Methamphetamine (contracted from N-methylamphetamine) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational or performance-enhancing drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder (ADHD). It has also been researched as a potential treatment for traumatic brain injury. Methamphetamine was discovered in 1893 and exists as two enantiomers: levo-methamphetamine and dextro-methamphetamine. Methamphetamine properly refers to a specific chemical substance, the racemic free base, which is an equal mixture of levomethamphetamine and dextromethamphetamine in their pure amine forms, but the hydrochloride salt, commonly called crystal meth, is widely used. Methamphetamine is rarely prescribed over concerns involving its 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 such as Adderall and Vyvanse. While pharmaceutical formulations of methamphetamine in the United States are labeled as methamphetamine hydrochloride, they contain dextromethamphetamine as the active ingredient. Dextromethamphetamine is a stronger CNS stimulant than levomethamphetamine.
Both racemic 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 and Oceania, and in the United States, where racemic methamphetamine 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, owing 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 illicitly produced more often, owing to the relative ease of synthesis and regulatory limits of chemical precursor availability.
In low to moderate doses, methamphetamine can elevate mood, increase alertness, concentration and energy in fatigued individuals, reduce appetite, and promote weight loss. At very high doses, it can induce psychosis, breakdown of skeletal muscle, seizures, and bleeding in the brain. Chronic high-dose use can precipitate unpredictable and rapid mood swings, stimulant psychosis (e.g., paranoia, hallucinations, delirium, 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 while binging the drug. 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). Discontinuing methamphetamine after heavy use may lead to a post-acute-withdrawal syndrome, which can persist for months beyond the typical withdrawal period. At high doses, methamphetamine is neurotoxic to human midbrain dopaminergic neurons and, to a lesser extent, serotonergic neurons. Methamphetamine neurotoxicity causes adverse changes in brain structure and function, such as reductions in grey matter volume in several brain regions, as well as adverse changes in markers of metabolic integrity.
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 formula C10H15N.
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InChI=1S/C6H6AsNO6/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14/h1-3,9H,(H2,10,11,12) |
XMVJITFPVVRMHC-UHFFFAOYSA-N |
Oc1ccc(cc1[N+]([O-])=O)[As](O)(O)=O |
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antibacterial drug
A drug used to treat or prevent bacterial infections.
coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
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antibacterial drug
A drug used to treat or prevent bacterial infections.
coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
animal growth promotant
Substances that are administered to farmed animals to improve productivity by promoting weight gain, increasing muscle mass, limiting fat deposition, reducing feed consumption, and reducing waste production.
agrochemical
An agrochemical is a substance that is used in agriculture or horticulture.
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View more via ChEBI Ontology
(4-hydroxy-3-nitrophenyl)arsonic acid
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roxarson
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ChemIDplus
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roxarsone
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ChemIDplus
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roxarsonum
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ChemIDplus
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2-nitro-1-hydroxybenzene-4-arsonic acid
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ChemIDplus
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3-nitro-4-hydroxybenzenearsonic acid
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ChemIDplus
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3-nitro-4-hydroxyphenylarsonic acid
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ChemIDplus
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4-hydroxy-3-nitrobenzenearsonic acid
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ChEBI
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4-hydroxy-3-nitrophenylarsonic acid
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ChEBI
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NSC-2101
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ChemIDplus
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3-Nitro
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ChEBI
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Ren-O-Sal
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ChemIDplus
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121-19-7
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CAS Registry Number
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ChemIDplus
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1221211
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Gmelin Registry Number
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Gmelin
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1976533
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Reaxys Registry Number
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Reaxys
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12724787
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PubMed citation
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Europe PMC
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12731831
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PubMed citation
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Europe PMC
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12731832
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PubMed citation
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Europe PMC
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18414637
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PubMed citation
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Europe PMC
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21388897
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PubMed citation
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Europe PMC
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2011-07-25
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Roxarsone has been widely used agriculturally in feed for chickens, turkeys and pigs as an antibacterial agent and growth promoter. It was primarily used to improve the effectiveness of the animal drugs, narasin or salinomycin, to control coccidiosis, a parasitic disease that infects the intestinal tracts of poultry and can lead to death in animals. Following concerns about arsenic contamination of the food chain and increased levels of inorganic arsenic detected in broiler chickens treated with roxarsone compared with untreated chickens, in June 2011 the U.S. Food and Drug Administration ordered the manufacturer Pfizer to suspend sales of roxarsone within 30 days.
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