Amphetamine

Amphetamine
Clinical data
AHFS/Drugs.com	entry
Leecence data	US FDA: Adderall;
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	N06BA01 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled) ; CA: Schedule I ; UK: Class B ; US: Schedule II ; UN: Psychotropic Schedule II ; Rx-anly;
Pharmacokinetic data
Bioavailability	Rectal 95–100%; Oral 75–100%
Protein bindin	15–40%
Metabolism	CYP2D6, DBH, FMO3, XM-ligase, an ACGNAT
Onset o action	Immediate
Biological hauf-life	D-amph:9–11h; L-amph:11–14h
Excretion	Renal; pH-dependent range: 1–75%
Identifiers
	IUPAC name (RS)-1-phenylpropan-2-amine; (RS)-1-phenyl-2-aminopropane;
Synonyms	α-methylphenethylamine
CAS Nummer	300-62-9 ;
PubChem CID	3007;
IUPHAR/BPS	4804;
DrugBank	DB00182 ;
ChemSpider	13852819 ;
UNII	CK833KGX7E;
KEGG	D07445 ;
ChEBI	CHEBI:2679 ;
ChEMBL	CHEMBL405 ;
NIAID ChemDB	018564;
PDB ligand	FRD (PDBe, RCSB PDB);
ECHA InfoCard	100.005.543
Chemical and physical data
Formula	C9H13N
Molar mass	135.2084 g/mol
3D model (Jmol)	Interactive eemage;
Density	0.9±0.1 g/cm3
Meltin pynt	11.3 °C (52.3 °F)
Bylin pynt	203 °C (397 °F)
	SMILES NC(CC1=CC=CC=C1)C;
	InChI InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 ; Key:KWTSXDURSIMDCE-UHFFFAOYSA-N ;
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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.

References

↑ "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.
1 2 3 4 "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.
1 2 "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.

[Drugbank-dexamph-1] "Pharmacology". Dextroamphetamine. DrugBank. University of Alberta. 8 Februar 2013. Retrieved 5 November 2013.

[Drugbank-amph-2] "Pharmacology". Amphetamine. DrugBank. University of Alberta. 8 Februar 2013. Retrieved 5 November 2013.

[FDA_Pharmacokinetics-3] 1 2 3 4 "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. Shire US Inc. December 2013. pp. 12–13. Retrieved 30 December 2013.

[DBH_ref-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)

[DBH_amph_primary-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.

[DBH_4-HA_primary-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)

[FMO-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.

[FMO3-Primary-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)

[Benzoic1-9] "Substrate/Product". butyrate-CoA ligase. BRENDA. Technische Universität Braunschweig. Retrieved 7 Mey 2014.

[Benzoic2-10] "Substrate/Product". glycine N-acyltransferase. BRENDA. Technische Universität Braunschweig. Retrieved 7 Mey 2014.

[Adderall_IR-11] 1 2 "Adderall IR Prescribing Information" (PDF). United States Food and Drug Administration. Barr Laboratories, Inc. Mairch 2007. pp. 4–5. Retrieved 2 November 2013.

[Chemspider-12] "Properties: Predicted – EP|Suite". Amphetamine. Chemspider. Retrieved 6 November 2013.

[Properties-13] "Chemical and Physical Properties". Amphetamine. PubChem Compound. National Center for Biotechnology Information. Retrieved 13 October 2013.

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