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Identification
NameAmphetamine
Accession NumberDB00182  (APRD00480)
TypeSmall Molecule
GroupsApproved, Illicit
Description

Amphetamine is a chiral compound. The racemic mixture can be divided into its optical antipodes: levo- and dextro-amphetamine. Amphetamine is the parent compound of its own structural class, comprising a broad range of psychoactive derivatives, e.g., MDMA (Ecstasy) and the N-methylated form, methamphetamine. Amphetamine is a homologue of phenethylamine.

Structure
Thumb
Synonyms
1-phenyl-2-aminopropane
1-Phenylpropan-2-amin
alpha-Methylbenzeneethaneamine
alpha-Methylphenylethylamine
Amfetamine
Amfetaminum
Amphetamin
Amphetamine
beta-Aminopropylbenzene
beta-Phenylisopropylamin
beta-Phenylisopropylamine
Desoxynorephedrine
α-methylbenzeneethaneamine
α-methylphenethylamine
β-aminopropylbenzene
β-phenylisopropylamine
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dyanavel XRsuspension, extended release2.5 mg/mLoralTris Pharma Inc2015-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Evekeotablet5 mg/1oralArbor Pharmaceuticals, Inc.2015-02-012017-09-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Evekeotablet10 mg/1oralArbor Pharmaceuticals2015-11-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Evekeotablet5 mg/1oralArbor Pharmaceuticals2015-11-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Evekeotablet10 mg/1oralArbor Pharmaceuticals, Inc.2015-02-012017-10-11Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
AdderallTeva Select Brands
Adderall XRShire US Manufacturing Inc.
Dextroamphetamine Saccharate and Amphetamine Aspartate and Dextroamphetamine Sulfate and Amphetamine SulfateMallinckrodt, Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate (monohydrate), Dextroamphetamine Sulfate, Amphetamine SulfateMylan Pharmaceuticals Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate Monohydrate, Dextroamphetamine Sulfate and Amphetamine SulfateEon Labs, Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate Monohydrate, Dextroamphetamine Sulfate, Amphetamine SulfateActavis Pharma, Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine SuflateSTAT Rx USA LLC
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine SulfateGlobal Pharmaceuticals, Division of Impax Laboratories Inc.
Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate, and Amphetamine SulfateBarr Laboratories Inc.
Salts
Name/CASStructureProperties
Amphetamine adipate
ThumbNot applicableDBSALT001323
Amphetamine aspartate
ThumbNot applicableDBSALT001345
Amphetamine aspartate monohydrate
ThumbNot applicableDBSALT001501
Amphetamine sulfate
ThumbNot applicableDBSALT001205
Categories
CAS number300-62-9
WeightAverage: 135.2062
Monoisotopic: 135.104799421
Chemical FormulaC9H13N
InChI KeyInChIKey=KWTSXDURSIMDCE-UHFFFAOYSA-N
InChI
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
IUPAC Name
1-phenylpropan-2-amine
SMILES
CC(N)CC1=CC=CC=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor treatment of Attention Deficit Disorder with Hyperactivity (ADDH) and narcolepsy in children.
PharmacodynamicsAmphetamine and dextroamphetamine, non-catechloamine sypathomimetic agents, are used in combination to treat attention-deficit hyperactivity disorder (ADHD) or narcolepsy. Adderall consists of equivalent amounts of amphetamine aspartate, amphetamine sulfate, dextroamphetamine saccharate, and dextroamphetamine sulfate.
Mechanism of actionAmphetamines stimulate the release of norepinephrine from central adrenergic receptors. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine 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. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT.
AbsorptionAmphetamine forms easily absorbed molecules that are highly lipid soluble
Volume of distributionNot Available
Protein binding15-40%
Metabolism

Hepatic

Route of eliminationNot Available
Half life10 hours
ClearanceNot Available
ToxicityLD50=180 mg/kg(subcutaneous injection in rat). The most common presenting symptoms seen are agitation, hallucinations, suicidal behaviour, and chest pain.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Lannett co inc
  • Akorn inc
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Capsule, extended releaseoral
Suspension, extended releaseoral2.5 mg/mL
Tabletoral10 mg/1
Tabletoral5 mg/1
Prices
Unit descriptionCostUnit
Desoxyn 5 mg tablet5.1USD tablet
Dexedrine 15 mg 24 Hour Capsule4.22USD capsule
Dexedrine 10 mg 24 Hour Capsule3.23USD capsule
Dexedrine 5 mg 24 Hour Capsule3.0USD capsule
Dexedrine spansule 15 mg2.45USD each
Dexedrine spansule 10 mg1.91USD each
Dexedrine spansule 5 mg1.91USD each
Amphetamine salts 12.5 mg tablet1.43USD tablet
Amphetamine salts 15 mg tablet1.43USD tablet
Amphetamine salts 7.5 mg tablet1.43USD tablet
Amphetamine salts 10 mg tablet1.37USD tablet
Amphetamine salts 20 mg tablet1.37USD tablet
Amphetamine salts 30 mg tablet1.37USD tablet
Amphetamine salts 5 mg tablet1.37USD tablet
Amphetamine Salt Combo 7.5 mg tablet1.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting pointVolatizes slowly at room temperatureNot Available
water solubilitySlightlyNot Available
logP1.76HANSCH,C ET AL. (1995)
pKa10.1 (at 20 °C)PERRIN,DD (1965)
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
Polarizability16.17 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.59 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-z200000000-98cd0a725199f943d6cfView in MoNA
References
Synthesis Reference

Guohong Wang, “Composition and methods for synthesis of novel tracers for detecting amphetamine and methamphetamine in samples.” U.S. Patent US20020090661, issued July 11, 2002.

US20020090661
General References
  1. Leith NJ, Kuczenski R: Chronic amphetamine: tolerance and reverse tolerance reflect different behavioral actions of the drug. Pharmacol Biochem Behav. 1981 Sep;15(3):399-404. Pubmed
  2. Chaudhry IA, Turkanis SA, Karler R: Characteristics of “reverse tolerance” to amphetamine-induced locomotor stimulation in mice. Neuropharmacology. 1988 Aug;27(8):777-81. Pubmed
  3. Sax KW, Strakowski SM: Behavioral sensitization in humans. J Addict Dis. 2001;20(3):55-65. Pubmed
  4. 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
External Links
ATC CodesN06BA01
AHFS Codes
  • 28:20.04
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Amphetamine.
AcepromazineAcepromazine may decrease the stimulatory activities of Amphetamine.
AcetaminophenThe risk or severity of adverse effects can be increased when Amphetamine is combined with Acetaminophen.
AcetazolamideAcetazolamide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Amphetamine.
Acetylsalicylic acidAmphetamine may increase the analgesic activities of Acetylsalicylic acid.
AlfentanilAmphetamine may increase the analgesic activities of Alfentanil.
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AminophyllineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Aminophylline.
AmisulprideAmisulpride may decrease the stimulatory activities of Amphetamine.
AmitriptylineAmitriptyline may increase the stimulatory activities of Amphetamine.
Ammonium chlorideThe serum concentration of Amphetamine can be decreased when it is combined with Ammonium chloride.
AmoxapineAmoxapine may increase the stimulatory activities of Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Arformoterol.
AripiprazoleAripiprazole may decrease the stimulatory activities of Amphetamine.
ArmodafinilThe risk or severity of adverse effects can be increased when Amphetamine is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Articaine.
AsenapineAsenapine may decrease the stimulatory activities of Amphetamine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Amphetamine.
AzelastineAmphetamine may decrease the sedative activities of Azelastine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Amphetamine.
BenzquinamideBenzquinamide may decrease the stimulatory activities of Amphetamine.
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of Amphetamine.
BrinzolamideThe serum concentration of Amphetamine can be increased when it is combined with Brinzolamide.
BrompheniramineAmphetamine may decrease the sedative activities of Brompheniramine.
BuprenorphineAmphetamine may increase the analgesic activities of Buprenorphine.
ButalbitalThe risk or severity of adverse effects can be increased when Amphetamine is combined with Butalbital.
ButorphanolAmphetamine may increase the analgesic activities of Butorphanol.
CaffeineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Caffeine.
Calcium AcetateCalcium Acetate may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Calcium carbonateCalcium carbonate may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
CarbinoxamineAmphetamine may decrease the sedative activities of Carbinoxamine.
CarphenazineCarphenazine may decrease the stimulatory activities of Amphetamine.
CetirizineAmphetamine may decrease the sedative activities of Cetirizine.
ChlormezanoneChlormezanone may decrease the stimulatory activities of Amphetamine.
ChlorphenamineAmphetamine may decrease the sedative activities of Chlorphenamine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Amphetamine.
ChlorpromazineChlorpromazine may decrease the stimulatory activities of Amphetamine.
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of Amphetamine.
ClemastineAmphetamine may decrease the sedative activities of Clemastine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Amphetamine.
ClofedanolAmphetamine may decrease the sedative activities of Clofedanol.
ClomipramineClomipramine may increase the stimulatory activities of Amphetamine.
ClozapineClozapine may decrease the stimulatory activities of Amphetamine.
CocaineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Cocaine.
CodeineAmphetamine may increase the analgesic activities of Codeine.
CyclizineAmphetamine may decrease the sedative activities of Cyclizine.
CyproheptadineAmphetamine may decrease the sedative activities of Cyproheptadine.
DesipramineDesipramine may increase the stimulatory activities of Amphetamine.
DesloratadineAmphetamine may decrease the sedative activities of Desloratadine.
DexbrompheniramineAmphetamine may decrease the sedative activities of Dexbrompheniramine.
Dexchlorpheniramine maleateAmphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Amphetamine is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Dextroamphetamine.
DiclofenamideDiclofenamide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
DiethylpropionThe risk or severity of adverse effects can be increased when Amphetamine is combined with Diethylpropion.
DihydrocodeineAmphetamine may increase the analgesic activities of Dihydrocodeine.
DimenhydrinateAmphetamine may decrease the sedative activities of Dimenhydrinate.
DiphenhydramineAmphetamine may decrease the sedative activities of Diphenhydramine.
DipivefrinThe risk or severity of adverse effects can be increased when Amphetamine is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Amphetamine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Amphetamine.
DorzolamideThe serum concentration of Amphetamine can be increased when it is combined with Dorzolamide.
DoxapramThe risk or severity of adverse effects can be increased when Amphetamine is combined with Doxapram.
DoxepinDoxepin may increase the stimulatory activities of Amphetamine.
DoxofyllineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Doxofylline.
DoxylamineAmphetamine may decrease the sedative activities of Doxylamine.
DronabinolDronabinol may increase the tachycardic activities of Amphetamine.
DroperidolDroperidol may decrease the stimulatory activities of Amphetamine.
DyphyllineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Amphetamine.
EsomeprazoleEsomeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with Amphetamine.
EthoxzolamideEthoxzolamide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
FencamfamineFencamfamine may decrease the stimulatory activities of Amphetamine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Amphetamine.
FentanylAmphetamine may increase the analgesic activities of Fentanyl.
FexofenadineAmphetamine may decrease the sedative activities of Fexofenadine.
FlupentixolFlupentixol may decrease the stimulatory activities of Amphetamine.
FluphenazineFluphenazine may decrease the stimulatory activities of Amphetamine.
FluspirileneFluspirilene may decrease the stimulatory activities of Amphetamine.
Fluticasone PropionateAmphetamine may decrease the sedative activities of Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Amphetamine.
HaloperidolHaloperidol may decrease the stimulatory activities of Amphetamine.
HexamethylenetetramineThe serum concentration of Amphetamine can be decreased when it is combined with Hexamethylenetetramine.
HydrocodoneAmphetamine may increase the analgesic activities of Hydrocodone.
HydromorphoneAmphetamine may increase the analgesic activities of Hydromorphone.
HydroxyzineAmphetamine may decrease the sedative activities of Hydroxyzine.
IloperidoneIloperidone may decrease the stimulatory activities of Amphetamine.
ImipramineImipramine may increase the stimulatory activities of Amphetamine.
IndacaterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Amphetamine.
Ioflupane I 123Amphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ipratropium bromide.
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Amphetamine.
IsomethepteneThe risk or severity of adverse effects can be increased when Amphetamine is combined with Isometheptene.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Amphetamine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Amphetamine.
LansoprazoleLansoprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
LevocetirizineAmphetamine may decrease the sedative activities of Levocetirizine.
LevonordefrinThe risk or severity of adverse effects can be increased when Amphetamine is combined with Levonordefrin.
LevorphanolAmphetamine may increase the analgesic activities of Levorphanol.
LinezolidLinezolid may increase the hypertensive activities of Amphetamine.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Lisdexamfetamine.
LithiumLithium may decrease the stimulatory activities of Amphetamine.
LoratadineAmphetamine may decrease the sedative activities of Loratadine.
LoxapineLoxapine may decrease the stimulatory activities of Amphetamine.
LurasidoneLurasidone may decrease the stimulatory activities of Amphetamine.
Magnesium hydroxideMagnesium hydroxide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Magnesium oxideMagnesium oxide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
MeclizineAmphetamine may decrease the sedative activities of Meclizine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Amphetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Mepivacaine.
MesoridazineMesoridazine may decrease the stimulatory activities of Amphetamine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Amphetamine.
MethadoneAmphetamine may increase the analgesic activities of Methadone.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Amphetamine.
MethazolamideMethazolamide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of Amphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Amphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Amphetamine is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Amphetamine.
MoclobemideMoclobemide may increase the hypertensive activities of Amphetamine.
ModafinilThe risk or severity of adverse effects can be increased when Amphetamine is combined with Modafinil.
MolindoneMolindone may decrease the stimulatory activities of Amphetamine.
MorphineAmphetamine may increase the analgesic activities of Morphine.
NabiloneNabilone may increase the tachycardic activities of Amphetamine.
NalbuphineAmphetamine may increase the analgesic activities of Nalbuphine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Amphetamine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Amphetamine.
NortriptylineNortriptyline may increase the stimulatory activities of Amphetamine.
OlanzapineOlanzapine may decrease the stimulatory activities of Amphetamine.
OlodaterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Olodaterol.
OlopatadineAmphetamine may decrease the sedative activities of Olopatadine.
OmeprazoleOmeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
OndansetronOndansetron may decrease the stimulatory activities of Amphetamine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Amphetamine.
OxycodoneAmphetamine may increase the analgesic activities of Oxycodone.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Amphetamine.
OxymorphoneAmphetamine may increase the analgesic activities of Oxymorphone.
PaliperidonePaliperidone may decrease the stimulatory activities of Amphetamine.
PantoprazolePantoprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
PentazocineAmphetamine may increase the analgesic activities of Pentazocine.
PerphenazinePerphenazine may decrease the stimulatory activities of Amphetamine.
PethidineAmphetamine may increase the analgesic activities of Pethidine.
PhendimetrazineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Phendimetrazine.
PhenelzinePhenelzine may increase the hypertensive activities of Amphetamine.
PheniramineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Pheniramine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Amphetamine.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Amphetamine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Amphetamine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Amphetamine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Amphetamine.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Amphetamine.
PimozidePimozide may decrease the stimulatory activities of Amphetamine.
PiperacetazinePiperacetazine may decrease the stimulatory activities of Amphetamine.
PirbuterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Pirbuterol.
PizotifenAmphetamine may decrease the sedative activities of Pizotifen.
ProcarbazineProcarbazine may increase the hypertensive activities of Amphetamine.
ProchlorperazineProchlorperazine may decrease the stimulatory activities of Amphetamine.
PromazinePromazine may decrease the stimulatory activities of Amphetamine.
PropylhexedrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Propylhexedrine.
ProtriptylineProtriptyline may increase the stimulatory activities of Amphetamine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Pseudoephedrine.
QuetiapineQuetiapine may decrease the stimulatory activities of Amphetamine.
RabeprazoleRabeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
RacepinephrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Racepinephrine.
RasagilineRasagiline may increase the hypertensive activities of Amphetamine.
RemifentanilAmphetamine may increase the analgesic activities of Remifentanil.
RemoxiprideRemoxipride may decrease the stimulatory activities of Amphetamine.
ReserpineReserpine may decrease the stimulatory activities of Amphetamine.
RisperidoneRisperidone may decrease the stimulatory activities of Amphetamine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Amphetamine.
SalbutamolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Amphetamine.
SelegilineSelegiline may increase the hypertensive activities of Amphetamine.
SertindoleSertindole may decrease the stimulatory activities of Amphetamine.
Sodium bicarbonateThe serum concentration of Amphetamine can be increased when it is combined with Sodium bicarbonate.
Sodium lactateThe serum concentration of Amphetamine can be increased when it is combined with Sodium lactate.
SufentanilAmphetamine may increase the analgesic activities of Sufentanil.
SulpirideSulpiride may decrease the stimulatory activities of Amphetamine.
TapentadolAmphetamine may increase the analgesic activities of Tapentadol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Amphetamine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Amphetamine.
TheophyllineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Theophylline.
ThioridazineThioridazine may decrease the stimulatory activities of Amphetamine.
ThiothixeneThiothixene may decrease the stimulatory activities of Amphetamine.
TopiramateTopiramate may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
TramadolAmphetamine may increase the analgesic activities of Tramadol.
TranylcypromineTranylcypromine may increase the hypertensive activities of Amphetamine.
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of Amphetamine.
TriflupromazineTriflupromazine may decrease the stimulatory activities of Amphetamine.
TrimipramineTrimipramine may increase the stimulatory activities of Amphetamine.
TriprolidineAmphetamine may decrease the sedative activities of Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Vilanterol.
Vitamin CThe serum concentration of Amphetamine can be decreased when it is combined with Vitamin C.
ZiprasidoneZiprasidone may decrease the stimulatory activities of Amphetamine.
ZonisamideZonisamide may decrease the excretion rate of Amphetamine which could result in a lower serum level and potentially a reduction in efficacy.
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of Amphetamine.
Food InteractionsNot Available

Targets

1. Synaptic vesicular amine transporter

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Synaptic vesicular amine transporter Q05940 Details

References:

  1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed
  2. 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
  3. Teng L, Crooks PA, Dwoskin LP: Lobeline displaces [3H]dihydrotetrabenazine binding and releases [3H]dopamine from rat striatal synaptic vesicles: comparison with d-amphetamine. J Neurochem. 1998 Jul;71(1):258-65. Pubmed
  4. Eiden LE, Weihe E: VMAT2: a dynamic regulator of brain monoaminergic neuronal function interacting with drugs of abuse. Ann N Y Acad Sci. 2011 Jan;1216:86-98. doi: 10.1111/j.1749-6632.2010.05906.×. Pubmed

2. Sodium-dependent dopamine transporter

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: negative modulator

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. Lott DC, Kim SJ, Cook EH Jr, de Wit H: Dopamine transporter gene associated with diminished subjective response to amphetamine. Neuropsychopharmacology. 2005 Mar;30(3):602-9. Pubmed
  2. Fone KC, Nutt DJ: Stimulants: use and abuse in the treatment of attention deficit hyperactivity disorder. Curr Opin Pharmacol. 2005 Feb;5(1):87-93. Pubmed
  3. 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
  4. Garcia BG, Wei Y, Moron JA, Lin RZ, Javitch JA, Galli A: Akt is essential for insulin modulation of amphetamine-induced human dopamine transporter cell-surface redistribution. Mol Pharmacol. 2005 Jul;68(1):102-9. Epub 2005 Mar 28. Pubmed
  5. Madras BK, Miller GM, Fischman AJ: The dopamine transporter and attention-deficit/hyperactivity disorder. Biol Psychiatry. 2005 Jun 1;57(11):1397-409. Epub 2005 Jan 5. Pubmed
  6. Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. Pubmed

3. Cocaine- and amphetamine-regulated transcript protein

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Cocaine- and amphetamine-regulated transcript protein Q16568 Details

References:

  1. Loos RJ, Rankinen T, Tremblay A, Perusse L, Chagnon Y, Bouchard C: Melanocortin-4 receptor gene and physical activity in the Quebec Family Study. Int J Obes (Lond). 2005 Apr;29(4):420-8. Pubmed
  2. McAlister ED, Van Vugt DA: Effect of leptin administration versus re-feeding on hypothalamic neuropeptide gene expression in fasted male rats. Can J Physiol Pharmacol. 2004 Dec;82(12):1128-34. Pubmed
  3. Muhlhausler BS, Adam CL, Marrocco EM, Findlay PA, Roberts CT, McFarlane JR, Kauter KG, McMillen IC: Impact of glucose infusion on the structural and functional characteristics of adipose tissue and on hypothalamic gene expression for appetite regulatory neuropeptides in the sheep fetus during late gestation. J Physiol. 2005 May 15;565(Pt 1):185-95. Epub 2005 Jan 20. Pubmed
  4. Scruggs P, Lai CC, Scruggs JE, Dun NJ: Cocaine- and amphetamine-regulated transcript peptide potentiates spinal glutamatergic sympathoexcitation in anesthetized rats. Regul Pept. 2005 Apr 15;127(1-3):79-85. Pubmed
  5. Oliveira VX Jr, Fazio MA, Miranda MT, da Silva JM, Bittencourt JC, Elias CF, Miranda A: Leptin fragments induce Fos immunoreactivity in rat hypothalamus. Regul Pept. 2005 Apr 15;127(1-3):123-32. Pubmed
  6. Vicentic A, Lakatos A, Jones D: The CART receptors: background and recent advances. Peptides. 2006 Aug;27(8):1934-7. Epub 2006 May 19. Pubmed

4. Trace amine-associated receptor 1

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Trace amine-associated receptor 1 Q96RJ0 Details

References:

  1. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. Pubmed
  2. Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. Pubmed
  3. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. Pubmed
  4. Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. Pubmed
  5. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. Pubmed

5. Sodium-dependent noradrenaline transporter

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: stimulator

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA: In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J Pharmacol Exp Ther. 2003 Oct;307(1):138-45. Epub 2003 Sep 3. Pubmed
  2. Wall SC, Gu H, Rudnick G: Biogenic amine flux mediated by cloned transporters stably expressed in cultured cell lines: amphetamine specificity for inhibition and efflux. Mol Pharmacol. 1995 Mar;47(3):544-50. Pubmed

6. Alpha adrenergic receptor

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details
Alpha-1B adrenergic receptor P35368 Details
Alpha-1D adrenergic receptor P25100 Details
Alpha-2A adrenergic receptor P08913 Details
Alpha-2B adrenergic receptor P18089 Details
Alpha-2C adrenergic receptor P18825 Details

References:

  1. Leibowitz SF: Reciprocal hunger-regulating circuits involving alpha- and beta-adrenergic receptors located, respectively, in the ventromedial and lateral hypothalamus. Proc Natl Acad Sci U S A. 1970 Oct;67(2):1063-70. Pubmed
  2. Reisine TD, U’Prichard DC, Wiech NL, Ursillo RC, Yamamura HI: Effects of combined administration of amphetamine and iprindole on brain adrenergic receptors. Brain Res. 1980 Apr 28;188(2):587-92. Pubmed

7. Beta adrenergic receptor

Kind: Protein group

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details
Beta-2 adrenergic receptor P07550 Details
Beta-3 adrenergic receptor P13945 Details

References:

  1. Leibowitz SF: Reciprocal hunger-regulating circuits involving alpha- and beta-adrenergic receptors located, respectively, in the ventromedial and lateral hypothalamus. Proc Natl Acad Sci U S A. 1970 Oct;67(2):1063-70. Pubmed
  2. Reisine TD, U’Prichard DC, Wiech NL, Ursillo RC, Yamamura HI: Effects of combined administration of amphetamine and iprindole on brain adrenergic receptors. Brain Res. 1980 Apr 28;188(2):587-92. Pubmed

8. D(2) dopamine receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

References:

  1. Innis RB, Malison RT, al-Tikriti M, Hoffer PB, Sybirska EH, Seibyl JP, Zoghbi SS, Baldwin RM, Laruelle M, Smith EO, et al.: Amphetamine-stimulated dopamine release competes in vivo for [123I]IBZM binding to the D2 receptor in nonhuman primates. Synapse. 1992 Mar;10(3):177-84. Pubmed

9. Amine oxidase [flavin-containing] B

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details

References:

  1. Clarke DE, Lyles GA, Callingham BA: A comparison of cardiac and vascular clorgyline-resistant amine oxidase and monoamine oxidase. Inhibition by amphetamine, mexiletine and other drugs. Biochem Pharmacol. 1982 Jan 1;31(1):27-35. Pubmed

10. Sodium-dependent serotonin transporter

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

References:

  1. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. Pubmed

Enzymes

1. Cytochrome P450 2D6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. Wu D, Otton SV, Inaba T, Kalow W, Sellers EM: Interactions of amphetamine analogs with human liver CYP2D6. Biochem Pharmacol. 1997 Jun 1;53(11):1605-12. Pubmed

2. Cytochrome P450 2A6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Siu EC, Tyndale RF: Selegiline is a mechanism-based inactivator of CYP2A6 inhibiting nicotine metabolism in humans and mice. J Pharmacol Exp Ther. 2008 Mar;324(3):992-9. Epub 2007 Dec 7. Pubmed

Transporters

1. Solute carrier family 22 member 3

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 3 O75751 Details

References:

  1. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. Pubmed
  2. Zhu HJ, Appel DI, Grundemann D, Markowitz JS: Interaction of organic cation transporter 3 (SLC22A3) and amphetamine. J Neurochem. 2010 Jul;114(1):142-9. doi: 10.1111/j.1471-4159.2010.06738.×. Epub 2010 Apr 6. Pubmed

2. Solute carrier family 22 member 5

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

References:

  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. Pubmed
  2. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. Pubmed
  3. Rytting E, Audus KL: Novel organic cation transporter 2-mediated carnitine uptake in placental choriocarcinoma (BeWo) cells. J Pharmacol Exp Ther. 2005 Jan;312(1):192-8. Epub 2004 Aug 17. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on December 03, 2015 09:51