Methamphetamines

Methamphetamine
INN: Metamfetamine

Clinical data
Pronunciation	/ˌmɛθæmˈfɛtəmiːn/
Trade names	Desoxyn
AHFS/Drugs.com	Monograph
License data	US FDA: Methamphetamine
Pregnancy category	US: C (Risk not ruled out)
Dependence liability	Physical: none Psychological: high
Addiction liability	High
Routes of administration	Medical: oral (ingestion), intravenous Recreational: oral, intravenous, intramuscular, subcutaneous, smoke inhalation, insufflation, rectal, vaginal
ATC code	N06BA03 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage II (Prohibited) NZ: Class A UK: Class A US: Schedule II UN: Psychotropic Schedule II
Pharmacokinetic data
Bioavailability	Oral: 70% IV: 100%
Protein binding	Varies widely
Metabolism	CYP2D6 and FMO3
Onset of action	Rapid
Biological half-life	5–30 hours
Duration of action	10–20 hours
Excretion	Primarily renal
Identifiers
IUPAC name (RS)-N-methyl-1-phenylpropan-2-amine
Synonyms	N-methylamphetamine, N,α-dimethylphenethylamine, desoxyephedrine
CAS Number	537-46-2 Y
PubChem (CID)	1206
IUPHAR/BPS	4803
DrugBank	DB01577 Y
ChemSpider	1169 Y
UNII	44RAL3456C Y
KEGG	D08187 Y
ChEBI	CHEBI:6809 Y
ChEMBL	CHEMBL1201201 Y
PDB ligand ID	B40 (PDBe, RCSB PDB)
ECHA InfoCard	100.007.882
Chemical and physical data
Formula	C10H15N
Molar mass	149.24 g·mol−1
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Melting point	3 °C (37 °F) (predicted)
Boiling point	212 °C (414 °F) at 760 mmHg
SMILES N(C(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 Y Key:MYWUZJCMWCOHBA-UHFFFAOYSA-N Y

Methamphetamine (contracted from N-methylamphetamine) is a strong central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a treatment for attention deficit hyperactivity disorder and obesity. Methamphetamine was discovered in 1893 and exists as two enantiomers: levo-methamphetamine and dextro-methamphetamine.Methamphetamine properly refers to a specific chemical, the racemic free base, which is an equal mixture of levomethamphetamine and dextromethamphetamine in their pure amine forms. It is rarely prescribed due to concerns involving human neurotoxicity and potential for recreational use as an aphrodisiac and euphoriant, among other concerns, as well as the availability of safer substitute drugs with comparable treatment efficacy. Dextromethamphetamine is a much stronger CNS stimulant than levomethamphetamine.

Both methamphetamine and dextromethamphetamine are illicitly trafficked and sold owing to their potential for recreational use. The highest prevalence of illegal methamphetamine use occurs in parts of Asia, Oceania, and in the United States, where racemic methamphetamine, levomethamphetamine, and dextromethamphetamine are classified as schedule II controlled substances. Levomethamphetamine is available as an over-the-counter (OTC) drug for use as an inhaled nasal decongestant in the United States. Internationally, the production, distribution, sale, and possession of methamphetamine is restricted or banned in many countries, due to its placement in schedule II of the United Nations Convention on Psychotropic Substances treaty. While dextromethamphetamine is a more potent drug, racemic methamphetamine is sometimes illicitly produced due to the relative ease of synthesis and limited availability of chemical precursors.