Levoamphetamine

Not to be confused with Lisdexamfetamine.
Levoamphetamine
Names
Systematic IUPAC name
(2R)-1-Phenylpropan-2-amine[1]
Identifiers
156-34-3 YesY
3D model (Jmol) Interactive image
Interactive image
2432739
ChEBI CHEBI:42724 YesY
ChEMBL ChEMBL19393 YesY
ChemSpider 30477 YesY
ECHA InfoCard 100.005.320
EC Number 205-850-8
1125855
2146
PubChem 32893
Properties
C9H13N
Molar mass 135.2062 g mol−1
log P 1.789
Pharmacology
Legal status
Oral (as part of Adderall, Evekeo, and generic amphetamine sulfate[2][3])
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

Levoamphetamine is the levorotary stereoisomer of the amphetamine molecule. Racemic amphetamine contains two optical isomers, dextroamphetamine and levoamphetamine.[5]

Formulations

Racemic amphetamine

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;[6] however, racemic (50:50) amphetamine sulfate is still prescribed under other brand names (e.g., Evekeo) and as their generic equivalents.[3][7]

Adderall

Adderall is an amphetamine pharmaceutical that contains 25% levoamphetamine salts and 75% dextroamphetamine salts.[5]


Evekeo

Evekeo is an amphetamine medication FDA approved as therapeutic equivalent, (for ADHD & Exogenous obesity) that contains 50% levoamphetamine salts and 50% dextroamphetamine salts.[5]

Others

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

See also

References

  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. 1 2 3 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. 1 2 3 "Evekeo prescribing information" (PDF). Arbor Pharmaceuticals LLC. April 2014. pp. 1–2. Retrieved 11 August 2015.
  4. 1 2 3 "R(-)amphetamine". IUPHAR/BPS Guide to PHARMACOLOGY. Retrieved 30 March 2016.
  5. 1 2 3 "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.

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