Amphetamine
Amphetamine (pronunciation: i/æmˈfɛtəmiːn/; contractit frae alpha‑methylphenethylamine) is a potent central nervous seestem (CNS) stimulant o the phenethylamine class that is uised in the treatment o attention deficit hyperacteevity disorder (ADHD) an narcolepsy.
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Dependence liability | Pheesical: none Psychological: moderate |
Addiction liability | Moderate |
Routes o admeenistration | Medical: oral, nasal inhalation Recreational: oral, nasal inhalation, insufflation, rectal, intravenous |
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Pharmacokinetic data | |
Bioavailability | Rectal 95–100%; Oral 75–100%[1] |
Protein bindin | 15–40%[2] |
Metabolism | CYP2D6,[3] DBH,[4][5][6] FMO3,[7][8] XM-ligase,[9] an ACGNAT[10] |
Onset o action | Immediate |
Biological hauf-life | D-amph:9–11h;[3][11] L-amph:11–14h[3][11] |
Excretion | Renal; pH-dependent range: 1–75%[3] |
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Synonyms | α-methylphenethylamine |
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ECHA InfoCard | 100.005.543 |
Chemical and physical data | |
Formula | C9H13N |
Molar mass | 135.2084 g/mol |
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Density | 0.9±0.1 g/cm3 |
Meltin pynt | 11.3 °C (52.3 °F) [12] |
Bylin pynt | 203 °C (397 °F) [13] |
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References
eedit- ↑ "Pharmacology". Dextroamphetamine. DrugBank. University of Alberta. 8 Februar 2013. Retrieved 5 November 2013.
- ↑ "Pharmacology". Amphetamine. DrugBank. University of Alberta. 8 Februar 2013. Retrieved 5 November 2013.
- ↑ 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.
- ↑ 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) - ↑ 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.
- ↑ 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) - ↑ 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.
- ↑ 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)
- ↑ "Substrate/Product". butyrate-CoA ligase. BRENDA. Technische Universität Braunschweig. Retrieved 7 Mey 2014.
- ↑ "Substrate/Product". glycine N-acyltransferase. BRENDA. Technische Universität Braunschweig. Retrieved 7 Mey 2014.
- ↑ 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.
- ↑ "Properties: Predicted – EP|Suite". Amphetamine. Chemspider. Retrieved 6 November 2013.
- ↑ "Chemical and Physical Properties". Amphetamine. PubChem Compound. National Center for Biotechnology Information. Retrieved 13 October 2013.