Levomethamphetamine

Levomethamphetamine
INN: Levmetamfetamine
Clinical data
Trade names	Vicks VapoInhaler, Everclear Inhaler, others
Other names	l-methamphetamine; (-)-methamphetamine; (R)-methamphetamine; (R)-(-)-methamphetamine; l-desoxyephedrine; levodesoxyephedrine
Routes of; administration	Medical: Intranasal; Recreational: By mouth, intravenous, insufflation, inhalation, suppository
Drug class	Norepinephrine releasing agent; Decongestant
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule II and for specific formulations OTC; UN: Psychotropic Schedule II;
Pharmacokinetic data
Bioavailability	Oral: ~100%
Metabolism	Liver (CYP2D6)
Metabolites	Levoamphetamine
Elimination half-life	10–15 hours
Excretion	Urine (41–49% unchanged, 2–3% as levoamphetamine)
Identifiers
	IUPAC name (R)-N-methyl-1-phenylpropan-2-amine;
CAS Number	33817-09-3 ;
PubChem CID	36604;
DrugBank	DB09571;
ChemSpider	33634 ;
UNII	Y24T9BT2Q2;
KEGG	D02291 ;
CompTox Dashboard (EPA)	DTXSID30187474 ;
ECHA InfoCard	100.046.974
Chemical and physical data
Formula	C10H15N
Molar mass	149.237 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Levorotatory enantiomer
	SMILES N([C@@H](Cc1ccccc1)C)C;
	InChI 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 ; Key:MYWUZJCMWCOHBA-SECBINFHSA-N ;
	(verify)

Levomethamphetamine^[a] (INN: levmetamfetamine) is an optical isomer of methamphetamine primarily used as a topical nasal decongestant.^[2] Levomethamphetamine is used to treat nasal congestion from allergies and the common cold.^[7] It was first used medically as decongestant beginning in 1958 and has been used for such purposes, primarily in the United States, since then.^[8]

^ Anvisa (28 May 2024). "RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 25 September 2024. Retrieved 25 September 2024.
^ ^a ^b ^c ^d ^e 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.
^ ^a ^b ^c ^d Cite error: The named reference LiLopezGalloway2010 was invoked but never defined (see the help page).
^ ^a ^b ^c Cite error: The named reference MendelsonUemuraHarris2006 was invoked but never defined (see the help page).
^ Cite error: The named reference KraemerMaurer2002 was invoked but never defined (see the help page).
^ Cite error: The named reference ScheininAnttilaDahl1998 was invoked but never defined (see the help page).
^ "Cold, Cough, Allergy, Bronchodilator, and Antiasthmatic Drug Products for Over-the-Counter Human Use". FDA. 7 June 2023. Archived from the original on 6 July 2023.
^ Cite error: The named reference WessonSmithMorgan1986 was invoked but never defined (see the help page).

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

[1] Anvisa (28 May 2024). "RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 25 September 2024. Retrieved 25 September 2024.

[BarkholtzHadzimaMiles2023-2] 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.

[LiLopezGalloway2010-3] Cite error: The named reference LiLopezGalloway2010 was invoked but never defined (see the help page).

[MendelsonUemuraHarris2006-4] Cite error: The named reference MendelsonUemuraHarris2006 was invoked but never defined (see the help page).

[KraemerMaurer2002-5] Cite error: The named reference KraemerMaurer2002 was invoked but never defined (see the help page).

[ScheininAnttilaDahl1998-6] Cite error: The named reference ScheininAnttilaDahl1998 was invoked but never defined (see the help page).

[8] "Cold, Cough, Allergy, Bronchodilator, and Antiasthmatic Drug Products for Over-the-Counter Human Use". FDA. 7 June 2023. Archived from the original on 6 July 2023.

[WessonSmithMorgan1986-9] Cite error: The named reference WessonSmithMorgan1986 was invoked but never defined (see the help page).

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