Dextroamphetamine (CHEM002398)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:52 UTC
Update Date2026-04-05 15:27:58 UTC
Accession NumberCHEM002398
Identification
Common NameDextroamphetamine
ClassSmall Molecule
DescriptionDextroamphetamine 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • 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)-AmphetamineChEBI
(+)-alpha-MethylphenethylamineChEBI
(+)-alpha-MethylphenylethylamineChEBI
(+)-AmphetamineChEBI
(AlphaS)-alpha-methylbenzeneethanamineChEBI
(S)-(+)-AmphetamineChEBI
(S)-(+)-beta-PhenylisopropylamineChEBI
(S)-1-Phenyl-2-aminopropaneChEBI
(S)-1-Phenyl-2-propylamineChEBI
(S)-alpha-MethylbenzeneethanamineChEBI
D-AmphetamineChEBI
DexamphetamineChEBI
DexamfetamineKegg
(+)-a-MethylphenethylamineGenerator
(+)-Α-methylphenethylamineGenerator
(+)-a-MethylphenylethylamineGenerator
(+)-Α-methylphenylethylamineGenerator
(AlphaS)-a-methylbenzeneethanamineGenerator
(AlphaS)-α-methylbenzeneethanamineGenerator
(S)-(+)-b-PhenylisopropylamineGenerator
(S)-(+)-Β-phenylisopropylamineGenerator
(S)-a-MethylbenzeneethanamineGenerator
(S)-Α-methylbenzeneethanamineGenerator
(S)-AmphetamineHMDB
Celltech brand OF dextroamphetamine sulfateHMDB
OxydessHMDB
Sulfate, dextroamphetamineHMDB
D AmphetamineHMDB
CurbanHMDB
Dextro-amphetamine sulfateHMDB
GlaxoSmithKline brand OF dextroamphetamine sulfateHMDB
Dextro-amphetamineHMDB
Dextro amphetamine sulfateHMDB
DextroStatHMDB
Shire brand OF dextroamphetamine sulfateHMDB
D-Amphetamine sulfateHMDB
DexedrineHMDB
Dextroamphetamine sulfateHMDB
Mallinckrodt brand OF dextroamphetamine sulfateHMDB
Pasadena brand OF dextroamphetamineHMDB
Vortech brand OF dextroamphetamine sulfateHMDB
D Amphetamine sulfateHMDB
Dextro amphetamineHMDB
DextroamphetamineChEBI
Chemical FormulaC9H13N
Average Molecular Mass135.206 g/mol
Monoisotopic Mass135.105 g/mol
CAS Registry Number51-64-9
IUPAC Name(2S)-1-phenylpropan-2-amine
Traditional Nameamphetamine
SMILESC[C@H](N)CC1=CC=CC=C1
InChI IdentifierInChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
InChI KeyKWTSXDURSIMDCE-QMMMGPOBSA-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
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25°C
Boiling Point203°C
Solubility1.74e+00 g/L
Predicted Properties
PropertyValueSource
Water Solubility1.74 g/LALOGPS
logP1.85ALOGPS
logP1.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.71 m³·mol⁻¹ChemAxon
Polarizability16.08 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, Positivesplash10-0006-9100000000-41224b447ebed58b4d86Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9000000000-6e32961bde8922a0f2f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-e842cf90085d664ef1c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2900000000-2b5fda1ab431107344f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9400000000-b1a9d46f37313e323a64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-0e421d19515a1429b103Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-fff6e7346b2c36a8ab21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-7900000000-3cd62c7239479d83b257Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-6900000000-4f5d22828acdcb13d83eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-c5766ace6b2031302336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c8535cbb285cac999590Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9200000000-0f66be3239e5e65d6028Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-6720c563d36a88e31cd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9000000000-f91f5b5177c2d32668fdSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f40d32a5bced4783345aSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral bioavailability is over 75%.
Mechanism of ToxicityThe 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.
MetabolismHepatic. Half Life: 10-28 hours (average is approximately 12 hours)
Toxicity ValuesLD50: 96.8 mg/kg (oral, rat).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed to treat attention deficit hyperactivity disorder (ADHD). Used as a psychostimulant drug. [Wikipedia]
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 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.
TreatmentManagement 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. (11)
Concentrations
Not Available
DrugBank IDDB01576
HMDB IDHMDB0015516
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDextroamphetamine
Chemspider ID5621
ChEBI ID4469
PubChem Compound ID5826
Kegg Compound IDC07884
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Nabenhauer, F.P.; US. Patent 2,276,508; March 17,1942; assigned to Smith, Kline & French
Laboratories.

MSDSNot Available
General References
1. Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10.
2. Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6.
3. Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40.
4. Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68.
5. Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6.
6. Greer CA, Alpern HP: Maturational changes related to dopamine in the effects of d-amphetamine, cocaine, nicotine, and strychnine on seizure susceptibility. Psychopharmacology (Berl). 1979 Sep;64(3):255-60.
7. Lile JA, Stoops WW, Durell TM, Glaser PE, Rush CR: Discriminative-stimulus, self-reported, performance, and cardiovascular effects of atomoxetine in methylphenidate-trained humans. Exp Clin Psychopharmacol. 2006 May;14(2):136-47.
8. Patel JB, Migler B: A sensitive and selective monkey conflict test. Pharmacol Biochem Behav. 1982 Oct;17(4):645-9.
9. Chiueh CC, Moore KE: D-amphetamine-induced release of "newly synthesized" and "stored" dopamine from the caudate nucleus in vivo. J Pharmacol Exp Ther. 1975 Mar;192(3):642-53.
10. Glick SD, Cox RD, Greenstein S: Relationship of rats' spatial preferences to effects of d-amphetamine on timing behavior. Eur J Pharmacol. 1975 Aug;33(1):173-82.
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22129527
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22894820
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23360956
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23851485
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23881044
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23907377
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24349338