Wednesday, August 1, 2018

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Methamphetamine

Methamphetamine
INN:Metamfetamine
An image of the methamphetamine compound
Ball-and-stick model of the methamphetamine molecule
Clinical data
Pronunciation/ˌmɛθæmˈfɛtəmn/
Trade namesDesoxyn, Methedrine
SynonymsN-methylamphetamineN,α-dimethylphenethylamine, desoxyephedrine
AHFS/Drugs.comMonograph
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[1]
    Recreational: oralintravenousintramuscularsubcutaneoussmoke inhalationinsufflationrectalvaginal
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    BioavailabilityOral: 70%[6]
    IV: 100%[6]
    Protein bindingVaries widely[7]
    MetabolismCYP2D6[2][3] and FMO3[4][5]
    Onset of actionRapid[8]
    Elimination half-life5–30 hours[9]
    Duration of action10–20 hours[8]
    ExcretionPrimarily renal
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    PDB ligand
    ECHA InfoCard100.007.882 Edit this at Wikidata
    Chemical and physical data
    FormulaC10H15N
    Molar mass149.24 g·mol−1
    3D model (JSmol)
    ChiralityRacemic mixture
    Melting point3 °C (37 °F) (predicted)[10]
    Boiling point212 °C (414 °F) at 760 mmHg[11]
      (verify)
    Methamphetamine[note 1] (contracted from N-methylamphetamine) is a potent central nervous system (CNS) stimulantthat is mainly used as a recreational drugand less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity.[17]Methamphetamine was discovered in 1893 and exists as two enantiomers:  levo-methamphetamine and dextro-methamphetamine.[note 2]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 over concerns involving human neurotoxicityand 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.[note 3] 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.
    In low to moderate doses, methamphetamine can elevate mood, increase alertness, concentration and energy in fatigued individuals, reduce appetite, and promote weight loss. At relatively high doses, it can induce psychosisbreakdown of skeletal muscleseizures and bleeding in the brain. Chronic high-dose use can precipitate unpredictable and rapid mood swingsstimulant psychosis (e.g., paranoiahallucinationsdelirium, and delusions) and violent behavior. Recreationally, methamphetamine's ability to increase energy has been reported to lift mood and increase sexual desire to such an extent that users are able to engage in sexual activity continuously for several days.[20]Methamphetamine is known to possess a high addiction liability (i.e., a high likelihood that long-term or high dose use will lead to compulsive drug use) and high dependence liability (i.e. a high likelihood that withdrawal symptoms will occur when methamphetamine use ceases). Heavy recreational use of methamphetamine may lead to a post-acute-withdrawal syndrome, which can persist for months beyond the typical withdrawal period. Unlike amphetamine, methamphetamine is neurotoxic to human midbrain dopaminergic neurons.[21] It has also been shown to damage serotoninneurons in the CNS.[22][23] This damage includes adverse changes in brain structure and function, such as reductions in grey matter volume in several brain regions and adverse changes in markers of metabolic integrity.[23]
    Methamphetamine belongs to the substituted phenethylamine and substituted amphetamine chemical classes. It is related to the other dimethylphenethylamines as a positional isomer of these compounds, which share the common chemical formulaC10H15N1.

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