hr 10.1124/dmd.108.020479
None ADMET Vdss 4.3 L.kg-1 10.1124/dmd.108.020479
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None Hepatotoxicity HepSE_bilirubinemia 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholecystitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholelithiasis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cirrhosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_Combined Scores 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_elevated liver function tests 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic failure 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic necrosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatomegaly 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_jaundice 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver disease 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver fatty 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver function tests abnormal 0.0 None 10.1371/journal.pcbi.1002310
None NON-PROTEIN TARGET Fu 0.85 None 10.1124/dmd.108.020479
None No relevant target Log PNalk 1.24 None 10.1021/jm048980b
None No relevant target pKa 9.99 None 10.1007/s11095-013-1232-z
None Unchecked EC50 4440.0 nM 10.1016/j.bmc.2011.10.007
None Unchecked Ratio EC50 10.0 None 10.1021/jm401316v

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010787 CN[C@@H](C)Cc1ccccc1>>C[C@@H](Cc1ccccc1)N(C)O RXN-19393