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
156-34-3 YesY
2432739
ChEBI CHEBI:42724 YesY
ChEMBL ChEMBL19393 YesY
ChemSpider 30477 YesY
EC Number 205-850-8
1125855
2146
Jmol 3D model Interactive image
Interactive image
PubChem 32893
  • InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1 YesY
    Key: KWTSXDURSIMDCE-MRVPVSSYSA-N YesY
  • 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
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 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

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

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

Adderall

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]

See also

References

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