Back دكستروأمفيتامين Arabic دقزامفتامین AZB Декстроамфетамин Bulgarian Dextroamfetamin Czech Decstroamffetamin Welsh Dextroamphetamin German Dextroanfetamina Spanish Dextroanfetamina Basque دگزامفتامین Persian Deksamfetamiini Finnish

Dextroamphetamine

Dextroamphetamine
INN: dexamfetamine
Clinical data
Pronunciation/ˌdɛkstroʊæmˈfɛtəmiːn/
Trade namesDexedrine, Zenzedi, Xelstrym, 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
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: ~90%[13]
Protein binding15–40%[14]
MetabolismCYP2D6,[19] DBH,[25] FMO3[26]
Onset of actionIR dosing: 0.5–1.5 hours[15][16]
XR dosing: 1.5–2 hours[17][18]
Elimination half-life9–11 hours[19][20]
pH-dependent: 7–34 hours[21]
Duration of actionIR dosing: 3–6 hours[17][22]
XR dosing: 8–12 hours[23][17][22]
ExcretionKidney (45%);[24] 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)
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.[10][27] It is also used as an athletic performance and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant.

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 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[29] and it releases these neurotransmitters from synaptic vesicles via vesicular monoamine transporter 2.[30] 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.

  1. ^ a b Vitiello B (April 2008). "Understanding the risk of using medications for attention deficit hyperactivity disorder with respect to physical growth and cardiovascular function". Child and Adolescent Psychiatric Clinics of North America. 17 (2): 459–74, xi. doi:10.1016/j.chc.2007.11.010. PMC 2408826. PMID 18295156.
  2. ^ a b Graham J, Banaschewski T, Buitelaar J, Coghill D, Danckaerts M, Dittmann RW, et al. (January 2011). "European guidelines on managing adverse effects of medication for ADHD". European Child & Adolescent Psychiatry. 20 (1): 17–37. doi:10.1007/s00787-010-0140-6. eISSN 1435-165X. PMC 3012210. PMID 21042924.
  3. ^ a b Kociancic T, Reed MD, Findling RL (March 2004). "Evaluation of risks associated with short- and long-term psychostimulant therapy for treatment of ADHD in children". Expert Opinion on Drug Safety. 3 (2): 93–100. doi:10.1517/14740338.3.2.93. eISSN 1744-764X. PMID 15006715. S2CID 31114829.
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  6. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
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  15. ^ Green-Hernandez C, Singleton JK, Aronzon DZ (1 January 2001). Primary Care Pediatrics. Lippincott Williams & Wilkins. p. 243. ISBN 978-0-7817-2008-3.|quote = Table 21.2 Medications for ADHD ... D-amphetamine ... Onset: 30 min.
  16. ^ "Dexedrine, ProCentra(dextroamphetamine) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Retrieved 4 October 2015. Onset of action: 1–1.5 hr
  17. ^ a b c Millichap JG (2010). "Chapter 9: Medications for ADHD". In Millichap JG (ed.). Attention Deficit Hyperactivity Disorder Handbook: A Physician's Guide to ADHD (2nd ed.). New York, USA: Springer. p. 112. ISBN 978-1-4419-1396-8.
    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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  20. ^ "Adderall- dextroamphetamine saccharate, amphetamine aspartate, dextroamphetamine sulfate, and amphetamine sulfate tablet". DailyMed. 27 February 2022. Retrieved 21 January 2023.
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  22. ^ 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.
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  24. ^ "dextrostat (dextroamphetamine sulfate) tablet [Shire US Inc.]". DailyMed. Wayne, PA: Shire US Inc. August 2006. Retrieved 8 November 2013.
  25. ^ Lemke TL, Williams DA, Roche VF, Zito W (2013). Foye's Principles of Medicinal Chemistry (7th ed.). Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 648. ISBN 978-1-60913-345-0. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.
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  27. ^ Cite error: The named reference Amph Uses was invoked but never defined (see the help page).
  28. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "enantiomer". doi:10.1351/goldbook.E02069
  29. ^ Cite error: The named reference Miller was invoked but never defined (see the help page).
  30. ^ Cite error: The named reference E Weihe was invoked but never defined (see the help page).


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