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<compound>
  <id type="integer">3094</id>
  <title>T3D3052</title>
  <common-name>Methamphetamine</common-name>
  <description>Methamphetamine (C10H15N) is an exogenous organic compound with an average molecular weight of 149.23 g/mol that exists as a solid at room temperature. Methamphetamine belongs to the phenethylamines, a subclass of benzene and substituted derivatives within the organic compounds. It is classified as a drug, neurotoxin, central nervous system stimulant, and psychotropic drug (PMC12241196). It has been detected in the liver and kidney.

The compound acts as an agonist of the sodium-dependent dopamine transporter (SLC6A3), the sodium-dependent serotonin transporter (SLC6A4), the synaptic vesicular amine transporter (SLC18A2), and the trace amine-associated receptor 1 (TAAR1), among 11 other protein targets. It also targets the alpha-1A (ADRA1A) and alpha-1B (ADRA1B) adrenergic receptors. Methamphetamine triggers a cascading release of serotonin, dopamine, and norepinephrine in the brain, acting as an adrenergic and dopaminergic reuptake inhibitor, and functioning as a monamine oxidase inhibitor (MAOI) in high concentrations.

Methamphetamine is used in healthcare, pharmaceuticals, and veterinary products as a nootropic, a psychostimulant, and an agent for ADHD. It is found in drinking water and various other sources, including household cleaning and consumer products, food processing, and electrical equipment. Exposure routes include oral ingestion and smoking (PMC9988231). Health effects associated with the compound include inflammation (PMC9434488), pain and fatigue (PMC3573677), hyperthermia (PMC7735854), and placental abruption (PMC8763371). Additionally, it is associated with increases in fever, paresthesia, and seizures (PMC9988231), as well as anxiety and depression (PMC11728700).</description>
  <cas>537-46-2</cas>
  <pubchem-id>10836</pubchem-id>
  <chemical-formula>C10H15N</chemical-formula>
  <weight>149.120450</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>9.28e-01 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Methamphetamine is rapidly absorbed from the gastrointestinal tract with peak methamphetamine concentrations occurring in 3.13 to 6.3 hours post ingestion. Methamphetamine is also well absorbed following inhalation and following intranasal administration. It is distributed to most parts of the body. Because methamphetamine has a high lipophilicity it is distributed across the blood brain barrier and crosses the placenta.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Methamphetamine enters the brain and triggers a cascading release of norepinephrine, dopamine and serotonin. To a lesser extent methamphetamine acts as a dopaminergic and adrenergic reuptake inhibitor and in high concentrations as a monamine oxidase inhibitor (MAOI). The mechanism of action involved in producing the beneficial behavioral changes seen in hyperkinetic children receiving methamphetamine is unknown.</mechanism-of-toxicity>
  <metabolism>Hepatic. The primary site of metabolism is in the liver by aromatic hydroxylation, N-dealkylation and deamination. At least seven metabolites have been identified in the urine, with the main metabolites being amphetamine (active) and 4-hydroxymethamphetamine. Other minor metabolites include 4-hydroxyamphetamine, norephedrine, and 4-hydroxynorephedrine.Route of Elimination: Excretion occurs primarily in the urine, the rate of which is dependent on urine pH. Between 30-54% of an oral dose is excreted in urine as unchanged methamphetamine and 10-23% as unchanged amphetamine. Following an intravenous dose, 45% is excreted as unchanged parent drug and 7% amphetamine.Half Life: The biological half-life has been reported in the range of 4 to 5 hours.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of Attention Deficit Disorder with Hyperactivity (ADHD) and exogenous obesity.</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 methamphetamine include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, panic states, hyperpyrexia, and rhabdomyolysis. 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 usually terminates in convulsions and coma.</symptoms>
  <treatment>Management of acute methamphetamine intoxication is largely symptomatic and includes gastric evacuation, administration of activated charcoal, and sedation. Experience with hemodialysis or peritoneal dialysis is inadequate to permit recommendations in this regard. Acidification of urine increases methamphetamine excretion, but is believed to increase risk of acute renal failure if myoglobinuria is present. Intravenous phentolamine has been suggested for possible acute, severe hypertension, if this complicates methamphetamine overdosage. Usually a gradual drop in blood pressure will result when sufficient sedation has been achieved. Chlorpromazine has been reported to be useful in decreasing CNS stimulation and sympathomimetic effects. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:53Z</created-at>
  <updated-at type="dateTime">2026-05-14T17:09:48Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Methamphetamine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07164</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>6809</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Methamphetamine</stitch-id>
  <drugbank-id>DB01577</drugbank-id>
  <pdb-id>B40</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CN[C@@H](C)CC1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C10H15N</moldb-formula>
  <moldb-inchi>InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m0/s1</moldb-inchi>
  <moldb-inchikey>MYWUZJCMWCOHBA-VIFPVBQESA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">149.2328</moldb-average-mass>
  <moldb-mono-mass type="decimal">149.120449485</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.07</logp>
  <hmdb-id>HMDB15517</hmdb-id>
  <chembl-id>CHEMBL1201201</chembl-id>
  <chemspider-id>10379</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;Nobuyuki Shigetoh, Hiroshi Nakayama, Jinsei Miyazaki, Tadayasu Mitsumata, &amp;#8220;Labelling colors for detecting cocaine or methamphetamine, method of preparing the same and detector for cocaine or methamphetamine.&amp;#8221; U.S. Patent US5571727, issued October, 1981.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002399</chemdb-id>
  <dsstox-id>DTXSID8037128</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00000412</susdat-id>
  <iupac>methyl[(2S)-1-phenylpropan-2-yl]amine</iupac>
  <moldb-polar-surface-area>12.03</moldb-polar-surface-area>
  <moldb-refractivity>48.47980000000001</moldb-refractivity>
  <moldb-polarizability>18.039597610039042</moldb-polarizability>
  <moldb-rotatable-bond-count>3</moldb-rotatable-bond-count>
  <moldb-acceptor-count>1</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>10.20988414728296</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>2.23</moldb-alogps-logp>
  <moldb-alogps-logs>-2.21</moldb-alogps-logs>
  <moldb-alogps-solubility>9.28e-01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Benzenoids</superklass>
  <klass>Benzene and substituted derivatives</klass>
  <subklass>Phenethylamines</subklass>
  <paper-count type="integer">18645</paper-count>
  <sync-id>CED0001381</sync-id>
  <structure-inchikey>MYWUZJCMWCOHBA-VIFPVBQESA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:43Z</structure-indexed-at>
</compound>
