Dextroamphetamine

Dextroamphetamine
INN: Dexamfetamine
Clinical data
Pronunciation/ˌdɛkstroʊæmˈfɛtəmiːn/
Trade namesDexedrine, others
Other namesd-Amphetamine, (S)-Amphetamine, S(+)-Amphetamine
AHFS/Drugs.comMonograph
MedlinePlusa605027
License data
Pregnancy
category
  • AU: B3
Dependence
liability		Moderate[1][2] – high[3][4][5]
Addiction
liability		Moderate[1][2] – high[3][4][5]
Routes of
administration		By mouth, transdermal
Drug classStimulant
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: ~90%[14]
Protein binding15–40%[15]
MetabolismCYP2D6,[20] DBH,[26] FMO3[27]
Onset of actionIR dosing: 0.5–1.5 hours[16][17]
XR dosing: 1.5–2 hours[18][19]
Elimination half-life9–11 hours[20][21]
pH-dependent: 7–34 hours[22]
Duration of actionIR dosing: 3–6 hours[18][23]
XR dosing: 8–12 hours[24][18][23]
ExcretionKidney (45%);[25] 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 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N
Molar mass135.210 g·mol−1
3D model (JSmol)
ChiralityDextrorotatory enantiomer
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 checkY
 ☒NcheckY (what is this?)  (verify)

Dextroamphetamine (INN: dexamfetamine) is a potent central nervous system (CNS) stimulant and enantiomer[note 1] of amphetamine that is prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.[11][28] It is also used as an athletic performance and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.

The amphetamine molecule exists as two enantiomers,[note 1] 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, which is converted into dextroamphetamine after absorption.

Side effects of dextroamphetamine at therapeutic doses include elevated mood, decreased appetite, dry mouth, excessive grinding of the teeth, headache, increased heart rate, increased wakefulness or insomnia, anxiety, and irritability, among others.[30] At excessively high doses, psychosis (i.e., hallucinations, delusions), addiction, and rapid muscle breakdown may occur. However, for individuals with pre-existing psychotic disorders, there may be a risk of psychosis even at therapeutic doses.[31]

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[32] and it releases these neurotransmitters from synaptic vesicles via vesicular monoamine transporter 2.[33] 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. It is available as a generic medication.[30] In 2022, mixed amphetamine salts (Adderall) was the 14th most commonly prescribed medication in the United States, with more than 34 million prescriptions.[34][35]

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    Table 9.2 Dextroamphetamine formulations of stimulant medication
    Dexedrine [Peak:2–3 h] [Duration:5–6 h] ...
    Adderall [Peak:2–3 h] [Duration:5–7 h]
    Dexedrine spansules [Peak:7–8 h] [Duration:12 h] ...
    Adderall XR [Peak:7–8 h] [Duration:12 h]
    Vyvanse [Peak:3–4 h] [Duration:12 h]
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  23. ^ a b Mignot EJ (October 2012). "A practical guide to the therapy of narcolepsy and hypersomnia syndromes". Neurotherapeutics. 9 (4): 739–752. doi:10.1007/s13311-012-0150-9. PMC 3480574. PMID 23065655.
  24. ^ Stahl SM (March 2017). "Amphetamine (D)". Prescriber's Guide: Stahl's Essential Psychopharmacology (6th ed.). Cambridge, United Kingdom: Cambridge University Press. pp. 39–44. ISBN 978-1-108-22874-9. Retrieved 8 August 2017.
  25. ^ "dextrostat (dextroamphetamine sulfate) tablet [Shire US Inc.]". DailyMed. Wayne, PA: Shire US Inc. August 2006. Retrieved 8 November 2013.
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  29. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "enantiomer". doi:10.1351/goldbook.E02069
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