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