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		Physical: None
Psychological: Moderate[1]
Addiction
liability		Moderate[2][3] – high[4][5][1]
Routes of
administration		By mouth, transdermal, intravenous, insufflation, rectal
Drug classStimulant
ATC code
Legal status
Legal status
  • AU: S8 (Controlled drug)[6][7]
  • BR: Class A3 (Psychoactive drugs)[8]
  • CA: ℞-only / Schedule G (CDSA I)[9]
  • DE: Anlage III (Special prescription form required)
  • UK: Class B
  • US: Schedule II[10][11]
  • UN: Psychotropic Schedule II
  • EU: Rx-only[12]
  • SE: Förteckning II
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
IUPAC name
  • (2S)-1-Phenylpropan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.103
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 water20mg per ml
SMILES
  • C[C@@H](Cc1ccccc1)N
InChI
  • 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 Y
 NY (what is this?)  (verify)

Dextroamphetamine is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.[10][27] It is also used illicitly to enhance cognitive and athletic performance, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.

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.

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.[28] 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.[29]

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[30] and it releases these neurotransmitters from synaptic vesicles via vesicular monoamine transporter 2 (VMAT2).[31] 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.[28] In 2022, mixed amphetamine salts (Adderall) was the 14th most commonly prescribed medication in the United States, with more than 34 million prescriptions.[32][33]

  1. ^ a b Cite error: The named reference Stahl's Essential Psychopharmacology was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Vitiello2008 was invoked but never defined (see the help page).
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  5. ^ Cite error: The named reference ClemowWalker2014 was invoked but never defined (see the help page).
  6. ^ "Therapeutic Goods (Poisons Standard—February 2023) Instrument 2022". Australian Government Federal Register of Legislation. 26 September 2022. Retrieved 9 January 2023.
  7. ^ Fuller K (20 February 2022). "ADHD Stimulant Prescribing Regulations & Authorities in Australia & New Zealand". AADPA. Retrieved 9 January 2023.
  8. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  9. ^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
  10. ^ a b "Dexedrine spansule- dextroamphetamine sulfate capsule, extended release". DailyMed. 10 January 2022. Retrieved 28 March 2022.
  11. ^ "Xelstrym- dextroamphetamine patch, extended release". DailyMed. 6 January 2023. Retrieved 21 January 2023.
  12. ^ "List of nationally authorised medicinal products : Active substance(s): dexamfetamine : Procedure No. PSUSA/00000986/202109" (PDF). Ema.europa.eu. Retrieved 5 June 2022.
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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]
  18. ^ Brams M, Mao AR, Doyle RL (September 2008). "Onset of efficacy of long-acting psychostimulants in pediatric attention-deficit/hyperactivity disorder". Postgrad. Med. 120 (3): 69–88. doi:10.3810/pgm.2008.09.1909. PMID 18824827. S2CID 31791162. Onset of efficacy was earliest for d-MPH-ER at 0.5 hours, followed by d, l-MPH-LA at 1 to 2 hours, MCD at 1.5 hours, d, l-MPH-OR at 1 to 2 hours, MAS-XR at 1.5 to 2 hours, MTS at 2 hours, and LDX at approximately 2 hours. ... MAS-XR, and LDX have a long duration of action at 12 hours postdose
  19. ^ a b Cite error: The named reference FDA Pharmacokinetics was invoked but never defined (see the help page).
  20. ^ "Adderall- dextroamphetamine saccharate, amphetamine aspartate, dextroamphetamine sulfate, and amphetamine sulfate tablet". DailyMed. 27 February 2022. Retrieved 21 January 2023.
  21. ^ Cite error: The named reference HSDB Toxnet October 2017 Full archived record was invoked but never defined (see the help page).
  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.
  23. ^ 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.
  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. ^ a b "Dextroamphetamine Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 3 February 2019. Retrieved 2 February 2019.
  29. ^ Cite error: The named reference Adderall XR FDA label was invoked but never defined (see the help page).
  30. ^ Cite error: The named reference Miller was invoked but never defined (see the help page).
  31. ^ Cite error: The named reference E Weihe was invoked but never defined (see the help page).
  32. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  33. ^ "Dextroamphetamine; Dextroamphetamine Saccharate; Amphetamine; Amphetamine Aspartate Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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