Levoamphetamine

Levoamphetamine
Names

Systematic IUPAC name (2R)-1-Phenylpropan-2-amine
Identifiers
CAS Number	156-34-3^Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	2432739
ChEBI	CHEBI:42724^Y
ChEMBL	ChEMBL19393^Y
ChemSpider	30477^Y
ECHA InfoCard	100.005.320
EC Number	205-850-8
Gmelin Reference	1125855
IUPHAR/BPS	2146
PubChem	32893
InChI InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1^Y Key: KWTSXDURSIMDCE-MRVPVSSYSA-N^Y
SMILES C[C@@H](N)Cc1ccccc1 C[C@@H](N)CC1=CC=CC=C1
Properties
Chemical formula	C₉H₁₃N
Molar mass	135.2062 g mol⁻¹
log P	1.789
Pharmacology
Routes of administration	Oral (as part of Adderall, Evekeo, and generic amphetamine sulfate)
Legal status	US: Schedule II
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Levoamphetamine, also known as levamfetamine (INN),(R)-amphetamine,(−)-amphetamine, 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.

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

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. It was later realized that the amphetamine enantiomers could treat obesity, narcolepsy, and ADHD. 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. However, in 2012 racemic amphetamine sulfate was reintroduced as the Evekeo brandname.

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