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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
SynonymLanguageCode
(+)-(S)-amphetamineNot AvailableNot Available
(S)-amphetamineNot AvailableNot Available
d-amphetamineNot AvailableNot Available
dexamphetamineNot AvailableNot Available
DextroamphetamineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Dextroamphetamine sulfate
Thumb
  • InChI Key: SOFQDLYSFOWTJX-QRPNPIFTSA-N
  • Monoisotopic Mass: 233.072178663
  • Average Mass: 233.285
DBSALT000046
Brand names
NameCompany
AttentinMedice
DexamphetamineSigma
DexedrineCorePharma
ProCentraNot Available
ZenzediNot Available
Brand mixtures
Brand NameIngredients
Adderall XRAmphetamine Aspartate Monohydrate + Amphetamine Sulfate + Dextroamphetamine Saccharate + Dextroamphetamine Sulfate
Categories
CAS number51-64-9
WeightAverage: 135.2062
Monoisotopic: 135.104799421
Chemical FormulaC9H13N
InChI KeyKWTSXDURSIMDCE-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
Mass Specshow(6.85 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsPolyamines; Monoalkylamines
Substituentspolyamine; primary amine; primary aliphatic amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
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
Property Value Probability
Human Intestinal Absorption + 0.9972
Blood Brain Barrier + 0.9565
Caco-2 permeable + 0.8395
P-glycoprotein substrate Non-substrate 0.7379
P-glycoprotein inhibitor I Non-inhibitor 0.9519
P-glycoprotein inhibitor II Non-inhibitor 0.9859
Renal organic cation transporter Non-inhibitor 0.8002
CYP450 2C9 substrate Non-substrate 0.8114
CYP450 2D6 substrate Substrate 0.8919
CYP450 3A4 substrate Non-substrate 0.795
CYP450 1A2 substrate Non-inhibitor 0.5697
CYP450 2C9 substrate Non-inhibitor 0.9313
CYP450 2D6 substrate Inhibitor 0.657
CYP450 2C19 substrate Non-inhibitor 0.8445
CYP450 3A4 substrate Non-inhibitor 0.8709
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8732
Ames test Non AMES toxic 0.93
Carcinogenicity Non-carcinogens 0.6869
Biodegradation Not ready biodegradable 0.6575
Rat acute toxicity 3.2491 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9452
hERG inhibition (predictor II) Non-inhibitor 0.9231
Pharmacoeconomics
Manufacturers
  • Smithkline beecham corp dba glaxosmithkline
  • Able laboratories inc
  • Barr laboratories inc
  • Mallinckrodt inc
  • Teva pharmaceuticals usa inc
  • Glaxosmithkline
  • Outlook pharmaceuticals inc
  • Endo pharmaceuticals inc
  • Halsey drug co inc
  • Kv pharmaceutical co
  • Lannett co inc
  • Mm mast and co
  • Purepac pharmaceutical co
  • Sandoz inc
  • Vitarine pharmaceuticals inc
  • Shire development inc
  • Ferndale laboratories inc
Packagers
Dosage forms
FormRouteStrength
Capsule, extended releaseOral
TabletOral
Prices
Unit descriptionCostUnit
D-amphetamine sulfate powder900.0USDg
Desoxyn 5 mg tablet5.1USDtablet
Dexedrine 15 mg 24 Hour Capsule4.22USDcapsule
Dextroamphetamine Sulfate CR 15 mg 24 Hour Capsule3.47USDcapsule
Dexedrine 10 mg 24 Hour Capsule3.23USDcapsule
Dexedrine 5 mg 24 Hour Capsule3.0USDcapsule
Dextroamphetamine Sulfate CR 10 mg 24 Hour Capsule2.96USDcapsule
Dexedrine spansule 15 mg2.45USDeach
Dextroamphetamine Sulfate CR 5 mg 24 Hour Capsule2.06USDcapsule
Dexedrine spansule 10 mg1.91USDeach
Dexedrine spansule 5 mg1.91USDeach
Dexedrine 15 mg Sustained-Release Capsule1.08USDcapsule
Dextroamphetamine Sulfate 10 mg tablet0.92USDtablet
Dexedrine 10 mg Sustained-Release Capsule0.89USDcapsule
Dextroamphetamine Sulfate 5 mg tablet0.65USDtablet
Dexedrine 5 mg Tablet0.62USDtablet
Dextroamphetamine 10 mg tablet0.56USDtablet
Dextrostat 10 mg tablet0.48USDtablet
Dextroamphetamine 5 mg tablet0.28USDtablet
Dextrostat 5 mg tablet0.25USDtablet
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 solubility1.74e+00 g/lALOGPS
logP1.85ALOGPS
logP1.8ChemAxon
logS-1.9ALOGPS
pKa (strongest basic)10.01ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area26.02ChemAxon
rotatable bond count2ChemAxon
refractivity43.71ChemAxon
polarizability16.08ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

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

General Reference
  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
ResourceLink
KEGG DrugD03740
KEGG CompoundC07884
PubChem Compound5826
PubChem Substance46506252
ChemSpider5621
ChEBI4469
ChEMBLCHEMBL612
Therapeutic Targets DatabaseDAP001470
PharmGKBPA449269
IUPHAR2147
Guide to Pharmacology2147
Drug Product Database1924516
RxListhttp://www.rxlist.com/cgi/generic/dextroamphetamine.htm
Drugs.comhttp://www.drugs.com/cdi/dextroamphetamine.html
WikipediaDextroamphetamine
ATC CodesN06BA02
AHFS Codes
  • 28:20.04
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ChlorpromazineDecreased anorexic effect, may increases psychotic symptoms
FluoxetineRisk of serotoninergic syndrome
FluphenazineDecreased anorexic effect, may increase psychotic symptoms
FluvoxamineRisk of serotoninergic syndrome
GuanethidineDextroamphetamine may decrease the effect of guanethidine.
IsocarboxazidPossible hypertensive crisis
MesoridazineDecreased anorexic effect, may increase psychotic symptoms
MethotrimeprazineDecreased anorexic effect, may increase psychotic symptoms
ParoxetineRisk of serotoninergic syndrome
PerphenazineDecreased anorexic effect, may increase psychotic symptoms
PhenelzinePossible hypertensive crisis
ProchlorperazineDecreased anorexic effect, may increase pyschotic symptoms
PromethazineDecreased anorexic effect, may increase pyschotic symptoms
PropericiazineDecreased anorexic effect, may increase pyschotic symptoms
RasagilinePossible hypertensive crisis
ThioridazineDecreased anorexic effect, may increase psychotic symptoms
TramadolIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
TrandolaprilDextroamphetamine may reduce the efficacy of Trandolapril.
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Dextroamphetamine. Concomitant therapy should be avoided.
TrifluoperazineDecreased anorexic effect, may increase psychotic symptoms
TriprolidineTriprolidine may reduce the sedative effect of the antihistamine, 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 April 10, 2014 14:08