Identification

Name
MMDA
Accession Number
DB01442
Type
Small Molecule
Groups
Experimental, Illicit
Description

MMDA, 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 IDs
DEA No. 7401
Categories
UNII
RG7FY73ZAA
CAS number
13674-05-0
Weight
Average: 209.2417
Monoisotopic: 209.105193351
Chemical Formula
C11H15NO3
InChI Key
YQYUWUKDEVZFDB-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

Indication

MMDA 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
Pharmacodynamics
Not Available
Mechanism of action

The 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.

TargetActionsOrganism
A5-hydroxytryptamine receptor 2A
agonist
Human
ASodium-dependent dopamine transporter
negative modulator
Human
ASodium-dependent serotonin transporter
negative modulator
Human
ASodium-dependent noradrenaline transporter
negative modulator
Human
ASynaptic vesicular amine transporter
inhibitor
Human
AChromaffin granule amine transporter
inhibitor
Human
AAmine oxidase [flavin-containing] A
inhibitor
Human
AAmine oxidase [flavin-containing] B
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of 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
AlgeldrateAlgeldrate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
AlimemazineMMDA may decrease the sedative activities of Alimemazine.Approved, Vet Approved
AlmagateAlmagate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
AlmasilateAlmasilate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
AloglutamolAloglutamol may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
AlphacetylmethadolMMDA may increase the analgesic activities of Alphacetylmethadol.Experimental, Illicit
AlphaprodineMMDA may increase the analgesic activities of Alphaprodine.Illicit
AluminiumAluminium may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
Aluminium acetoacetateAluminium acetoacetate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
Aluminium glycinateAluminium glycinate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
Aluminum hydroxideAluminum hydroxide 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
BamipineMMDA may decrease the sedative activities of Bamipine.Experimental
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
Bismuth subnitrateBismuth subnitrate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of MMDA.Approved
BrofaromineThe risk or severity of adverse effects can be increased when MMDA is combined with Brofaromine.Experimental
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
ButaperazineButaperazine may decrease the stimulatory activities of MMDA.Experimental
ButorphanolMMDA may increase the analgesic activities of Butorphanol.Approved, Illicit, Vet Approved
Butyric AcidMMDA may decrease the sedative activities of Butyric Acid.Experimental
Calcium CarbonateCalcium Carbonate may decrease the excretion rate of MMDA which could result in a higher serum level.Approved
Calcium silicateCalcium silicate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
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
ChlorproethazineChlorproethazine may decrease the stimulatory activities of MMDA.Experimental
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
ClopenthixolClopenthixol may decrease the stimulatory activities of MMDA.Experimental
ClothiapineClothiapine may decrease the stimulatory activities of MMDA.Experimental
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
DexchlorpheniramineMMDA may decrease the sedative activities of Dexchlorpheniramine.Experimental
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
DibenzepinDibenzepin may increase the stimulatory activities of MMDA.Experimental
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
DixyrazineDixyrazine may decrease the stimulatory activities of MMDA.Experimental
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
FluanisoneFluanisone may decrease the stimulatory activities of MMDA.Experimental
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
Glutamic AcidThe serum concentration of MMDA can be decreased when it is combined with Glutamic Acid.Approved, Nutraceutical
GuanethidineThe serum concentration of MMDA can be decreased when it is combined with Guanethidine.Approved
HaloperidolHaloperidol may decrease the stimulatory activities of MMDA.Approved
HarmalineThe risk or severity of adverse effects can be increased when MMDA is combined with Harmaline.Experimental
HeroinMMDA may increase the analgesic activities of Heroin.Approved, Illicit
HydracarbazineHydracarbazine may increase the hypertensive activities of MMDA.Experimental
HydrocodoneMMDA may increase the analgesic activities of Hydrocodone.Approved, Illicit
HydromorphoneMMDA may increase the analgesic activities of Hydromorphone.Approved, Illicit
HydrotalciteHydrotalcite may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
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
IprindoleIprindole may increase the stimulatory activities of MMDA.Experimental
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
KetobemidoneMMDA may increase the analgesic activities of Ketobemidone.Approved
KetotifenMMDA may decrease the sedative activities of Ketotifen.Approved
LafutidineMMDA may decrease the sedative activities of Lafutidine.Investigational
LavoltidineMMDA may decrease the sedative activities of Lavoltidine.Investigational
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
LofepramineLofepramine may increase the stimulatory activities of MMDA.Experimental
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 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 peroxideMagnesium peroxide may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
Magnesium silicateMagnesium silicate may decrease the excretion rate of MMDA which could result in a higher serum level.Experimental
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
MeptazinolMMDA may increase the analgesic activities of Meptazinol.Experimental
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
MethenamineThe serum concentration of MMDA can be decreased when it is combined with Methenamine.Approved, Vet 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
MoperoneMoperone may decrease the stimulatory activities of MMDA.Experimental
MorphineMMDA may increase the analgesic activities of Morphine.Approved, Investigational
MosapramineMosapramine may decrease the stimulatory activities of MMDA.Experimental
NalbuphineMMDA may increase the analgesic activities of Nalbuphine.Approved
NialamideNialamide may increase the hypertensive activities of MMDA.Withdrawn
NicomorphineMMDA may increase the analgesic activities of Nicomorphine.Experimental
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
OxatomideMMDA may decrease the sedative activities of Oxatomide.Investigational
OxycodoneMMDA may increase the analgesic activities of Oxycodone.Approved, Illicit, Investigational
OxymorphoneMMDA may increase the analgesic activities of Oxymorphone.Approved, Investigational, Vet Approved
OxypertineOxypertine may decrease the stimulatory activities of MMDA.Experimental
OzagrelMMDA may decrease the sedative activities of Ozagrel.Investigational
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
PenfluridolPenfluridol may decrease the stimulatory activities of MMDA.Experimental
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
PhenazocineMMDA may increase the analgesic activities of Phenazocine.Experimental
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
PhenoperidineMMDA may increase the analgesic activities of Phenoperidine.Experimental
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
QuifenadineMMDA may decrease the sedative activities of Quifenadine.Experimental
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
SelegilineThe risk or severity of adverse effects can be increased when MMDA is combined with Selegiline.Approved, Investigational, Vet Approved
SertindoleSertindole may decrease the stimulatory activities of MMDA.Approved, Withdrawn
SufentanilMMDA may increase the analgesic activities of Sufentanil.Approved, Investigational
SulpirideSulpiride may decrease the stimulatory activities of MMDA.Approved
SultoprideSultopride may decrease the stimulatory activities of MMDA.Experimental
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
TetrahydropalmatineTetrahydropalmatine may decrease the stimulatory activities of MMDA.Investigational
ThiopropazateThiopropazate may decrease the stimulatory activities of MMDA.Experimental
ThioproperazineThioproperazine may decrease the stimulatory activities of MMDA.Approved
ThioridazineThioridazine may decrease the stimulatory activities of MMDA.Withdrawn
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.Approved, Investigational
TilidineMMDA may increase the analgesic activities of Tilidine.Experimental
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
TrifluperidolTrifluperidol may decrease the stimulatory activities of MMDA.Experimental
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
TritoqualineMMDA may decrease the sedative activities of Tritoqualine.Experimental
VeraliprideVeralipride may decrease the stimulatory activities of MMDA.Experimental
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 Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
PubChem Compound
26175
PubChem Substance
46506802
ChemSpider
24386
ChEMBL
CHEMBL126506
Wikipedia
MMDA_%28psychedelic%29
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of chemical entities 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.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organoheterocyclic compounds
Sub Class
Benzodioxoles
Direct Parent
Benzodioxoles
Alternative Parents
Anisoles / Aralkylamines / Alkyl aryl ethers / Oxacyclic compounds / Acetals / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Benzodioxole / Anisole / Alkyl aryl ether / Aralkylamine / Benzenoid / Acetal / Oxacycle / Ether / Organic nitrogen compound / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
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
Uniprot Name
Sodium-dependent dopamine transporter
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 t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
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
Uniprot Name
Sodium-dependent noradrenaline transporter
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...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
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
Uniprot Name
Chromaffin granule amine transporter
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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
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 ]

Drug created on July 31, 2007 07:09 / Updated on October 02, 2017 04:58