CHEBI:4469 - (S)-amphetamine

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ChEBI Name (S)-amphetamine
ChEBI ID CHEBI:4469
ChEBI ASCII Name (S)-amphetamine
Definition A 1-phenylpropan-2-amine that has S configuration.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H13N
Net Charge 0
Average Mass 135.20626
Monoisotopic Mass 135.105
InChI InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
InChIKey KWTSXDURSIMDCE-QMMMGPOBSA-N
SMILES C[C@H](N)Cc1ccccc1
Roles Classification
Biological Role(s): sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
adrenergic agent
Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopaminergic agent
A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
neurotoxin
A poison that interferes with the functions of the nervous system.
Application(s): sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
adrenergic agent
Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopaminergic agent
A drug used for its effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-amphetamine (CHEBI:4469) has role adrenergic agent (CHEBI:37962)
(S)-amphetamine (CHEBI:4469) has role adrenergic uptake inhibitor (CHEBI:35640)
(S)-amphetamine (CHEBI:4469) has role dopamine uptake inhibitor (CHEBI:51039)
(S)-amphetamine (CHEBI:4469) has role dopaminergic agent (CHEBI:48560)
(S)-amphetamine (CHEBI:4469) has role neurotoxin (CHEBI:50910)
(S)-amphetamine (CHEBI:4469) has role sympathomimetic agent (CHEBI:35524)
(S)-amphetamine (CHEBI:4469) is a 1-phenylpropan-2-amine (CHEBI:132233)
(S)-amphetamine (CHEBI:4469) is enantiomer of (R)-amphetamine (CHEBI:42724)
Incoming methamphetamine (CHEBI:6809) has functional parent (S)-amphetamine (CHEBI:4469)
(S)-amphetamine sulfate (CHEBI:51064) has part (S)-amphetamine (CHEBI:4469)
amphetamine (CHEBI:2679) has part (S)-amphetamine (CHEBI:4469)
(R)-amphetamine (CHEBI:42724) is enantiomer of (S)-amphetamine (CHEBI:4469)
IUPAC Name
(2S)-1-phenylpropan-2-amine
Synonyms Sources
(+)-(S)-amphetamine ChemIDplus
(+)-α-methylphenethylamine NIST Chemistry WebBook
(+)-α-methylphenylethylamine NIST Chemistry WebBook
(+)-amphetamine ChEBI
S)-α-methylbenzeneethanamine ChemIDplus
(S)-(+)-amphetamine ChemIDplus
(S)-(+)-β-phenylisopropylamine NIST Chemistry WebBook
(S)-1-phenyl-2-aminopropane ChemIDplus
(S)-1-phenyl-2-propylamine ChemIDplus
(S)-α-methylbenzeneethanamine ChemIDplus
(S)-amphetamine NIST Chemistry WebBook
d-amphetamine ChemIDplus
dexamphetamine NIST Chemistry WebBook
Dextroamphetamine KEGG COMPOUND
Database Links Databases
841 DrugCentral
C07884 KEGG COMPOUND
D03740 KEGG DRUG
DB01576 DrugBank
Dextroamphetamine Wikipedia
View more database links
Registry Numbers Types Sources
1125854 Gmelin Registry Number Gmelin
2205872 Beilstein Registry Number ChemIDplus
51-64-9 CAS Registry Number ChemIDplus
51-64-9 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
22129527 PubMed citation Europe PMC
22894820 PubMed citation Europe PMC
23360956 PubMed citation Europe PMC
23851485 PubMed citation Europe PMC
23881044 PubMed citation Europe PMC
23907377 PubMed citation Europe PMC
24349338 PubMed citation Europe PMC
Last Modified
22 February 2017