Identification

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

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

Structure
Thumb
Synonyms
  • (+)-(S)-amphetamine
  • (+)-alpha-Methylphenethylamine
  • (+)-alpha-Methylphenylethylamine
  • (+)-Amphetamine
  • (AlphaS)-alpha-methylbenzeneethanamine
  • (S)-(+)-Amphetamine
  • (S)-(+)-beta-Phenylisopropylamine
  • (S)-1-Phenyl-2-aminopropane
  • (S)-1-Phenyl-2-propylamine
  • (S)-alpha-Methylbenzeneethanamine
  • (S)-amphetamine
  • d-amphetamine
  • Dexamfetamine
  • dexamphetamine
  • Dextroamphetamine
External 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 release15 mg/1OralGlaxosmithkline Inc2007-10-052013-01-31Us
DexedrineCapsule, extended release10 mg/1OralGlaxosmithkline Inc2007-10-052013-01-31Us
DexedrineCapsule, extended release5 mg/1OralGlaxosmithkline Inc2007-11-142012-05-31Us
Dexedrine SpansuleCapsule, extended release15 mg/1OralAmedra Pharmaceuticals LLC1976-08-02Not applicableUs
Dexedrine SpansuleCapsule, extended release10 mg/1OralAmedra Pharmaceuticals LLC1976-08-02Not applicableUs
DEXEDRINE SpansuleCapsule, extended release10 mg/1OralPhysicians Total Care, Inc.2007-10-052010-06-30Us
Dexedrine SpansuleCapsule, extended release5 mg/1OralAmedra Pharmaceuticals LLC1976-08-02Not applicableUs
DEXEDRINE SpansuleCapsule, extended release5 mg/1OralPhysicians Total Care, Inc.2007-11-142011-06-30Us
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 SulfateTablet10 mg/1OralNovel Laboratories, Inc.2016-03-16Not applicableUs
Dextroamphetamine SulfateTablet7.5 mg/1OralMikart, Inc.2011-10-25Not applicableUs
Dextroamphetamine SulfateTablet5 mg/1OralWilshire Pharmaceuticals, Inc.2012-07-16Not applicableUs
Dextroamphetamine SulfateTablet5 mg/1OralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2011-12-072014-12-31Us
Dextroamphetamine SulfateTablet5 mg/1OralAurolife Pharma, LLC2013-07-31Not applicableUs
Dextroamphetamine SulfateTablet5 mg/1OralZydus Pharmaceuticals Usa, Inc.2016-03-28Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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 (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 (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 (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 (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 (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 (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 (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 (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 (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
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DexedrineDextroamphetamine sulfate (5 mg/1)TabletOralGlaxoSmithKline2007-04-302007-04-30Us
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, Amphetamine SulfateDextroamphetamine saccharate (3.125 mg/1) + Dextroamphetamine sulfate (3.125 mg/1) + Amphetamine aspartate (3.125 mg/1) + Amphetamine sulfate (3.125 mg/1)TabletOralMallinckrodt Inc.2006-10-232006-10-23Us
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, Amphetamine SulfateDextroamphetamine saccharate (3.125 mg/1) + Dextroamphetamine sulfate (3.125 mg/1) + Amphetamine aspartate (3.125 mg/1) + Amphetamine sulfate (3.125 mg/1)TabletOralMallinckrodt Inc.2006-10-232006-10-23Us
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateDextroamphetamine saccharate (1.875 mg/1) + Dextroamphetamine sulfate (1.875 mg/1) + Amphetamine aspartate (1.875 mg/1) + Amphetamine sulfate (1.875 mg/1)TabletOralMutual Pharmaceutical Company2007-03-27Not applicableUs
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateDextroamphetamine saccharate (1.25 mg/1) + Dextroamphetamine sulfate (1.25 mg/1) + Amphetamine aspartate (1.25 mg/1) + Amphetamine sulfate (1.25 mg/1)TabletOralMutual Pharmaceutical Company2007-03-27Not applicableUs
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateDextroamphetamine saccharate (7.5 mg/1) + Dextroamphetamine sulfate (7.5 mg/1) + Amphetamine aspartate (7.5 mg/1) + Amphetamine sulfate (7.5 mg/1)TabletOralMutual Pharmaceutical Company2007-03-27Not applicableUs
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateDextroamphetamine saccharate (5 mg/1) + Dextroamphetamine sulfate (5 mg/1) + Amphetamine aspartate (5 mg/1) + Amphetamine sulfate (5 mg/1)TabletOralMutual Pharmaceutical Company2007-03-27Not applicableUs
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateDextroamphetamine saccharate (3.75 mg/1) + Dextroamphetamine sulfate (3.75 mg/1) + Amphetamine aspartate (3.75 mg/1) + Amphetamine sulfate (3.75 mg/1)TabletOralMutual Pharmaceutical Company2007-03-27Not applicableUs
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateDextroamphetamine saccharate (2.5 mg/1) + Dextroamphetamine sulfate (2.5 mg/1) + Amphetamine aspartate (2.5 mg/1) + Amphetamine sulfate (2.5 mg/1)TabletOralMutual Pharmaceutical Company2007-03-27Not applicableUs
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateDextroamphetamine saccharate (1.875 mg/1) + Dextroamphetamine sulfate (1.875 mg/1) + Amphetamine aspartate (1.875 mg/1) + Amphetamine sulfate (1.875 mg/1)TabletOralMutual Pharmaceutical Company2007-03-27Not applicableUs
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

Used to treat attention deficit hyperactivity disorder (ADHD).

Associated Conditions
Pharmacodynamics

Amphetamines such as dextroamphetamine are noncatecholamine, sympathomimetic amines with CNS stimulant activity. Peripheral actions include elevations of systolic and diastolic blood pressures and weak bronchodilator and respiratory stimulant action. There is neither specific evidence that clearly establishes the mechanism whereby amphetamines produce mental and behavioral effects in children, nor conclusive evidence regarding how these effects relate to the condition of the central nervous system.

Mechanism of action

The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect.

TargetActionsOrganism
ASynaptic vesicular amine transporter
inducer
Human
ASodium-dependent noradrenaline transporter
negative modulator
Human
ASodium-dependent dopamine transporter
negative modulator
Human
UTrace amine-associated receptor 1
agonist
Human
UAlpha-1A adrenergic receptorNot AvailableHuman
UAlpha-1B adrenergic receptor
antagonist
Human
Absorption

Oral bioavailability is over 75%.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life

10-28 hours (average is approximately 12 hours)

Clearance
Not Available
Toxicity

In rats, the oral LD50 of dextroamphetamine sulfate is 96.8 mg/kg. Manifestations of acute overdosage with amphetamines include restlessness, tremor, hyperreflexia, rhabdomyolysis, rapid respiration, hyperpyrexia, confusion, assaultiveness, hallucinations, panic states. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension, and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Fatal poisoning is usually preceded by convulsions and coma.

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

Interactions

Drug Interactions
DrugInteraction
4-MethoxyamphetamineDextroamphetamine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of Dextroamphetamine.
AbirateroneThe serum concentration of Dextroamphetamine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Dextroamphetamine.
AcepromazineAcepromazine may increase the antihypertensive activities of Dextroamphetamine.
AceprometazineAceprometazine may decrease the stimulatory activities of Dextroamphetamine.
AcetazolamideAcetazolamide may decrease the excretion rate of Dextroamphetamine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Dextroamphetamine.
AcrivastineDextroamphetamine may decrease the sedative activities of Acrivastine.
AdrafinilDextroamphetamine may decrease the vasoconstricting activities of Adrafinil.
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. Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6. [PubMed:6506758]
  2. Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. [PubMed:2180548]
  3. Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40. [PubMed:10901342]
  4. Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6. [PubMed:14520168]
  5. Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68. [PubMed:11782985]
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
IUPHAR
2147
Guide to Pharmacology
GtP Drug Page
HET
1WE
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dextroamphetamine
ATC Codes
N06BA02 — Dexamfetamine
AHFS Codes
  • 28:20.04 — Amphetamines
PDB Entries
4lar / 4xp9

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentDependence, Cocaine1
0RecruitingBasic ScienceCocaine-Related Disorders1
0RecruitingBasic ScienceDependence, Cocaine1
0RecruitingOtherCardiovascular System / Hemodynamics1
1CompletedNot AvailableHealthy Volunteers1
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
2Active Not RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Deficient Emotional Self-Regulation (DESR)1
2CompletedDiagnosticPathological Gambling1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity1
2CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentCocaine-Related Disorders / Opioid-Related Disorders1
2CompletedTreatmentCocaine-Related Disorders / Substance-Related Disorders1
2CompletedTreatmentMethamphetamine Addiction1
2CompletedTreatmentMethamphetamine Dependence1
2CompletedTreatmentStrokes2
2RecruitingTreatmentAnhedonia / Cocaine-Related Disorders1
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
4RecruitingTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)2
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 AvailableNot Yet RecruitingNot AvailableAttention Deficit Disorder With Hyperactivity (ADHD) / Problem Behavior1
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)
US6384020Yes2001-01-062021-01-06Us
USRE42096Yes1999-04-212019-04-21Us
US6605300Yes1999-04-212019-04-21Us
US6322819Yes1999-04-212019-04-21Us
USRE41148Yes1999-04-212019-04-21Us
US9173857No2006-05-122026-05-12Us
US6913768No2003-05-242023-05-24Us
US8846100No2009-08-242029-08-24Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)203 °CPhysProp
logP1.76SANGSTER (1994); similar isomer
pKa9.9SANGSTER (1994); similar isomer
Predicted Properties
PropertyValueSource
Water Solubility1.74 mg/mLALOGPS
logP1.85ALOGPS
logP1.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.71 m3·mol-1ChemAxon
Polarizability16.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose 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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on August 29, 2007 08:50 / Updated on September 22, 2018 22:33