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Identification
NameDextroamphetamine
Accession NumberDB01576
TypeSmall Molecule
GroupsApproved, Illicit
Description

Dextroamphetamine is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. It is a slightly polar, weak base and is lipophilic.

Structure
Thumb
Synonyms
(+)-(S)-amphetamine
(+)-alpha-Methylphenethylamine
(+)-alpha-Methylphenylethylamine
(+)-Amphetamine
(AlphaS)-alpha-methylbenzeneethanamine
(S)-(+)-Amphetamine
(S)-(+)-beta-Phenylisopropylamine
(S)-1-Phenyl-2-aminopropane
(S)-1-Phenyl-2-propylamine
(S)-alpha-Methylbenzeneethanamine
(S)-amphetamine
d-amphetamine
Dexamfetamine
dexamphetamine
Dextroamphetamine
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Dextroamphetamine SRcapsule (sustained-release)15 mgoralActavis Pharma CompanyNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Act Dextroamphetamine SRcapsule (sustained-release)10 mgoralActavis Pharma CompanyNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Dexedrine Spansulecapsule, extended release5 mg/1oralAmedra Pharmaceuticals LLC1976-08-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dexedrine Spansulecapsule, extended release15 mg/1oralAmedra Pharmaceuticals LLC1976-08-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dexedrine Spansulecapsule, extended release10 mg/1oralAmedra Pharmaceuticals LLC1976-08-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dexedrine Spansule Src 10mgcapsule (sustained-release)10 mgoralPaladin Labs Inc1992-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Dexedrine Spansule Src 15mgcapsule (sustained-release)15 mgoralPaladin Labs Inc1992-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Dexedrine Tablets (5mg)tablet5 mgoralPaladin Labs Inc1992-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Dextroamphetamine Sulfate Extended-releasecapsule, extended release15 mg/1oralLineage Therapeutics1976-08-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfate Extended-releasecapsule, extended release10 mg/1oralLineage Therapeutics1976-08-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfate Extended-releasecapsule, extended release5 mg/1oralLineage Therapeutics1976-08-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-dextroamphetaminetablet5 mgoralApotex Inc2015-08-28Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Dexedrinetablet10 mg/1oralAmedra Pharmaceuticals LLC2014-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dexedrinetablet5 mg/1oralAmedra Pharmaceuticals LLC2014-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetaminesolution5 mg/5mLoralTris Pharma Inc2013-05-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralMallinckrodt, Inc.2010-02-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet20 mg/1oralMikart, Inc.2011-10-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release10 mg/1oralPhysicians Total Care, Inc.2005-11-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release5 mg/1oralBarr Laboratories Inc.2002-02-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralCore Pharma, Llc2014-05-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet7.5 mg/1oralMikart, Inc.2011-10-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralBarr Laboratories Inc.2001-02-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release15 mg/1oralPhysicians Total Care, Inc.2005-08-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralAurolife Pharma, LLC2012-02-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralCore Pharma, Llc2014-05-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralMikart, Inc.2011-10-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralBarr Laboratories Inc.2001-02-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralWilshire Pharmaceuticals, Inc.2012-07-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralAurolife Pharma, LLC2012-02-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet2.5 mg/1oralMikart, Inc.2011-10-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralWilshire Pharmaceuticals, Inc.2012-07-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralKvk Tech, Inc.2015-11-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release10 mg/1oralAmerican Health Packaging2015-03-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatesolution5 mg/5mLoralMikart, Inc.2008-01-29Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralKvk Tech, Inc.2015-11-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralAmerican Health Packaging2015-03-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release15 mg/1oralActavis Pharma, Inc.2014-06-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release15 mg/1oralBarr Laboratories Inc.2002-02-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralEthex Corporation2009-11-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release10 mg/1oralActavis Pharma, Inc.2014-06-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet15 mg/1oralMikart, Inc.2011-10-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralMallinckrodt, Inc.2010-02-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet30 mg/1oralMikart, Inc.2011-10-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet5 mg/1oralEthex Corporation2009-11-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release5 mg/1oralActavis Pharma, Inc.2014-06-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatecapsule, extended release10 mg/1oralBarr Laboratories Inc.2002-02-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatesolution5 mg/5mLoralTalec Pharma, LLC2014-01-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfatetablet10 mg/1oralMikart, Inc.2011-10-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfate Extended-releasecapsule, extended release15 mg/1oralAmerican Health Packaging2015-06-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfate Extended-releasecapsule, extended release15 mg/1oralMallinckrodt, Inc.2011-10-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfate Extended-releasecapsule, extended release10 mg/1oralMallinckrodt, Inc.2011-10-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Dextroamphetamine Sulfate Extended-releasecapsule, extended release5 mg/1oralMallinckrodt, Inc.2011-10-07Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Procentraliquid5 mg/5mLoralFSC Laboratories, Inc2010-08-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Procentrasolution5 mg/5mLoralIndependence Pharmaceuticals, LLC2014-05-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zenzeditablet5 mg/1oralArbor Pharmaceuticals, Inc.2013-05-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zenzeditablet30 mg/1oralArbor Pharmaceuticals, Inc.2014-05-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zenzeditablet20 mg/1oralArbor Pharmaceuticals, Inc.2014-05-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zenzeditablet15 mg/1oralArbor Pharmaceuticals, Inc.2014-05-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zenzeditablet10 mg/1oralArbor Pharmaceuticals, Inc.2013-05-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zenzeditablet2.5 mg/1oralArbor Pharmaceuticals, Inc.2013-05-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zenzeditablet7.5 mg/1oralArbor Pharmaceuticals, Inc.2013-05-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AttentinMedice
DexamphetamineSigma
Brand mixtures
NameLabellerIngredients
AdderallTeva Select Brands
Adderall XRShire US Manufacturing Inc.
Dextroamphetamine Saccharate and Amphetamine Aspartate and Dextroamphetamine Sulfate and Amphetamine SulfateMallinckrodt, Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate (monohydrate), Dextroamphetamine Sulfate, Amphetamine SulfateMylan Pharmaceuticals Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate Monohydrate, Dextroamphetamine Sulfate and Amphetamine SulfateEon Labs, Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate Monohydrate, Dextroamphetamine Sulfate, Amphetamine SulfateActavis Pharma, Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine SuflateSTAT Rx USA LLC
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine SulfateGlobal Pharmaceuticals, Division of Impax Laboratories Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateBarr Laboratories Inc.
Salts
Name/CASStructureProperties
Dextroamphetamine adipate
ThumbNot applicableDBSALT001324
Dextroamphetamine saccharate
ThumbNot applicableDBSALT001346
Dextroamphetamine sulfate
Thumb
  • InChI Key: SOFQDLYSFOWTJX-QRPNPIFTSA-N
  • Monoisotopic Mass: 233.072178663
  • Average Mass: 233.285
DBSALT000046
Categories
CAS number51-64-9
WeightAverage: 135.2062
Monoisotopic: 135.104799421
Chemical FormulaC9H13N
InChI KeyInChIKey=KWTSXDURSIMDCE-QMMMGPOBSA-N
InChI
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
IUPAC Name
(2S)-1-phenylpropan-2-amine
SMILES
C[C@H](N)CC1=CC=CC=C1
Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed to treat attention deficit hyperactivity disorder (ADHD).
PharmacodynamicsAmphetamines such as dextroamphetamine are noncatecholamine, sympathomimetic amines with CNS stimulant activity. Peripheral actions include elevations of systolic and diastolic blood pressures and weak bronchodilator and respiratory stimulant action. There is neither specific evidence that clearly establishes the mechanism whereby amphetamines produce mental and behavioral effects in children, nor conclusive evidence regarding how these effects relate to the condition of the central nervous system.
Mechanism of actionThe 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.
AbsorptionOral bioavailability is over 75%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half life10-28 hours (average is approximately 12 hours)
ClearanceNot Available
ToxicityIn rats, the oral LD50 of dextroamphetamine sulfate is 96.8 mg/kg. 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.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9972
Blood Brain Barrier+0.9565
Caco-2 permeable+0.8395
P-glycoprotein substrateNon-substrate0.7379
P-glycoprotein inhibitor INon-inhibitor0.9519
P-glycoprotein inhibitor IINon-inhibitor0.9859
Renal organic cation transporterNon-inhibitor0.8002
CYP450 2C9 substrateNon-substrate0.8114
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.795
CYP450 1A2 substrateNon-inhibitor0.5697
CYP450 2C9 inhibitorNon-inhibitor0.9313
CYP450 2D6 inhibitorInhibitor0.657
CYP450 2C19 inhibitorNon-inhibitor0.8445
CYP450 3A4 inhibitorNon-inhibitor0.8709
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8732
Ames testNon AMES toxic0.93
CarcinogenicityNon-carcinogens0.6869
BiodegradationNot ready biodegradable0.6575
Rat acute toxicity3.2491 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9452
hERG inhibition (predictor II)Non-inhibitor0.9231
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsule (sustained-release)oral10 mg
Capsule (sustained-release)oral15 mg
Tabletoral5 mg
Tabletoral
Capsule, extended releaseoral
Tabletoral10 mg/1
Tabletoral5 mg/1
Capsule, extended releaseoral10 mg/1
Capsule, extended releaseoral15 mg/1
Capsule, extended releaseoral5 mg/1
Liquidoral5 mg/5mL
Solutionoral5 mg/5mL
Tabletoral15 mg/1
Tabletoral2.5 mg/1
Tabletoral20 mg/1
Tabletoral30 mg/1
Tabletoral7.5 mg/1
Prices
Unit descriptionCostUnit
D-amphetamine sulfate powder900.0USD g
Desoxyn 5 mg tablet5.1USD tablet
Dexedrine 15 mg 24 Hour Capsule4.22USD capsule
Dextroamphetamine Sulfate CR 15 mg 24 Hour Capsule3.47USD capsule
Dexedrine 10 mg 24 Hour Capsule3.23USD capsule
Dexedrine 5 mg 24 Hour Capsule3.0USD capsule
Dextroamphetamine Sulfate CR 10 mg 24 Hour Capsule2.96USD capsule
Dexedrine spansule 15 mg2.45USD each
Dextroamphetamine Sulfate CR 5 mg 24 Hour Capsule2.06USD capsule
Dexedrine spansule 10 mg1.91USD each
Dexedrine spansule 5 mg1.91USD each
Dexedrine 15 mg Sustained-Release Capsule1.08USD capsule
Dextroamphetamine Sulfate 10 mg tablet0.92USD tablet
Dexedrine 10 mg Sustained-Release Capsule0.89USD capsule
Dextroamphetamine Sulfate 5 mg tablet0.65USD tablet
Dexedrine 5 mg Tablet0.62USD tablet
Dextroamphetamine 10 mg tablet0.56USD tablet
Dextrostat 10 mg tablet0.48USD tablet
Dextroamphetamine 5 mg tablet0.28USD tablet
Dextrostat 5 mg tablet0.25USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point203 °CPhysProp
logP1.76SANGSTER (1994); similar isomer
pKa9.9SANGSTER (1994); similar isomer
Predicted Properties
PropertyValueSource
Water Solubility1.74 mg/mLALOGPS
logP1.85ALOGPS
logP1.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.71 m3·mol-1ChemAxon
Polarizability16.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (6.85 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-z100000000-f40d32a5bced4783345aView in MoNA
References
Synthesis Reference

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

General References
  1. 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. Pubmed
  2. Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. Pubmed
  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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
External Links
ATC CodesN06BA02
AHFS Codes
  • 28:20.04
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Dextroamphetamine.
AcepromazineAcepromazine may decrease the stimulatory activities of Dextroamphetamine.
AcetazolamideAcetazolamide may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Dextroamphetamine.
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AmisulprideAmisulpride may decrease the stimulatory activities of Dextroamphetamine.
AmitriptylineAmitriptyline may increase the stimulatory activities of Dextroamphetamine.
Ammonium chlorideThe serum concentration of Dextroamphetamine can be decreased when it is combined with Ammonium chloride.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with DextroAmphetamine.
AripiprazoleAripiprazole may decrease the stimulatory activities of Dextroamphetamine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Dextroamphetamine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Dextroamphetamine.
BenzquinamideBenzquinamide may decrease the stimulatory activities of Dextroamphetamine.
BrompheniramineDextroamphetamine may decrease the sedative activities of Brompheniramine.
Calcium AcetateCalcium Acetate may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Calcium carbonateCalcium carbonate may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
CarphenazineCarphenazine may decrease the stimulatory activities of Dextroamphetamine.
ChlormezanoneChlormezanone may decrease the stimulatory activities of Dextroamphetamine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Dextroamphetamine.
ChlorpromazineChlorpromazine may decrease the stimulatory activities of Dextroamphetamine.
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of Dextroamphetamine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dextroamphetamine.
ClozapineClozapine may decrease the stimulatory activities of Dextroamphetamine.
DiclofenamideDiclofenamide may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Dextroamphetamine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Dextroamphetamine.
DoxofyllineThe risk or severity of adverse effects can be increased when Dextroamphetamine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Dextroamphetamine.
DroperidolDroperidol may decrease the stimulatory activities of Dextroamphetamine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Dextroamphetamine.
EsomeprazoleEsomeprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with Dextroamphetamine.
EthoxzolamideEthoxzolamide may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
FencamfamineFencamfamine may decrease the stimulatory activities of Dextroamphetamine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Dextroamphetamine.
FlupentixolFlupentixol may decrease the stimulatory activities of Dextroamphetamine.
FluphenazineFluphenazine may decrease the stimulatory activities of Dextroamphetamine.
FluspirileneFluspirilene may decrease the stimulatory activities of Dextroamphetamine.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Dextroamphetamine.
HaloperidolHaloperidol may decrease the stimulatory activities of Dextroamphetamine.
HexamethylenetetramineThe serum concentration of Dextroamphetamine can be decreased when it is combined with Hexamethylenetetramine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dextroamphetamine.
Ioflupane I 123Dextroamphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Dextroamphetamine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Dextroamphetamine.
LansoprazoleLansoprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
LinezolidLinezolid may increase the hypertensive activities of Dextroamphetamine.
LithiumLithium may decrease the stimulatory activities of Dextroamphetamine.
LoxapineLoxapine may decrease the stimulatory activities of Dextroamphetamine.
Magnesium oxideMagnesium oxide may decrease the excretion rate of Dextroamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dextroamphetamine.
MesoridazineMesoridazine may decrease the stimulatory activities of Dextroamphetamine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dextroamphetamine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Dextroamphetamine.
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of Dextroamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dextroamphetamine.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Dextroamphetamine.
MolindoneMolindone may decrease the stimulatory activities of Dextroamphetamine.
MorphineDextroamphetamine may increase the analgesic activities of Morphine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Dextroamphetamine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Dextroamphetamine.
OlanzapineOlanzapine may decrease the stimulatory activities of Dextroamphetamine.
OmeprazoleOmeprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
OndansetronOndansetron may decrease the stimulatory activities of Dextroamphetamine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Dextroamphetamine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Dextroamphetamine.
PaliperidonePaliperidone may decrease the stimulatory activities of Dextroamphetamine.
PantoprazolePantoprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
PerphenazinePerphenazine may decrease the stimulatory activities of Dextroamphetamine.
PhenelzinePhenelzine may increase the hypertensive activities of Dextroamphetamine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Dextroamphetamine.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Dextroamphetamine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Dextroamphetamine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Dextroamphetamine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Dextroamphetamine.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Dextroamphetamine.
PimozidePimozide may decrease the stimulatory activities of Dextroamphetamine.
PiperacetazinePiperacetazine may decrease the stimulatory activities of Dextroamphetamine.
ProchlorperazineProchlorperazine may decrease the stimulatory activities of Dextroamphetamine.
PromazinePromazine may decrease the stimulatory activities of Dextroamphetamine.
QuetiapineQuetiapine may decrease the stimulatory activities of Dextroamphetamine.
RabeprazoleRabeprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
RemoxiprideRemoxipride may decrease the stimulatory activities of Dextroamphetamine.
ReserpineReserpine may decrease the stimulatory activities of Dextroamphetamine.
RisperidoneRisperidone may decrease the stimulatory activities of Dextroamphetamine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Dextroamphetamine.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Dextroamphetamine.
SertindoleSertindole may decrease the stimulatory activities of Dextroamphetamine.
SulpirideSulpiride may decrease the stimulatory activities of Dextroamphetamine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Dextroamphetamine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Dextroamphetamine.
ThioridazineThioridazine may decrease the stimulatory activities of Dextroamphetamine.
ThiothixeneThiothixene may decrease the stimulatory activities of Dextroamphetamine.
TranylcypromineTranylcypromine may increase the hypertensive activities of Dextroamphetamine.
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of Dextroamphetamine.
TriflupromazineTriflupromazine may decrease the stimulatory activities of Dextroamphetamine.
Vitamin CThe serum concentration of Dextroamphetamine can be decreased when it is combined with Vitamin C.
ZiprasidoneZiprasidone may decrease the stimulatory activities of Dextroamphetamine.
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of Dextroamphetamine.
Food InteractionsNot Available

Targets

1. Synaptic vesicular amine transporter

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
Synaptic vesicular amine transporter Q05940 Details

References:

  1. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. Pubmed
  2. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed

2. Sodium-dependent noradrenaline transporter

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: negative modulator

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Dlugos A, Freitag C, Hohoff C, McDonald J, Cook EH, Deckert J, de Wit H: Norepinephrine transporter gene variation modulates acute response to D-amphetamine. Biol Psychiatry. 2007 Jun 1;61(11):1296-305. Epub 2007 Jan 17. Pubmed
  2. Dlugos AM, Hamidovic A, Palmer AA, de Wit H: Further evidence of association between amphetamine response and SLC6A2 gene variants. Psychopharmacology (Berl). 2009 Oct;206(3):501-11. Pubmed
  3. Burnette WB, Bailey MD, Kukoyi S, Blakely RD, Trowbridge CG, Justice JB Jr: Human norepinephrine transporter kinetics using rotating disk electrode voltammetry. Anal Chem. 1996 Sep 1;68(17):2932-8. Pubmed

3. Sodium-dependent dopamine transporter

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: negative modulator

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. Zhen J, Chen N, Reith ME: Differences in interactions with the dopamine transporter as revealed by diminishment of Na(+) gradient and membrane potential: dopamine versus other substrates. Neuropharmacology. 2005 Nov;49(6):769-79. Epub 2005 Aug 24. Pubmed
  2. Kuczenski R, Segal DS, Cho AK, Melega W: Hippocampus norepinephrine, caudate dopamine and serotonin, and behavioral responses to the stereoisomers of amphetamine and methamphetamine. J Neurosci. 1995 Feb;15(2):1308-17. Pubmed
  3. Rothman RB, Dersch CM, Ananthan S, Partilla JS: Studies of the biogenic amine transporters. 13. Identification of “agonist” and “antagonist” allosteric modulators of amphetamine-induced dopamine release. J Pharmacol Exp Ther. 2009 May;329(2):718-28. Epub 2009 Feb 24. Pubmed

4. Trace amine-associated receptor 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Trace amine-associated receptor 1 Q96RJ0 Details

References:

  1. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. Pubmed
  2. Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. Pubmed
  3. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. Pubmed
  4. Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. Pubmed
  5. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. Pubmed

5. Alpha-1A adrenergic receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

6. Alpha-1B adrenergic receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 2D6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on August 29, 2007 08:50 / Updated on November 27, 2015 13:13