Levoamphetamine

Not to be confused with Lisdexamfetamine or Levomethamphetamine.
For the racemate, see Amphetamine.

Levoamphetamine
INN: Levamfetamine
Clinical data
Trade namesCydril, others
Other namesl-Amphetamine;[1] Levafetamine; C-105; C105
Routes of
administration		Oral (as part of Adderall, Evekeo, and generic amphetamine[2][3])
Drug classStimulant; Norepinephrine releasing agent
Legal status
Legal status
  • US: Schedule II
Pharmacokinetic data
Protein binding31.7%[4]
MetabolismHydroxylation (CYP2D6), oxidative deamination[3]
MetabolitesL-4-Hydroxyamphetamine[3]
Elimination half-life11.7–15.2 hours[5][3]
ExcretionUrine[6][7]
Identifiers
IUPAC name
  • (2R)-1-Phenylpropan-2-amine[8]
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.320
Chemical and physical data
FormulaC9H13N
Molar mass135.210 g·mol−1
3D model (JSmol)
ChiralityLevorotatory enantiomer
SMILES
  • C[C@@H](N)Cc1ccccc1
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

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 such as Adderall.[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]

  1. ^ CID 32893 from PubChem
  2. ^ Cite error: The named reference Amph Uses was invoked but never defined (see the help page).
  3. ^ a b c d Cite error: The named reference Evekeo FDA label was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference LosackerRoehrich2021 was invoked but never defined (see the help page).
  5. ^ a b c d e Markowitz JS, Patrick KS (October 2017). "The Clinical Pharmacokinetics of Amphetamines Utilized in the Treatment of Attention-Deficit/Hyperactivity Disorder". J Child Adolesc Psychopharmacol. 27 (8): 678–689. doi:10.1089/cap.2017.0071. PMID 28910145.
  6. ^ Cite error: The named reference PatrickMarkowitz1997 was invoked but never defined (see the help page).
  7. ^ a b Heinonen EH, Lammintausta R (1991). "A review of the pharmacology of selegiline". Acta Neurol Scand Suppl. 136: 44–59. doi:10.1111/j.1600-0404.1991.tb05020.x. PMID 1686954.
  8. ^ a b "L-Amphetamine". PubChem Compound. United States National Library of Medicine – National Center for Biotechnology Information. 30 December 2017. Retrieved 2 January 2018.
  9. ^ "R(-)amphetamine". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 2 January 2018.
  10. ^ a b c d e f g h i Heal DJ, Smith SL, Gosden J, Nutt DJ (June 2013). "Amphetamine, past and present--a pharmacological and clinical perspective". J Psychopharmacol. 27 (6): 479–496. doi:10.1177/0269881113482532. PMC 3666194. PMID 23539642.
  11. ^ Cite error: The named reference SilverstoneWells1980 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference SmithDavis1977 was invoked but never defined (see the help page).
  13. ^ Simola N, Carta M (2016). "Amphetamine Usage, Misuse, and Addiction Processes". Neuropathology of Drug Addictions and Substance Misuse. Elsevier. pp. 14–24. doi:10.1016/b978-0-12-800212-4.00002-9. ISBN 978-0-12-800212-4.
  14. ^ Cite error: The named reference BielBopp1978 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference ArnoldWenderMcCloskey1972 was invoked but never defined (see the help page).
  16. ^ Barkholtz HM, Hadzima R, Miles A (July 2023). "Pharmacology of R-(-)-Methamphetamine in Humans: A Systematic Review of the Literature". ACS Pharmacol Transl Sci. 6 (7): 914–924. doi:10.1021/acsptsci.3c00019. PMC 10353062. PMID 37470013.
  17. ^ Cite error: The named reference KraemerMaurer2002 was invoked but never defined (see the help page).


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