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Amphetamine

This article is about mixtures of levoamphetamine and dextroamphetamine. For other uses, see Amphetamine (disambiguation).

Amphetamine
INN: Amfetamine
An image of the amphetamine compound
Clinical data
Pronunciation/æmˈfɛtəmiːn/
Trade namesEvekeo, Adderall,[note 1] others
Other namesα-methylphenethylamine
AHFS/Drugs.comMonograph
MedlinePlusa616004
License data
Dependence
liability		Physical: None
Psychological: Moderate[1]
Addiction
liability		Moderate
Routes of
administration		Medical: Oral, intravenous[2]
Recreational: Oral, insufflation, rectal, intravenous, intramuscular
Drug class
ATC code
Physiological data
ReceptorsTAAR1, VMAT2, 5HT1A
MetabolismCYP2D6,[3] DBH,[4][5] FMO3[4][6][7]
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: ~90%[11]
Protein binding20%[12]
MetabolismCYP2D6,[3] DBH,[4][5] FMO3[4][6][7]
Metabolites4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, benzoic acid, hippuric acid, norephedrine, phenylacetone[3][13]
Onset of actionIR dosing: 30–60 minutes[14]
XR dosing: 1.5–2 hours[15][16]
Elimination half-lifeD-amph: 9–11 hours[3][17]
L-amph: 11–14 hours[3][17]
pH-dependent: 7–34 hours[18]
Duration of actionIR dosing: 3–6 hours[1][15][19]
XR dosing: 8–12 hours[1][15][19]
ExcretionPrimarily renal;
pH-dependent range: 1–75%[3]
Identifiers
  • (RS)-1-phenylpropan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.005.543 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N
Molar mass135.210 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture[20]
Density.936 g/cm3 at 25 °C[21]
Melting point146 °C (295 °F) [22]
Boiling point203 °C (397 °F) at 760 mmHg[23]
  • NC(C)Cc1ccccc1
  • InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 checkY
  • Key:KWTSXDURSIMDCE-UHFFFAOYSA-N checkY
  (verify)

Amphetamine[note 2] (contracted from alpha-methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity; it is also used to treat binge eating disorder in the form of its inactive prodrug lisdexamfetamine. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers:[note 3] levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.[sources 1]

The first amphetamine pharmaceutical was Benzedrine, a brand which was used to treat a variety of conditions. Currently, pharmaceutical amphetamine is prescribed as racemic amphetamine, Adderall,[note 4] dextroamphetamine, or the inactive prodrug lisdexamfetamine. Amphetamine increases monoamine and excitatory neurotransmission in the brain, with its most pronounced effects targeting the norepinephrine and dopamine neurotransmitter systems.[sources 2]

At therapeutic doses, amphetamine causes emotional and cognitive effects such as euphoria, change in desire for sex, increased wakefulness, and improved cognitive control. It induces physical effects such as improved reaction time, fatigue resistance, decreased appetite, elevated heart rate, and increased muscle strength. Larger doses of amphetamine may impair cognitive function and induce rapid muscle breakdown. Addiction is a serious risk with heavy recreational amphetamine use, but is unlikely to occur from long-term medical use at therapeutic doses. Very high doses can result in psychosis (e.g., hallucinations, delusions and paranoia) which rarely occurs at therapeutic doses even during long-term use. Recreational doses are generally much larger than prescribed therapeutic doses and carry a far greater risk of serious side effects.[sources 3]

Amphetamine belongs to the phenethylamine class. It is also the parent compound of its own structural class, the substituted amphetamines,[note 5] which includes prominent substances such as bupropion, cathinone, MDMA, and methamphetamine. As a member of the phenethylamine class, amphetamine is also chemically related to the naturally occurring trace amine neuromodulators, specifically phenethylamine and N-methylphenethylamine, both of which are produced within the human body. Phenethylamine is the parent compound of amphetamine, while N-methylphenethylamine is a positional isomer of amphetamine that differs only in the placement of the methyl group.[sources 4]


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    Table 9.2 Dextroamphetamine formulations of stimulant medication
    Dexedrine [Peak:2–3 h] [Duration:5–6 h] ...
    Adderall [Peak:2–3 h] [Duration:5–7 h]
    Dexedrine spansules [Peak:7–8 h] [Duration:12 h] ...
    Adderall XR [Peak:7–8 h] [Duration:12 h]
    Vyvanse [Peak:3–4 h] [Duration:12 h]
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