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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 KeySHXWCVYOXRDMCX-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
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.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium-dependent serotonin transporterProteinyes
negative modulator
HumanP31645 details
Synaptic vesicular amine transporterProteinyes
inhibitor
HumanQ05940 details
Sodium-dependent dopamine transporterProteinunknown
negative modulator
HumanQ01959 details
5-hydroxytryptamine receptor 2AProteinunknown
agonist
HumanP28223 details
5-hydroxytryptamine receptor 2BProteinunknown
agonist
HumanP41595 details
5-hydroxytryptamine receptor 2CProteinunknown
agonist
HumanP28335 details
Sodium-dependent noradrenaline transporterProteinyes
negative modulator
HumanP23975 details
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
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 3,4-Methylenedioxymethamphetamine.Experimental
AcepromazineAcepromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
AceprometazineAceprometazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
AcetazolamideAcetazolamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved, Vet Approved
AcetophenazineAcetophenazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Acrivastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Acrivastine.Approved
Alcaftadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Alcaftadine.Approved
Alfentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Alfentanil.Approved, Illicit
Alimemazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Alimemazine.Approved, Vet Approved
Alphacetylmethadol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Alphacetylmethadol.Experimental, Illicit
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
Aluminum phosphateAluminum phosphate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
AmineptineAmineptine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Illicit, Withdrawn
AmisulprideAmisulpride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Investigational
AmitriptylineAmitriptyline may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Ammonium chlorideThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Ammonium chloride.Approved, Vet Approved
AmperozideAmperozide may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Experimental
Antazoline3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Antazoline.Approved
AripiprazoleAripiprazole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Investigational
AsenapineAsenapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Astemizole3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Astemizole.Approved, Withdrawn
AzaperoneAzaperone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Vet Approved
Azatadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Azatadine.Approved
Azelastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Azelastine.Approved
BenmoxinBenmoxin may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
BenperidolBenperidol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Bezitramide3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Bezitramide.Experimental, Illicit, Withdrawn
BifeprunoxBifeprunox may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Bismuth SubcitrateBismuth Subcitrate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
BromperidolBromperidol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Brompheniramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Brompheniramine.Approved
Buclizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Buclizine.Approved
Buprenorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
Butanoic Acid3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Butanoic Acid.Experimental
Butorphanol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Butorphanol.Approved, Illicit, Vet Approved
Calcium carbonateCalcium carbonate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
Carbinoxamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Carbinoxamine.Approved
Carfentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Carfentanil.Illicit, Vet Approved
CariprazineCariprazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
Cetirizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cetirizine.Approved
Chloropyramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Chloropyramine.Approved
Chlorphenamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Chlorphenamine.Approved
Chlorphenoxamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Chlorphenoxamine.Withdrawn
ChlorpromazineChlorpromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Withdrawn
Cimetidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cimetidine.Approved
Cinnarizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cinnarizine.Approved
Clemastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Clemastine.Approved
ClomipramineClomipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
ClozapineClozapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Codeine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Codeine.Approved, Illicit
CyamemazineCyamemazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Cyclizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cyclizine.Approved
CyclobenzaprineCyclobenzaprine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Cyproheptadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Cyproheptadine.Approved
DapiprazoleDapiprazole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
DesipramineDesipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Desloratadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Desloratadine.Approved, Investigational
Dexbrompheniramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dexbrompheniramine.Approved
Dexchlorpheniramine maleate3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
Dextromoramide3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dextromoramide.Experimental, Illicit
Dextropropoxyphene3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dextropropoxyphene.Approved, Illicit, Withdrawn
Dezocine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dezocine.Approved
DiclofenamideDiclofenamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
Dihydrocodeine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dihydrocodeine.Approved, Illicit
Dihydroetorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dihydroetorphine.Experimental, Illicit
Dihydromorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Dihydromorphine.Experimental, Illicit
Dimenhydrinate3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dimenhydrinate.Approved
Dimetindene3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dimetindene.Approved
Dimetotiazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dimetotiazine.Approved
Diphenhydramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Diphenhydramine.Approved
Diphenoxylate3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Diphenoxylate.Approved, Illicit
DosulepinDosulepin may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Doxepin3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Doxepin.Approved
Doxylamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Doxylamine.Approved, Vet Approved
DPDPE3,4-Methylenedioxymethamphetamine may increase the analgesic activities of DPDPE.Investigational
DroperidolDroperidol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
Ebastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ebastine.Investigational
EcopipamEcopipam may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Emedastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Emedastine.Approved
Epinastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Epinastine.Approved, Investigational
Esmirtazapine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Esmirtazapine.Investigational
Ethopropazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ethopropazine.Approved
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with 3,4-Methylenedioxymethamphetamine.Approved
EthoxzolamideEthoxzolamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Withdrawn
Ethylmorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Ethylmorphine.Approved, Illicit
Etorphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Etorphine.Illicit, Vet Approved
Famotidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Famotidine.Approved
FencamfamineFencamfamine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Illicit, Withdrawn
Fentanyl3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Fentanyl.Approved, Illicit, Investigational, Vet Approved
Fexofenadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Fexofenadine.Approved
Flunarizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Flunarizine.Approved
FlupentixolFlupentixol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Withdrawn
FluphenazineFluphenazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
FluspirileneFluspirilene may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
FurazolidoneFurazolidone may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
GuanethidineThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Guanethidine.Approved
HaloperidolHaloperidol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Heroin3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Heroin.Approved, Illicit
HexamethylenetetramineThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Hexamethylenetetramine.Approved, Vet Approved
HydracarbazineHydracarbazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
Hydrocodone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Hydrocodone.Approved, Illicit
Hydromorphone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Hydromorphone.Approved, Illicit
Hydroxyzine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Hydroxyzine.Approved
IloperidoneIloperidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
ImipramineImipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Ioflupane I-1233,4-Methylenedioxymethamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IproclozideIproclozide may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
Isothipendyl3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Isothipendyl.Approved
Kct 08093,4-Methylenedioxymethamphetamine may decrease the sedative activities of Kct 0809.Investigational
Ketobemidone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Ketobemidone.Approved
Ketotifen3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ketotifen.Approved
L-Glutamic AcidThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with L-Glutamic Acid.Nutraceutical
Levocabastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Levocabastine.Approved
Levocetirizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Levocetirizine.Approved
Levomethadyl Acetate3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Levomethadyl Acetate.Approved
Levorphanol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Levorphanol.Approved
LithiumLithium may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Lodoxamide3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Lodoxamide.Approved
Lofentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Lofentanil.Illicit
Loratadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Loratadine.Approved
LoxapineLoxapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
LurasidoneLurasidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
MagaldrateMagaldrate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Withdrawn
Magnesium carbonateMagnesium carbonate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
Magnesium hydroxideMagnesium hydroxide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
Magnesium oxideMagnesium oxide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
Magnesium TrisilicateMagnesium Trisilicate may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
MebanazineMebanazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
Meclizine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Meclizine.Approved
MelperoneMelperone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Mepyramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mepyramine.Approved, Vet Approved
Mequitazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mequitazine.Approved
MesoridazineMesoridazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Methadone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Methadone.Approved
Methadyl Acetate3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Methadyl Acetate.Approved, Illicit
Methapyrilene3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Methapyrilene.Withdrawn
MethazolamideMethazolamide may decrease the excretion rate of 3,4-Methylenedioxymethamphetamine which could result in a higher serum level.Approved
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Methylene blueMethylene blue may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Investigational
Metiamide3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Metiamide.Experimental
Mianserin3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mianserin.Approved
MinaprineMinaprine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
Mirtazapine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mirtazapine.Approved
Mizolastine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mizolastine.Investigational
MoclobemideMoclobemide may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
MolindoneMolindone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Morphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Morphine.Approved, Investigational
Nalbuphine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Nalbuphine.Approved
NialamideNialamide may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
Nizatidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Nizatidine.Approved
Normethadone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Normethadone.Approved, Illicit
NortriptylineNortriptyline may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
OctamoxinOctamoxin may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
OlanzapineOlanzapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Investigational
Olopatadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Olopatadine.Approved
OndansetronOndansetron may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
OpipramolOpipramol may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Opium3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Opium.Approved, Illicit
OsanetantOsanetant may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Oxycodone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Oxycodone.Approved, Illicit, Investigational
Oxymorphone3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Oxymorphone.Approved, Investigational, Vet Approved
PaliperidonePaliperidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
PargylinePargyline may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
Pemirolast3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Pemirolast.Approved
Pentazocine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Pentazocine.Approved, Vet Approved
PerazinePerazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
PerospironePerospirone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
PerphenazinePerphenazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Pethidine3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Pethidine.Approved
PhenelzinePhenelzine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
Phenindamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Phenindamine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
Pheniramine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Pheniramine.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with 3,4-Methylenedioxymethamphetamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
PimozidePimozide may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
PipamperonePipamperone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
PipotiazinePipotiazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Piritramide3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Piritramide.Investigational
PirlindolePirlindole may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
ProchlorperazineProchlorperazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
PromazinePromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
Promethazine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Promethazine.Approved
PropericiazinePropericiazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
ProthipendylProthipendyl may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
ProtriptylineProtriptyline may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
QuetiapineQuetiapine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
RacloprideRaclopride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Ranitidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ranitidine.Approved
RasagilineRasagiline may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
Remifentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Remifentanil.Approved
RemoxiprideRemoxipride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Withdrawn
ReserpineReserpine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
RisperidoneRisperidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Investigational
RitanserinRitanserin may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
Roxatidine acetate3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Roxatidine acetate.Approved
SafrazineSafrazine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved, Investigational, Vet Approved
SertindoleSertindole may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Withdrawn
Spaglumic Acid3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Spaglumic Acid.Approved
Sufentanil3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Sufentanil.Approved, Investigational
SulpirideSulpiride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Tapentadol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Tapentadol.Approved
Terfenadine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Terfenadine.Withdrawn
Tesmilifene3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Tesmilifene.Investigational
ThioproperazineThioproperazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
ThioridazineThioridazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
ThiothixeneThiothixene may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Thonzylamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Thonzylamine.Approved
TianeptineTianeptine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
TiaprideTiapride may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Investigational
ToloxatoneToloxatone may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
Tramadol3,4-Methylenedioxymethamphetamine may increase the analgesic activities of Tramadol.Approved, Investigational
Tranilast3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Tranilast.Approved, Investigational
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of 3,4-Methylenedioxymethamphetamine.Approved
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
TriflupromazineTriflupromazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Vet Approved
TrimipramineTrimipramine may increase the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
Tripelennamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Tripelennamine.Approved, Vet Approved
Triprolidine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Triprolidine.Approved
Vitamin CThe serum concentration of 3,4-Methylenedioxymethamphetamine can be decreased when it is combined with Vitamin C.Approved, Nutraceutical
ZiprasidoneZiprasidone may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
ZotepineZotepine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Approved, Investigational
Food InteractionsNot 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
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
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

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