Methamphetamine (CHEM002399)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:53 UTC
Update Date2026-03-26 18:30:50 UTC
Accession NumberCHEM002399
Identification
Common NameMethamphetamine
ClassSmall Molecule
DescriptionMethamphetamine is a psychostimulant and sympathomimetic drug. It is a member of the amphetamine group of sympathomimetic amines. Methamphetamine can induce effects such as euphoria, increased alertness and energy, and enhanced self-esteem. It is a scheduled drug in most countries due to its high potential for addiction and abuse.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
Contaminant Type
  • Adrenergic Agent
  • Adrenergic Uptake Inhibitor
  • Amine
  • Central Nervous System Stimulant
  • Dopamine Agent
  • Dopamine Uptake Inhibitor
  • Drug
  • Metabolite
  • Organic Compound
  • Sympathomimetic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-(S)-N-alpha-DimethylphenethylamineChEBI
(AlphaS)-N,alpha-dimethylbenzeneethanamineChEBI
(S)-N,alpha-DimethylbenzeneethanamineChEBI
D-1-Phenyl-2-methylaminopropaneChEBI
D-DeoxyephedrineChEBI
D-DesoxyephedrineChEBI
D-N-MethylamphetamineChEBI
D-PhenylisopropylmethylamineChEBI
DextromethamphetamineChEBI
MetamfetamineChEBI
MetamfetaminumChEBI
MetanfetaminaChEBI
Methyl-beta-phenylisopropylamineChEBI
(+)-(S)-N-a-DimethylphenethylamineGenerator
(+)-(S)-N-Α-dimethylphenethylamineGenerator
(AlphaS)-N,a-dimethylbenzeneethanamineGenerator
(AlphaS)-N,α-dimethylbenzeneethanamineGenerator
(S)-N,a-DimethylbenzeneethanamineGenerator
(S)-N,Α-dimethylbenzeneethanamineGenerator
Methyl-b-phenylisopropylamineGenerator
Methyl-β-phenylisopropylamineGenerator
(+ )-MethylamphetamineHMDB
(+)-(S)-DeoxyephedrineHMDB
(+)-2-(N-Methylamino)-1-phenylpropaneHMDB
(+)-MethamphetamineHMDB
(+)-MethylamphetamineHMDB
(+)-N,alpha-Dimethyl-beta-phenylethylamineHMDB
(+)-N,alpha-DimethylphenethylamineHMDB
(+)-N-MethylamphetamineHMDB
(2S)-N-Methyl-1-phenylpropan-2-amineHMDB
(S)-(+)-DeoxyephedrineHMDB
(S)-(+)-MethamphetamineHMDB
(S)-(+)-N,alpha,DimethylphenethylamineHMDB
(S)-MethamphetamineHMDB
(S)-MethylamphetamineHMDB
(S)-N,alpha-DimethylbenzeneethanoamineHMDB
1-Phenyl-2-methylaminopropaneHMDB
2S-(+)-MethamphetamineHMDB
D-(S)-MethamphetamineHMDB
D-MethamphetamineHMDB
D-MethylamphetamineHMDB
D-N,alpha-DimethylphenethylamineHMDB
Desoxyephedrine hydrochlorideHMDB
IceHMDB
L-MethamphetamineHMDB
MetamphetamineHMDB
MethHMDB
MethylamphetamineHMDB
N-Methyl-1-phenyl-2-propanamineHMDB
N-Methyl-beta-phenylisopropylamineHMDB
N-MethylamphetamineHMDB
S-(+)-MethamphetamineHMDB
Abbott brand OF methamphetamine hydrochlorideHMDB
Hydrochloride, methamphetamineHMDB
MadrineHMDB
DesoxyephedrineHMDB
DesoxynHMDB
Methamphetamine hydrochlorideHMDB
N MethylamphetamineHMDB
DeoxyephedrineHMDB
Langly brand OF methamphetamine hydrochlorideHMDB
MethamphetamineKEGG
Chemical FormulaC10H15N
Average Molecular Mass149.233 g/mol
Monoisotopic Mass149.120 g/mol
CAS Registry Number537-46-2
IUPAC Namemethyl[(2S)-1-phenylpropan-2-yl]amine
Traditional Namemeth
SMILESCN[C@@H](C)CC1=CC=CC=C1
InChI IdentifierInChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m0/s1
InChI KeyMYWUZJCMWCOHBA-VIFPVBQESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility9.28e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.93 g/LALOGPS
logP2.23ALOGPS
logP2.24ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.48 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-d5c137de90ac4540f8bbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-2900000000-9f47787fb23e13a87dadSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-7337ca7928cea10bffe5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udl-5900000000-03d47250c7a980a66e20Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9300000000-d10984417cc7279a776bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9000000000-ba626750e38f88879a89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9000000000-3e56ce6f6bf92f4b0a14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9000000000-4095966beeb0165843c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-7337ca7928cea10bffe5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udl-5900000000-bb1f4cbf0ac7cca4d691Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9300000000-6e88a7d0ffb252a513daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9000000000-70ddbc2127d9ecc43ec0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9000000000-faa0136ac65ec9065e49Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-9000000000-ce6e9f98d322c724f026Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0gb9-2900000000-753b4591b9e358e01e68Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kf-9800000000-94af1bb67acf7028de89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kf-9800000000-904b385cb2c1370393d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9200000000-49618d55cba0c2470ba6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9000000000-3167ad4af9af7ec20657Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9000000000-351c5861a20ce31f40a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-6ca41b91a4dd107137f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-3900000000-7fa23fc8e2e96d14abccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-104f35aae3c1bcbc7887Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-503d557b64d8fcd09a36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-d34387a31168c299ab03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ku6-9400000000-3a9b55d0b53a10725f67Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-fd0454cafd58d60de713Spectrum
Toxicity Profile
Route of ExposureMethamphetamine 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.
Mechanism of ToxicityMethamphetamine 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.
MetabolismHepatic. 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.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of Attention Deficit Disorder with Hyperactivity (ADHD) and exogenous obesity.
Minimum Risk LevelNot Available
Health EffectsUsing 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.
SymptomsManifestations 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.
TreatmentManagement 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. (7)
Concentrations
Not Available
DrugBank IDDB01577
HMDB IDHMDB0015517
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00042732
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMethamphetamine
Chemspider ID10379
ChEBI ID6809
PubChem Compound ID10836
Kegg Compound IDC07164
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Nobuyuki Shigetoh, Hiroshi Nakayama, Jinsei Miyazaki, Tadayasu Mitsumata, “Labelling colors for detecting cocaine or methamphetamine, method of preparing the same and detector for cocaine or methamphetamine.” U.S. Patent US5571727, issued October, 1981.

MSDSNot Available
General References
1. Bennett BA, Hollingsworth CK, Martin RS, Harp JJ: Methamphetamine-induced alterations in dopamine transporter function. Brain Res. 1998 Jan 26;782(1-2):219-27.
2. Shaner JW: Caries associated with methamphetamine abuse. J Mich Dent Assoc. 2002 Sep;84(9):42-7.
3. Schepers RJ, Oyler JM, Joseph RE Jr, Cone EJ, Moolchan ET, Huestis MA: Methamphetamine and amphetamine pharmacokinetics in oral fluid and plasma after controlled oral methamphetamine administration to human volunteers. Clin Chem. 2003 Jan;49(1):121-32.
4. Hasan AA, Ciancio S: Relationship between amphetamine ingestion and gingival enlargement. Pediatr Dent. 2004 Sep-Oct;26(5):396-400.
5. McGregor C, Srisurapanont M, Jittiwutikarn J, Laobhripatr S, Wongtan T, White JM: The nature, time course and severity of methamphetamine withdrawal. Addiction. 2005 Sep;100(9):1320-9.
6. Ko BJ, Suh S, Suh YJ, In MK, Kim SH, Kim JH: (1S,2S)-1-Methylamino-1-phenyl-2-chloropropane: Route specific marker impurity of methamphetamine synthesized from ephedrine via chloroephedrine. Forensic Sci Int. 2012 Sep 10;221(1-3):92-7. doi: 10.1016/j.forsciint.2012.04.008. Epub 2012 May 2.
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17. https://www.ncbi.nlm.nih.gov/pubmed/?term=14769818
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=15380623
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