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Dextroamphetamine information


Dextroamphetamine
INN: dexamfetamine
Clinical data
Pronunciation/ˌdɛkstræmˈfɛtəmn/
Trade namesDexedrine, Dextrostat, Xelstrym, others
Other namesd-Amphetamine, (S)-Amphetamine, S(+)-Amphetamine
AHFS/Drugs.comMonograph
MedlinePlusa605027
License data
  • US DailyMed: Dextroamphetamine
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
  • N06BA02 (WHO)
Legal status
Legal status
  • AU: S8 (Controlled drug)[7][8]
  • BR: Class A3 (Psychoactive drugs)[9]
  • CA: Schedule I
  • DE: Anlage III (Special prescription form required)
  • UK: Class B
  • US: WARNING[6]Schedule II[10][11]
  • UN: Psychotropic Schedule II
  • EU: Rx-only[12]
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
  • 51-64-9 checkY
PubChem CID
  • 5826
IUPHAR/BPS
  • 2147
DrugBank
  • DB01576 checkY
ChemSpider
  • 5621 checkY
UNII
  • TZ47U051FI
KEGG
  • D03740 checkY
ChEBI
  • CHEBI:4469 checkY
ChEMBL
  • ChEMBL612 checkY
CompTox Dashboard (EPA)
  • DTXSID8022907 Edit this at Wikidata
ECHA InfoCard100.000.103 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N
Molar mass135.210 g·mol−1
3D model (JSmol)
  • Interactive image
Density0.913 g/cm3
Boiling point201.5 °C (394.7 °F)
Solubility in water20
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 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.
  4. ^ a b Clemow DB, Walker DJ (September 2014). "The potential for misuse and abuse of medications in ADHD: a review". Postgraduate Medicine. 126 (5): 64–81. doi:10.3810/pgm.2014.09.2801. eISSN 1941-9260. PMID 25295651. S2CID 207580823.
  5. ^ a b Cite error: The named reference Stahl's Essential Psychopharmacology was invoked but never defined (see the help page).
  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.
  7. ^ "Therapeutic Goods (Poisons Standard—February 2023) Instrument 2022". Australian Government Federal Register of Legislation. 26 September 2022. Retrieved 9 January 2023.
  8. ^ Fuller K (20 February 2022). "ADHD Stimulant Prescribing Regulations & Authorities in Australia & New Zealand". AADPA. Retrieved 9 January 2023.
  9. ^ 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.
  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.
  13. ^ Cite error: The named reference handbook2022 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Drugbank-amph was invoked but never defined (see the help page).
  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.
  26. ^ Cite error: The named reference FMO was invoked but never defined (see the help page).
  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).


Cite error: There are <ref group=note> tags on this page, but the references will not show without a {{reflist|group=note}} template (see the help page).

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Dextroamphetamine

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Dextroamphetamine (INN:dexamfetamine) is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is prescribed for the treatment...

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Adderall

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of equal parts racemic amphetamine and dextroamphetamine, which produces a (3:1) ratio between dextroamphetamine and levoamphetamine, the two enantiomers...

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Lisdexamfetamine

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inactive prodrug that works after being converted by the body into dextroamphetamine, a central nervous system (CNS) stimulant. Chemically, lisdexamfetamine...

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Amphetamine

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the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free...

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Levoamphetamine

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amphetamine molecule. Racemic amphetamine contains two optical isomers, dextroamphetamine, and levoamphetamine. The first patented amphetamine brand, Benzedrine...

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Dexamyl

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amobarbital (previously called amylbarbitone and its brand name Amytal) and dextroamphetamine sulfate (Dexedrine) within the same pill. It was widely abused, and...

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List of polysubstance combinations

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deliriant. The prescription medicine Adderall (dextroamphetamine sulfate/amphetamine sulfate/dextroamphetamine saccharate/amphetamine aspartate monohydrate)...

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Obetrol

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Obetrol (and Adderall) contained equal portions of: Dextroamphetamine sulfate Dextroamphetamine saccharine Amphetamine sulfate Amphetamine aspartate...

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Ortetamine

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substituted for dextroamphetamine more closely than either 3- or 4-methylamphetamine, although with only around 1/10 the potency of dextroamphetamine itself....

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Substituted amphetamine

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methamphetamine and the dextrorotatory optical isomer of amphetamine, dextroamphetamine, were synthesized. This synthesis was a by-product of a search for...

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Eskatrol

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States. Others included Dexamyl and Desbutal pills. Eskatrol contained dextroamphetamine sulfate (Dexedrine) and prochlorperazine (Compazine), a typical antipsychotic...

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Stimulant

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containing all or mostly dextroamphetamine. Presently, it is typically prescribed as mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine. Amphetamine...

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Polysubstance use

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treat motion sickness and nausea Adderall (dextroamphetamine sulfate/amphetamine sulfate/dextroamphetamine saccharate/amphetamine aspartate monohydrate)...

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Brompton cocktail

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in place of the chlorpromazine; and methamphetamine, amphetamine, dextroamphetamine, co-phenylcaine (lidocaine and phenylephrine hydrochloride), methylphenidate...

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Racemic mixture

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enantiomers. A single Adderall dose combines the neutral sulfate salts of dextroamphetamine and amphetamine, with the dextro isomer of amphetamine saccharate...

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MDMA

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2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine...

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Cocaine

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2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine...

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List of investigational attention deficit hyperactivity disorder drugs

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inhibitor [29] Dextroamphetamine [abuse-resistant] (PF-08, PFR 08001, PFR08026) – norepinephrine–dopamine releasing agent [30] Dextroamphetamine sulfate [modified...

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Combination drug

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and vomiting Prescription drugs: Adderall (dextroamphetamine sulfate/amphetamine sulfate/dextroamphetamine saccharate/amphetamine aspartate monohydrate)...

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Clobenzorex

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after ingestion; however, small amounts are also metabolized into dextroamphetamine. In commercial production, clobenzorex is supplied as the hydrochloride...

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C9H13N

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Dimethylbenzylamine Methylphenethylamines Amphetamine (Benzedrine, Adderall) Dextroamphetamine Levoamphetamine β-Methylphenethylamine N-Methylphenethylamine 2-Methylphenethylamine...

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Amphetamine type stimulant

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there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine. Amphetamine was first synthesized in 1887 by...

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Dexys Midnight Runners

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Dexys "song". The band's name was derived from Dexedrine, a brand of dextroamphetamine used as a recreational drug among Northern soul fans to give them...

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Anorectic

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suppressant activity include: Amphetamine-Dextroamphetamine is known to hamper appetite. Amphetamine-Dextroamphetamine is used to treat Attention deficit hyperactivity...

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Livedo reticularis

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Livedo reticularis associated with rasagiline Methylphenidate and dextroamphetamine-induced peripheral vasculopathy Gefitinib Obstruction of capillaries:...

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Vietnam veteran

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large amounts of "speed" (stimulants), in the form of Dexedrine (dextroamphetamine), an amphetamine twice as strong as Benzedrine, to American servicemen...

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