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Identification
NameMMDA
Accession NumberDB01442
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionMMDA, or 3-methoxy-4,5-methylenedioxyamphetamine, is a stimulant and psychedelic drug of the amphetamine class. It also acts as an entheogen and an entactogen. MMDA bears resemblance to the psychopharmacologically active essential oils elemicin and myristicin found in nutmeg. The effects of MMDA includes feelings of euphoria and warmth, as well as realistic closed-eye visuals.
Structure
Thumb
Synonyms
(+-)-mmda
3-Methoxy-4,5-methylenedioxyphenylisopropylamine
3-Methoxy-alpha-methyl-4,5-methylenedioxyphenethylamine
3-METHOXY-METHYLENEDIOXYAMPHETAMINE
5-Methoxy-3,4-methylenedioxyamphetamine
Amphetamine, 3,4-methylenedioxy-5-methoxy
External Identifiers
  • DEA No. 7401
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
UNIIRG7FY73ZAA
CAS number13674-05-0
WeightAverage: 209.2417
Monoisotopic: 209.105193351
Chemical FormulaC11H15NO3
InChI KeyYQYUWUKDEVZFDB-UHFFFAOYSA-N
InChI
InChI=1S/C11H15NO3/c1-7(12)3-8-4-9(13-2)11-10(5-8)14-6-15-11/h4-5,7H,3,6,12H2,1-2H3
IUPAC Name
1-(7-methoxy-2H-1,3-benzodioxol-5-yl)propan-2-amine
SMILES
COC1=CC(CC(C)N)=CC2=C1OCO2
Pharmacology
IndicationMMDA is a recreational drug. It has no current medical uses and is a Schedule I controlled substance in the USA at present.
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionThe mechanism that produces the psychedelic activity of MMDA has not been definitively established. There are, as of the present time, no reported studies on the human pharmacokinetics or metabolism of MMDA. Based on its structural relationship with other similar drugs for which the pharmacology is known, it is likely that MMDA has multiple mechanisms of action, and probably acts both as a 5HT2A agonist in a similar manner to hallucinogenic amphetamines such as DOM, and also as a serotonin releaser by reversing the direction of the serotonin reuptake transporter in a similar manner to MDMA.
TargetKindPharmacological actionActionsOrganismUniProt ID
5-hydroxytryptamine receptor 2AProteinyes
agonist
HumanP28223 details
Sodium-dependent dopamine transporterProteinyes
negative modulator
HumanQ01959 details
Sodium-dependent serotonin transporterProteinyes
negative modulator
HumanP31645 details
Sodium-dependent noradrenaline transporterProteinyes
negative modulator
HumanP23975 details
Synaptic vesicular amine transporterProteinyes
inhibitor
HumanQ05940 details
Chromaffin granule amine transporterProteinyes
inhibitor
HumanP54219 details
Amine oxidase [flavin-containing] AProteinyes
inhibitor
HumanP21397 details
Amine oxidase [flavin-containing] BProteinyes
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 organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of MMDA.Experimental
AcepromazineAcepromazine may decrease the stimulatory activities of MMDA.Approved, Vet Approved
AceprometazineAceprometazine may decrease the stimulatory activities of MMDA.Approved
AcetazolamideAcetazolamide may decrease the excretion rate of MMDA which could result in a higher serum level.Approved, Vet Approved
AcetophenazineAcetophenazine may decrease the stimulatory activities of MMDA.Approved
AcrivastineMMDA may decrease the sedative activities of Acrivastine.Approved
AlcaftadineMMDA may decrease the sedative activities of Alcaftadine.Approved
AlfentanilMMDA may increase the analgesic activities of Alfentanil.Approved, Illicit
AlimemazineMMDA may decrease the sedative activities of Alimemazine.Approved, Vet Approved
AlphacetylmethadolMMDA may increase the analgesic activities of Alphacetylmethadol.Experimental, Illicit
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
Aluminum phosphateAluminum phosphate may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
AmineptineAmineptine may increase the stimulatory activities of MMDA.Illicit, Withdrawn
AmisulprideAmisulpride may decrease the stimulatory activities of MMDA.Approved, Investigational
AmitriptylineAmitriptyline may increase the stimulatory activities of MMDA.Approved
Ammonium chlorideThe serum concentration of MMDA can be decreased when it is combined with Ammonium chloride.Approved, Vet Approved
AmperozideAmperozide may decrease the stimulatory activities of MMDA.Experimental
AntazolineMMDA may decrease the sedative activities of Antazoline.Approved
AripiprazoleAripiprazole may decrease the stimulatory activities of MMDA.Approved, Investigational
AsenapineAsenapine may decrease the stimulatory activities of MMDA.Approved
AstemizoleMMDA may decrease the sedative activities of Astemizole.Approved, Withdrawn
AzaperoneAzaperone may decrease the stimulatory activities of MMDA.Vet Approved
AzatadineMMDA may decrease the sedative activities of Azatadine.Approved
AzelastineMMDA may decrease the sedative activities of Azelastine.Approved
BenmoxinBenmoxin may increase the hypertensive activities of MMDA.Withdrawn
BenperidolBenperidol may decrease the stimulatory activities of MMDA.Investigational
BezitramideMMDA may increase the analgesic activities of Bezitramide.Experimental, Illicit, Withdrawn
BifeprunoxBifeprunox may decrease the stimulatory activities of MMDA.Investigational
Bismuth SubcitrateBismuth Subcitrate may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of MMDA.Approved
BromperidolBromperidol may decrease the stimulatory activities of MMDA.Investigational
BrompheniramineMMDA may decrease the sedative activities of Brompheniramine.Approved
BuclizineMMDA may decrease the sedative activities of Buclizine.Approved
BuprenorphineMMDA may increase the analgesic activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
Butanoic AcidMMDA may decrease the sedative activities of Butanoic Acid.Experimental
ButorphanolMMDA may increase the analgesic activities of Butorphanol.Approved, Illicit, Vet Approved
Calcium carbonateCalcium carbonate may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
CarbinoxamineMMDA may decrease the sedative activities of Carbinoxamine.Approved
CarfentanilMMDA may increase the analgesic activities of Carfentanil.Illicit, Vet Approved
CariprazineCariprazine may decrease the stimulatory activities of MMDA.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of MMDA.Withdrawn
CetirizineMMDA may decrease the sedative activities of Cetirizine.Approved
ChloropyramineMMDA may decrease the sedative activities of Chloropyramine.Approved
ChlorphenamineMMDA may decrease the sedative activities of Chlorphenamine.Approved
ChlorphenoxamineMMDA may decrease the sedative activities of Chlorphenoxamine.Withdrawn
ChlorpromazineChlorpromazine may decrease the stimulatory activities of MMDA.Approved, Vet Approved
ChlorprothixeneChlorprothixene may decrease the stimulatory activities of MMDA.Approved, Withdrawn
CimetidineMMDA may decrease the sedative activities of Cimetidine.Approved
CinnarizineMMDA may decrease the sedative activities of Cinnarizine.Approved
ClemastineMMDA may decrease the sedative activities of Clemastine.Approved
ClomipramineClomipramine may increase the stimulatory activities of MMDA.Approved, Vet Approved
ClozapineClozapine may decrease the stimulatory activities of MMDA.Approved
CodeineMMDA may increase the analgesic activities of Codeine.Approved, Illicit
CyamemazineCyamemazine may decrease the stimulatory activities of MMDA.Approved
CyclizineMMDA may decrease the sedative activities of Cyclizine.Approved
CyclobenzaprineCyclobenzaprine may increase the stimulatory activities of MMDA.Approved
CyproheptadineMMDA may decrease the sedative activities of Cyproheptadine.Approved
DapiprazoleDapiprazole may decrease the stimulatory activities of MMDA.Approved
DesipramineDesipramine may increase the stimulatory activities of MMDA.Approved
DesloratadineMMDA may decrease the sedative activities of Desloratadine.Approved, Investigational
DexbrompheniramineMMDA may decrease the sedative activities of Dexbrompheniramine.Approved
Dexchlorpheniramine maleateMMDA may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
DextromoramideMMDA may increase the analgesic activities of Dextromoramide.Experimental, Illicit
DextropropoxypheneMMDA may increase the analgesic activities of Dextropropoxyphene.Approved, Illicit, Withdrawn
DezocineMMDA may increase the analgesic activities of Dezocine.Approved
DiclofenamideDiclofenamide may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
DihydrocodeineMMDA may increase the analgesic activities of Dihydrocodeine.Approved, Illicit
DihydroetorphineMMDA may increase the analgesic activities of Dihydroetorphine.Experimental, Illicit
DihydromorphineMMDA may increase the analgesic activities of Dihydromorphine.Experimental, Illicit
DimenhydrinateMMDA may decrease the sedative activities of Dimenhydrinate.Approved
DimetindeneMMDA may decrease the sedative activities of Dimetindene.Approved
DimetotiazineMMDA may decrease the sedative activities of Dimetotiazine.Approved
DiphenhydramineMMDA may decrease the sedative activities of Diphenhydramine.Approved
DiphenoxylateMMDA may increase the analgesic activities of Diphenoxylate.Approved, Illicit
DosulepinDosulepin may increase the stimulatory activities of MMDA.Approved
DoxepinMMDA may decrease the sedative activities of Doxepin.Approved
DoxylamineMMDA may decrease the sedative activities of Doxylamine.Approved, Vet Approved
DPDPEMMDA may increase the analgesic activities of DPDPE.Investigational
DroperidolDroperidol may decrease the stimulatory activities of MMDA.Approved, Vet Approved
EbastineMMDA may decrease the sedative activities of Ebastine.Investigational
EcopipamEcopipam may decrease the stimulatory activities of MMDA.Investigational
EmedastineMMDA may decrease the sedative activities of Emedastine.Approved
EpinastineMMDA may decrease the sedative activities of Epinastine.Approved, Investigational
EsmirtazapineMMDA may decrease the sedative activities of Esmirtazapine.Investigational
EthopropazineMMDA may decrease the sedative activities of Ethopropazine.Approved
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with MMDA.Approved
EthoxzolamideEthoxzolamide may decrease the excretion rate of MMDA which could result in a higher serum level.Withdrawn
EthylmorphineMMDA may increase the analgesic activities of Ethylmorphine.Approved, Illicit
EtorphineMMDA may increase the analgesic activities of Etorphine.Illicit, Vet Approved
FamotidineMMDA may decrease the sedative activities of Famotidine.Approved
FencamfamineFencamfamine may decrease the stimulatory activities of MMDA.Approved, Illicit, Withdrawn
FentanylMMDA may increase the analgesic activities of Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineMMDA may decrease the sedative activities of Fexofenadine.Approved
FlunarizineMMDA may decrease the sedative activities of Flunarizine.Approved
FlupentixolFlupentixol may decrease the stimulatory activities of MMDA.Approved, Withdrawn
FluphenazineFluphenazine may decrease the stimulatory activities of MMDA.Approved
FluspirileneFluspirilene may decrease the stimulatory activities of MMDA.Approved
FurazolidoneFurazolidone may increase the hypertensive activities of MMDA.Approved, Vet Approved
GuanethidineThe serum concentration of MMDA can be decreased when it is combined with Guanethidine.Approved
HaloperidolHaloperidol may decrease the stimulatory activities of MMDA.Approved
HeroinMMDA may increase the analgesic activities of Heroin.Approved, Illicit
HexamethylenetetramineThe serum concentration of MMDA can be decreased when it is combined with Hexamethylenetetramine.Approved, Vet Approved
HydracarbazineHydracarbazine may increase the hypertensive activities of MMDA.Approved
HydrocodoneMMDA may increase the analgesic activities of Hydrocodone.Approved, Illicit
HydromorphoneMMDA may increase the analgesic activities of Hydromorphone.Approved, Illicit
HydroxyzineMMDA may decrease the sedative activities of Hydroxyzine.Approved
IloperidoneIloperidone may decrease the stimulatory activities of MMDA.Approved
ImipramineImipramine may increase the stimulatory activities of MMDA.Approved
Ioflupane I-123MMDA may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IproclozideIproclozide may increase the hypertensive activities of MMDA.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of MMDA.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of MMDA.Approved
IsothipendylMMDA may decrease the sedative activities of Isothipendyl.Approved
Kct 0809MMDA may decrease the sedative activities of Kct 0809.Investigational
KetobemidoneMMDA may increase the analgesic activities of Ketobemidone.Approved
KetotifenMMDA may decrease the sedative activities of Ketotifen.Approved
L-Glutamic AcidThe serum concentration of MMDA can be decreased when it is combined with L-Glutamic Acid.Nutraceutical
LevocabastineMMDA may decrease the sedative activities of Levocabastine.Approved
LevocetirizineMMDA may decrease the sedative activities of Levocetirizine.Approved
Levomethadyl AcetateMMDA may increase the analgesic activities of Levomethadyl Acetate.Approved
LevorphanolMMDA may increase the analgesic activities of Levorphanol.Approved
LithiumLithium may decrease the stimulatory activities of MMDA.Approved
LodoxamideMMDA may decrease the sedative activities of Lodoxamide.Approved
LofentanilMMDA may increase the analgesic activities of Lofentanil.Illicit
LoratadineMMDA may decrease the sedative activities of Loratadine.Approved
LoxapineLoxapine may decrease the stimulatory activities of MMDA.Approved
LurasidoneLurasidone may decrease the stimulatory activities of MMDA.Approved
MagaldrateMagaldrate may decrease the excretion rate of MMDA which could result in a higher serum level.Withdrawn
Magnesium carbonateMagnesium carbonate may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
Magnesium hydroxideMagnesium hydroxide may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
Magnesium oxideMagnesium oxide may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
Magnesium TrisilicateMagnesium Trisilicate may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
MebanazineMebanazine may increase the hypertensive activities of MMDA.Withdrawn
MeclizineMMDA may decrease the sedative activities of Meclizine.Approved
MelperoneMelperone may decrease the stimulatory activities of MMDA.Approved
MepyramineMMDA may decrease the sedative activities of Mepyramine.Approved, Vet Approved
MequitazineMMDA may decrease the sedative activities of Mequitazine.Approved
MesoridazineMesoridazine may decrease the stimulatory activities of MMDA.Approved
MethadoneMMDA may increase the analgesic activities of Methadone.Approved
Methadyl AcetateMMDA may increase the analgesic activities of Methadyl Acetate.Approved, Illicit
MethapyrileneMMDA may decrease the sedative activities of Methapyrilene.Withdrawn
MethazolamideMethazolamide may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of MMDA.Approved
Methylene blueMethylene blue may increase the hypertensive activities of MMDA.Investigational
MetiamideMMDA may decrease the sedative activities of Metiamide.Experimental
MianserinMMDA may decrease the sedative activities of Mianserin.Approved
MinaprineMinaprine may increase the hypertensive activities of MMDA.Approved
MirtazapineMMDA may decrease the sedative activities of Mirtazapine.Approved
MizolastineMMDA may decrease the sedative activities of Mizolastine.Investigational
MoclobemideMoclobemide may increase the hypertensive activities of MMDA.Approved
MolindoneMolindone may decrease the stimulatory activities of MMDA.Approved
MorphineMMDA may increase the analgesic activities of Morphine.Approved, Investigational
NalbuphineMMDA may increase the analgesic activities of Nalbuphine.Approved
NialamideNialamide may increase the hypertensive activities of MMDA.Withdrawn
NizatidineMMDA may decrease the sedative activities of Nizatidine.Approved
NormethadoneMMDA may increase the analgesic activities of Normethadone.Approved, Illicit
NortriptylineNortriptyline may increase the stimulatory activities of MMDA.Approved
OctamoxinOctamoxin may increase the hypertensive activities of MMDA.Withdrawn
OlanzapineOlanzapine may decrease the stimulatory activities of MMDA.Approved, Investigational
OlopatadineMMDA may decrease the sedative activities of Olopatadine.Approved
OndansetronOndansetron may decrease the stimulatory activities of MMDA.Approved
OpipramolOpipramol may increase the stimulatory activities of MMDA.Investigational
OpiumMMDA may increase the analgesic activities of Opium.Approved, Illicit
OsanetantOsanetant may decrease the stimulatory activities of MMDA.Investigational
OxycodoneMMDA may increase the analgesic activities of Oxycodone.Approved, Illicit, Investigational
OxymorphoneMMDA may increase the analgesic activities of Oxymorphone.Approved, Investigational, Vet Approved
PaliperidonePaliperidone may decrease the stimulatory activities of MMDA.Approved
PargylinePargyline may increase the hypertensive activities of MMDA.Approved
PemirolastMMDA may decrease the sedative activities of Pemirolast.Approved
PentazocineMMDA may increase the analgesic activities of Pentazocine.Approved, Vet Approved
PerazinePerazine may decrease the stimulatory activities of MMDA.Investigational
PerospironePerospirone may decrease the stimulatory activities of MMDA.Approved
PerphenazinePerphenazine may decrease the stimulatory activities of MMDA.Approved
PethidineMMDA may increase the analgesic activities of Pethidine.Approved
PhenelzinePhenelzine may increase the hypertensive activities of MMDA.Approved
PhenindamineMMDA may decrease the sedative activities of Phenindamine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of MMDA.Withdrawn
PheniramineMMDA may decrease the sedative activities of Pheniramine.Approved
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with MMDA.Approved
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of MMDA.Withdrawn
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with MMDA.Approved, Vet Approved
PimozidePimozide may decrease the stimulatory activities of MMDA.Approved
PipamperonePipamperone may decrease the stimulatory activities of MMDA.Approved
PipotiazinePipotiazine may decrease the stimulatory activities of MMDA.Approved
PiritramideMMDA may increase the analgesic activities of Piritramide.Investigational
PirlindolePirlindole may increase the hypertensive activities of MMDA.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of MMDA.Withdrawn
ProchlorperazineProchlorperazine may decrease the stimulatory activities of MMDA.Approved, Vet Approved
PromazinePromazine may decrease the stimulatory activities of MMDA.Approved, Vet Approved
PromethazineMMDA may decrease the sedative activities of Promethazine.Approved
PropericiazinePropericiazine may decrease the stimulatory activities of MMDA.Approved
ProthipendylProthipendyl may decrease the stimulatory activities of MMDA.Investigational
ProtriptylineProtriptyline may increase the stimulatory activities of MMDA.Approved
QuetiapineQuetiapine may decrease the stimulatory activities of MMDA.Approved
RacloprideRaclopride may decrease the stimulatory activities of MMDA.Investigational
RanitidineMMDA may decrease the sedative activities of Ranitidine.Approved
RasagilineRasagiline may increase the hypertensive activities of MMDA.Approved
RemifentanilMMDA may increase the analgesic activities of Remifentanil.Approved
RemoxiprideRemoxipride may decrease the stimulatory activities of MMDA.Approved, Withdrawn
ReserpineReserpine may decrease the stimulatory activities of MMDA.Approved
RisperidoneRisperidone may decrease the stimulatory activities of MMDA.Approved, Investigational
RitanserinRitanserin may decrease the stimulatory activities of MMDA.Investigational
Roxatidine acetateMMDA may decrease the sedative activities of Roxatidine acetate.Approved
SafrazineSafrazine may increase the hypertensive activities of MMDA.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of MMDA.Approved, Investigational, Vet Approved
SertindoleSertindole may decrease the stimulatory activities of MMDA.Approved, Withdrawn
Spaglumic AcidMMDA may decrease the sedative activities of Spaglumic Acid.Approved
SufentanilMMDA may increase the analgesic activities of Sufentanil.Approved, Investigational
SulpirideSulpiride may decrease the stimulatory activities of MMDA.Approved
TapentadolMMDA may increase the analgesic activities of Tapentadol.Approved
TerfenadineMMDA may decrease the sedative activities of Terfenadine.Withdrawn
TesmilifeneMMDA may decrease the sedative activities of Tesmilifene.Investigational
ThioproperazineThioproperazine may decrease the stimulatory activities of MMDA.Approved
ThioridazineThioridazine may decrease the stimulatory activities of MMDA.Approved
ThiothixeneThiothixene may decrease the stimulatory activities of MMDA.Approved
ThonzylamineMMDA may decrease the sedative activities of Thonzylamine.Approved
TianeptineTianeptine may increase the stimulatory activities of MMDA.Approved
TiaprideTiapride may decrease the stimulatory activities of MMDA.Investigational
ToloxatoneToloxatone may increase the hypertensive activities of MMDA.Approved
TramadolMMDA may increase the analgesic activities of Tramadol.Approved, Investigational
TranilastMMDA may decrease the sedative activities of Tranilast.Approved, Investigational
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of MMDA.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of MMDA.Approved
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of MMDA.Approved
TriflupromazineTriflupromazine may decrease the stimulatory activities of MMDA.Approved, Vet Approved
TrimipramineTrimipramine may increase the stimulatory activities of MMDA.Approved
TripelennamineMMDA may decrease the sedative activities of Tripelennamine.Approved, Vet Approved
TriprolidineMMDA may decrease the sedative activities of Triprolidine.Approved
Vitamin CThe serum concentration of MMDA can be decreased when it is combined with Vitamin C.Approved, Nutraceutical
ZiprasidoneZiprasidone may decrease the stimulatory activities of MMDA.Approved
ZotepineZotepine may decrease the stimulatory activities of MMDA.Approved
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of MMDA.Approved, Investigational
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+0.9972
Blood Brain Barrier+0.9147
Caco-2 permeable+0.6269
P-glycoprotein substrateNon-substrate0.6271
P-glycoprotein inhibitor INon-inhibitor0.8586
P-glycoprotein inhibitor IINon-inhibitor0.9336
Renal organic cation transporterNon-inhibitor0.7891
CYP450 2C9 substrateNon-substrate0.8935
CYP450 2D6 substrateNon-substrate0.6434
CYP450 3A4 substrateNon-substrate0.5519
CYP450 1A2 substrateInhibitor0.7772
CYP450 2C9 inhibitorNon-inhibitor0.7849
CYP450 2D6 inhibitorInhibitor0.7001
CYP450 2C19 inhibitorNon-inhibitor0.5393
CYP450 3A4 inhibitorInhibitor0.5469
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6085
Ames testNon AMES toxic0.5878
CarcinogenicityNon-carcinogens0.9168
BiodegradationNot ready biodegradable0.7228
Rat acute toxicity2.5346 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9776
hERG inhibition (predictor II)Non-inhibitor0.957
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 Solubility2.71 mg/mLALOGPS
logP1.07ALOGPS
logP1.27ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)9.99ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.71 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.94 m3·mol-1ChemAxon
Polarizability22.38 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
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
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. 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 ]
  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 ]
  4. Kokoshka JM, Metzger RR, Wilkins DG, Gibb JW, Hanson GR, Fleckenstein AE: Methamphetamine treatment rapidly inhibits serotonin, but not glutamate, transporters in rat brain. Brain Res. 1998 Jul 13;799(1):78-83. [PubMed:9666084 ]
  5. Haughey HM, Fleckenstein AE, Metzger RR, Hanson GR: The effects of methamphetamine on serotonin transporter activity: role of dopamine and hyperthermia. J Neurochem. 2000 Oct;75(4):1608-17. [PubMed:10987842 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
negative modulator
General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
References
  1. 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 ]
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. 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 ]
  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 ]
  4. 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 ]
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. 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:
Monoamine transmembrane transporter activity
Specific Function:
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis.
Gene Name:
SLC18A2
Uniprot ID:
Q05940
Molecular Weight:
55712.075 Da
References
  1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613 ]
  2. Henry JP, Sagne C, Bedet C, Gasnier B: The vesicular monoamine transporter: from chromaffin granule to brain. Neurochem Int. 1998 Mar;32(3):227-46. [PubMed:9587917 ]
  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
yes
Actions
inhibitor
General Function:
Serotonin transmembrane transporter activity
Specific Function:
Involved in the transport of biogenic monoamines, such as serotonin, from the cytoplasm into the secretory vesicles of neuroendocrine and endocrine cells.
Gene Name:
SLC18A1
Uniprot ID:
P54219
Molecular Weight:
56256.71 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. Henry JP, Sagne C, Bedet C, Gasnier B: The vesicular monoamine transporter: from chromaffin granule to brain. Neurochem Int. 1998 Mar;32(3):227-46. [PubMed:9587917 ]
  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
yes
Actions
inhibitor
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular Weight:
59681.27 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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
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. 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 ]
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Drug created on July 31, 2007 07:09 / Updated on August 17, 2016 12:23