<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3093</id>
  <title>T3D3051</title>
  <common-name>Dextroamphetamine</common-name>
  <description>Dextroamphetamine is only found in individuals that have used or taken this drug. It is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. It is a slightly polar, weak base and is lipophilic. The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect.</description>
  <cas>51-64-9</cas>
  <pubchem-id>5826</pubchem-id>
  <chemical-formula>C9H13N</chemical-formula>
  <weight>135.104800</weight>
  <appearance nil="true"/>
  <melting-point>&lt; 25°C</melting-point>
  <boiling-point>203°C</boiling-point>
  <density nil="true"/>
  <solubility>1.74e+00 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral bioavailability is over 75%.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect.</mechanism-of-toxicity>
  <metabolism>Hepatic.Half Life: 10-28 hours (average is approximately 12 hours)</metabolism>
  <toxicity>LD50: 96.8 mg/kg (oral, rat).</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used to treat attention deficit hyperactivity disorder (ADHD). Used as a psychostimulant drug. [Wikipedia]</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.</health-effects>
  <symptoms>Manifestations of acute overdosage with amphetamines include restlessness, tremor, hyperreflexia, rhabdomyolysis, rapid respiration, hyperpyrexia, confusion, assaultiveness, hallucinations, panic states. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension, and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Fatal poisoning is usually preceded by convulsions and coma.</symptoms>
  <treatment>Management of acute amphetamine intoxication is largely symptomatic and includes gastric lavage, administration of activated charcoal, administration of a cathartic, and sedation. Experience with hemodialysis or peritoneal dialysis is inadequate to permit recommendation in this regard. Acidification of the urine increases amphetamine excretion, but is believed to increase risk of acute renal failure if myoglobinuria is present. If acute, severe hypertension complicates amphetamine overdosage, administration of intravenous phentolamine has been suggested. However, a gradual drop in blood pressure will usually result when sufficient sedation has been achieved. Chlorpromazine antagonizes the central stimulant effects of amphetamines and can be used to treat amphetamine intoxication. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:52Z</created-at>
  <updated-at type="dateTime">2026-04-05T15:27:58Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Dextroamphetamine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07884</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>4469</chebi-id>
  <biocyc-id>CPD-7658</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Dextroamphetamine</stitch-id>
  <drugbank-id>DB01576</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>C[C@H](N)CC1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C9H13N</moldb-formula>
  <moldb-inchi>InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1</moldb-inchi>
  <moldb-inchikey>KWTSXDURSIMDCE-QMMMGPOBSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">135.2062</moldb-average-mass>
  <moldb-mono-mass type="decimal">135.104799421</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp>1.76</logp>
  <hmdb-id>HMDB15516</hmdb-id>
  <chembl-id>CHEMBL612</chembl-id>
  <chemspider-id>5621</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Nabenhauer, F.P.; US. Patent 2,276,508; March 17,1942; assigned to Smith, Kline &amp;amp; French&lt;br /&gt;
Laboratories.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002398</chemdb-id>
  <dsstox-id>DTXSID8022907</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00075524</susdat-id>
  <iupac>(2S)-1-phenylpropan-2-amine</iupac>
</compound>
