Levoamphetamine

Levoamphetamine
Names
	Systematic IUPAC name (2R)-1-Phenylpropan-2-amine
Identifiers
CAS Number	156-34-3
Beilstein Reference	2432739
ChEBI	CHEBI:42724
ChEMBL	ChEMBL19393
ChemSpider	30477
EC Number	205-850-8
Gmelin Reference	1125855
IUPHAR/BPS	2146
Jmol interactive 3D	Image; Image
PubChem	32893
	InChI InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1 Key: KWTSXDURSIMDCE-MRVPVSSYSA-N ;
	SMILES C[C@@H](N)Cc1ccccc1 ; C[C@@H](N)CC1=CC=CC=C1 ;
Properties
Chemical formula	C9H13N
Molar mass	135.2062 g mol−1
log P	1.789
Pharmacology
Legal status	US: Schedule II;
Routes of; administration	Oral (as part of Adderall, Evekeo, and generic amphetamine sulfate)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Levoamphetamine (also levamfetamine (INN), (R)-amphetamine or (−)-amphetamine) is a central nervous system (CNS) stimulant known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries.

Levoamphetamine is the levorotatory stereoisomer of the amphetamine molecule.

Chemistry[edit]

Levoamphetamine is the levorotary stereoisomer of the amphetamine molecule. Racemic amphetamine contains two optical isomers, dextroamphetamine and levoamphetamine.^[4]

Formulations[edit]

Racemic amphetamine[edit]

The first patented amphetamine brand, Benzedrine, was a racemic (i.e., equal parts) mixture of the freebases or sulfate salts of both amphetamine enantiomers (levoamphetamine and dextroamphetamine) that was introduced in the United States in 1934 as an inhaler for treating nasal congestion.^[2] It was later realized that the amphetamine enantiomers could treat obesity, narcolepsy, and ADHD.^[2]^[3] The Benzedrine brand is no longer marketed;^[5] however, racemic amphetamine sulfate is still prescribed under other brand names (e.g., Evekeo) and as their generic equivalents.^[3]^[6]

Adderall[edit]

Adderall (nonproprietary name: dextroamphetamine sulfate, dextroamphetamine saccharate, amphetamine sulfate and amphetamine aspartate)^[7] is an amphetamine pharmaceutical that contains 25% levoamphetamine salts and 75% dextroamphetamine salts.^[4]

References[edit]

^ "Amphetamine - PubChem Public Chemical Project". The PubChem Project. USA: National Center for Biotechnology Information. 8 August 2005. Descriptors Computed from Structure. Retrieved 26 September 2011.
^ ^a ^b ^c Heal DJ, Smith SL, Gosden J, Nutt DJ (June 2013). "Amphetamine, past and present – a pharmacological and clinical perspective". J. Psychopharmacol. 27 (6): 479–496. doi:10.1177/0269881113482532. PMC 3666194. PMID 23539642.
^ ^a ^b ^c "Evekeo prescribing information" (PDF). Arbor Pharmaceuticals LLC. April 2014. pp. 1–2. Retrieved 11 August 2015.
^ ^a ^b "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. December 2013. Retrieved 30 December 2013.
^ "Benzedrine". United States Food and Drug Administration. Retrieved 4 September 2015.
^ "Evekeo". United States Food and Drug Administration. Retrieved 11 August 2015.
^ "National Drug Code Amphetamine Search Results". National Drug Code Directory. United States Food and Drug Administration. Archived from the original on 7 February 2014. Retrieved 16 December 2013.

[1] "Amphetamine - PubChem Public Chemical Project". The PubChem Project. USA: National Center for Biotechnology Information. 8 August 2005. Descriptors Computed from Structure. Retrieved 26 September 2011.

[Amph_Uses-2] Heal DJ, Smith SL, Gosden J, Nutt DJ (June 2013). "Amphetamine, past and present – a pharmacological and clinical perspective". J. Psychopharmacol. 27 (6): 479–496. doi:10.1177/0269881113482532. PMC 3666194. PMID 23539642.

[Evekeo-3] "Evekeo prescribing information" (PDF). Arbor Pharmaceuticals LLC. April 2014. pp. 1–2. Retrieved 11 August 2015.

[FDA-4] "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. December 2013. Retrieved 30 December 2013.

[Racemic_amph_-_FDA_Benzedrine_status-5] "Benzedrine". United States Food and Drug Administration. Retrieved 4 September 2015.

[Racemic_amph_-_FDA_Evekeo_status-6] "Evekeo". United States Food and Drug Administration. Retrieved 11 August 2015.

[NDCD-7] "National Drug Code Amphetamine Search Results". National Drug Code Directory. United States Food and Drug Administration. Archived from the original on 7 February 2014. Retrieved 16 December 2013.

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Levoamphetamine

Contents

Chemistry[edit]

Formulations[edit]

Racemic amphetamine[edit]

Adderall[edit]

See also[edit]

References[edit]

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