NAV

Dextroamphetamine

Identification

Summary

Dextroamphetamineis a sympathomimetic agent used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.

Brand Names
Adderall, Dexedrine, Mydayis, Procentra, Xelstrym, Zenzedi
Generic Name
Dextroamphetamine
DrugBank Accession Number
DB01576
Background

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
 3D
Similar Structures
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

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Associated Conditions
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Pharmacodynamics

Dextroamphetamine is a noncatecholamine, sympathomimetic amine that acts as a CNS stimulant.LabelDextroamphetamine raises systolic and diastolic blood pressure, acts as a weak bronchodilator, and also acts as a respiratory stimulant.LabelThe general mechanism of action of dextroamphetamine has not been well established.Label

Mechanism of action

安非他命的确切机制作为一个类not known. Dextroamphetamine acts by preventing reuptake, increasing release, and stimulating reverse-transport of dopamine in synaptic clefts in the striatum.4Newer evidence shows amphetamines may also alter the number of dopamine transporters in synaptic clefts.2

Target Actions Organism
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肾上腺素的衰退ptor
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 meal.Label

Volume of distribution

195L.3

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 glucoronyltransferase.1

Hover over products below to view reaction partners

Route of elimination

A third of the drug is eliminated renally.5

Half-life

11.75 hours.LabelIn a study of post-stroke patients the half life was 16.0 hours in females and 12.4 hours in males.5Studies in healthy populations show a half life of 7.9 hours.3

Clearance

17L/h.3

Adverse Effects
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Toxicity

Dextroamphetamine has been shown to be teratogenic and embryotoxic in mice at 41 times the maximum human dose.LabelThese effects were not seen in rat or rabbit studies, and the effects on human pregnancy have not been studied.LabelThe 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 pregnancy.LabelMothers should not take amphetamines while nursing as the drug is excreted in breast milk.LabelLong term effects of dextroamphetamine have not bee determined in pediatric patients and dextroamphetamine should be avoided in children under 3 years.Label

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
Drug Interaction
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Abatacept The metabolism of Dextroamphetamine can be increased when combined with Abatacept.
Abiraterone The metabolism of Dextroamphetamine can be decreased when combined with Abiraterone.
Acebutolol The therapeutic efficacy of Acebutolol can be decreased when used in combination with Dextroamphetamine.
Aceclofenac The risk or severity of hypertension can be increased when Dextroamphetamine is combined with Aceclofenac.
Acemetacin The risk or severity of hypertension can be increased when Dextroamphetamine is combined with Acemetacin.
Acetaminophen The metabolism of Dextroamphetamine can be decreased when combined with Acetaminophen.
Acetazolamide Acetazolamide may decrease the excretion rate of Dextroamphetamine which could result in a higher serum level.
Acetophenazine Acetophenazine may decrease the stimulatory activities of Dextroamphetamine.
Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Dextroamphetamine.
Aclidinium The risk or severity of Tachycardia can be increased when Dextroamphetamine is combined with Aclidinium.
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Food Interactions
  • Avoid fruit juice. Fruit juice may acidify the gastrointestinal tract, decreasing absorption of amphetamines.

Products

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Product Ingredients
Ingredient UNII CAS InChI Key
Dextroamphetamine adipate YYI1A8W4TQ 64770-52-1 OFCJKOOVFDGTLY-QRPNPIFTSA-N
Dextroamphetamine saccharate G83415V073 350708-40-6 CXFNVDBOUVJOQO-OUDZKKFGSA-N
Dextroamphetamine sulfate JJ768O327N 51-63-8 SOFQDLYSFOWTJX-QRPNPIFTSA-N
Product Images
International/Other Brands
Attentin (Medice)/Dexamphetamine (Sigma)
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Act Dextroamphetamine SR Capsule, extended release 15 mg Oral TEVA Canada Limited 2017-10-06 Not applicable Canada flag
Act Dextroamphetamine SR Capsule, extended release 10 mg Oral TEVA Canada Limited 2017-10-06 Not applicable Canada flag
Adderall XR Capsule, extended release 6.25 mg Oral Takeda 2004-01-30 Not applicable Canada flag
Adderall XR Capsule, extended release 6.25 mg Oral Takeda 2004-01-30 Not applicable Canada flag
Dexedrine Capsule, extended release 5 mg/1 Oral Glaxosmithkline Inc 2007-11-14 2012-05-31 US flag
Dexedrine Capsule, extended release 15 mg/1 Oral Glaxosmithkline Inc 2007-10-05 2013-01-31 US flag
Dexedrine Tablet 5 mg/1 Oral GlaxoSmithKline 2007-04-10 Not applicable US flag
Dexedrine Capsule, extended release 10 mg/1 Oral Glaxosmithkline Inc 2007-10-05 2013-01-31 US flag
Dexedrine Spansule Capsule, extended release 15 mg/1 Oral Amedra Pharmaceuticals LLC 1976-08-02 2019-12-01 US flag
DEXEDRINE Spansule Capsule, extended release 5 mg/1 Oral Physicians Total Care, Inc. 2007-11-14 2011-06-30 US flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Apo-dextroamphetamine SR Capsule, extended release 15 mg Oral Apotex Corporation Not applicable Not applicable Canada flag
Apo-dextroamphetamine SR Capsule, extended release 10 mg Oral Apotex Corporation Not applicable Not applicable Canada flag
Dexedrine Tablet 10 mg/1 Oral Amedra Pharmaceuticals LLC 2014-07-01 2016-09-30 US flag
Dexedrine Tablet 5 mg/1 Oral Physicians Total Care, Inc. 2004-12-16 2011-05-31 US flag
Dexedrine Tablet 5 mg/1 Oral Amedra Pharmaceuticals LLC 2014-07-01 2016-09-30 US flag
Dextroamphetamine Solution 5 mg/5mL Oral Tris Pharma Inc 2013-05-31 Not applicable US flag
硫酸右旋安非他命 Tablet 5 mg/1 Oral Wilshire Pharmaceuticals, Inc. 2012-07-16 Not applicable US flag
硫酸右旋安非他命 Capsule, extended release 15 mg/1 Oral Mayne Pharma Inc. 2016-08-05 2024-02-29 US flag
硫酸右旋安非他命 Tablet 5 mg/1 Oral bryant ranch prepack 2018-07-04 Not applicable US flag
硫酸右旋安非他命 Tablet 5 mg/1 Oral Core Pharma, Llc 2014-05-15 2016-09-30 US flag
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Adderall Dextroamphetamine saccharate(5 mg/1)+Dextroamphetamine sulfate(5 mg/1)+Amphetamine aspartate(5 mg/1)+Amphetamine sulfate(5 mg/1) Tablet Oral bryant ranch prepack 1996-02-13 Not applicable US flag
Adderall Dextroamphetamine saccharate(5 mg/1)+Dextroamphetamine sulfate(5 mg/1)+Amphetamine aspartate(5 mg/1)+Amphetamine sulfate(5 mg/1) Tablet Oral bryant ranch prepack 1996-02-13 Not applicable US flag
Adderall Dextroamphetamine saccharate(2.5 mg/1)+Dextroamphetamine sulfate(2.5 mg/1)+Amphetamine aspartate(2.5 mg/1)+Amphetamine sulfate(2.5 mg/1) Tablet Oral bryant ranch prepack 1996-02-13 Not applicable US flag
Adderall Dextroamphetamine saccharate(2.5 mg/1)+Dextroamphetamine sulfate(2.5 mg/1)+Amphetamine aspartate(2.5 mg/1)+Amphetamine sulfate(2.5 mg/1) Tablet Oral bryant ranch prepack 1996-02-13 Not applicable US flag
Adderall Dextroamphetamine saccharate(1.25 mg/1)+Dextroamphetamine sulfate(1.25 mg/1)+Amphetamine aspartate(1.25 mg/1)+Amphetamine sulfate(1.25 mg/1) Tablet Oral Physicians Total Care, Inc. 1997-10-02 2011-07-31 US flag
Adderall Dextroamphetamine saccharate(1.25 mg/1)+Dextroamphetamine sulfate(1.25 mg/1)+Amphetamine aspartate(1.25 mg/1)+Amphetamine sulfate(1.25 mg/1) Tablet Oral Physicians Total Care, Inc. 1997-10-02 2011-07-31 US flag
Adderall Dextroamphetamine saccharate(2.5 mg/1)+Dextroamphetamine sulfate(2.5 mg/1)+Amphetamine aspartate(2.5 mg/1)+Amphetamine sulfate(2.5 mg/1) Tablet Oral Physicians Total Care, Inc. 2006-03-07 2011-07-31 US flag
Adderall Dextroamphetamine saccharate(2.5 mg/1)+Dextroamphetamine sulfate(2.5 mg/1)+Amphetamine aspartate(2.5 mg/1)+Amphetamine sulfate(2.5 mg/1) Tablet Oral Physicians Total Care, Inc. 2006-03-07 2011-07-31 US flag
Adderall Dextroamphetamine saccharate(5 mg/1)+Dextroamphetamine sulfate(5 mg/1)+Amphetamine aspartate(5 mg/1)+Amphetamine sulfate(5 mg/1) Tablet Oral Physicians Total Care, Inc. 2005-08-01 2011-07-31 US flag
Adderall Dextroamphetamine saccharate(5 mg/1)+Dextroamphetamine sulfate(5 mg/1)+Amphetamine aspartate(5 mg/1)+Amphetamine sulfate(5 mg/1) Tablet Oral Physicians Total Care, Inc. 2005-08-01 2011-07-31 US flag

Categories

ATC Codes
N06BA02 — Dexamfetamine
Drug Categories
Chemical TaxonomyProvided byClassyfire
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)
Affected organisms
  • Humans and other mammals

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.
一般References
  1. de la Torre R, Farre M,纳瓦罗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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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药物页面
Wikipedia
Dextroamphetamine
PDB Entries
4lar/4xp9
FDA label
Download (97.5 KB)
MSDS
Download (145 KB)

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Completed Health Services Research Expectancy Versus Pharmacotherapy Effect of Adderall 1
4 Completed Treatment Alzheimer's Disease (AD)/Dementia 1
4 Completed Treatment Attention Deficit Hyperactivity Disorder (ADHD) 2
4 Completed Treatment Attention Deficit Hyperactivity Disorder (ADHD)/Defiant Disorder, Oppositional 1
4 Completed Treatment Attention Deficit Hyperactivity Disorder (ADHD)/Deficient Emotional Self-Regulation (DESR) 1
4 Completed Treatment Attention Deficit Hyperactivity Disorder (ADHD)/Reading Disability 1
4 Completed Treatment Major Depressive Disorder (MDD) 1
4 Not Yet Recruiting Health Services Research Deception/Expectations/Prescription Stimulants 1
4 Recruiting Basic Science Attention Deficit Hyperactivity Disorder (ADHD)/Defiant Disorder, Oppositional/Substance Abuse 1
4 Recruiting Treatment Attention Deficit Hyperactivity Disorder (ADHD)/Behavioural Problem 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Abbott Laboratories Ltd.
  • Actavis Group
  • Auriga Pharmaceuticals LLC
  • Barr Pharmaceuticals
  • Bryant Ranch Prepack
  • Cardinal Health
  • Catalent制药公司的解决方案
  • 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
Form Route Strength
Capsule, extended release Oral 6.25 mg
Capsule, extended release Oral 10 mg/1
Capsule, extended release Oral 15 mg/1
Capsule, extended release Oral 5 mg/1
Tablet Oral 5 mg/1
Capsule, extended release Oral 10 mg
Capsule, extended release Oral 15 mg
Tablet Oral 5 mg
Capsule Oral
Capsule, extended release Oral
Tablet Oral
Solution Oral 5 mg/5mL
Tablet Oral 10 mg/1
液体 Oral 5 mg/5mL
Patch, extended release Transdermal 13.5 mg/1
Patch, extended release Transdermal 18 mg/1
Patch, extended release Transdermal 4.5 mg/1
Patch, extended release Transdermal 9 mg/1
Tablet Oral 15 mg/1
Tablet Oral 2.5 mg/1
Tablet Oral 20 mg/1
Tablet Oral 30 mg/1
Tablet Oral 7.5 mg/1
Prices
Unit description Cost Unit
D-amphetamine sulfate powder 900.0USD g
Desoxyn 5 mg tablet 5.1 uSD tablet
Dexedrine 15 mg 24 Hour Capsule 4.22USD capsule
硫酸右旋安非他命CR 15 mg 24 Hour Capsule 3.47USD capsule
Dexedrine 10 mg 24 Hour Capsule 3.23USD capsule
Dexedrine 5 mg 24 Hour Capsule 3.0USD capsule
硫酸右旋安非他命CR 10 mg 24 Hour Capsule 2.96USD capsule
Dexedrine spansule 15 mg 2.45USD each
硫酸右旋安非他命CR 5 mg 24 Hour Capsule 2.06USD capsule
Dexedrine spansule 10 mg 1.91USD each
Dexedrine spansule 5 mg 1.91USD each
Dexedrine 15 mg Sustained-Release Capsule 1.08USD capsule
硫酸右旋安非他命10 mg tablet 0.92USD tablet
Dexedrine 10 mg Sustained-Release Capsule 0.89USD capsule
硫酸右旋安非他命5 mg tablet 0.65USD tablet
Dexedrine 5 mg Tablet 0.62USD tablet
Dextroamphetamine 10 mg tablet 0.56USD tablet
Dextrostat 10 mg tablet 0.48USD tablet
Dextroamphetamine 5 mg tablet 0.28USD tablet
Dextrostat 5 mg tablet 0.25USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region
US6384020 Yes 2002-05-07 2021-01-06 US flag
USRE42096 Yes 2011-02-01 2019-04-21 US flag
US6605300 Yes 2003-08-12 2019-04-21 US flag
US6322819 Yes 2001-11-27 2019-04-21 US flag
USRE41148 Yes 2010-02-23 2019-04-21 US flag
US8632802 No 2014-01-21 2025-10-07 US flag
US9034370 No 2015-05-19 2025-10-07 US flag
US9173857 No 2015-11-03 2026-05-12 US flag
US6913768 No 2005-07-05 2023-05-24 US flag
US8846100 No 2014-09-30 2029-08-24 US flag
US9456993 No 2016-10-04 2033-10-24 US flag
US9474722 No 2016-10-25 2033-10-24 US flag
US8591941 No 2013-11-26 2025-10-07 US flag
US11559501 No 2022-01-06 2042-01-06 US flag

Properties

State
液体
Experimental Properties
Property Value Source
melting point (°C) -98 [MSDS]
boiling point (°C) 64.7 [MSDS]
water solubility 适度的可溶性 [MSDS]
Predicted Properties
Property Value Source
Water Solubility 1.74 mg/mL ALOGPS
logP 1.85 ALOGPS
logP 1.8 Chemaxon
logS -1.9 ALOGPS
pKa (Strongest Basic) 10.01 Chemaxon
Physiological Charge 1 Chemaxon
Hydrogen Acceptor Count 1 Chemaxon
Hydrogen Donor Count 1 Chemaxon
Polar Surface Area 26.02 Å2 Chemaxon
Rotatable Bond Count 2 Chemaxon
Refractivity 43.71 m3·mol-1 Chemaxon
Polarizability 16.08 Å3 Chemaxon
Number of Rings 1 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter No Chemaxon
Veber's Rule Yes Chemaxon
MDDR-like Rule No Chemaxon
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 inhibitor Non-inhibitor 0.9313
CYP450 2D6 inhibitor Inhibitor 0.657
CYP450 2C19 inhibitor Non-inhibitor 0.8445
CYP450 3A4 inhibitor 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
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (6.85 KB)
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Mass Spectrum (Electron Ionization) MS splash10-0006-9000000000-f40d32a5bced4783345a
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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Use our structured and evidence-based datasets tounlock new
insights and accelerate drug research.
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Learn more
Details 1.Synaptic vesicular amine transporter
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
一般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
分子量
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. [Article]
  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. [Article]
Details 2.Sodium-dependent noradrenaline transporter
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Negative modulator
一般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
分子量
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. [Article]
  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. [Article]
  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. [Article]
Details 3.Sodium-dependent dopamine transporter
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Negative modulator
一般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
分子量
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. [Article]
  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. [Article]
  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. [Article]
Details 4.Trace amine-associated receptor 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
一般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
分子量
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Details 5.Alpha-1B肾上腺素的衰退ptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
一般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肾上腺素的衰退ptor
分子量
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. [Article]
  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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details 6.Alpha adrenergic receptor (Protein Group)
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.
一般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:
Name UniProt ID
Alpha-1A adrenergic receptor P35348
Alpha-1B肾上腺素的衰退ptor P35368
Alpha-1D adrenergic receptor P25100
Alpha-2A adrenergic receptor P08913
Alpha-2B adrenergic receptor P18089
Alpha-2C adrenergic receptor P18825
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. [Article]
  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. [Article]

Enzymes

Details 1.Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
一般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
分子量
55768.94 Da
Details 2.Primary amine oxidase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
No
Actions
Substrate
一般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
分子量
84378.17 Da
References
  1. Kumar K, Dhoke全球之声,Sharma AK,贾斯瓦尔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. [Article]

Transporters

Details 1.Sodium-dependent dopamine transporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
一般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
分子量
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. [Article]

Drug created at August 29, 2007 14:50 / Updated at April 28, 2023 03:25