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Details

Stereochemistry RACEMIC
Molecular Formula C9H13N
Molecular Weight 135.2062
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPHETAMINE

SMILES

CC(N)CC1=CC=CC=C1

InChI

InChIKey=KWTSXDURSIMDCE-UHFFFAOYSA-N
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3

HIDE SMILES / InChI

Molecular Formula C9H13N
Molecular Weight 135.2062
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Amphetamine is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers: levoamphetamine and dextroamphetamine. The mode of therapeutic action in ADHD is not known. Amphetamines are thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT. Several currently prescribed amphetamine formulations contain both enantiomers, including Adderall, Dyanavel XR, and Evekeo, the last of which is racemic amphetamine sulfate. Amphetamine is also prescribed in enantiopure and prodrug form as dextroamphetamine and lisdexamfetamine respectively. Lisdexamfetamine is structurally different from amphetamine, and is inactive until it metabolizes into dextroamphetamine.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DYANAVEL XR

Cmax

ValueDoseCo-administeredAnalytePopulation
120 ng/mL
40.3 mg single, oral
AMPHETAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1727 ng × h/mL
40.3 mg single, oral
AMPHETAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.9 h
40.3 mg single, oral
AMPHETAMINE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
DYANAVEL XR (R (amphetamine) extended-release oral suspension) should be orally administered once daily in the morning with or without food. The dose should be individualized according to the needs and responses of the patient. Before administering the dose, shake the bottle of DYANAVEL XR. In children 6 years of age and older, start with 2.5 mg or 5 mg once daily in the morning. The dose may be increase
Route of Administration: Oral
In Vitro Use Guide
β-Phenylethylamine (βPEA) activates the amine-gated chloride channel LGC-55 more efficiently than amphetamine (Amph) (Km = 9 and 152 μm, respectively)
Substance Class Chemical
Record UNII
CK833KGX7E
Record Status Validated (UNII)
Record Version