Levoamphetamine

Source: Wikipedia, the free encyclopedia.
Not to be confused with Lisdexamfetamine or Levomethamphetamine.
For the
racemate, see Amphetamine
.

Levoamphetamine
Stereo, Kekulé, skeletal formula of levoamphetamine
Names
Preferred IUPAC name
(2R)-1-Phenylpropan-2-amine[2]
Other names
l-Amphetamine, Levamfetamine[1]
Identifiers
3D model (
JSmol
)
2432739
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.005.320 Edit this at Wikidata
EC Number
  • 205-850-8
1125855
IUPHAR/BPS
UNII
  • InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1 checkY
    Key: KWTSXDURSIMDCE-MRVPVSSYSA-N checkY
  • C[C@@H](N)Cc1ccccc1
  • C[C@@H](N)CC1=CC=CC=C1
Properties
C9H13N
Molar mass 135.2062 g mol−1
log P 1.789
Pharmacology
Oral (as part of Adderall, Evekeo, and generic amphetamine sulfate[3][4]
)
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Levoamphetamine

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

over-the-counter as a nasal decongestant
.

Chemistry

Levoamphetamine is the levorotatory stereoisomer of the amphetamine molecule.

Racemic amphetamine contains two optical isomers, dextroamphetamine, and levoamphetamine.[6][7]

Formulations

Racemic amphetamine

The first patented amphetamine brand,

dextrorotatory enantiomer (i.e., dextroamphetamine), sold as Dexedrine, prescription of the Benzedrine brand fell and was eventually discontinued.[8] However, in 2012, racemic amphetamine sulfate was reintroduced as the Evekeo brandname.[4][9]

Adderall

Adderall is a 3.1:1 mixture of dextro- to levo- amphetamine base equivalent pharmaceutical that contains equal amounts (by weight) of four salts: dextroamphetamine sulfate, amphetamine sulfate, dextroamphetamine saccharate and amphetamine (D,L)-aspartate monohydrate. This result is a 76% dextroamphetamine to 24% levoamphetamine, or 3⁄4 to 1⁄4 ratio.[6][7]

Evekeo

Evekeo is an FDA-approved medication that contains racemic amphetamine sulfate (i.e., 50% levoamphetamine sulfate and 50% dextroamphetamine sulfate).[4] It is approved for the treatment of narcolepsy, ADHD, and exogenous obesity.[4] The orally disintegrating tablets are approved for the treatment of attention deficit hyperactivity disorder (ADHD) in children and adolescents aged six to 17 years of age.[10]

Others

Products using amphetamine base are now marketed. Dyanavel XR, a liquid suspension form became available in 2015, and contains about 24% levoamphetamine.[11] Adzenys XR, an orally dissolving tablet came to market in 2016 and contains 25% levoamphetamine.[12][13]

See also

Notes

  1. International Nonproprietary Name [INN]), (R)-amphetamine, (−)-amphetamine, l-amphetamine, and L-amphetamine.[2][5]

References

  1. ^ CID 32893 from PubChem
  2. ^ a b "L-Amphetamine". PubChem Compound. United States National Library of Medicine – National Center for Biotechnology Information. 30 December 2017. Retrieved 2 January 2018.
  3. ^
    PMID 23539642
    .
  4. ^ a b c d e "Evekeo- amphetamine sulfate tablet". DailyMed. 14 August 2019. Retrieved 7 April 2020.
  5. ^ "R(-)amphetamine". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 2 January 2018.
  6. ^ a b "Adderall XR- dextroamphetamine sulfate, dextroamphetamine saccharate, amphetamine sulfate and amphetamine aspartate capsule, extended release". DailyMed. 17 July 2019. Retrieved 7 April 2020.
  7. ^ a b "Adderall- dextroamphetamine saccharate, amphetamine aspartate, dextroamphetamine sulfate, and amphetamine sulfate tablet". DailyMed. 8 November 2019. Retrieved 7 April 2020.
  8. ^ "Benzedrine: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 4 September 2015.
  9. ^ "Evekeo: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 11 August 2015.
  10. ^ "Evekeo ODT- amphetamine sulfate tablet, orally disintegrating". DailyMed. 20 February 2020. Retrieved 7 April 2020.
  11. ^ "Dyanavel XR Prescribing Information". January 2017. Retrieved 14 May 2017.
  12. ^ "Adzenys XR-ODT- amphetamine tablet, orally disintegrating". DailyMed. 22 January 2020. Retrieved 7 April 2020. 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.
  13. ^ "Adzenys ER- amphetamine suspension, extended release". DailyMed. 21 January 2020. Retrieved 7 April 2020.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Levoamphetamine&oldid=1213561661"