Amphetamine

Amphetamine
INN: Amfetamine
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
  • AU: S8 (Controlled drug)
  • BR: Class A3 (Psychoactive drugs)
  • CA: Schedule I
  • DE: Anlage III (Special prescription form required)
  • NZ: Class B
  • UK: Class B
  • US: Schedule II[8]
  • UN: Psychotropic Schedule II
Pharmacokinetic data
BioavailabilityOral: ~90%[9]
Protein binding20%[10]
MetabolismCYP2D6,[3] DBH,[4][5] FMO3[4][6][7]
Metabolites4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, benzoic acid, hippuric acid, norephedrine, phenylacetone[3][11]
Onset of actionIR dosing: 30–60 minutes[12]
XR dosing: 1.5–2 hours[13][14]
Elimination half-lifeD-amph: 9–11 hours[3][15]
L-amph: 11–14 hours[3][15]
pH-dependent: 7–34 hours[16]
Duration of actionIR dosing: 3–6 hours[1][13][17]
XR dosing: 8–12 hours[1][13][17]
ExcretionPrimarily renal;
pH-dependent range: 1–75%[3]
Identifiers
IUPAC name
  • (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
Chemical and physical data
FormulaC9H13N
Molar mass135.210 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture[18]
Density.936 g/cm3 at 25 °C[19]
Melting point146 °C (295 °F) [20]
Boiling point203 °C (397 °F) at 760 mmHg[21]
SMILES
  • NC(C)Cc1ccccc1
InChI
  • InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 Y
  • Key:KWTSXDURSIMDCE-UHFFFAOYSA-N Y
  (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. 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]


Cite error: There are <ref group=note> tags on this page, but the references will not show without a {{reflist|group=note}} template (see the help page).

  1. ^ a b c Cite error: The named reference Stahl's Essential Psychopharmacology was invoked but never defined (see the help page).
  2. ^ a b c Cite error: The named reference Amph Uses was invoked but never defined (see the help page).
  3. ^ a b c d e Cite error: The named reference FDA Pharmacokinetics was invoked but never defined (see the help page).
  4. ^ a b c Cite error: The named reference Substituted amphetamines, FMO, and DBH was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference DBH amph primary was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference FMO was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference FMO3-Primary was invoked but never defined (see the help page).
  8. ^ Ingersoll J (7 July 1971). "Amphetamine, Methamphetamine, and Optical Isomers" (PDF). Federal Register. Bureau of Narcotics and Dangerous Drugs. Archived (PDF) from the original on 27 November 2024. Retrieved 27 November 2024.
  9. ^ Cite error: The named reference Antunes_2022 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference Drugbank-amph was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Metabolites was invoked but never defined (see the help page).
  12. ^ "Pharmacology". amphetamine/dextroamphetamine. Medscape - WebMD. Retrieved 21 January 2016. Onset of action: 30–60 min
  13. ^ a b c Millichap JG (2010). "Chapter 9: Medications for ADHD". In Millichap JG (ed.). Attention Deficit Hyperactivity Disorder Handbook: A Physician's Guide to ADHD (2nd ed.). New York: Springer. p. 112. ISBN 9781441913968.
    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]
  14. ^ Brams M, Mao AR, Doyle RL (September 2008). "Onset of efficacy of long-acting psychostimulants in pediatric attention-deficit/hyperactivity disorder". Postgraduate Medicine. 120 (3): 69–88. doi:10.3810/pgm.2008.09.1909. PMID 18824827. S2CID 31791162.
  15. ^ a b c d "Adderall- dextroamphetamine saccharate, amphetamine aspartate, dextroamphetamine sulfate, and amphetamine sulfate tablet". DailyMed. Teva Pharmaceuticals USA, Inc. 8 November 2019. Retrieved 22 December 2019.
  16. ^ Cite error: The named reference HSDB Toxnet October 2017 Full archived record was invoked but never defined (see the help page).
  17. ^ a b Cite error: The named reference Narcolepsy guide was invoked but never defined (see the help page).
  18. ^ a b c d e Yoshida T (1997). "Chapter 1: Use and Misuse of Amphetamines: An International Overview". In Klee H (ed.). Amphetamine Misuse: International Perspectives on Current Trends. Amsterdam, Netherlands: Harwood Academic Publishers. p. 2. ISBN 9789057020810. Amphetamine, in the singular form, properly applies to the racemate of 2-amino-1-phenylpropane. ... In its broadest context, however, the term [amphetamines] can even embrace a large number of structurally and pharmacologically related substances.
  19. ^ "Density". Amphetamine. United States National Library of Medicine – National Center for Biotechnology Information. PubChem Compound Database. 5 November 2016. Retrieved 9 November 2016.
  20. ^ Amphetamine. American Chemical Society. CAS Common Chemistry. Retrieved 25 October 2022.
  21. ^ Cite error: The named reference Properties was invoked but never defined (see the help page).
  22. ^ a b Cite error: The named reference PubChem Header was invoked but never defined (see the help page).
  23. ^ Cite error: The named reference Acute amph toxicity was invoked but never defined (see the help page).
  24. ^ "Enantiomer". IUPAC Compendium of Chemical Terminology. International Union of Pure and Applied Chemistry. IUPAC Goldbook. 2009. doi:10.1351/goldbook.E02069. ISBN 9780967855097. Archived from the original on 17 March 2013. Retrieved 14 March 2014. One of a pair of molecular entities which are mirror images of each other and non-superposable.
  25. ^ Rasmussen N (January 2015). Taba P, Lees A, Sikk K (eds.). "Amphetamine-Type Stimulants: The Early History of Their Medical and Non-Medical Uses". International Review of Neurobiology. The Neuropsychiatric Complications of Stimulant Abuse. 120. Academic Press: 9–25. doi:10.1016/bs.irn.2015.02.001. hdl:1959.4/unsworks_47518. PMID 26070751.
  26. ^ a b c Cite error: The named reference Malenka_2009 was invoked but never defined (see the help page).
  27. ^ a b Cite error: The named reference Ergogenics was invoked but never defined (see the help page).
  28. ^ a b Cite error: The named reference FDA was invoked but never defined (see the help page).
  29. ^ a b Cite error: The named reference Benzedrine was invoked but never defined (see the help page).
  30. ^ Cite error: The named reference UN Convention was invoked but never defined (see the help page).
  31. ^ Cite error: The named reference Nonmedical was invoked but never defined (see the help page).
  32. ^ a b Cite error: The named reference Libido was invoked but never defined (see the help page).
  33. ^ "Amphetamine". Medical Subject Headings. United States National Library of Medicine. Retrieved 16 December 2013.
  34. ^ "Guidelines on the Use of International Nonproprietary Names (INNS) for Pharmaceutical Substances". World Health Organization. 1997. Archived from the original on 9 January 2015. Retrieved 1 December 2014. In principle, INNs are selected only for the active part of the molecule which is usually the base, acid or alcohol. In some cases, however, the active molecules need to be expanded for various reasons, such as formulation purposes, bioavailability or absorption rate. In 1975 the experts designated for the selection of INN decided to adopt a new policy for naming such molecules. In future, names for different salts or esters of the same active substance should differ only with regard to the inactive moiety of the molecule. ... The latter are called modified INNs (INNMs).
  35. ^ a b Cite error: The named reference Evekeo was invoked but never defined (see the help page).
  36. ^ Cite error: The named reference BED rapid review was invoked but never defined (see the help page).
  37. ^ "National Drug Code Amphetamine Search Results". National Drug Code Directory. United States Food and Drug Administration. Archived from the original on 16 December 2013. Retrieved 16 December 2013.
  38. ^ Cite error: The named reference Miller was invoked but never defined (see the help page).
  39. ^ Cite error: The named reference Miller+Grandy 2016 was invoked but never defined (see the help page).
  40. ^ Cite error: The named reference Westfall was invoked but never defined (see the help page).
  41. ^ Cite error: The named reference Cochrane was invoked but never defined (see the help page).
  42. ^ Cite error: The named reference Amphetamine-induced psychosis was invoked but never defined (see the help page).
  43. ^ Cite error: The named reference Stimulant Misuse was invoked but never defined (see the help page).
  44. ^ Cite error: The named reference Long-Term Outcomes Medications was invoked but never defined (see the help page).
  45. ^ Cite error: The named reference NHMH_3e-Addiction doses was invoked but never defined (see the help page).
  46. ^ Cite error: The named reference Addiction risk was invoked but never defined (see the help page).
  47. ^ Cite error: The named reference narcolepsy addiction was invoked but never defined (see the help page).
  48. ^ Cite error: The named reference Trace Amines was invoked but never defined (see the help page).
  49. ^ "Amphetamine". European Monitoring Centre for Drugs and Drug Addiction. Retrieved 19 October 2013.
  50. ^ Cite error: The named reference Amphetamine - a substituted amphetamine was invoked but never defined (see the help page).


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