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| 2'-deoxyadenosine 5'-monophosphate |
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| CHEBI:17713 |
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| A purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:40419, CHEBI:40544, CHEBI:40499, CHEBI:40607, CHEBI:40614, CHEBI:40505, CHEBI:41864, CHEBI:41870, CHEBI:41815, CHEBI:10490, CHEBI:19236, CHEBI:14068
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| eMolecules:36759798, ZINC000006021043 |
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Molfile
XML
SDF
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more structures >>
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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js
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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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Read full article at Wikipedia
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InChI=1S/C10H14N5O6P/c11- 9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 |
| KHWCHTKSEGGWEX-RRKCRQDMSA-N |
| Nc1ncnc2n(cnc12)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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fundamental metabolite
Any metabolite produced by all living cells.
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View more via ChEBI Ontology
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Outgoing
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2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
has role
fundamental metabolite
(CHEBI:78675)
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
is a
2'-deoxyadenosine 5'-phosphate
(CHEBI:19237)
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
is a
purine 2'-deoxyribonucleoside 5'-monophosphate
(CHEBI:36993)
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
is conjugate acid of
2'-deoxyadenosine 5'-monophosphate(2−)
(CHEBI:58245)
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Incoming
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8,5'-cyclo-2'-deoxyadenosine monophosphate
(CHEBI:131827)
has functional parent
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
8-hydroxy-dAMP
(CHEBI:70964)
has functional parent
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
8-oxo-dAMP
(CHEBI:71403)
has functional parent
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
N6-carbamoylmethyl-2'-deoxyadenosine 5'-monophosphate
(CHEBI:103067)
has functional parent
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
2'-deoxyadenosine 5'-monophosphate(2−)
(CHEBI:58245)
is conjugate base of
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
2'-deoxyadenosine 5'-monophosphate residue
(CHEBI:50323)
is substituent group from
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
dAMP 3'-end residue
(CHEBI:53113)
is substituent group from
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
dAMP 5'-end residue
(CHEBI:53099)
is substituent group from
2'-deoxyadenosine 5'-monophosphate
(CHEBI:17713)
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2'-deoxy-5'-adenylic acid
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2'-dAMP
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ChemIDplus
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2'-deoxy-5'-adenosine monophosphate
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ChemIDplus
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2'-deoxy-AMP
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ChemIDplus
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2'-deoxyadenosine 5'-(dihydrogen phosphate)
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ChemIDplus
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2'-deoxyadenosine 5'-monophosphate
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ChEBI
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2'-Deoxyadenosine 5'-monophosphate
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KEGG COMPOUND
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2'-Deoxyadenosine 5'-phosphate
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KEGG COMPOUND
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2'-deoxyadenosine monophosphate
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ChemIDplus
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2'-DEOXYADENOSINE-5'-MONOPHOSPHATE
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PDBeChem
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2'-deoxyadenylic acid
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ChemIDplus
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dAMP
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KEGG COMPOUND
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deoxy-5'-adenylic acid
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ChemIDplus
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deoxy-AMP
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ChemIDplus
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deoxyadenosine 5'-monophosphate
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ChemIDplus
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deoxyadenosine 5'-phosphate
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ChemIDplus
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Deoxyadenosine monophosphate
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KEGG COMPOUND
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Deoxyadenylic acid
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KEGG COMPOUND
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56028
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Reaxys Registry Number
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Reaxys
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653-63-4
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CAS Registry Number
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ChemIDplus
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8645724
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PubMed citation
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Europe PMC
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