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Dextroamphetamine or dexamfetamine is a potent central nervous system stimulant and amphetamine enantiomer that is prescribed for the treatment of attention deficit hyperactivity disorder and narcolepsy. It is also used as an athletic performance and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is also widely used by military air forces as a 'go-pill' during fatigue-inducing mission profiles such as night-time bombing missions. Preparations containing dextroamphetamine were also used in World War II as a treatment against fatigue.

Dextroamphetamine
D-amphetamine.svg
Clinical data
Trade names Dexedrine, Metamina, Attentin, Zenzedi, Procentra, Amfexa
AHFS/Drugs.com Monograph
MedlinePlus a605027
License data
Pregnancy
category
  • B3
  • C (Risk not ruled out)
Dependence
liability
Physical: None
Psychological: Moderate
Addiction
liability
Moderate
Routes of
administration
oral
ATC code N06BA02 (WHO)
Legal status
Legal status
  • S8 (Controlled)
  • : Schedule I
  • : Anlage III (Prescription only)
  • Class B
  • Schedule II
Pharmacokinetic data
Bioavailability Oral 75–100%
Protein binding 15–40%
Metabolism CYP2D6, DBH, FMO3
Onset of action IR dosing: 0.5-1.5 hours
XR dosing: 1.5–2 hours
Biological half-life 9–11 hours
pH-dependent: 8–31 hours
Duration of action IR dosing: 3–7 hours
XR dosing: 12 hours
Excretion Renal (45%); urinary pH-dependent
Identifiers
CAS Number 51-64-9
PubChem (CID) 5826
IUPHAR/BPS 2147
DrugBank DB01576
ChemSpider 5621
UNII TZ47U051FI
KEGG D03740
ChEBI CHEBI:4469
ChEMBL CHEMBL612
ECHA InfoCard 100.000.103
Chemical and physical data
Formula C9H13N
Molar mass 135.20622
3D model (Jmol) Interactive image
Density 0.913 g/cm
Boiling point 201.5 °C (394.7 °F)
Solubility in water 20 mg/mL (20 °C)
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Dextroamphetamine (American English) or dexamfetamine (Commonwealth English) is a potent central nervous system (CNS) stimulant and amphetamine enantiomer 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 is also widely used by military air forces as a 'go-pill' during fatigue-inducing mission profiles such as night-time bombing missions. Preparations containing dextroamphetamine were also used in World War II as a treatment against fatigue.

The amphetamine molecule exists as two enantiomers (in other words, two different molecules that are mirror images of one another), levoamphetamine and dextroamphetamine. Dextroamphetamine is the more active dextrorotatory, or 'right-handed', enantiomer of the amphetamine molecule. 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.