DEXTROAMPHETAMINE

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Synonyms
Status
Molecule Category Free-form
UNII TZ47U051FI
EPA CompTox DTXSID8022907

Structure

InChI Key KWTSXDURSIMDCE-QMMMGPOBSA-N
Smiles C[C@H](N)Cc1ccccc1
InChI
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H13N
Molecular Weight 135.21
AlogP 1.58
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 26.02
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 10.0

Bioactivity

Mechanism of Action Action Reference
Dopamine transporter releasing agent RELEASING AGENT PubMed PubMed PubMed
Protein: Norepinephrine transporter
Description: Sodium-dependent noradrenaline transporter
Organism : Homo sapiens
P23975 ENSG00000103546
Protein: Dopamine transporter
Description: Sodium-dependent dopamine transporter
Organism : Homo sapiens
Q01959 ENSG00000142319
Protein: Synaptic vesicular amine transporter
Description: Synaptic vesicular amine transporter
Organism : Homo sapiens
Q05940 ENSG00000165646
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- - - 12200 -
Ion channel Ligand-gated ion channel 5HT3 receptor
- - 4467 - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - 4467 - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Trace amine receptor
14-1200 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
1765-1770 16596 - 101 -
Assay Description Organism Bioactivity Reference
Effective concentration was measured for the release of accumulated [3H]NE from chopped cortex of rat Rattus norvegicus 800.0 nM
Inhibitory concentration against uptake of [3H]NE into chopped cerebral cortical tissue from rat brain Rattus norvegicus 200.0 nM
Agonist activity at human trace amine associated receptor 1 expressed in RD-HGA16 CHO-K1 cells coexpressed with Galpha16 protein assessed as internal calcium mobilization by calcium 3 assay Homo sapiens 935.0 nM
Activation of C-terminal HA epitope tagged human TAAR1 expressed in RD-HGA16 cells co-expressing Gq protein, Galpha16 by cAMP accumulation assay Homo sapiens 600.0 nM
Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3H]cAMP after 1 hr by liquid scintillation counting Rattus norvegicus 810.0 nM
Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3H]cAMP after 1 hr by competitive binding assay Rattus norvegicus 440.0 nM
Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulation of [3H]cAMP after 1 hr by liquid scintillation counting Mus musculus 210.0 nM
Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulation of cAMP after 15 mins Mus musculus 2.0 nM
Activation of human TAAR1 expressed in Syrian hamster AV12-664 cells co-expressing GalphaS protein assessed as accumulation of cAMP after 30 mins using cAMP XS EA/CL as substrate by luminescence method in presence of RX821002 and alprenolol Homo sapiens 990.0 nM
Activation of human TAAR1 expressed in human HEK293T cells assessed as cAMP accumulation after 10 mins by BRET assay Homo sapiens 140.0 nM
Inhibition of [3H]norepinephrine reuptake at human NET cloned in rat brain synaptosome by scintillation counting Homo sapiens 7.1 nM
Inhibition of [3H]dopamine reuptake at human DAT cloned in rat brain synaptosome by scintillation counting Homo sapiens 24.8 nM
Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay Homo sapiens 101.0 nM Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay Homo sapiens 630.96 nM
Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay Homo sapiens 109.0 nM Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay Homo sapiens 288.4 nM
Activation of mouse TAAR1 transmembrane domain 7 Tyr287(7.39)Asn mutant expressed in HEK293 cells assessed as stimulation of cAMP production after 1 hr by chemiluminescent assay Mus musculus 218.8 nM
Activation of rat TAAR1 transmembrane domain 7 Asn287(7.39)Tyr mutant expressed in HEK293 cells assessed as stimulation of cAMP production after 1 hr by chemiluminescent assay Rattus norvegicus 13.9 nM
Activation of mouse TAAR1 transmembrane domain 6 Thr268(6.55)Met mutant expressed in HEK293 cells assessed as stimulation of cAMP production after 1 hr by chemiluminescent assay Mus musculus 3.98 nM
Activation of rat TAAR1 transmembrane domain 6 Met268(6.55)Thr mutant expressed in HEK293 cells assessed as stimulation of cAMP production after 1 hr by chemiluminescent assay Rattus norvegicus 677.4 nM
Activation of mouse wild type TAAR1 expressed in HEK293 cells assessed as stimulation of cAMP production after 1 hr by chemiluminescent assay Mus musculus 84.6 nM
Activation of rat wild type TAAR1 expressed in HEK293 cells assessed as stimulation of cAMP production after 1 hr by chemiluminescent assay Rattus norvegicus 55.6 nM
Activity at DAT in rat synaptosomes obtained from striatum assessed as release of [3H]MPP+ by liquid scintillation counting method Rattus norvegicus 24.8 nM
Activity at NET in rat synaptosomes obtained from whole brain minus striatum and cerebellum assessed as release of [3H]MPP+ by liquid scintillation counting method Rattus norvegicus 7.1 nM
Activity at DAT in rat synaptosomes assessed as release of [3H]DA after 5 mins by liquid scintillation counting method Rattus norvegicus 25.0 nM
Activity at NET in rat synaptosomes assessed as release of [3H]NE after 30 mins by liquid scintillation counting method Rattus norvegicus 7.0 nM

Cross References

Resources Reference
ChEBI 4469
ChEMBL CHEMBL612
DrugBank DB01576
DrugCentral 841
FDA SRS TZ47U051FI
Human Metabolome Database HMDB0015516
Guide to Pharmacology 2147
KEGG C07884
PDB 1WE
PharmGKB PA448408
PubChem 5826
SureChEMBL SCHEMBL8859
ZINC ZINC000006021033
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