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.
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Pronunciation | /ˌdɛkstroʊæmˈfɛtəmiːn/ |
Trade names | Dexedrine, Dextrostat, Xelstrym, Zenzedi, others |
Other names | d-Amphetamine, (S)-Amphetamine, S(+)-Amphetamine |
AHFS/Drugs.com | Monograph |
MedlinePlus | a605027 |
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Dependence liability | Moderate - high |
Addiction liability | Moderate - high |
Routes of administration | By mouth, transdermal |
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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 |
Elimination half-life | 9–11 hours pH-dependent: 7–34 hours |
Duration of action | IR dosing: 3–6 hours XR dosing: 8–12 hours |
Excretion | Kidney (45%); urinary pH-dependent |
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ECHA InfoCard | 100.000.103 |
Chemical and physical data | |
Formula | C9H13N |
Molar mass | 135.210 g·mol−1 |
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Density | 0.913 g/cm3 |
Boiling point | 201.5 °C (394.7 °F) |
Solubility in water | 20 |
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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.