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Identification
Name4-Methoxyamphetamine
Accession NumberDB01472  (EXPT03303)
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionNot 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 Identifiers
  • J213.549C
  • J434.573H
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIOVB8F8P39Q
CAS number64-13-1
WeightAverage: 165.2322
Monoisotopic: 165.115364107
Chemical FormulaC10H15NO
InChI KeyNEGYEDYHPHMHGK-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action4-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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium-dependent dopamine transporterProteinyes
inhibitor
HumanQ01959 details
Sodium-dependent serotonin transporterProteinyes
inhibitor
HumanP31645 details
Synaptic vesicular amine transporterProteinyes
inhibitor
HumanQ05940 details
Alpha-1A adrenergic receptorProteinyes
agonist
HumanP35348 details
Alpha-2A adrenergic receptorProteinyes
agonist
HumanP08913 details
Amine oxidase [flavin-containing] AProteinunknown
inhibitor
HumanP21397 details
Amine oxidase [flavin-containing] BProteinunknown
inhibitor
HumanP27338 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
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
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
Aop2007044-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Aop200704.Investigational
Arotinolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Arotinolol.Approved
ArtemetherThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Artemether.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
Betaxolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Betaxolol.Approved
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
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
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
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, Vet Approved
ChlorpromazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Chlorpromazine.Approved, 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
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
ClobazamThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineClomipramine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved, Vet Approved
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
CyclobenzaprineCyclobenzaprine may decrease the antihypertensive 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
DesvenlafaxineDesvenlafaxine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
DiphenhydramineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Diphenhydramine.Approved
DosulepinDosulepin may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
DoxepinDoxepin may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
DronedaroneThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Eliglustat.Approved
EsmirtazapineEsmirtazapine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Investigational
Esmolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Esmolol.Approved
FluoxetineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Fluvoxamine.Approved, Investigational
HaloperidolThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Haloperidol.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
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with 4-Methoxyamphetamine.Approved
IsoniazidThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Isoniazid.Approved
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
LevomilnacipranLevomilnacipran may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
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
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
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
MilnacipranMilnacipran may decrease the antihypertensive 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
Nadolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Nadolol.Approved
NevirapineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nevirapine.Approved
NicardipineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Nilotinib.Approved, Investigational
NortriptylineNortriptyline may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
OpipramolOpipramol may decrease the antihypertensive activities of 4-Methoxyamphetamine.Investigational
Oxprenolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Oxprenolol.Approved
PanobinostatThe serum concentration of 4-Methoxyamphetamine can be increased when it is combined with Panobinostat.Approved, Investigational
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
Pindolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Pindolol.Approved
Practolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Practolol.Approved
PromazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Promazine.Approved, Vet Approved
Propranolol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Propranolol.Approved, Investigational
ProtriptylineProtriptyline may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
QuinidineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ranolazine.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
RopiniroleThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ropinirole.Approved, Investigational
SertralineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Sertraline.Approved
Sotalol4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Sotalol.Approved
StiripentolThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Stiripentol.Approved
TerbinafineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThioridazineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Thioridazine.Approved
TianeptineTianeptine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
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
TranylcypromineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Tranylcypromine.Approved
TrimipramineTrimipramine may decrease the antihypertensive activities of 4-Methoxyamphetamine.Approved
VenlafaxineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Venlafaxine.Approved
ZiprasidoneThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.19 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Ether
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • 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:
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. 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 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. 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. Requisite for vesicular amine storage prior to secretion via exocytosis.
Gene Name:
SLC18A2
Uniprot ID:
Q05940
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23