Dextroamphetamine

Dextroamphetamine is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used as an athletic performance and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant.

Dextroamphetamine
INN: dexamfetamine
Clinical data
Pronunciation/ˌdɛkstræmˈfɛtəmn/
Trade namesDexedrine, Dextrostat, Xelstrym, Zenzedi, others
Other namesd-Amphetamine, (S)-Amphetamine, S(+)-Amphetamine
AHFS/Drugs.comMonograph
MedlinePlusa605027
License data
Pregnancy
category
  • AU: B3
Dependence
liability
Moderate - high
Addiction
liability
Moderate - high
Routes of
administration
By mouth, transdermal
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 75–100%
Protein binding15–40%
MetabolismCYP2D6, DBH, FMO3
Onset of actionIR dosing: 0.5–1.5 hours
XR dosing: 1.5–2 hours
Elimination half-life9–11 hours
pH-dependent: 7–34 hours
Duration of actionIR dosing: 3–6 hours
XR dosing: 8–12 hours
ExcretionKidney (45%); urinary pH-dependent
Identifiers
  • (2S)-1-Phenylpropan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.103
Chemical and physical data
FormulaC9H13N
Molar mass135.210 g·mol−1
3D model (JSmol)
Density0.913 g/cm3
Boiling point201.5 °C (394.7 °F)
Solubility in water20
  • C[C@@H](Cc1ccccc1)N
  • InChI=InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1 N
  • Key:KWTSXDURSIMDCE-QMMMGPOBSA-N Y
 NY (what is this?)  (verify)

The amphetamine molecule exists as two enantiomers, levoamphetamine and dextroamphetamine. Dextroamphetamine is the dextrorotatory, or 'right-handed', enantiomer and exhibits more pronounced effects on the central nervous system than levoamphetamine. Pharmaceutical dextroamphetamine sulfate is available as both a brand name and generic drug in a variety of dosage forms. Dextroamphetamine is sometimes prescribed as the inactive prodrug lisdexamfetamine dimesylate, which is converted into dextroamphetamine after absorption.

Dextroamphetamine, like other amphetamines, elicits its stimulating effects via several distinct actions: it inhibits or reverses the transporter proteins for the monoamine neurotransmitters (namely the serotonin, norepinephrine and dopamine transporters) either via trace amine-associated receptor 1 (TAAR1) or in a TAAR1 independent fashion when there are high cytosolic concentrations of the monoamine neurotransmitters and it releases these neurotransmitters from synaptic vesicles via vesicular monoamine transporter 2. It also shares many chemical and pharmacological properties with human trace amines, particularly phenethylamine and N-methylphenethylamine, the latter being an isomer of amphetamine produced within the human body.

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