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Identification
NameAmphetamine
Accession NumberDB00182  (APRD00480)
TypeSmall Molecule
GroupsApproved, Illicit
DescriptionAmphetamines are non-catecholamine sympathomimetic amines with CNS stimulant activity. By mimicking the structures of the catecholamine neurotransmitters, noradrenaline and dopamine, amphetamines modulate monoamine release, reuptake, and signalling within the brain. Although "amphetamine" is used as a descriptor of its own structural class, amphetamine properly refers to a racemic free base composed of equal parts of its two optical antipodes: levo-amphetamine and dextro-amphetamine. Used in the past for the treatment of depression, stress, and for concentration improvement, it is currently available as a prescription drug for the treatment of attention hyperactivity disorder (ADHD), narcolepsy, and as an adjunct in the treatment of exogenous obesity. Amphetamine is also available in a mixed salt/mixed enantiomer form (Adderall), where d-amphetamine and l-amphetamine are available in a ratio of 3:1. It is also available in a prodrug form as lisdexamfetamine.
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
rac-(2R)-1-phenylpropan-2-amine
rac-amphetamine
α-methylbenzeneethaneamine
α-methylphenethylamine
β-aminopropylbenzene
β-phenylisopropylamine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Adzenys XR-odtTablet, orally disintegrating12.5 mg/1OralNeos Therapeutics, Lp2016-02-16Not applicableUs
Adzenys XR-odtTablet, orally disintegrating3.1 mg/1OralNeos Therapeutics, Lp2016-02-16Not applicableUs
Adzenys XR-odtTablet, orally disintegrating15.7 mg/1OralNeos Therapeutics, Lp2016-02-16Not applicableUs
Adzenys XR-odtTablet, orally disintegrating6.3 mg/1OralNeos Therapeutics, Lp2016-02-16Not applicableUs
Adzenys XR-odtTablet, orally disintegrating18.8 mg/1OralNeos Therapeutics, Lp2016-02-16Not applicableUs
Adzenys XR-odtTablet, orally disintegrating9.4 mg/1OralNeos Therapeutics, Lp2016-02-16Not applicableUs
Dyanavel XRSuspension, extended release2.5 mg/mLOralTris Pharma Inc2015-10-01Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EvekeoTablet5 mg/1OralArbor Pharmaceuticals, Inc.2015-02-01Not applicableUs
EvekeoTablet10 mg/1OralArbor Pharmaceuticals, Inc.2015-02-01Not applicableUs
EvekeoTablet5 mg/1OralArbor Pharmaceuticals2015-11-01Not applicableUs
EvekeoTablet10 mg/1OralArbor Pharmaceuticals2015-11-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Act Amphetamine XRActavis Pharma Company
Adderallbryant ranch prepack
Adderall XRShire US Manufacturing Inc.
Apo-amphetamine XRApotex 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.
PMS-amphetamines XRPharmascience Inc
Sandoz Amphetamine XRSandoz Canada Incorporated
Salts
Name/CASStructureProperties
Amphetamine adipate
64770-51-0
Thumb
  • InChI Key: OFCJKOOVFDGTLY-UHFFFAOYSA-N
  • Monoisotopic Mass: 281.162708225
  • Average Mass: 281.352
DBSALT001323
Amphetamine aspartate
25333-81-7
Thumb
  • InChI Key: OJNSNSZTGUACNI-VAGRMJETSA-N
  • Monoisotopic Mass: 403.247106555
  • Average Mass: 403.523
DBSALT001345
Amphetamine aspartate monohydrate
851591-76-9
Thumb
  • InChI Key: DAWXRFCLWKUCNS-MNTSKLTCSA-N
  • Monoisotopic Mass: 421.257671239
  • Average Mass: 421.538
DBSALT001501
Amphetamine sulfate
60-13-9
Thumb
  • InChI Key: PYHRZPFZZDCOPH-UHFFFAOYSA-N
  • Monoisotopic Mass: 368.176978564
  • Average Mass: 368.49
DBSALT001205
Categories
UNIICK833KGX7E
CAS number300-62-9
WeightAverage: 135.2062
Monoisotopic: 135.104799421
Chemical FormulaC9H13N
InChI KeyKWTSXDURSIMDCE-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
Pharmacology
IndicationFor treatment of Attention Deficit Disorder with Hyperactivity (ADDH), narcolepsy, and exogenous obesity as a short term (a few weeks) adjunct in a regimen of weight reduction based on caloric restriction for patients refractory to alternative therapy.
Structured Indications
PharmacodynamicsNot Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Synaptic vesicular amine transporterProteinyes
inhibitor
HumanQ05940 details
Sodium-dependent dopamine transporterProteinyes
negative modulator
HumanQ01959 details
Cocaine- and amphetamine-regulated transcript proteinProteinyes
agonist
HumanQ16568 details
Trace amine-associated receptor 1Proteinyes
agonist
HumanQ96RJ0 details
Sodium-dependent noradrenaline transporterProteinunknown
stimulator
HumanP23975 details
Alpha adrenergic receptorProtein groupunknown
agonist
Humannot applicabledetails
Beta adrenergic receptorProtein groupunknown
agonist
Humannot applicabledetails
D(2) dopamine receptorProteinunknown
binder
HumanP14416 details
Amine oxidase [flavin-containing] BProteinunknownNot AvailableHumanP27338 details
Sodium-dependent serotonin transporterProteinunknown
binder
HumanP31645 details
Monoamine oxidaseProtein groupyes
inhibitor
Humannot applicabledetails
vesicular monoamine transporter 2 (VMAT2)ProteinyesNot AvailableHumanQ99870 details
Related Articles
AbsorptionAmphetamine forms easily absorbed molecules that are highly lipid soluble. D-amphetamine mean peak plasma concentrations of 44.9 ng/mL occurred at a median time of 5.0 hours after dosing, and L-amphetamine mean peak plasma concentrations of 14.5 ng/mL occurred at a median time of 5.25 hours after dosing.
Volume of distributionNot Available
Protein binding15-40%
Metabolism

Amphetamine is reported to be oxidized at the 4 position of the benzene ring to form 4-hydroxyamphetamine, or on the side chain α or β carbons to form alpha-hydroxy-amphetamine or norephedrine, respectively. Norephedrine and 4-hydroxy-amphetamine are both active and each is subsequently oxidized to form 4-hydroxy-norephedrine. Alpha-hydroxy-amphetamine undergoes deamination to form phenylacetone, which ultimately forms benzoic acid and its glucuronide and the glycine conjugate hippuric acid. Although the enzymes involved in amphetamine metabolism have not been clearly defined, CYP2D6 is known to be involved with formation of 4-hydroxy-amphetamine. Since CYP2D6 is genetically polymorphic, population variations in amphetamine metabolism are a possibility.

Route of eliminationWith normal urine pHs, approximately half of an administered dose of amphetamine is recoverable in urine as derivatives of alpha-hydroxy-amphetamine and approximately another 30-40% of the dose is recoverable in urine as amphetamine itself. Since amphetamine has a pKa of 9 .9, urinary recovery of amphetamine is highly dependent on pH and urine flow rates. Alkaline urine pHs result in less ionization and reduced renal elimination, and acidic pHs and high flow rates result in increased renal elimination with clearances greater than glomerular filtration rates, indicating the involvement of active secretion.
Half lifeThe half life for adults in the fasted state was found to be 11.25 hr.
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
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of Amphetamine.Experimental
AbirateroneThe serum concentration of Amphetamine can be increased when it is combined with Abiraterone.Approved
AcebutololThe risk or severity of adverse effects can be increased when Amphetamine is combined with Acebutolol.Approved
AcepromazineAcepromazine may decrease the stimulatory activities of Amphetamine.Approved, Vet Approved
AceprometazineAceprometazine may decrease the stimulatory activities of Amphetamine.Approved
AcetazolamideAcetazolamide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved, Vet Approved
AcetophenazineAcetophenazine may decrease the stimulatory activities of Amphetamine.Approved
AcrivastineAmphetamine may decrease the sedative activities of Acrivastine.Approved
AlcaftadineAmphetamine may decrease the sedative activities of Alcaftadine.Approved
AlfentanilAmphetamine may increase the analgesic activities of Alfentanil.Approved, Illicit
AlimemazineAmphetamine may decrease the sedative activities of Alimemazine.Approved, Vet Approved
AlphacetylmethadolAmphetamine may increase the analgesic activities of Alphacetylmethadol.Experimental, Illicit
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
Aluminum phosphateAluminum phosphate may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
AmineptineAmineptine may increase the stimulatory activities of Amphetamine.Illicit, Withdrawn
AmiodaroneThe metabolism of Amphetamine can be decreased when combined with Amiodarone.Approved, Investigational
AmisulprideAmisulpride may decrease the stimulatory activities of Amphetamine.Approved, Investigational
AmitriptylineAmitriptyline may increase the stimulatory activities of Amphetamine.Approved
Ammonium chlorideThe serum concentration of Amphetamine can be decreased when it is combined with Ammonium chloride.Approved, Vet Approved
AmperozideAmperozide may decrease the stimulatory activities of Amphetamine.Experimental
AntazolineAmphetamine may decrease the sedative activities of Antazoline.Approved
AripiprazoleAripiprazole may decrease the stimulatory activities of Amphetamine.Approved, Investigational
ArtemetherThe metabolism of Amphetamine can be decreased when combined with Artemether.Approved
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Amphetamine resulting in a loss in efficacy.Approved
AsenapineAsenapine may decrease the stimulatory activities of Amphetamine.Approved
AstemizoleAmphetamine may decrease the sedative activities of Astemizole.Approved, Withdrawn
AtomoxetineAtomoxetine may increase the hypertensive activities of Amphetamine.Approved
AzaperoneAzaperone may decrease the stimulatory activities of Amphetamine.Vet Approved
AzatadineAmphetamine may decrease the sedative activities of Azatadine.Approved
AzelastineAmphetamine may decrease the sedative activities of Azelastine.Approved
BenmoxinBenmoxin may increase the hypertensive activities of Amphetamine.Withdrawn
BenperidolBenperidol may decrease the stimulatory activities of Amphetamine.Investigational
BenzphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Benzphetamine.Approved, Illicit
BetaxololThe metabolism of Amphetamine can be decreased when combined with Betaxolol.Approved
BezitramideAmphetamine may increase the analgesic activities of Bezitramide.Experimental, Illicit, Withdrawn
BifeprunoxBifeprunox may decrease the stimulatory activities of Amphetamine.Investigational
Bismuth SubcitrateBismuth Subcitrate may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of Amphetamine.Approved
BromperidolBromperidol may decrease the stimulatory activities of Amphetamine.Investigational
BrompheniramineAmphetamine may decrease the sedative activities of Brompheniramine.Approved
BucindololThe risk or severity of adverse effects can be increased when Amphetamine is combined with Bucindolol.Investigational
BuclizineAmphetamine may decrease the sedative activities of Buclizine.Approved
BuprenorphineAmphetamine may increase the analgesic activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BupropionThe metabolism of Amphetamine can be decreased when combined with Bupropion.Approved
Butanoic AcidAmphetamine may decrease the sedative activities of Butanoic Acid.Experimental
ButorphanolAmphetamine may increase the analgesic activities of Butorphanol.Approved, Illicit, Vet Approved
Calcium carbonateCalcium carbonate may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
CarbinoxamineAmphetamine may decrease the sedative activities of Carbinoxamine.Approved
CarfentanilAmphetamine may increase the analgesic activities of Carfentanil.Illicit, Vet Approved
CariprazineCariprazine may decrease the stimulatory activities of Amphetamine.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of Amphetamine.Withdrawn
CelecoxibThe metabolism of Amphetamine can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Amphetamine is combined with Celiprolol.Approved, Investigational
CetirizineAmphetamine may decrease the sedative activities of Cetirizine.Approved
ChloropyramineAmphetamine may decrease the sedative activities of Chloropyramine.Approved
ChloroquineThe metabolism of Amphetamine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorphenamineAmphetamine may decrease the sedative activities of Chlorphenamine.Approved
ChlorphenoxamineAmphetamine may decrease the sedative activities of Chlorphenoxamine.Withdrawn
ChlorphentermineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Chlorphentermine.Illicit, Withdrawn
ChlorpromazineThe metabolism of Amphetamine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of Amphetamine.Approved, Withdrawn
CholecalciferolThe metabolism of Amphetamine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Amphetamine can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Amphetamine can be decreased when combined with Cinacalcet.Approved
CinnarizineAmphetamine may decrease the sedative activities of Cinnarizine.Approved
CitalopramThe metabolism of Amphetamine can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Amphetamine can be decreased when combined with Clemastine.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Clenbuterol.Approved, Vet Approved
ClobazamThe metabolism of Amphetamine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Amphetamine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Amphetamine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Amphetamine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Amphetamine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Amphetamine can be decreased when combined with Cocaine.Approved, Illicit
CodeineAmphetamine may increase the analgesic activities of Codeine.Approved, Illicit
CyamemazineCyamemazine may decrease the stimulatory activities of Amphetamine.Approved
CyclizineAmphetamine may decrease the sedative activities of Cyclizine.Approved
CyclobenzaprineCyclobenzaprine may increase the stimulatory activities of Amphetamine.Approved
CyproheptadineAmphetamine may decrease the sedative activities of Cyproheptadine.Approved
DapiprazoleDapiprazole may decrease the stimulatory activities of Amphetamine.Approved
DarifenacinThe metabolism of Amphetamine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Amphetamine can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Amphetamine can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Amphetamine can be decreased when combined with Desipramine.Approved
DesloratadineAmphetamine may decrease the sedative activities of Desloratadine.Approved, Investigational
DexbrompheniramineAmphetamine may decrease the sedative activities of Dexbrompheniramine.Approved
Dexchlorpheniramine maleateAmphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
DextromoramideAmphetamine may increase the analgesic activities of Dextromoramide.Experimental, Illicit
DextropropoxypheneAmphetamine may increase the analgesic activities of Dextropropoxyphene.Approved, Illicit, Withdrawn
DezocineAmphetamine may increase the analgesic activities of Dezocine.Approved
DiclofenamideDiclofenamide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
DihydrocodeineAmphetamine may increase the analgesic activities of Dihydrocodeine.Approved, Illicit
DihydroetorphineAmphetamine may increase the analgesic activities of Dihydroetorphine.Experimental, Illicit
DihydromorphineAmphetamine may increase the analgesic activities of Dihydromorphine.Experimental, Illicit
DimenhydrinateAmphetamine may decrease the sedative activities of Dimenhydrinate.Approved
DimetindeneAmphetamine may decrease the sedative activities of Dimetindene.Approved
DimetotiazineAmphetamine may decrease the sedative activities of Dimetotiazine.Approved
DiphenhydramineThe metabolism of Amphetamine can be decreased when combined with Diphenhydramine.Approved
DiphenoxylateAmphetamine may increase the analgesic activities of Diphenoxylate.Approved, Illicit
DobutamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Dopamine.Approved
DosulepinDosulepin may increase the stimulatory activities of Amphetamine.Approved
DoxepinAmphetamine may decrease the sedative activities of Doxepin.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Doxofylline.Approved
DoxylamineAmphetamine may decrease the sedative activities of Doxylamine.Approved, Vet Approved
DPDPEAmphetamine may increase the analgesic activities of DPDPE.Investigational
DronabinolDronabinol may increase the tachycardic activities of Amphetamine.Approved, Illicit
DronedaroneThe metabolism of Amphetamine can be decreased when combined with Dronedarone.Approved
DroperidolDroperidol may decrease the stimulatory activities of Amphetamine.Approved, Vet Approved
DuloxetineThe metabolism of Amphetamine can be decreased when combined with Duloxetine.Approved
EbastineAmphetamine may decrease the sedative activities of Ebastine.Investigational
EcopipamEcopipam may decrease the stimulatory activities of Amphetamine.Investigational
EliglustatThe metabolism of Amphetamine can be decreased when combined with Eliglustat.Approved
EmedastineAmphetamine may decrease the sedative activities of Emedastine.Approved
EphedrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ephedrine.Approved
EpinastineAmphetamine may decrease the sedative activities of Epinastine.Approved, Investigational
EpinephrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Epinephrine.Approved, Vet Approved
EsmirtazapineAmphetamine may decrease the sedative activities of Esmirtazapine.Investigational
EsomeprazoleEsomeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
EthopropazineAmphetamine may decrease the sedative activities of Ethopropazine.Approved
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with Amphetamine.Approved
EthoxzolamideEthoxzolamide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Withdrawn
EthylmorphineAmphetamine may increase the analgesic activities of Ethylmorphine.Approved, Illicit
EtilefrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Etilefrine.Withdrawn
EtorphineAmphetamine may increase the analgesic activities of Etorphine.Illicit, Vet Approved
FamotidineAmphetamine may decrease the sedative activities of Famotidine.Approved
FencamfamineFencamfamine may decrease the stimulatory activities of Amphetamine.Approved, Illicit, Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Fenoterol.Approved
FentanylAmphetamine may increase the analgesic activities of Fentanyl.Approved, Illicit, Investigational, Vet Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Amphetamine.Approved
FexofenadineAmphetamine may decrease the sedative activities of Fexofenadine.Approved
FlunarizineAmphetamine may decrease the sedative activities of Flunarizine.Approved
FluoxetineThe metabolism of Amphetamine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlupentixolFlupentixol may decrease the stimulatory activities of Amphetamine.Approved, Withdrawn
FluphenazineFluphenazine may decrease the stimulatory activities of Amphetamine.Approved
FluspirileneFluspirilene may decrease the stimulatory activities of Amphetamine.Approved
FluvoxamineThe metabolism of Amphetamine can be decreased when combined with Fluvoxamine.Approved, Investigational
FurazolidoneFurazolidone may increase the hypertensive activities of Amphetamine.Approved, Vet Approved
GuanethidineThe serum concentration of Amphetamine can be decreased when it is combined with Guanethidine.Approved
HaloperidolThe metabolism of Amphetamine can be decreased when combined with Haloperidol.Approved
HeroinAmphetamine may increase the analgesic activities of Heroin.Approved, Illicit
HexamethylenetetramineThe serum concentration of Amphetamine can be decreased when it is combined with Hexamethylenetetramine.Approved, Vet Approved
HydracarbazineHydracarbazine may increase the hypertensive activities of Amphetamine.Approved
HydrocodoneAmphetamine may increase the analgesic activities of Hydrocodone.Approved, Illicit
HydromorphoneAmphetamine may increase the analgesic activities of Hydromorphone.Approved, Illicit
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Amphetamine is combined with Hydroxyamphetamine hydrobromide.Approved
HydroxyzineAmphetamine may decrease the sedative activities of Hydroxyzine.Approved
IloperidoneIloperidone may decrease the stimulatory activities of Amphetamine.Approved
ImipramineThe metabolism of Amphetamine can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Amphetamine can be decreased when combined with Indinavir.Approved
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Amphetamine.Approved
Ioflupane I-123Amphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IproclozideIproclozide may increase the hypertensive activities of Amphetamine.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Amphetamine.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Amphetamine.Approved
IsoniazidThe metabolism of Amphetamine can be decreased when combined with Isoniazid.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Isoprenaline.Approved
IsothipendylAmphetamine may decrease the sedative activities of Isothipendyl.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Isoxsuprine.Approved, Withdrawn
Kct 0809Amphetamine may decrease the sedative activities of Kct 0809.Investigational
KetobemidoneAmphetamine may increase the analgesic activities of Ketobemidone.Approved
KetoconazoleThe metabolism of Amphetamine can be decreased when combined with Ketoconazole.Approved, Investigational
KetotifenAmphetamine may decrease the sedative activities of Ketotifen.Approved
L-Glutamic AcidThe serum concentration of Amphetamine can be decreased when it is combined with L-Glutamic Acid.Nutraceutical
LabetalolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Labetalol.Approved
LansoprazoleLansoprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
LevocabastineAmphetamine may decrease the sedative activities of Levocabastine.Approved
LevocetirizineAmphetamine may decrease the sedative activities of Levocetirizine.Approved
Levomethadyl AcetateAmphetamine may increase the analgesic activities of Levomethadyl Acetate.Approved
LevorphanolAmphetamine may increase the analgesic activities of Levorphanol.Approved
LinezolidLinezolid may increase the hypertensive activities of Amphetamine.Approved, Investigational
LithiumLithium may decrease the stimulatory activities of Amphetamine.Approved
LodoxamideAmphetamine may decrease the sedative activities of Lodoxamide.Approved
LofentanilAmphetamine may increase the analgesic activities of Lofentanil.Illicit
LopinavirThe metabolism of Amphetamine can be decreased when combined with Lopinavir.Approved
LoratadineAmphetamine may decrease the sedative activities of Loratadine.Approved
LorcaserinThe metabolism of Amphetamine can be decreased when combined with Lorcaserin.Approved
LoxapineLoxapine may decrease the stimulatory activities of Amphetamine.Approved
LumefantrineThe metabolism of Amphetamine can be decreased when combined with Lumefantrine.Approved
LurasidoneLurasidone may decrease the stimulatory activities of Amphetamine.Approved
MagaldrateMagaldrate may decrease the excretion rate of Amphetamine which could result in a higher serum level.Withdrawn
Magnesium carbonateMagnesium carbonate may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
Magnesium hydroxideMagnesium hydroxide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
Magnesium oxideMagnesium oxide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
Magnesium TrisilicateMagnesium Trisilicate may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
MebanazineMebanazine may increase the hypertensive activities of Amphetamine.Withdrawn
MeclizineAmphetamine may decrease the sedative activities of Meclizine.Approved
MelperoneMelperone may decrease the stimulatory activities of Amphetamine.Approved
MephentermineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Mephentermine.Approved
MepyramineAmphetamine may decrease the sedative activities of Mepyramine.Approved, Vet Approved
MequitazineAmphetamine may decrease the sedative activities of Mequitazine.Approved
MesoridazineMesoridazine may decrease the stimulatory activities of Amphetamine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Metaraminol.Approved, Investigational
MethadoneThe metabolism of Amphetamine can be decreased when combined with Methadone.Approved
Methadyl AcetateAmphetamine may increase the analgesic activities of Methadyl Acetate.Approved, Illicit
MethamphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Methamphetamine.Approved, Illicit
MethapyrileneAmphetamine may decrease the sedative activities of Methapyrilene.Withdrawn
MethazolamideMethazolamide may decrease the excretion rate of Amphetamine which could result in a higher serum level.Approved
MethotrimeprazineThe metabolism of Amphetamine can be decreased when combined with Methotrimeprazine.Approved
MethoxamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Methoxamine.Approved
Methylene blueMethylene blue may increase the hypertensive activities of Amphetamine.Investigational
MetiamideAmphetamine may decrease the sedative activities of Metiamide.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Amphetamine.Approved, Investigational
MianserinAmphetamine may decrease the sedative activities of Mianserin.Approved
MidodrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Midodrine.Approved
MinaprineMinaprine may increase the hypertensive activities of Amphetamine.Approved
MirabegronThe metabolism of Amphetamine can be decreased when combined with Mirabegron.Approved
MirtazapineAmphetamine may decrease the sedative activities of Mirtazapine.Approved
MizolastineAmphetamine may decrease the sedative activities of Mizolastine.Investigational
MoclobemideMoclobemide may increase the hypertensive activities of Amphetamine.Approved
MolindoneMolindone may decrease the stimulatory activities of Amphetamine.Approved
MorphineAmphetamine may increase the analgesic activities of Morphine.Approved, Investigational
NabiloneNabilone may increase the tachycardic activities of Amphetamine.Approved, Investigational
NalbuphineAmphetamine may increase the analgesic activities of Nalbuphine.Approved
NevirapineThe metabolism of Amphetamine can be decreased when combined with Nevirapine.Approved
NialamideNialamide may increase the hypertensive activities of Amphetamine.Withdrawn
NicardipineThe metabolism of Amphetamine can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Amphetamine can be decreased when combined with Nilotinib.Approved, Investigational
NizatidineAmphetamine may decrease the sedative activities of Nizatidine.Approved
NorepinephrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Norepinephrine.Approved
NormethadoneAmphetamine may increase the analgesic activities of Normethadone.Approved, Illicit
NortriptylineNortriptyline may increase the stimulatory activities of Amphetamine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Amphetamine is combined with Nylidrin.Approved
OctamoxinOctamoxin may increase the hypertensive activities of Amphetamine.Withdrawn
OlanzapineOlanzapine may decrease the stimulatory activities of Amphetamine.Approved, Investigational
OlopatadineAmphetamine may decrease the sedative activities of Olopatadine.Approved
OmeprazoleOmeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational, Vet Approved
OndansetronOndansetron may decrease the stimulatory activities of Amphetamine.Approved
OpipramolOpipramol may increase the stimulatory activities of Amphetamine.Investigational
OpiumAmphetamine may increase the analgesic activities of Opium.Approved, Illicit
OrciprenalineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Orciprenaline.Approved
OsanetantOsanetant may decrease the stimulatory activities of Amphetamine.Investigational
OxycodoneAmphetamine may increase the analgesic activities of Oxycodone.Approved, Illicit, Investigational
OxymetazolineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Oxymetazoline.Approved
OxymorphoneAmphetamine may increase the analgesic activities of Oxymorphone.Approved, Investigational, Vet Approved
PaliperidonePaliperidone may decrease the stimulatory activities of Amphetamine.Approved
PanobinostatThe serum concentration of Amphetamine can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazolePantoprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
PargylinePargyline may increase the hypertensive activities of Amphetamine.Approved
ParoxetineThe metabolism of Amphetamine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Amphetamine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PemirolastAmphetamine may decrease the sedative activities of Pemirolast.Approved
PentazocineAmphetamine may increase the analgesic activities of Pentazocine.Approved, Vet Approved
PerazinePerazine may decrease the stimulatory activities of Amphetamine.Investigational
PerospironePerospirone may decrease the stimulatory activities of Amphetamine.Approved
PerphenazinePerphenazine may decrease the stimulatory activities of Amphetamine.Approved
PethidineAmphetamine may increase the analgesic activities of Pethidine.Approved
PhenelzinePhenelzine may increase the hypertensive activities of Amphetamine.Approved
PhenindamineAmphetamine may decrease the sedative activities of Phenindamine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of Amphetamine.Withdrawn
PheniramineAmphetamine may decrease the sedative activities of Pheniramine.Approved
PhenmetrazineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Phenmetrazine.Approved, Illicit
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Amphetamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Amphetamine.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Phentermine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Phenylephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Phenylpropanolamine.Approved, Vet Approved, Withdrawn
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Amphetamine.Approved, Vet Approved
PimozidePimozide may decrease the stimulatory activities of Amphetamine.Approved
PipamperonePipamperone may decrease the stimulatory activities of Amphetamine.Approved
PipotiazinePipotiazine may decrease the stimulatory activities of Amphetamine.Approved
PiritramideAmphetamine may increase the analgesic activities of Piritramide.Investigational
PirlindolePirlindole may increase the hypertensive activities of Amphetamine.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Amphetamine.Withdrawn
ProcaterolThe risk or severity of adverse effects can be increased when Amphetamine is combined with Procaterol.Approved
ProchlorperazineProchlorperazine may decrease the stimulatory activities of Amphetamine.Approved, Vet Approved
PromazineThe metabolism of Amphetamine can be decreased when combined with Promazine.Approved, Vet Approved
PromethazineAmphetamine may decrease the sedative activities of Promethazine.Approved
PropericiazinePropericiazine may decrease the stimulatory activities of Amphetamine.Approved
ProthipendylProthipendyl may decrease the stimulatory activities of Amphetamine.Investigational
ProtriptylineProtriptyline may increase the stimulatory activities of Amphetamine.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Pseudoephedrine.Approved
QuetiapineQuetiapine may decrease the stimulatory activities of Amphetamine.Approved
QuinidineThe metabolism of Amphetamine can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Amphetamine can be decreased when combined with Quinine.Approved
RabeprazoleRabeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
RacepinephrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Racepinephrine.Approved
RacloprideRaclopride may decrease the stimulatory activities of Amphetamine.Investigational
RanitidineAmphetamine may decrease the sedative activities of Ranitidine.Approved
RanolazineThe metabolism of Amphetamine can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the hypertensive activities of Amphetamine.Approved
RemifentanilAmphetamine may increase the analgesic activities of Remifentanil.Approved
RemoxiprideRemoxipride may decrease the stimulatory activities of Amphetamine.Approved, Withdrawn
ReserpineReserpine may decrease the stimulatory activities of Amphetamine.Approved
RisperidoneRisperidone may decrease the stimulatory activities of Amphetamine.Approved, Investigational
RitanserinRitanserin may decrease the stimulatory activities of Amphetamine.Investigational
RitodrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ritodrine.Approved
RitonavirThe metabolism of Amphetamine can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Amphetamine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Amphetamine can be decreased when combined with Ropinirole.Approved, Investigational
Roxatidine acetateAmphetamine may decrease the sedative activities of Roxatidine acetate.Approved
SafrazineSafrazine may increase the hypertensive activities of Amphetamine.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Amphetamine.Approved, Investigational, Vet Approved
SertindoleSertindole may decrease the stimulatory activities of Amphetamine.Approved, Withdrawn
SertralineThe metabolism of Amphetamine can be decreased when combined with Sertraline.Approved
Spaglumic AcidAmphetamine may decrease the sedative activities of Spaglumic Acid.Approved
StiripentolThe metabolism of Amphetamine can be decreased when combined with Stiripentol.Approved
SufentanilAmphetamine may increase the analgesic activities of Sufentanil.Approved, Investigational
SulpirideSulpiride may decrease the stimulatory activities of Amphetamine.Approved
SynephrineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Synephrine.Experimental
TAK-390MRTAK-390MR can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Investigational
TapentadolAmphetamine may increase the analgesic activities of Tapentadol.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Amphetamine.Approved
TerbinafineThe metabolism of Amphetamine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerbutalineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Terbutaline.Approved
TerfenadineAmphetamine may decrease the sedative activities of Terfenadine.Withdrawn
TesmilifeneAmphetamine may decrease the sedative activities of Tesmilifene.Investigational
TetryzolineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Tetryzoline.Approved
ThioproperazineThioproperazine may decrease the stimulatory activities of Amphetamine.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Amphetamine.Approved
ThiothixeneThiothixene may decrease the stimulatory activities of Amphetamine.Approved
ThonzylamineAmphetamine may decrease the sedative activities of Thonzylamine.Approved
TianeptineTianeptine may increase the stimulatory activities of Amphetamine.Approved
TiaprideTiapride may decrease the stimulatory activities of Amphetamine.Investigational
TiclopidineThe metabolism of Amphetamine can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Amphetamine can be decreased when combined with Tipranavir.Approved, Investigational
ToloxatoneToloxatone may increase the hypertensive activities of Amphetamine.Approved
TramadolAmphetamine may increase the analgesic activities of Tramadol.Approved, Investigational
TranilastAmphetamine may decrease the sedative activities of Tranilast.Approved, Investigational
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Amphetamine.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Amphetamine.Approved
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of Amphetamine.Approved
TriflupromazineTriflupromazine may decrease the stimulatory activities of Amphetamine.Approved, Vet Approved
TrimipramineTrimipramine may increase the stimulatory activities of Amphetamine.Approved
TripelennamineAmphetamine may decrease the sedative activities of Tripelennamine.Approved, Vet Approved
TriprolidineAmphetamine may decrease the sedative activities of Triprolidine.Approved
TyramineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Tyramine.Investigational, Nutraceutical
VenlafaxineThe metabolism of Amphetamine can be decreased when combined with Venlafaxine.Approved
Vitamin CThe serum concentration of Amphetamine can be decreased when it is combined with Vitamin C.Approved, Nutraceutical
ZiprasidoneThe metabolism of Amphetamine can be decreased when combined with Ziprasidone.Approved
ZotepineZotepine may decrease the stimulatory activities of Amphetamine.Approved
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of Amphetamine.Approved, Investigational
Food InteractionsNot Available
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:7291243 ]
  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:3216957 ]
  3. Sax KW, Strakowski SM: Behavioral sensitization in humans. J Addict Dis. 2001;20(3):55-65. [PubMed:11681593 ]
  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:15955613 ]
  5. Heal DJ, Smith SL, Gosden J, Nutt DJ: Amphetamine, past and present--a pharmacological and clinical perspective. J Psychopharmacol. 2013 Jun;27(6):479-96. doi: 10.1177/0269881113482532. Epub 2013 Mar 28. [PubMed:23539642 ]
External Links
ATC CodesN06BA01
AHFS Codes
  • 28:20.04
PDB EntriesNot Available
FDA labelDownload (10.4 MB)
MSDSNot 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
Tablet, orally disintegratingOral12.5 mg/1
Tablet, orally disintegratingOral15.7 mg/1
Tablet, orally disintegratingOral18.8 mg/1
Tablet, orally disintegratingOral3.1 mg/1
Tablet, orally disintegratingOral6.3 mg/1
Tablet, orally disintegratingOral9.4 mg/1
CapsuleOral
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6322819 Yes1999-04-212019-04-21Us
US6384020 Yes2001-01-062021-01-06Us
US6605300 Yes1999-04-212019-04-21Us
US8062667 No2009-03-292029-03-29Us
US8597684 No2007-03-152027-03-15Us
US8709491 No2012-06-282032-06-28Us
US8747902 No2007-03-152027-03-15Us
US8840924 No2006-06-052026-06-05Us
US8883217 No2007-03-152027-03-15Us
US9017731 No2012-06-282032-06-28Us
US9265737 No2012-06-282032-06-28Us
USRE41148 Yes1999-04-212019-04-21Us
USRE42096 Yes1999-04-212019-04-21Us
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)splash10-0006-9000000000-98cd0a725199f943d6cfView in MoNA
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

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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. Requisite for vesicular amine storage prior to secretion via exocytosis.
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular Weight:
55712.075 Da
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:15955613 ]
  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:7751968 ]
  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:9648873 ]
  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.x. [PubMed:21272013 ]
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
Molecular Weight:
68494.255 Da
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:15602501 ]
  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:15661631 ]
  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:15764732 ]
  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:15795321 ]
  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:15950014 ]
  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:15728379 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Not Available
Specific Function:
Satiety factor closely associated with the actions of leptin and neuropeptide y; this anorectic peptide inhibits both normal and starvation-induced feeding and completely blocks the feeding response induced by neuropeptide Y and regulated by leptin in the hypothalamus. It promotes neuronal development and survival in vitro.
Gene Name:
CARTPT
Uniprot ID:
Q16568
Molecular Weight:
12828.975 Da
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:15597110 ]
  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:15644956 ]
  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:15661821 ]
  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:15680473 ]
  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:15680478 ]
  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:16713658 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
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 amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace ami...
Gene Name:
TAAR1
Uniprot ID:
Q96RJ0
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
Actions
stimulator
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
Molecular Weight:
69331.42 Da
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:12954796 ]
  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:7700252 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
Actions
agonist
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Components:
NameUniProt IDDetails
Alpha-1A adrenergic receptorP35348 Details
Alpha-1B adrenergic receptorP35368 Details
Alpha-1D adrenergic receptorP25100 Details
Alpha-2A adrenergic receptorP08913 Details
Alpha-2B adrenergic receptorP18089 Details
Alpha-2C adrenergic receptorP18825 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:4399738 ]
  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:6245760 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Components:
NameUniProt IDDetails
Beta-1 adrenergic receptorP08588 Details
Beta-2 adrenergic receptorP07550 Details
Beta-3 adrenergic receptorP13945 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:4399738 ]
  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:6245760 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
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:1532675 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular Weight:
58762.475 Da
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:7059347 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Serotonin:sodium symporter activity
Specific Function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin an...
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular Weight:
70324.165 Da
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:17209801 ]
Kind
Protein group
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Components:
NameUniProt IDDetails
Amine oxidase [flavin-containing] AP21397 Details
Amine oxidase [flavin-containing] BP27338 Details
References
  1. Heal DJ, Smith SL, Gosden J, Nutt DJ: Amphetamine, past and present--a pharmacological and clinical perspective. J Psychopharmacol. 2013 Jun;27(6):479-96. doi: 10.1177/0269881113482532. Epub 2013 Mar 28. [PubMed:23539642 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q99870
Molecular Weight:
Not Available
References
  1. Heal DJ, Smith SL, Gosden J, Nutt DJ: Amphetamine, past and present--a pharmacological and clinical perspective. J Psychopharmacol. 2013 Jun;27(6):479-96. doi: 10.1177/0269881113482532. Epub 2013 Mar 28. [PubMed:23539642 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 ]
  2. 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:9264312 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 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 ]
  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:18065502 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
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:9830022 ]
  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.x. Epub 2010 Apr 6. [PubMed:20402963 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
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:9618255 ]
  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:10454528 ]
  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:15316089 ]
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Drug created on June 13, 2005 07:24 / Updated on December 10, 2016 03:55