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Clinical data | |
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Trade names | Cydril, Adderall, Evekeo, Benzedrine, others |
Other names | l-Amphetamine, Levamfetamine[1] |
Routes of administration | Oral (as part of Adderall, Evekeo, and generic amphetamine sulfate[2][3]) |
Drug class | Amphetamine; Stimulant; Sympathomimetic; Norepinephrine releasing agent; TAAR1 agonist |
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Pharmacokinetic data | |
Protein binding | 31.7%[4] |
Metabolism | Hydroxylation (CYP2D6), oxidative deamination[3] |
Metabolites | L-4-Hydroxyamphetamine[3] |
Elimination half-life | 11.7–15.2 hours[5][3] |
Excretion | Urine[6][7] |
Identifiers | |
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CAS Number | |
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ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.005.320 |
Chemical and physical data | |
Formula | C9H13N |
Molar mass | 135.210 g·mol−1 |
3D model (JSmol) | |
Chirality | Levorotatory enantiomer |
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Levoamphetamine[note 1] is a stimulant medication which is used in the treatment of certain medical conditions.[10] It was previously marketed by itself under the brand name Cydril, but is now available only in combination with dextroamphetamine in varying ratios under brand names like Adderall and Evekeo.[10][5] The drug is known to increase wakefulness and concentration in association with decreased appetite and fatigue.[11][12] Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries.[10][5][13] Levoamphetamine is taken by mouth.[10][5]
Levoamphetamine acts as a releasing agent of the monoamine neurotransmitters norepinephrine and dopamine.[10] It is similar to dextroamphetamine in its ability to release norepinephrine and in its sympathomimetic effects but is a few times weaker than dextroamphetamine in its capacity to release dopamine and in its psychostimulant effects.[10][14][12] Levoamphetamine is the levorotatory stereoisomer of the racemic amphetamine molecule, whereas dextroamphetamine is the dextrorotatory isomer.[10][5]
Levoamphetamine was first introduced in the form of racemic amphetamine under the brand name Benzedrine in 1935 and as an enantiopure drug under the brand name Cydril in the 1970s.[10][15] While pharmaceutical formulations containing enantiopure levoamphetamine are no longer manufactured,[10] levomethamphetamine (levmetamfetamine) is still marketed and sold over-the-counter as a nasal decongestant.[16] In addition to being used in pharmaceutical drugs itself, levoamphetamine is a known active metabolite of certain other drugs, such as selegiline (L-deprenyl).[17][7]
Amph Uses
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