Back لوومت‌آمفتامین Persian Levometamfetamiini Finnish Levometamfetamin Croatian Lewometamfetamina Polish Levometanfetamina Portuguese Levometamfetamin Serbo-Croatian Template:Nasal preparations SIMPLE Levometamfetamin Serbian Levomethamphetamine Vietnamese 左旋甲基苯丙胺 Chinese

Levomethamphetamine

Levomethamphetamine
INN: Levmetamfetamine
Clinical data
Trade namesVicks Inhaler; Vicks Vapor Inhaler; Pervitin
Other namesLevmetamfetamine; L-Methamphetamine; R-(-)-Methamphetamine; Levodesoxyephedrine; L-Desoxyephedrine
Routes of
administration		Medical: Inhalation (nasal)
Recreational: Oral, intravenous, insufflation, inhalation, suppository
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: ~100%[2][3]
MetabolismLiver (CYP2D6)[5][6]
MetabolitesLevoamphetamine[2][4][3]
Elimination half-life10–15 hours[2][4][3]
ExcretionUrine (41–49% unchanged, 2–3% as levoamphetamine)[2][4][3]
Identifiers
  • (R)-N-methyl-1-phenylpropan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.046.974 Edit this at Wikidata
Chemical and physical data
FormulaC10H15N
Molar mass149.237 g·mol−1
3D model (JSmol)
ChiralityLevorotatory enantiomer
  • N([C@@H](Cc1ccccc1)C)C
  • InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m1/s1 checkY
  • Key:MYWUZJCMWCOHBA-SECBINFHSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Levomethamphetamine, also known as l-desoxyephedrine[note 1] and sold under the brand name Vicks Vapor Inhaler among others, is a sympathomimetic, decongestant, and stimulant medication which is used to treat nasal congestion.[2] It is available over-the-counter at low doses as a decongestant in the United States and is taken by inhalation for this use.[2]

Levomethamphetamine act as a selective releasing agent of norepinephrine.[7][8][4] It also induces the release of dopamine to a far lesser extent.[7][9][4] Levomethamphetamine is an amphetamine and is the levorotatory enantiomer of the better-known methamphetamine.[2] The effects of levomethamphetamine are distinct from those of racemic methamphetamine and dextromethamphetamine and it does not have the same misuse potential as these substances.[2][10][11][4][12]

Methamphetamine was first discovered in 1919[13][14] and was introduced for medical use in oral form in 1938 under the brand name Pervitin.[15] Decongestant inhalers containing enantiopure levomethamphetamine were introduced in 1958 under the brand name Vicks Inhaler.[15] In addition to being used in pharmaceutical drugs itself, levomethamphetamine is a known active metabolite of certain other drugs, such as selegiline (L-deprenyl).[5][16]

  1. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  2. ^ a b c d e f g h 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.
  3. ^ a b c d Cite error: The named reference LiLopezGalloway2010 was invoked but never defined (see the help page).
  4. ^ a b c d e f Cite error: The named reference MendelsonUemuraHarris2006 was invoked but never defined (see the help page).
  5. ^ a b Kraemer T, Maurer HH (April 2002). "Toxicokinetics of amphetamines: metabolism and toxicokinetic data of designer drugs, amphetamine, methamphetamine, and their N-alkyl derivatives". Ther Drug Monit. 24 (2): 277–89. doi:10.1097/00007691-200204000-00009. PMID 11897973.
  6. ^ Cite error: The named reference ScheininAnttilaDahl1998 was invoked but never defined (see the help page).
  7. ^ a b Cite error: The named reference RothmanBaumann2003 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference RothmanBaumannDersch2001 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference KohutJacobsRothman2017 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference PaulyBhimaniLi2023 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference MelegaChoSchmitz1999 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference KuczenskiSegalCho1995 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference VearrierGreenbergMiller2012 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Ciccarone2011 was invoked but never defined (see the help page).
  15. ^ a b Cite error: The named reference WessonSmithMorgan1986 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference HeinonenLammintausta1991 was invoked but never defined (see the help page).


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