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Identification
Name3,4-Methylenedioxymethamphetamine
Accession NumberDB01454
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionAn N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy. [PubChem]
Structure
Thumb
Synonyms
Ecstasy
MDMA
External Identifiers Not Available
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
UNIIKE1SEN21RM
CAS number42542-10-9
WeightAverage: 193.2423
Monoisotopic: 193.110278729
Chemical FormulaC11H15NO2
InChI KeyInChIKey=SHXWCVYOXRDMCX-UHFFFAOYSA-N
InChI
InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
IUPAC Name
[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine
SMILES
CNC(C)CC1=CC2=C(OCO2)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Aralkylamine
  • Benzenoid
  • Oxacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationClinical trials are now testing the therapeutic potential of MDMA for post-traumatic stress disorder (PTSD) and anxiety associated with terminal cancer. MDMA is one of the four most widely used illicit drugs in the U.S.
PharmacodynamicsMDMA acts as a releasing agent of serotonin, norepinephrine, and dopamine.
Mechanism of actionIt enters neurons via carriage by the monoamine transporters. Once inside, MDMA inhibits the vesicular monoamine transporter, which results in increased concentrations of serotonin, norepinephrine, and dopamine into the cytoplasm, and induces their release by reversing their respective transporters through a process known as phosphorylation. It also acts as a weak 5-HT1 and 5-HT2 receptor agonist. MDMA's unusual entactogenic effects have been hypothesized to be, at least partly, the result of indirect oxytocin secretion via activation of the serotonin system. Oxytocin is a hormone released following events like hugging, orgasm, and childbirth, and is thought to facilitate bonding and the establishment of trust. Based on studies in rats, MDMA is believed to cause the release of oxytocin, at least in part, by both directly and indirectly agonizing the serotonin 5-HT1A receptor.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic: CYP450 extensively involved, especially CYP2D6 MDMA is known to be metabolized by two main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. The metabolism may be primarily by cytochrome P450 (CYP450) enzymes (CYP2D6 (in humans, but CYP2D1 in mice), and CYP3A4) and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug.

Route of eliminationrenal
Half life6–10 (though duration of effects is typically actually 3–5 hours)
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9639
Caco-2 permeable+0.6781
P-glycoprotein substrateNon-substrate0.6447
P-glycoprotein inhibitor INon-inhibitor0.8631
P-glycoprotein inhibitor IINon-inhibitor0.8926
Renal organic cation transporterNon-inhibitor0.7568
CYP450 2C9 substrateNon-substrate0.8507
CYP450 2D6 substrateNon-substrate0.5776
CYP450 3A4 substrateNon-substrate0.5325
CYP450 1A2 substrateInhibitor0.7626
CYP450 2C9 inhibitorNon-inhibitor0.8324
CYP450 2D6 inhibitorInhibitor0.7708
CYP450 2C19 inhibitorNon-inhibitor0.6331
CYP450 3A4 inhibitorNon-inhibitor0.6106
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5857
Ames testNon AMES toxic0.6597
CarcinogenicityNon-carcinogens0.9001
BiodegradationReady biodegradable0.5643
Rat acute toxicity2.7501 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9585
hERG inhibition (predictor II)Non-inhibitor0.9417
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 Solubility3.22 mg/mLALOGPS
logP1.65ALOGPS
logP1.86ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)10.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area30.49 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.25 m3·mol-1ChemAxon
Polarizability21.49 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Freudenmann RW, Oxler F, Bernschneider-Reif S: The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents. Addiction. 2006 Sep;101(9):1241-5. [PubMed:16911722 ]
  2. Jayanthi LD, Ramamoorthy S: Regulation of monoamine transporters: influence of psychostimulants and therapeutic antidepressants. AAPS J. 2005 Oct 27;7(3):E728-38. [PubMed:16353949 ]
  3. Verrico CD, Miller GM, Madras BK: MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Psychopharmacology (Berl). 2007 Jan;189(4):489-503. Epub 2005 Oct 12. [PubMed:16220332 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
AcepromazineAcepromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
AceprometazineAceprometazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
AcetazolamideAcetazolamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AcetophenazineAcetophenazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Acrivastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Acrivastine.
Alcaftadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Alcaftadine.
Alfentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Alfentanil.
Alimemazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Alimemazine.
Alphacetylmethadol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Alphacetylmethadol.
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Aluminum phosphateAluminum phosphate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
AmineptineAmineptine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
AmisulprideAmisulpride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
AmitriptylineAmitriptyline may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Ammonium chlorideThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Ammonium chloride.
AmperozideAmperozide may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Antazoline3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Antazoline.
AripiprazoleAripiprazole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
AsenapineAsenapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Astemizole3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Astemizole.
AzaperoneAzaperone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Azatadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Azatadine.
Azelastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Azelastine.
BenmoxinBenmoxin may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Bezitramide3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Bezitramide.
BifeprunoxBifeprunox may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Bismuth SubcitrateBismuth Subcitrate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Brompheniramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Brompheniramine.
Buclizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Buclizine.
Buprenorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Buprenorphine.
Butanoic Acid3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Butanoic Acid.
Butorphanol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Butorphanol.
Calcium carbonateCalcium carbonate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Carbinoxamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Carbinoxamine.
Carfentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Carfentanil.
CariprazineCariprazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
CaroxazoneCaroxazone may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Cetirizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cetirizine.
Chloropyramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Chloropyramine.
Chlorphenamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Chlorphenamine.
Chlorphenoxamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Chlorphenoxamine.
ChlorpromazineChlorpromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Cimetidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cimetidine.
Cinnarizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cinnarizine.
Clemastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Clemastine.
ClomipramineClomipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ClozapineClozapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Codeine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Codeine.
CyamemazineCyamemazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Cyclizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cyclizine.
CyclobenzaprineCyclobenzaprine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Cyproheptadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cyproheptadine.
DapiprazoleDapiprazole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
DesipramineDesipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Desloratadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Desloratadine.
Dexbrompheniramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dexbrompheniramine.
Dexchlorpheniramine maleate3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.
Dextromoramide3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dextromoramide.
Dextropropoxyphene3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dextropropoxyphene.
Dezocine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dezocine.
DiclofenamideDiclofenamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Dihydrocodeine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dihydrocodeine.
Dihydroetorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dihydroetorphine.
Dihydromorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dihydromorphine.
Dimenhydrinate3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dimenhydrinate.
Dimetindene3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dimetindene.
Dimetotiazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dimetotiazine.
Diphenhydramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Diphenhydramine.
Diphenoxylate3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Diphenoxylate.
DosulepinDosulepin may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Doxepin3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Doxepin.
DoxepinDoxepin may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Doxylamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Doxylamine.
DPDPE3,4-Methylenedioxymethamphetamine may increase the analgesic activities of DPDPE.
DroperidolDroperidol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Emedastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Emedastine.
Epinastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Epinastine.
Esmirtazapine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Esmirtazapine.
EsmirtazapineEsmirtazapine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Ethopropazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ethopropazine.
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with 3,4-Methylenedioxymethamphetamine.
EthoxzolamideEthoxzolamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Ethylmorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Ethylmorphine.
Etorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Etorphine.
Famotidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Famotidine.
FencamfamineFencamfamine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Fentanyl3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Fentanyl.
Fexofenadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Fexofenadine.
Flunarizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Flunarizine.
FlupentixolFlupentixol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
FluphenazineFluphenazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
FluspirileneFluspirilene may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
FurazolidoneFurazolidone may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
GuanethidineThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Guanethidine.
HaloperidolHaloperidol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Heroin3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Heroin.
HexamethylenetetramineThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Hexamethylenetetramine.
HydracarbazineHydracarbazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Hydrocodone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Hydrocodone.
Hydromorphone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Hydromorphone.
Hydroxyzine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Hydroxyzine.
IloperidoneIloperidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ImipramineImipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Ioflupane I-1233,4-Methylenedioxymethamphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
IproclozideIproclozide may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
IproniazidIproniazid may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
IsocarboxazidIsocarboxazid may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Isothipendyl3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Isothipendyl.
Ketobemidone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Ketobemidone.
Ketotifen3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ketotifen.
L-Glutamic AcidThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with L-Glutamic Acid.
Levocabastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Levocabastine.
Levocetirizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Levocetirizine.
Levomethadyl Acetate3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Levomethadyl Acetate.
Levorphanol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Levorphanol.
LithiumLithium may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Lodoxamide3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Lodoxamide.
Lofentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Lofentanil.
Loratadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Loratadine.
LoxapineLoxapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
LurasidoneLurasidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
MagaldrateMagaldrate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Magnesium carbonateMagnesium carbonate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Magnesium hydroxideMagnesium hydroxide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Magnesium oxideMagnesium oxide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
Magnesium TrisilicateMagnesium Trisilicate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
MebanazineMebanazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Meclizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Meclizine.
MelperoneMelperone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Mepyramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mepyramine.
Mequitazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mequitazine.
MesoridazineMesoridazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Methadone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Methadone.
Methadyl Acetate3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Methadyl Acetate.
Methapyrilene3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Methapyrilene.
MethazolamideMethazolamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a lower serum level and potentially a reduction in efficacy.
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Methylene blueMethylene blue may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Metiamide3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Metiamide.
Mianserin3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mianserin.
MinaprineMinaprine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Mirtazapine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mirtazapine.
MirtazapineMirtazapine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
MoclobemideMoclobemide may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
MolindoneMolindone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Morphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Morphine.
Nalbuphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Nalbuphine.
NialamideNialamide may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Nizatidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Nizatidine.
Normethadone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Normethadone.
NortriptylineNortriptyline may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
OctamoxinOctamoxin may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
OlanzapineOlanzapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Olopatadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Olopatadine.
OndansetronOndansetron may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Opium3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Opium.
OsanetantOsanetant may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Oxycodone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Oxycodone.
Oxymorphone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Oxymorphone.
PaliperidonePaliperidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
PargylinePargyline may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Pemirolast3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Pemirolast.
Pentazocine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Pentazocine.
PerospironePerospirone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
PerphenazinePerphenazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Pethidine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Pethidine.
PhenelzinePhenelzine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Phenindamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Phenindamine.
PheniprazinePheniprazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Pheniramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Pheniramine.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with 3,4-Methylenedioxymethamphetamine.
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with 3,4-Methylenedioxymethamphetamine.
PimozidePimozide may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
PipamperonePipamperone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
PipotiazinePipotiazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
PirlindolePirlindole may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
PivhydrazinePivhydrazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
ProchlorperazineProchlorperazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
PromazinePromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Promethazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Promethazine.
PropericiazinePropericiazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ProtriptylineProtriptyline may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
QuetiapineQuetiapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Ranitidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ranitidine.
RasagilineRasagiline may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Remifentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Remifentanil.
RemoxiprideRemoxipride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ReserpineReserpine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
RisperidoneRisperidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Roxatidine acetate3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Roxatidine acetate.
SafrazineSafrazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
SelegilineSelegiline may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
SertindoleSertindole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Spaglumic Acid3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Spaglumic Acid.
Sufentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Sufentanil.
SulpirideSulpiride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Tapentadol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Tapentadol.
Terfenadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Terfenadine.
Tesmilifene3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Tesmilifene.
ThioproperazineThioproperazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ThioridazineThioridazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ThiothixeneThiothixene may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Thonzylamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Thonzylamine.
TianeptineTianeptine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ToloxatoneToloxatone may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
Tramadol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Tramadol.
Tranilast3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Tranilast.
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
TranylcypromineTranylcypromine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
TriflupromazineTriflupromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
TrimipramineTrimipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Tripelennamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Tripelennamine.
Triprolidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Triprolidine.
Vitamin CThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Vitamin C.
ZiprasidoneZiprasidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ZotepineZotepine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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
unknown
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. 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 ]
  2. 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 ]
  3. 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
unknown
Actions
agonist
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
References
  1. Lyon RA, Glennon RA, Titeler M: 3,4-Methylenedioxymethamphetamine (MDMA): stereoselective interactions at brain 5-HT1 and 5-HT2 receptors. Psychopharmacology (Berl). 1986;88(4):525-6. [PubMed:2871581 ]
  2. Nash JF, Roth BL, Brodkin JD, Nichols DE, Gudelsky GA: Effect of the R(-) and S(+) isomers of MDA and MDMA on phosphatidyl inositol turnover in cultured cells expressing 5-HT2A or 5-HT2C receptors. Neurosci Lett. 1994 Aug 15;177(1-2):111-5. [PubMed:7824160 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins ...
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular Weight:
54297.41 Da
References
  1. Lyon RA, Glennon RA, Titeler M: 3,4-Methylenedioxymethamphetamine (MDMA): stereoselective interactions at brain 5-HT1 and 5-HT2 receptors. Psychopharmacology (Berl). 1986;88(4):525-6. [PubMed:2871581 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modul...
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular Weight:
51820.705 Da
References
  1. Nash JF, Roth BL, Brodkin JD, Nichols DE, Gudelsky GA: Effect of the R(-) and S(+) isomers of MDA and MDMA on phosphatidyl inositol turnover in cultured cells expressing 5-HT2A or 5-HT2C receptors. Neurosci Lett. 1994 Aug 15;177(1-2):111-5. [PubMed:7824160 ]
  2. Lyon RA, Glennon RA, Titeler M: 3,4-Methylenedioxymethamphetamine (MDMA): stereoselective interactions at brain 5-HT1 and 5-HT2 receptors. Psychopharmacology (Berl). 1986;88(4):525-6. [PubMed:2871581 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 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. 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 ]
  3. Haughey HM, Brown JM, Wilkins DG, Hanson GR, Fleckenstein AE: Differential effects of methamphetamine on Na(+)/Cl(-)-dependent transporters. Brain Res. 2000 Apr 28;863(1-2):59-65. [PubMed:10773193 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
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. Verrico CD, Miller GM, Madras BK: MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Psychopharmacology (Berl). 2007 Jan;189(4):489-503. Epub 2005 Oct 12. [PubMed:16220332 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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. Verrico CD, Miller GM, Madras BK: MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Psychopharmacology (Berl). 2007 Jan;189(4):489-503. Epub 2005 Oct 12. [PubMed:16220332 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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. Verrico CD, Miller GM, Madras BK: MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Psychopharmacology (Berl). 2007 Jan;189(4):489-503. Epub 2005 Oct 12. [PubMed:16220332 ]
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Drug created on July 31, 2007 07:09 / Updated on August 17, 2016 12:23