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Methamphetamines

Methamphetamine
INN: Metamfetamine
An image of the methamphetamine compound
Ball-and-stick model of the methamphetamine molecule
Clinical data
Pronunciation /ˌmɛθæmˈfɛtəmn/
Trade names Desoxyn
AHFS/Drugs.com Monograph
License data
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
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
Synonyms N-methylamphetamine, N,α-dimethylphenethylamine, desoxyephedrine
CAS Number 537-46-2 YesY
PubChem (CID) 1206
IUPHAR/BPS 4803
DrugBank DB01577 YesY
ChemSpider 1169 YesY
UNII 44RAL3456C YesY
KEGG D08187 YesY
ChEBI CHEBI:6809 YesY
ChEMBL CHEMBL1201201 YesY
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
  

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.


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