Identification

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Name
Dextroamphetamine
Accession Number
DB01576
Type
Small Molecule
Groups
Approved, Illicit
Description

Dextroamphetamine is the dextrorotary enantiomer of amphetamine[A2505]. Dextroamphetamine was approved by the FDA in 2001 for the treatment of attention deficit hyperactivity disorder5,Label.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Dextroamphetamine adipateYYI1A8W4TQ64770-52-1OFCJKOOVFDGTLY-QRPNPIFTSA-N
Dextroamphetamine saccharateG83415V073350708-40-6CXFNVDBOUVJOQO-OUDZKKFGSA-N
Dextroamphetamine sulfateJJ768O327N51-63-8SOFQDLYSFOWTJX-QRPNPIFTSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Dextroamphetamine SRCapsule, extended release15 mgOralActavis Pharma Company2017-10-06Not applicableCanada
Act Dextroamphetamine SRCapsule, extended release10 mgOralActavis Pharma Company2017-10-06Not applicableCanada
DexedrineCapsule, extended release10 mg/1OralGlaxosmithkline Inc2007-10-052013-01-31Us
DexedrineCapsule, extended release5 mg/1OralGlaxosmithkline Inc2007-11-142012-05-31Us
DexedrineCapsule, extended release15 mg/1OralGlaxosmithkline Inc2007-10-052013-01-31Us
DexedrineTablet5 mg/1OralGlaxoSmithKline2007-04-302007-04-30Us
Dexedrine SpansuleCapsule, extended release15 mg/1OralAmedra Pharmaceuticals LLC1976-08-022019-12-01Us
DEXEDRINE SpansuleCapsule, extended release10 mg/1OralPhysicians Total Care, Inc.2007-10-052010-06-30Us
Dexedrine SpansuleCapsule, extended release15 mg/1OralImpax Specialty Pharma1976-08-02Not applicableUs
Dexedrine SpansuleCapsule, extended release10 mg/1OralAmedra Pharmaceuticals LLC1976-08-022019-12-01Us
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 End
DexedrineTablet5 mg/1OralPhysicians Total Care, Inc.2004-12-162011-05-31Us
DexedrineTablet10 mg/1OralAmedra Pharmaceuticals LLC2014-07-012016-09-30Us
DexedrineTablet5 mg/1OralAmedra Pharmaceuticals LLC2014-07-012016-09-30Us
DextroamphetamineSolution5 mg/5mLOralTris Pharma, Inc.2013-05-31Not applicableUs
Dextroamphetamine SulfateCapsule, extended release10 mg/1OralAmerincan Health Packaging2015-03-312018-04-30Us
Dextroamphetamine SulfateCapsule, extended release10 mg/1OralMayne Pharma Inc.2016-08-05Not applicableUs
Dextroamphetamine SulfateTablet10 mg/1OralMikart, Inc.2011-10-25Not applicableUs
Dextroamphetamine SulfateTablet10 mg/1OralWilshire Pharmaceuticals, Inc.2012-07-20Not applicableUs
Dextroamphetamine SulfateTablet5 mg/1OralLupin Pharmaceuticals2016-04-25Not applicableUs
Dextroamphetamine SulfateSolution5 mg/5mLOralMikart, Inc.2008-01-29Not applicableUs
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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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act Amphetamine XRDextroamphetamine saccharate (3.75 mg) + Dextroamphetamine sulfate (3.75 mg) + Amphetamine aspartate monohydrate (3.75 mg) + Amphetamine sulfate (3.75 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (1.25 mg) + Dextroamphetamine sulfate (1.25 mg) + Amphetamine aspartate monohydrate (1.25 mg) + Amphetamine sulfate (1.25 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (7.5 mg) + Dextroamphetamine sulfate (7.5 mg) + Amphetamine aspartate monohydrate (7.5 mg) + Amphetamine sulfate (7.5 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (1.25 mg) + Dextroamphetamine sulfate (1.25 mg) + Amphetamine aspartate monohydrate (1.25 mg) + Amphetamine sulfate (1.25 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (3.75 mg) + Dextroamphetamine sulfate (3.75 mg) + Amphetamine aspartate monohydrate (3.75 mg) + Amphetamine sulfate (3.75 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (7.5 mg) + Dextroamphetamine sulfate (7.5 mg) + Amphetamine aspartate monohydrate (7.5 mg) + Amphetamine sulfate (7.5 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (2.5 mg) + Dextroamphetamine sulfate (2.5 mg) + Amphetamine aspartate monohydrate (2.5 mg) + Amphetamine sulfate (2.5 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (5 mg) + Dextroamphetamine sulfate (5 mg) + Amphetamine aspartate monohydrate (5 mg) + Amphetamine sulfate (5 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (6.25 mg) + Dextroamphetamine sulfate (6.25 mg) + Amphetamine aspartate monohydrate (6.25 mg) + Amphetamine sulfate (6.25 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
Act Amphetamine XRDextroamphetamine saccharate (2.5 mg) + Dextroamphetamine sulfate (2.5 mg) + Amphetamine aspartate monohydrate (2.5 mg) + Amphetamine sulfate (2.5 mg)Capsule, extended releaseOralTeva2015-10-02Not applicableCanada
International/Other Brands
Attentin (Medice) / Dexamphetamine (Sigma)
Categories
UNII
TZ47U051FI
CAS number
51-64-9
Weight
Average: 135.2062
Monoisotopic: 135.104799421
Chemical Formula
C9H13N
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

Pharmacology

Indication

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

Associated Conditions
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-1A adrenergic receptorNot AvailableHumans
UAlpha-1B adrenergic receptor
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

Route of elimination

A third of the drug is eliminated renally[A2505].

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 males[A2505]. Studies in healthy populations show a half life of 7.9 hours3.

Clearance

17L/h3.

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
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when Dextroamphetamine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Dextroamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Dextroamphetamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Dextroamphetamine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe risk or severity of adverse effects can be increased when Dextroamphetamine is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Dextroamphetamine.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Dextroamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of hypertension can be increased when Dextroamphetamine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Dextroamphetamine is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Dextroamphetamine is combined with 7-Deazaguanine.
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

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  • Evidence Level
    Evidence Level

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  • Action
    Evidence Level

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Food Interactions
Not Available

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. FDA Drug Approval Package for Dextroamphetamine [Link]
External Links
Human Metabolome Database
HMDB0015516
KEGG Drug
D03740
KEGG Compound
C07884
PubChem Compound
5826
PubChem Substance
46506252
ChemSpider
5621
BindingDB
50022723
ChEBI
4469
ChEMBL
CHEMBL612
Therapeutic Targets Database
DAP001470
PharmGKB
PA449269
Guide to Pharmacology
GtP Drug Page
HET
1WE
Wikipedia
Dextroamphetamine
ATC Codes
N06BA02 — Dexamfetamine
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
0CompletedTreatmentDependence, Cocaine1
0RecruitingBasic ScienceCocaine-Related Disorders1
0RecruitingBasic ScienceDependence, Cocaine1
0RecruitingOtherCardiovascular System / Hemodynamics1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceBipolar II Disorder1
1CompletedBasic ScienceDependence, Cocaine1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentDrug Users / Healthy Volunteers1
1RecruitingBasic ScienceAnhedonia1
1TerminatedOtherAbuse Potential1
1TerminatedTreatmentCocaine-Related Disorders1
1, 2CompletedBasic ScienceAttention Deficit Disorder With Hyperactivity (ADHD)1
1, 2RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
1, 2RecruitingTreatmentDependence, Cocaine1
2CompletedDiagnosticPathological Gambling1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Deficient Emotional Self-Regulation (DESR)1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentCocaine-Related Disorders / Opioid-Related Disorders1
2CompletedTreatmentCocaine-Related Disorders / Substance-Related Disorders1
2CompletedTreatmentMethamphetamine Addiction1
2CompletedTreatmentMethamphetamine Dependence1
2CompletedTreatmentStrokes2
2Not Yet RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Change in Sustained Attention / Mood / Stimulant Use / Working Memory1
2RecruitingTreatmentAnhedonia / Cocaine-Related Disorders1
2RecruitingTreatmentIdiopathic Hypersomnia / Narcolepsy Without Cataplexy1
2RecruitingTreatmentSchizophrenic Disorders1
2, 3CompletedTreatmentCognitive Impairments / Disseminated Sclerosis / Impaired Processing Speed1
2, 3CompletedTreatmentDependence, Cocaine1
2, 3RecruitingTreatmentDisseminated Sclerosis1
3CompletedBasic ScienceHealthy Adults1
3CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
3CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)2
4CompletedBasic ScienceEating Disorder1
4CompletedTreatmentAlzheimer's Disease (AD) / Dementias1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)3
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Deficient Emotional Self-Regulation (DESR)1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Reading Disability1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity / Oppositional Defiant Disorder1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4Not Yet RecruitingHealth Services ResearchExpectancy Versus Pharmacotherapy Effect of Adderall1
4Not Yet RecruitingOtherHealthy Adults1
4Not Yet RecruitingTreatmentAttention Deficit-Hyperactivity1
4RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)2
4RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Problem Behavior1
4TerminatedTreatmentMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentAttention Deficit Disorder With Hyperactivity1
Not AvailableActive Not RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)3
Not AvailableCompletedNot AvailableNicotine Dependence1
Not AvailableCompletedBasic ScienceAOD Effects and Consequences1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedTreatmentAttention Deficit Disorder With Hyperactivity1
Not AvailableRecruitingNot AvailableAlcohol Dependence / Cocaine Abuse / Dependence, Cocaine / Opiate Dependence / Substance Abuse1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingBasic SciencePsychosis / Schizophrenic Disorders / Sensitization1
Not AvailableUnknown StatusTreatmentMajor 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 releaseOral
Capsule, extended releaseOral10 mg/1
Capsule, extended releaseOral15 mg/1
Capsule, extended releaseOral5 mg/1
TabletOral5 mg/1
Capsule, extended releaseOral10 mg
Capsule, extended releaseOral15 mg
TabletOral5 mg
SolutionOral5 mg/5mL
CapsuleOral
TabletOral
TabletOral15 mg/1
TabletOral2.5 mg/1
TabletOral20 mg/1
TabletOral30 mg/1
TabletOral7.5 mg/1
TabletOral10 mg/1
LiquidOral5 mg/5mL
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)
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.

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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

Taxonomy

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
Amphetamine or derivatives / Phenylpropane / Aralkylamine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Organonitrogen compound / Primary aliphatic amine / Amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
amphetamine (CHEBI:4469)

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
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
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 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]
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]

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 May 21, 2019 10:32