CHEBI:35817 - roxarsone

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ChEBI Name roxarsone
ChEBI ID CHEBI:35817
Definition An organoarsonic acid where the organyl group is 4-hydroxy-3-nitrophenyl.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information eMolecules:36759798, ZINC000006021043
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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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Formula C6H6AsNO6
Net Charge 0
Average Mass 263.03650
Monoisotopic Mass 262.94111
InChI 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)
InChIKey XMVJITFPVVRMHC-UHFFFAOYSA-N
SMILES Oc1ccc(cc1[N+]([O-])=O)[As](O)(O)=O
Roles Classification
Biological Role(s): 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.
Application(s): 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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ChEBI Ontology
Outgoing roxarsone (CHEBI:35817) has functional parent phenylarsonic acid (CHEBI:29851)
roxarsone (CHEBI:35817) has role agrochemical (CHEBI:33286)
roxarsone (CHEBI:35817) has role animal growth promotant (CHEBI:82655)
roxarsone (CHEBI:35817) has role antibacterial drug (CHEBI:36047)
roxarsone (CHEBI:35817) has role coccidiostat (CHEBI:35818)
roxarsone (CHEBI:35817) is a 2-nitrophenols (CHEBI:86421)
roxarsone (CHEBI:35817) is a organoarsonic acid (CHEBI:22638)
IUPAC Name
(4-hydroxy-3-nitrophenyl)arsonic acid
INNs Sources
roxarson ChemIDplus
roxarsone ChemIDplus
roxarsonum ChemIDplus
Synonyms Sources
2-nitro-1-hydroxybenzene-4-arsonic acid ChemIDplus
3-nitro-4-hydroxybenzenearsonic acid ChemIDplus
3-nitro-4-hydroxyphenylarsonic acid ChemIDplus
4-hydroxy-3-nitrobenzenearsonic acid ChEBI
4-hydroxy-3-nitrophenylarsonic acid ChEBI
NSC-2101 ChemIDplus
Brand Names Sources
3-Nitro ChEBI
Ren-O-Sal ChemIDplus
Manual Xrefs Databases
3003 VSDB
DE224953 Patent
GB226255 Patent
LSM-5383 LINCS
Roxarsone Wikipedia
View more database links
Registry Numbers Types Sources
121-19-7 CAS Registry Number ChemIDplus
1221211 Gmelin Registry Number Gmelin
1976533 Reaxys Registry Number Reaxys
Citations Types Sources
12724787 PubMed citation Europe PMC
12731831 PubMed citation Europe PMC
12731832 PubMed citation Europe PMC
18414637 PubMed citation Europe PMC
21388897 PubMed citation Europe PMC
Last Modified
25 February 2016
General Comment
2011-07-25 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.