Amphetamine (pronunciation: Listeni/æmˈfɛtəmn/; contractit frae alphamethylphenethylamine) is a potent central nervous seestem (CNS) stimulant o the phenethylamine class that is uised in the treatment o attention deficit hyperactivity disorder (ADHD) an narcolepsy.

Amphetamine
An image o the amphetamine compoond
A 3d image o the amphetamine compoond
Clinical data
AHFS/Drugs.comentry
Leecence data
Pregnancy
category
  • US: C (Risk nae ruled oot)
Dependence
liability
Pheesical: none
Psychological: moderate
Addiction
liability
Moderate
Routes o
admeenistration
Medical: oral, nasal inhalation
Recreational: oral, nasal inhalation, insufflation, rectal, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityRectal 95–100%; Oral 75–100%[1]
Protein bindin15–40%[2]
MetabolismCYP2D6,[3] DBH,[4][5][6] FMO3,[7][8] XM-ligase,[9] an ACGNAT[10]
Onset o actionImmediate
Biological hauf-lifeD-amph:9–11h;[3][11] L-amph:11–14h[3][11]
ExcretionRenal; pH-dependent range: 1–75%[3]
Identifiers
Synonymsα-methylphenethylamine
CAS Nummer
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
ECHA InfoCard100.005.543
Chemical and physical data
FormulaC9H13N
Molar mass135.2084 g/mol
3D model (Jmol)
Density0.9±0.1 g/cm3
Meltin pynt11.3 °C (52.3 °F) [12]
Bylin pynt203 °C (397 °F) [13]
  (verify)

ReferencesEedit

  1. "Pharmacology". Dextroamphetamine. DrugBank. University of Alberta. 8 Februar 2013. Retrieved 5 November 2013.
  2. "Pharmacology". Amphetamine. DrugBank. University of Alberta. 8 Februar 2013. Retrieved 5 November 2013.
  3. 3.0 3.1 3.2 3.3 "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. Shire US Inc. December 2013. pp. 12–13. Retrieved 30 December 2013.
  4. Lemke TL, Williams DA, Roche VF, Zito W (2013). Foye's Principles of Medicinal Chemistry (7th ed.). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 648. ISBN 9781609133450. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.CS1 maint: multiple names: authors leet (link)
  5. Taylor KB (Januar 1974). "Dopamine-beta-hydroxylase. Stereochemical course of the reaction" (PDF). J. Biol. Chem. 249 (2): 454–458. PMID 4809526. Retrieved 6 November 2014. Dopamine-β-hydroxylase catalyzed the removal of the pro-R hydrogen atom and the production of 1-norephedrine, (2S,1R)-2-amino-1-hydroxyl-1-phenylpropane, from d-amphetamine.
  6. Horwitz D, Alexander RW, Lovenberg W, Keiser HR (Mey 1973). "Human serum dopamine-β-hydroxylase. Relationship to hypertension and sympathetic activity". Circ. Res. 32 (5): 594–599. doi:10.1161/01.RES.32.5.594. PMID 4713201. Subjects with exceptionally low levels of serum dopamine-β-hydroxylase activity showed normal cardiovascular function and normal β-hydroxylation of an administered synthetic substrate, hydroxyamphetamine.CS1 maint: multiple names: authors leet (link)
  7. Krueger SK, Williams DE (Juin 2005). "Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism". Pharmacol. Ther. 106 (3): 357–387. doi:10.1016/j.pharmthera.2005.01.001. PMC 1828602. PMID 15922018.
  8. Cashman JR, Xiong YN, Xu L, Janowsky A (Mairch 1999). "N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication". J. Pharmacol. Exp. Ther. 288 (3): 1251–1260. PMID 10027866.CS1 maint: multiple names: authors leet (link)
  9. "Substrate/Product". butyrate-CoA ligase. BRENDA. Technische Universität Braunschweig. Retrieved 7 Mey 2014.
  10. "Substrate/Product". glycine N-acyltransferase. BRENDA. Technische Universität Braunschweig. Retrieved 7 Mey 2014.
  11. 11.0 11.1 "Adderall IR Prescribing Information" (PDF). United States Food and Drug Administration. Barr Laboratories, Inc. Mairch 2007. pp. 4–5. Retrieved 2 November 2013.
  12. "Properties: Predicted – EP|Suite". Amphetamine. Chemspider. Retrieved 6 November 2013.
  13. "Chemical and Physical Properties". Amphetamine. PubChem Compound. National Center for Biotechnology Information. Retrieved 13 October 2013.