Levomethamphetamine

Levomethamphetamine

Clinical data
Routes of administration	Medical: Inhalation (nasal) Recreational: Oral, intravenous, insufflation, inhalation, suppository
Legal status
Legal status	CA: Schedule I DE: Anlage II (Prohibited) UK: Class A US: Schedule II; specific formulations OTC UN: Psychotropic Schedule II
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name (R)-N-methyl-1-phenyl-propan-2-amine
CAS Number	33817-09-3 Y
PubChem (CID)	36604
ChemSpider	33634 Y
UNII	44RAL3456C Y
KEGG	D02291 Y
ECHA InfoCard	100.046.974
Chemical and physical data
Formula	C10H15N
Molar mass	149.2
3D model (Jmol)	Interactive image
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 Y Key:MYWUZJCMWCOHBA-SECBINFHSA-N Y

Levomethamphetamine is the levorotary (L-enantiomer) form of methamphetamine. Levomethamphetamine is a sympathomimetic vasoconstrictor which is the active ingredient in some over-the-counter (OTC) nasal decongestant inhalers in the United States.

Levomethamphetamine crosses the blood-brain-barrier and acts as a TAAR1 agonist, functioning as a selective norepinephrine releasing agent (with few or no effects on the release of dopamine), so it affects the central nervous system, although its effects are qualitatively distinct relative to those of dextromethamphetamine. It does not possess the potential for euphoria or addiction that dextromethamphetamine possesses. Among its physiological effects are the vasoconstriction that makes it useful for nasal decongestion. The elimination half-life of levomethamphetamine is between 13.3 and 15 hours, whereas dextromethamphetamine has a half-life of about 10.5 hours.

Levomethamphetamine is the chemical precursor of the antiparkinson's drug selegiline. Selegiline, a selective monoamine oxidase B (MAO_B) inhibitor at low doses, is also metabolized into levomethamphetamine and levoamphetamine. This has caused users to test positive for amphetamines.