D-amphetamine
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| Clinical data | |
|---|---|
| Trade names | Dexedrine, Metamina, Attentin, Zenzedi, Procentra, Amfexa |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a605027 |
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| Pregnancy category |
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| Dependence liability |
Physical: None Psychological: Moderate |
| Addiction liability |
Moderate |
| Routes of administration |
oral |
| ATC code | |
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| Legal status |
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| 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 |
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| ChEMBL | |
| ECHA InfoCard | 100.000.103 |
| Chemical and physical data | |
| Formula | C9H13N |
| Molar mass | 135.20622 |
| 3D model (Jmol) | |
| Density | 0.913 g/cm3 |
| Boiling point | 201.5 °C (394.7 °F) |
| Solubility in water | 20 mg/mL (20 °C) |
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Dextroamphetamine 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.
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Wikipedia