Levoamphetamine

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Levoamphetamine
Stereo, Kekulé, skeletal formula of levoamphetamine
Names
Systematic IUPAC name
(2R)-1-Phenylpropan-2-amine[1]
Identifiers
2432739
156-34-3 YesY
ChEBI CHEBI:42724 YesY
ChEMBL ChEMBL19393 YesY
ChemSpider 30477 YesY
EC number 205-850-8
1125855
Jmol-3D images Image
Image
PubChem 32893
Properties
C9H13N
Molar mass 135.21 g·mol−1
log P 1.789
Pharmacology
Oral (as part of Adderall)
Legal status
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
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. 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.[2]

Formulations[edit]

Adderall[edit]

Adderall (nonproprietary name: dextroamphetamine sulfate, dextroamphetamine saccharate, amphetamine sulfate and amphetamine aspartate)[3] is an amphetamine pharmaceutical that contains 25% levoamphetamine salts and 75% dextroamphetamine salts.[2]

Benzedrine[edit]

Benzedrine was a racemic (equal parts) mixture of levoamphetamine and dextroamphetamine introduced in the United States in 1934 as an inhaler for nasal decongestion.[4] It was later realized that amphetamine could treat narcolepsy and ADHD.[4]

See also[edit]

References[edit]

  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. 
  2. ^ a b "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. December 2013. Retrieved 30 December 2013. 
  3. ^ "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. 
  4. ^ a b 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.