Identification

Name
4-Methoxyamphetamine
Accession Number
DB01472  (EXPT03303)
Type
Small Molecule
Groups
Experimental, Illicit
Description
Not Available
Structure
Thumb
Synonyms
  • (2RS)-1-(4-methoxyphenyl)propan-2-amine
  • 4-methoxyamfetamine
  • D,L-p-methoxyamphetamine
  • Formoterol fumarate related compound G
  • P-methoxyamfetamine
  • P-methoxyamphetamine
  • Paramethoxyamphetamine
External IDs
J213.549C / J434.573H
Categories
UNII
OVB8F8P39Q
CAS number
64-13-1
Weight
Average: 165.2322
Monoisotopic: 165.115364107
Chemical Formula
C10H15NO
InChI Key
NEGYEDYHPHMHGK-UHFFFAOYSA-N
InChI
InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3
IUPAC Name
1-(4-methoxyphenyl)propan-2-amine
SMILES
COC1=CC=C(CC(C)N)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

4-Methoxyamphetamine is a seratogenic drug of the amphetamine class. The drug acts as a potent and selective serotonin releasing agent. It binds to alpha receptors to mediate these effects.

TargetActionsOrganism
ASodium-dependent dopamine transporter
inhibitor
Human
ASodium-dependent serotonin transporter
inhibitor
Human
ASynaptic vesicular amine transporter
inhibitor
Human
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
UAmine oxidase [flavin-containing] A
inhibitor
Human
UAmine oxidase [flavin-containing] B
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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 4-Methoxyamphetamine.Experimental
AbirateroneThe serum concentration of 4-Methoxyamphetamine can be increased when it is combined with Abiraterone.Approved
Acebutolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Acebutolol.Approved, Investigational
AcepromazineAcepromazine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Vet Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
Alprenolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Alprenolol.Approved, Withdrawn
AmineptineAmineptine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Illicit, Withdrawn
AmiodaroneThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineAmitriptyline may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
AmitriptylinoxideAmitriptylinoxide may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
AmoxapineAmoxapine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
AmphetamineAmphetamine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Illicit, Investigational
AripiprazoleAripiprazole may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
Arotinolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Arotinolol.Investigational
ArtemetherThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Artemether.Approved
Asenapine4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Asenapine.Approved
Atenolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Atenolol.Approved
AtomoxetineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Atomoxetine.Approved
Befunolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Befunolol.Experimental
BenmoxinBenmoxin may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
Benzylpenicilloyl Polylysine4-Methoxyamphetamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
Betaxolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved, Investigational
Bevantolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Bevantolol.Approved
Bisoprolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Bisoprolol.Approved
Bopindolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Bopindolol.Approved
BrexpiprazoleBrexpiprazole may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
BrofaromineBrofaromine may increase the hypertensive activities of 4-Methoxyamphetamine.Experimental
BromocriptineBromocriptine may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
Bucindolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Bucindolol.Investigational
Bufuralol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Bufuralol.Experimental, Investigational
BunazosinBunazosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Investigational
Bupranolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Bupranolol.Approved
BupropionThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Bupropion.Approved
ButriptylineButriptyline may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
CabergolineCabergoline may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
Carteolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Carteolol.Approved
Carvedilol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Carvedilol.Approved, Investigational
CelecoxibThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Celecoxib.Approved, Investigational
Celiprolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Celiprolol.Approved, Investigational
ChloroquineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Chloroquine.Approved, Investigational, Vet Approved
ChlorpromazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Chlorpromazine.Approved, Investigational, Vet Approved
CholecalciferolThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Cimetidine.Approved, Investigational
CinacalcetThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Clemastine.Approved, Investigational
ClobazamThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineClomipramine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved, Investigational, Vet Approved
Cloranolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Cloranolol.Experimental
ClotrimazoleThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of 4-Methoxyamphetamine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Cocaine.Approved, Illicit
CurcuminThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Curcumin.Approved, Investigational
DapiprazoleDapiprazole may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
DarifenacinThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of 4-Methoxyamphetamine can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Delavirdine.Approved
DesipramineDesipramine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of 4-Methoxyamphetamine.Approved, Investigational
DextroamphetamineDextroamphetamine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Illicit
DibenzepinDibenzepin may decrease the antihypertensive activities of 4-Methoxyamphetamine.Experimental
DihydroergocornineDihydroergocornine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
DihydroergocristineDihydroergocristine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Experimental
DihydroergocryptineDihydroergocryptine may increase the hypertensive activities of 4-Methoxyamphetamine.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
DimetacrineDimetacrine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved, Withdrawn
DiphenhydramineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Diphenhydramine.Approved, Investigational
DosulepinDosulepin may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
DoxepinDoxepin may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
DronedaroneThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Dronedarone.Approved
DroperidolDroperidol may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Vet Approved
DuloxetineDuloxetine may increase the tachycardic activities of 4-Methoxyamphetamine.Approved
EliglustatThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Eliglustat.Approved
Epanolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Epanolol.Experimental
EpinephrineEpinephrine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.Approved
ErgonovineErgonovine may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.Approved
ErgotamineErgotamine may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.Approved
Esatenolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Esatenolol.Experimental
EscitalopramEscitalopram may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
Esmolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with 4-Methoxyamphetamine.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlupentixolFlupentixol may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational, Withdrawn
FluvoxamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Fluvoxamine.Approved, Investigational
FurazolidoneFurazolidone may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational, Vet Approved
HaloperidolThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Haloperidol.Approved
HarmalineHarmaline may increase the hypertensive activities of 4-Methoxyamphetamine.Experimental
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypertensive activities of 4-Methoxyamphetamine.Experimental
IloperidoneIloperidone may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
ImipramineImipramine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
Indenolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Indenolol.Withdrawn
IndinavirThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Indinavir.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with 4-Methoxyamphetamine.Approved, Investigational
IprindoleIprindole may decrease the antihypertensive activities of 4-Methoxyamphetamine.Experimental
IproclozideIproclozide may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
IsocarboxazidThe therapeutic efficacy of 4-Methoxyamphetamine can be increased when used in combination with Isocarboxazid.Approved
IsoniazidThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Isoniazid.Approved, Investigational
KetoconazoleThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ketoconazole.Approved, Investigational
Labetalol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Labetalol.Approved
Landiolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Landiolol.Investigational
Levobetaxolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Levobetaxolol.Approved, Investigational
LevomilnacipranLevomilnacipran may increase the tachycardic activities of 4-Methoxyamphetamine.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
LisurideLisuride may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
LofepramineLofepramine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Experimental
LopinavirThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Lorcaserin.Approved
LumefantrineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Lumefantrine.Approved
Lysergic Acid DiethylamideLysergic Acid Diethylamide may increase the hypertensive activities of 4-Methoxyamphetamine.Illicit, Investigational, Withdrawn
ManidipineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Manidipine.Approved, Investigational
MebanazineMebanazine may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
MelitracenMelitracen may decrease the antihypertensive activities of 4-Methoxyamphetamine.Experimental, Investigational
Mepindolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Mepindolol.Experimental
MetergolineMetergoline may increase the hypertensive activities of 4-Methoxyamphetamine.Experimental
MethadoneThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Methotrimeprazine.Approved, Investigational
Methylene blueMethylene blue may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive and vasoconstricting activities of 4-Methoxyamphetamine.Approved
MethysergideMethysergide may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
Metoprolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Metoprolol.Approved, Investigational
MianserinThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Mianserin.Approved, Investigational
MidostaurinThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Midostaurin.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of 4-Methoxyamphetamine.Approved, Investigational
MinaprineMinaprine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
MirabegronThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Mirabegron.Approved
MirtazapineMirtazapine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
MoclobemideMoclobemide may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
Nadolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Nadolol.Approved
Nebivolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Nebivolol.Approved, Investigational
NefazodoneNefazodone may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Withdrawn
NevirapineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nevirapine.Approved
NialamideNialamide may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
NicardipineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nicardipine.Approved, Investigational
NicergolineNicergoline may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
NiguldipineNiguldipine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Experimental
NilotinibThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nilotinib.Approved, Investigational
NortriptylineNortriptyline may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
OctamoxinOctamoxin may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
OlanzapineOlanzapine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
OpipramolOpipramol may decrease the antihypertensive activities of 4-Methoxyamphetamine.Investigational
Oxprenolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Oxprenolol.Approved
PaliperidonePaliperidone may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
PanobinostatThe serum concentration of 4-Methoxyamphetamine can be increased when it is combined with Panobinostat.Approved, Investigational
PargylinePargyline may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
ParoxetineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of 4-Methoxyamphetamine can be decreased when it is combined with Peginterferon alfa-2b.Approved
Penbutolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Penbutolol.Approved, Investigational
PergolidePergolide may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational, Vet Approved, Withdrawn
PhenelzinePhenelzine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
PhenoxybenzaminePhenoxybenzamine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
PhentolaminePhentolamine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
Pindolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Pindolol.Approved, Investigational
PirlindolePirlindole may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
PitolisantThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Pitolisant.Approved, Investigational
PivhydrazinePivhydrazine may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
PizotifenPizotifen may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
Platelet Activating Factor4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Platelet Activating Factor.Experimental
Practolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
ProcaineProcaine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational, Vet Approved
ProcarbazineProcarbazine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
PromazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Promazine.Approved, Vet Approved
Propafenone4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Propafenone.Approved
PropericiazinePropericiazine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
PropiomazinePropiomazine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
PropiverinePropiverine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
Propranolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Propranolol.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
QuetiapineQuetiapine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
QuinidineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Quinidine.Approved, Investigational
QuinineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Quinine.Approved
RacepinephrineRacepinephrine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
RanolazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
RisperidoneRisperidone may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
RitonavirThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Rolapitant.Approved, Investigational
RopiniroleThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ropinirole.Approved, Investigational
RucaparibThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Rucaparib.Approved, Investigational
SafrazineSafrazine may increase the hypertensive activities of 4-Methoxyamphetamine.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational, Vet Approved
SertralineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Sertraline.Approved
SilodosinSilodosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
Sotalol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Sotalol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
StiripentolThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Stiripentol.Approved
Talinolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Talinolol.Investigational
TamsulosinTamsulosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
TerazosinTerazosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
TerbinafineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
Terbutaline4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Terbutaline.Approved
TergurideTerguride may increase the hypertensive activities of 4-Methoxyamphetamine.Experimental
Tertatolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Tertatolol.Experimental
ThioproperazineThioproperazine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
ThioridazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Thioridazine.Approved, Withdrawn
TianeptineTianeptine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
TiclopidineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ticlopidine.Approved
Timolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Timolol.Approved
TipranavirThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Tipranavir.Approved, Investigational
TolazolineTolazoline may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Vet Approved
ToloxatoneToloxatone may increase the hypertensive activities of 4-Methoxyamphetamine.Approved
TranylcypromineTranylcypromine may increase the hypertensive activities of 4-Methoxyamphetamine.Approved, Investigational
TrazodoneTrazodone may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
TrifluoperazineTrifluoperazine may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
TrimazosinTrimazosin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Experimental
TrimipramineTrimipramine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
UrapidilUrapidil may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of 4-Methoxyamphetamine.Approved
VerapamilVerapamil may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved
ZiprasidoneThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ziprasidone.Approved
ZuclopenthixolZuclopenthixol may decrease the vasoconstricting activities of 4-Methoxyamphetamine.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
31721
PubChem Substance
46507471
ChemSpider
29417
BindingDB
50024209
ChEMBL
CHEMBL278663
Wikipedia
4-Methoxyamphetamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.928 mg/mLALOGPS
logP1.74ALOGPS
logP1.65ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)10.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.25 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.17 m3·mol-1ChemAxon
Polarizability19.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9283
Caco-2 permeable+0.7646
P-glycoprotein substrateNon-substrate0.688
P-glycoprotein inhibitor INon-inhibitor0.9424
P-glycoprotein inhibitor IINon-inhibitor0.9812
Renal organic cation transporterNon-inhibitor0.7678
CYP450 2C9 substrateNon-substrate0.8422
CYP450 2D6 substrateSubstrate0.8336
CYP450 3A4 substrateNon-substrate0.6008
CYP450 1A2 substrateInhibitor0.6567
CYP450 2C9 inhibitorNon-inhibitor0.9747
CYP450 2D6 inhibitorInhibitor0.8492
CYP450 2C19 inhibitorNon-inhibitor0.6537
CYP450 3A4 inhibitorNon-inhibitor0.9431
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8424
Ames testNon AMES toxic0.6201
CarcinogenicityNon-carcinogens0.8044
BiodegradationNot ready biodegradable0.875
Rat acute toxicity2.8848 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8836
hERG inhibition (predictor II)Non-inhibitor0.8576
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.19 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Phenoxy compounds / Methoxybenzenes / Anisoles / Aralkylamines / Alkyl aryl ethers / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Amphetamine or derivatives / Phenylpropane / Anisole / Phenol ether / Phenoxy compound / Methoxybenzene / Aralkylamine / Alkyl aryl ether / Ether / Primary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F: Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77. [PubMed:11041537]
  2. Hansen JP, Riddle EL, Sandoval V, Brown JM, Gibb JW, Hanson GR, Fleckenstein AE: Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity. J Pharmacol Exp Ther. 2002 Mar;300(3):1093-100. [PubMed:11861820]
  3. Fitzgerald JL, Reid JJ: Effects of methylenedioxymethamphetamine on the release of monoamines from rat brain slices. Eur J Pharmacol. 1990 Nov 27;191(2):217-20. [PubMed:1982265]
  4. 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
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
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 t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F: Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77. [PubMed:11041537]
  2. Shankaran M, Yamamoto BK, Gudelsky GA: Involvement of the serotonin transporter in the formation of hydroxyl radicals induced by 3,4-methylenedioxymethamphetamine. Eur J Pharmacol. 1999 Dec 3;385(2-3):103-10. [PubMed:10607865]
  3. Whitworth TL, Herndon LC, Quick MW: Psychostimulants differentially regulate serotonin transporter expression in thalamocortical neurons. J Neurosci. 2002 Jan 1;22(1):RC192. [PubMed:11756522]
  4. Szabo Z, McCann UD, Wilson AA, Scheffel U, Owonikoko T, Mathews WB, Ravert HT, Hilton J, Dannals RF, Ricaurte GA: Comparison of (+)-(11)C-McN5652 and (11)C-DASB as serotonin transporter radioligands under various experimental conditions. J Nucl Med. 2002 May;43(5):678-92. [PubMed:11994534]
  5. Boot BP, Mechan AO, McCann UD, Ricaurte GA: MDMA- and p-chlorophenylalanine-induced reduction in 5-HT concentrations: effects on serotonin transporter densities. Eur J Pharmacol. 2002 Oct 25;453(2-3):239-44. [PubMed:12398910]
  6. Saldana SN, Barker EL: Temperature and 3,4-methylenedioxymethamphetamine alter human serotonin transporter-mediated dopamine uptake. Neurosci Lett. 2004 Jan 16;354(3):209-12. [PubMed:14700733]
  7. Bogen IL, Haug KH, Myhre O, Fonnum F: Short- and long-term effects of MDMA ("ecstasy") on synaptosomal and vesicular uptake of neurotransmitters in vitro and ex vivo. Neurochem Int. 2003 Sep-Oct;43(4-5):393-400. [PubMed:12742084]
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...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Biezonski DK, Meyer JS: Effects of 3,4-methylenedioxymethamphetamine (MDMA) on serotonin transporter and vesicular monoamine transporter 2 protein and gene expression in rats: implications for MDMA neurotoxicity. J Neurochem. 2010 Feb;112(4):951-62. doi: 10.1111/j.1471-4159.2009.06515.x. Epub 2009 Nov 30. [PubMed:20002520]
  2. Hansen JP, Riddle EL, Sandoval V, Brown JM, Gibb JW, Hanson GR, Fleckenstein AE: Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity. J Pharmacol Exp Ther. 2002 Mar;300(3):1093-100. [PubMed:11861820]
Kind
Protein
Organism
Human
Pharmacological action
Yes
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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Green AL, El Hait MA: p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J Pharm Pharmacol. 1980 Apr;32(4):262-6. [PubMed:6103055]
  2. Ask AL, Fagervall I, Ross SB: Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):79-87. [PubMed:6646243]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Green AL, El Hait MA: p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J Pharm Pharmacol. 1980 Apr;32(4):262-6. [PubMed:6103055]
  2. Ask AL, Fagervall I, Ross SB: Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):79-87. [PubMed:6646243]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. 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]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Drug created on June 13, 2005 07:24 / Updated on July 02, 2018 17:34