Amphetamine

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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)

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.

References[eedit | eedit soorce]

  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. a b c d "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. a b "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.