Levoamphetamine

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Not to be confused with Lisdexamfetamine.
Levoamphetamine
Stereo, Kekulé, skeletal formula of levoamphetamine
Names
Systematic IUPAC name
(2R)-1-Phenylpropan-2-amine[1]
Identifiers
3D model (Jmol)
2432739
ChEBI
ChemSpider
ECHA InfoCard 100.005.320
EC Number 205-850-8
1125855
Properties
C9H13N
Molar mass 135.2062 g mol−1
log P 1.789
Pharmacology
Oral (as part of Adderall, Evekeo, and generic amphetamine sulfate[2][3])
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Levoamphetamine, also known as levamfetamine (INN),[4] (R)-amphetamine,[4] (−)-amphetamine,[4] and L-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.[5]

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] Because of the greater central nervous system effect of the dextro enantiomer, sold as Dexedrine, prescription of the Benzedrine brand fell and was eventually discontinued.[6] However, in 2012 racemic amphetamine sulfate was reintroduced as the Evekeo brandname.[3][7]

Adderall[edit]

Adderall is an amphetamine pharmaceutical that contains 25% levoamphetamine salts.[5]

Evekeo[edit]

Evekeo is an amphetamine medication FDA approved as therapeutic equivalent that contains 50% levoamphetamine sulfate.[8] It is approved for narcolepsy, ADHD and exogenous obesity.

Others[edit]

Products using amphetamine base are now marketed. Dyanevel XR, a liquid suspension form became available in 2015, and contains about 24% levoamphetamine.[9] Adzenys XR, an orally dissolving tablet came to market in 2016 and contains 25% levoamphetamine.[10]

L-Amphetamine succinate was sold in Hungary between 1952 and 1955 under the brand name Cydril.

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 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 3666194Freely accessible. PMID 23539642. 
  3. ^ a b c "Evekeo prescribing information" (PDF). Arbor Pharmaceuticals LLC. April 2014. pp. 1–2. Retrieved 11 August 2015. 
  4. ^ a b c "R(-)amphetamine". IUPHAR/BPS Guide to PHARMACOLOGY. Retrieved 30 March 2016. 
  5. ^ a b "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. December 2013. Retrieved 30 December 2013. 
  6. ^ "Benzedrine". United States Food and Drug Administration. Retrieved 4 September 2015. 
  7. ^ "Evekeo". United States Food and Drug Administration. Retrieved 11 August 2015. 
  8. ^ "Evekeo Prescribing Information" (PDF). Evekeo (Arbor Pharmaceuticals, LLC). December 2016. Retrieved 6 December 2016. 
  9. ^ "Dyanavel XR Prescribing Information" (PDF). Tris Pharmaceuticals. October 2015. pp. 1–16. Retrieved 23 November 2015. DYANAVEL XR contains d-amphetamine and l-amphetamine in a ratio of 3.2 to 1 
  10. ^ "Adzenys XR Prescribing Information" (PDF). United States Food and Drug Administration. Neos Therapeutics, Inc. January 2016. p. 15. Retrieved 7 March 2016. ADZENYS XR-ODT (amphetamine extended-release orally disintegrating tablet) contains a 3 to 1 ratio of d- to l-amphetamine, a central nervous system stimulant.