Identification

Name
Dextroamphetamine
Accession Number
DB01576
Description

Dextroamphetamine is the dextrorotary enantiomer of amphetamine5. Dextroamphetamine was approved by the FDA in 2001 for the treatment of attention deficit hyperactivity disorder6,Label.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Thumb
Weight
Average: 135.2062
Monoisotopic: 135.104799421
Chemical Formula
C9H13N
Synonyms
  • (+)-(S)-amphetamine
  • (+)-amphetamine
  • (+)-α-methylphenethylamine
  • (+)-α-methylphenylethylamine
  • (S)-(+)-amphetamine
  • (S)-(+)-β-phenylisopropylamine
  • (S)-1-phenyl-2-aminopropane
  • (S)-1-phenyl-2-propylamine
  • (S)-amphetamine
  • (S)-α-methylbenzeneethanamine
  • (αS)-α-methylbenzeneethanamine
  • d-amphetamine
  • Desamfetamina
  • Dexamfetamina
  • Dexamfetamine
  • Dexamfetaminum
  • Dexamphetamine
  • Dexanfetamina
  • Dextroamphetamine
External IDs
  • NSC-73713

Pharmacology

Indication

Dextroamphetamine is indicated for the treatment of attention deficit hyperactivity disorder (ADHD)Label.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Dextroamphetamine is a noncatecholamine, sympathomimetic amine that acts as a CNS stimulantLabel. Dextroamphetamine raises systolic and diastolic blood pressure, acts as a weak bronchodilator, and also acts as a respiratory stimulantLabel. The general mechanism of action of dextroamphetamine has not been well establishedLabel.

Mechanism of action

The exact mechanism of amphetamines as a class is not known. Dextroamphetamine acts by preventing reuptake, increasing release, and stimulating reverse-transport of dopamine in synaptic clefts in the striatum4. Newer evidence shows amphetamines may also alter the number of dopamine transporters in synaptic clefts2.

TargetActionsOrganism
ASynaptic vesicular amine transporter
inducer
Humans
ASodium-dependent noradrenaline transporter
negative modulator
Humans
ASodium-dependent dopamine transporter
negative modulator
Humans
UTrace amine-associated receptor 1
agonist
Humans
UAlpha-1B adrenergic receptor
antagonist
Humans
UAlpha adrenergic receptor
inhibitor
inducer
Humans
Absorption

Bioavailability data of dextroamphetamine is not readily available, however there is no difference in bioavailability when taken with or without a mealLabel.

Volume of distribution

195L3.

Protein binding
Not Available
Metabolism

Dextroamphetamine is metabolized by cytochrome P-450 2D6 in the liver to 4-hydroxyamphetamine and later conjugated by sulfotransferase or glucoronyltransferase1.

Hover over products below to view reaction partners

Route of elimination

A third of the drug is eliminated renally5.

Half-life

11.75 hoursLabel. In a study of post-stroke patients the half life was 16.0 hours in females and 12.4 hours in males5. Studies in healthy populations show a half life of 7.9 hours3.

Clearance

17L/h3.

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Dexrtoamphetamine has been shown to be teratogenic and embryotoxic in mice at 41 times the maximum human doseLabel. These effects were not seen in rat or rabbit studies, and the effects on human pregnancy have not been studiedLabel. The risk and benefit of use during pregnancy should be weighed as bone deformities, tracheoesophageal fistula, anal atresia, low birthweight, and withdrawl have been reported in the children of mothers who were taking dextroamphetamine during pregnancyLabel. Mothers should not take amphetamines while nursing as the drug is excreted in breast milkLabel. Long term effects of dextroamphetamine have not bee determined in pediatric patients and dextroamphetamine should be avoided in children under 3 yearsLabel.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Dextroamphetamine is combined with Abaloparatide.
AbataceptThe metabolism of Dextroamphetamine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Dextroamphetamine can be decreased when combined with Abiraterone.
AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with Dextroamphetamine.
AceclofenacThe risk or severity of hypertension can be increased when Dextroamphetamine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Dextroamphetamine is combined with Acemetacin.
AcetaminophenThe metabolism of Dextroamphetamine can be decreased when combined with Acetaminophen.
AcetazolamideAcetazolamide may decrease the excretion rate of Dextroamphetamine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Dextroamphetamine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Dextroamphetamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid fruit juice. Fruit juice may acidify the gastrointestinal tract, decreasing absorption of amphetamines.

Products

Product Ingredients
IngredientUNIICASInChI Key
Dextroamphetamine adipateYYI1A8W4TQ64770-52-1OFCJKOOVFDGTLY-QRPNPIFTSA-N
Dextroamphetamine saccharateG83415V073350708-40-6CXFNVDBOUVJOQO-OUDZKKFGSA-N
Dextroamphetamine sulfateJJ768O327N51-63-8SOFQDLYSFOWTJX-QRPNPIFTSA-N
Product Images
International/Other Brands
Attentin (Medice) / Dexamphetamine (Sigma)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRCapsule, extended releaseOralTeva2015-10-02Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Apo-amphetamine XRCapsule, extended releaseOralApotex CorporationNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AdderallDextroamphetamine saccharate (7.5 mg/1) + Dextroamphetamine sulfate (7.5 mg/1) + Amphetamine aspartate (7.5 mg/1) + Amphetamine sulfate (7.5 mg/1)TabletOralPhysicians Total Care, Inc.2005-11-152011-07-31Us
AdderallDextroamphetamine saccharate (5 mg/1) + Dextroamphetamine sulfate (5 mg/1) + Amphetamine aspartate monohydrate (5 mg/1) + Amphetamine sulfate (5 mg/1)TabletOralTeva Pharmaceuticals USA, Inc.2014-02-11Not applicableUs
AdderallDextroamphetamine saccharate (1.25 mg/1) + Dextroamphetamine sulfate (1.25 mg/1) + Amphetamine aspartate (1.25 mg/1) + Amphetamine sulfate (1.25 mg/1)TabletOralPhysicians Total Care, Inc.1997-10-022011-07-31Us
AdderallDextroamphetamine saccharate (5 mg/1) + Dextroamphetamine sulfate (5 mg/1) + Amphetamine aspartate (5 mg/1) + Amphetamine sulfate (5 mg/1)TabletOralPhysicians Total Care, Inc.2005-08-012011-07-31Us
AdderallDextroamphetamine saccharate (1.875 mg/1) + Dextroamphetamine sulfate (1.875 mg/1) + Amphetamine aspartate monohydrate (1.875 mg/1) + Amphetamine sulfate (1.875 mg/1)TabletOralShire1996-02-132006-09-29Us
AdderallDextroamphetamine saccharate (2.5 mg/1) + Dextroamphetamine sulfate (2.5 mg/1) + Amphetamine aspartate monohydrate (2.5 mg/1) + Amphetamine sulfate (2.5 mg/1)TabletOralShire1996-02-132006-09-29Us
AdderallDextroamphetamine saccharate (5 mg/1) + Dextroamphetamine sulfate (5 mg/1) + Amphetamine aspartate monohydrate (5 mg/1) + Amphetamine sulfate (5 mg/1)TabletOralShire1996-02-132006-09-29Us
AdderallDextroamphetamine saccharate (3.75 mg/1) + Dextroamphetamine sulfate (3.75 mg/1) + Amphetamine aspartate monohydrate (3.75 mg/1) + Amphetamine sulfate (3.75 mg/1)TabletOralShire1996-02-132006-09-29Us
AdderallDextroamphetamine saccharate (1.25 mg/1) + Dextroamphetamine sulfate (1.25 mg/1) + Amphetamine aspartate monohydrate (1.25 mg/1) + Amphetamine sulfate (1.25 mg/1)TabletOralBarr Laboratories2008-08-112015-08-31Us0555 076220180907 15195 k2osd6
AdderallDextroamphetamine saccharate (1.875 mg/1) + Dextroamphetamine sulfate (1.875 mg/1) + Amphetamine aspartate monohydrate (1.875 mg/1) + Amphetamine sulfate (1.875 mg/1)TabletOralBarr Laboratories2008-08-112015-07-31Us0555 076320180907 15195 cc4t4y

Categories

ATC Codes
N06BA02 — Dexamfetamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Aralkylamines / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropane / Primary aliphatic amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
amphetamine (CHEBI:4469)

Chemical Identifiers

UNII
TZ47U051FI
CAS number
51-64-9
InChI Key
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

References

Synthesis Reference

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

General References
  1. de la Torre R, Farre M, Navarro M, Pacifici R, Zuccaro P, Pichini S: Clinical pharmacokinetics of amfetamine and related substances: monitoring in conventional and non-conventional matrices. Clin Pharmacokinet. 2004;43(3):157-85. doi: 10.2165/00003088-200443030-00002. [PubMed:14871155]
  2. Saunders C, Galli A: Insights in how amphetamine ROCKs (Rho-associated containing kinase) membrane protein trafficking. Proc Natl Acad Sci U S A. 2015 Dec 22;112(51):15538-9. doi: 10.1073/pnas.1520960112. Epub 2015 Nov 25. [PubMed:26607447]
  3. Dolder PC, Strajhar P, Vizeli P, Hammann F, Odermatt A, Liechti ME: Pharmacokinetics and Pharmacodynamics of Lisdexamfetamine Compared with D-Amphetamine in Healthy Subjects. Front Pharmacol. 2017 Sep 7;8:617. doi: 10.3389/fphar.2017.00617. eCollection 2017. [PubMed:28936175]
  4. Calipari ES, Ferris MJ: Amphetamine mechanisms and actions at the dopamine terminal revisited. J Neurosci. 2013 May 22;33(21):8923-5. doi: 10.1523/JNEUROSCI.1033-13.2013. [PubMed:23699503]
  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. [PubMed:14520168]
  6. FDA Drug Approval Package for Dextroamphetamine [Link]
  7. FDA Approved Drug Products: Adderall (dextroamphetamine) capsule [Link]
Human Metabolome Database
HMDB0015516
KEGG Drug
D03740
KEGG Compound
C07884
PubChem Compound
5826
PubChem Substance
46506252
ChemSpider
5621
BindingDB
50022723
RxNav
3288
ChEBI
4469
ChEMBL
CHEMBL612
ZINC
ZINC000006021033
Therapeutic Targets Database
DAP001470
PharmGKB
PA449269
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
1WE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dextroamphetamine
AHFS Codes
  • 28:20.04 — Amphetamines
PDB Entries
4lar / 4xp9
FDA label
Download (97.5 KB)
MSDS
Download (145 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceAttention Deficit Disorder With Hyperactivity / Oppositional Defiant Disorder / Substance Abuse1
4CompletedHealth Services ResearchExpectancy Versus Pharmacotherapy Effect of Adderall1
4CompletedTreatmentAlzheimer's Disease (AD) / Dementias1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity / Oppositional Defiant Disorder1
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD)1
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Attention Deficit/Hyperactivity Disorder2
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Attention Deficit/Hyperactivity Disorder / Deficient Emotional Self-Regulation (DESR)1
4CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Attention Deficit/Hyperactivity Disorder / Reading Disability1
4CompletedTreatmentMajor Depressive Disorder (MDD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Abbott Laboratories Ltd.
  • Actavis Group
  • Auriga Pharmaceuticals LLC
  • Barr Pharmaceuticals
  • Bryant Ranch Prepack
  • Cardinal Health
  • Catalent Pharma Solutions
  • Corepharma LLC
  • D.M. Graham Laboratories Inc.
  • Dispensing Solutions
  • DSM Corp.
  • Eon Labs
  • Ethex Corp.
  • GlaxoSmithKline Inc.
  • Global Pharmaceuticals
  • Lundbeck Inc.
  • Mallinckrodt Inc.
  • Mikart Inc.
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Professional Co.
  • Ranbaxy Laboratories
  • Shire Inc.
  • Stat Rx Usa
  • Tiber Pharmaceuticals LLC
Dosage Forms
FormRouteStrength
Capsule, extended releaseOral1.25 mg
Capsule, extended releaseOral2.5 mg
Capsule, extended releaseOral3.75 mg
Capsule, extended releaseOral5.00 mg
Capsule, extended releaseOral6.25 mg
Capsule, extended releaseOral7.5 mg
Capsule, extended releaseOral
Capsule, extended releaseOral10 mg/1
Capsule, extended releaseOral15 mg/1
Capsule, extended releaseOral5 mg/1
TabletOral5 mg/1
TabletOral
TabletOral5 mg
CapsuleOral
Capsule, extended releaseOral
TabletOral
SolutionOral5 mg/5mL
TabletOral10 mg/1
LiquidOral5 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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6384020Yes2002-05-072021-01-06Us
USRE42096Yes2011-02-012019-04-21Us
US6605300Yes2003-08-122019-04-21Us
US6322819Yes2001-11-272019-04-21Us
USRE41148Yes2010-02-232019-04-21Us
US9173857No2015-11-032026-05-12Us
US6913768No2005-07-052023-05-24Us
US8846100No2014-09-302029-08-24Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-98[MSDS]
boiling point (°C)64.7[MSDS]
water solubilityModerately Soluble[MSDS]
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (6.85 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-9000000000-f40d32a5bced4783345a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
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:7751968]
  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:15955613]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Negative modulator
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
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:17239355]
  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. doi: 10.1007/s00213-009-1628-y. [PubMed:19727679]
  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:8794928]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Negative modulator
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
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:16122767]
  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:7869099]
  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. doi: 10.1124/jpet.108.149088. Epub 2009 Feb 24. [PubMed:19244097]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Trace-amine receptor activity
Specific Function
Receptor for trace amines, including beta-phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amin...
Gene Name
TAAR1
Uniprot ID
Q96RJ0
Uniprot Name
Trace amine-associated receptor 1
Molecular Weight
39091.34 Da
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:17218486]
  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:17234900]
  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:17212650]
  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:17234899]
  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:15764732]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
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:17139284]
  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:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
Curator comments
There are limited data in the literature to support this target action. Adrenergic receptors are possible targets for dextroamphetamine based on indirect evidence.
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Nakamura S, Tepper JM, Young SJ, Groves PM: Changes in noradrenergic terminal excitability induced by amphetamine and their relation to impulse traffic. Neuroscience. 1982;7(9):2217-24. doi: 10.1016/0306-4522(82)90132-4. [PubMed:6292781]
  2. Shekim WO, Bylund DB, Hodges K, Glaser R, Ray-Prenger C, Oetting G: Platelet alpha 2-adrenergic receptor binding and the effects of d-amphetamine in boys with attention deficit hyperactivity disorder. Neuropsychobiology. 1994;29(3):120-4. doi: 10.1159/000119074. [PubMed:8022532]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
No
Actions
Substrate
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
The enzyme prefers aromatic over aliphatic amines.
Gene Name
tynA
Uniprot ID
P46883
Uniprot Name
Primary amine oxidase
Molecular Weight
84378.17 Da
References
  1. Kumar K, Dhoke GV, Sharma AK, Jaiswal SK, Sharma VK: Mechanistic elucidation of amphetamine metabolism by tyramine oxidase from human gut microbiota using molecular dynamics simulations. J Cell Biochem. 2019 Jan 30. doi: 10.1002/jcb.28396. [PubMed:30701587]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Saunders C, Galli A: Insights in how amphetamine ROCKs (Rho-associated containing kinase) membrane protein trafficking. Proc Natl Acad Sci U S A. 2015 Dec 22;112(51):15538-9. doi: 10.1073/pnas.1520960112. Epub 2015 Nov 25. [PubMed:26607447]

Drug created on August 29, 2007 08:50 / Updated on August 02, 2020 22:18

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