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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- 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
Structure for DB01442 (MMDA)
- 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.
- 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.
Target Actions Organism A5-hydroxytryptamine receptor 2A agonistHuman ASodium-dependent dopamine transporter negative modulatorHuman ASodium-dependent serotonin transporter negative modulatorHuman ASodium-dependent noradrenaline transporter negative modulatorHuman ASynaptic vesicular amine transporter inhibitorHuman AChromaffin granule amine transporter inhibitorHuman AAmine oxidase [flavin-containing] A inhibitorHuman AAmine oxidase [flavin-containing] B inhibitorHuman - 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
Drug Interaction Drug group 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of MMDA. Experimental Acepromazine Acepromazine may decrease the stimulatory activities of MMDA. Approved, Vet Approved Aceprometazine Aceprometazine may decrease the stimulatory activities of MMDA. Approved Acetazolamide Acetazolamide may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Vet Approved Acetophenazine Acetophenazine may decrease the stimulatory activities of MMDA. Approved Acrivastine MMDA may decrease the sedative activities of Acrivastine. Approved Alcaftadine MMDA may decrease the sedative activities of Alcaftadine. Approved Alfentanil MMDA may increase the analgesic activities of Alfentanil. Approved, Illicit Alimemazine MMDA may decrease the sedative activities of Alimemazine. Approved, Vet Approved Almasilate Almasilate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Experimental Aloglutamol Aloglutamol may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Alphacetylmethadol MMDA may increase the analgesic activities of Alphacetylmethadol. Experimental, Illicit Alphaprodine MMDA may increase the analgesic activities of Alphaprodine. Illicit Aluminium Aluminium may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Investigational Aluminium acetoacetate Aluminium acetoacetate may decrease the excretion rate of MMDA which could result in a higher serum level. Experimental Aluminium glycinate Aluminium glycinate may decrease the excretion rate of MMDA which could result in a higher serum level. Experimental Aluminum hydroxide Aluminum hydroxide may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Investigational Amineptine Amineptine may increase the stimulatory activities of MMDA. Illicit, Withdrawn Amisulpride Amisulpride may decrease the stimulatory activities of MMDA. Approved, Investigational Amitriptyline Amitriptyline may increase the stimulatory activities of MMDA. Approved Amitriptylinoxide Amitriptylinoxide may increase the stimulatory activities of MMDA. Approved, Investigational Ammonium chloride The serum concentration of MMDA can be decreased when it is combined with Ammonium chloride. Approved, Investigational, Vet Approved Amoxapine Amoxapine may increase the stimulatory activities of MMDA. Approved Amperozide Amperozide may decrease the stimulatory activities of MMDA. Experimental Amphetamine The risk or severity of adverse effects can be increased when MMDA is combined with Amphetamine. Approved, Illicit, Investigational Antazoline MMDA may decrease the sedative activities of Antazoline. Approved Aripiprazole Aripiprazole may decrease the stimulatory activities of MMDA. Approved, Investigational Asenapine Asenapine may decrease the stimulatory activities of MMDA. Approved Astemizole MMDA may decrease the sedative activities of Astemizole. Approved, Withdrawn Azaperone Azaperone may decrease the stimulatory activities of MMDA. Investigational, Vet Approved Azatadine MMDA may decrease the sedative activities of Azatadine. Approved Azelastine MMDA may decrease the sedative activities of Azelastine. Approved Bamipine MMDA may decrease the sedative activities of Bamipine. Experimental Benmoxin The risk or severity of adverse effects can be increased when MMDA is combined with Benmoxin. Withdrawn Benperidol Benperidol may decrease the stimulatory activities of MMDA. Approved, Investigational Benzatropine MMDA may decrease the sedative activities of Benzatropine. Approved Benzquinamide MMDA may decrease the sedative activities of Benzquinamide. Withdrawn Bepotastine MMDA may decrease the sedative activities of Bepotastine. Approved Betahistine MMDA may decrease the sedative activities of Betahistine. Approved, Investigational Bezitramide MMDA may increase the analgesic activities of Bezitramide. Experimental, Illicit, Withdrawn Bifeprunox Bifeprunox may decrease the stimulatory activities of MMDA. Investigational Bilastine MMDA may decrease the sedative activities of Bilastine. Approved, Investigational Bismuth Subcitrate Bismuth Subcitrate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Investigational Bismuth subnitrate Bismuth subnitrate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Brexpiprazole Brexpiprazole may decrease the stimulatory activities of MMDA. Approved, Investigational Brofaromine The risk or severity of adverse effects can be increased when MMDA is combined with Brofaromine. Experimental Bromodiphenhydramine MMDA may decrease the sedative activities of Bromodiphenhydramine. Approved Bromperidol Bromperidol may decrease the stimulatory activities of MMDA. Approved, Investigational Brompheniramine MMDA may decrease the sedative activities of Brompheniramine. Approved Buclizine MMDA may decrease the sedative activities of Buclizine. Approved Buprenorphine MMDA may increase the analgesic activities of Buprenorphine. Approved, Illicit, Investigational, Vet Approved Butaperazine Butaperazine may decrease the stimulatory activities of MMDA. Experimental Butorphanol MMDA may increase the analgesic activities of Butorphanol. Approved, Illicit, Vet Approved Butriptyline Butriptyline may increase the stimulatory activities of MMDA. Approved Butyric Acid MMDA may decrease the sedative activities of Butyric Acid. Experimental, Investigational Calcium Carbonate Calcium Carbonate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Investigational Calcium silicate Calcium silicate may decrease the excretion rate of MMDA which could result in a higher serum level. Experimental Carbinoxamine MMDA may decrease the sedative activities of Carbinoxamine. Approved Carfentanil MMDA may increase the analgesic activities of Carfentanil. Illicit, Investigational, Vet Approved Cariprazine Cariprazine may decrease the stimulatory activities of MMDA. Approved, Investigational Caroxazone The risk or severity of adverse effects can be increased when MMDA is combined with Caroxazone. Withdrawn Cetirizine MMDA may decrease the sedative activities of Cetirizine. Approved Chlorcyclizine MMDA may decrease the sedative activities of Chlorcyclizine. Approved Chloropyramine MMDA may decrease the sedative activities of Chloropyramine. Approved Chlorphenamine MMDA may decrease the sedative activities of Chlorphenamine. Approved Chlorphenoxamine MMDA may decrease the sedative activities of Chlorphenoxamine. Withdrawn Chlorproethazine Chlorproethazine may decrease the stimulatory activities of MMDA. Experimental Chlorpromazine Chlorpromazine may decrease the stimulatory activities of MMDA. Approved, Investigational, Vet Approved Chlorprothixene Chlorprothixene may decrease the stimulatory activities of MMDA. Approved, Investigational, Withdrawn Cimetidine MMDA may decrease the sedative activities of Cimetidine. Approved, Investigational Cinnarizine MMDA may decrease the sedative activities of Cinnarizine. Approved, Investigational Clemastine MMDA may decrease the sedative activities of Clemastine. Approved, Investigational Clofedanol MMDA may decrease the sedative activities of Clofedanol. Approved, Withdrawn Clomipramine Clomipramine may increase the stimulatory activities of MMDA. Approved, Investigational, Vet Approved Clopenthixol Clopenthixol may decrease the stimulatory activities of MMDA. Experimental Clothiapine Clothiapine may decrease the stimulatory activities of MMDA. Experimental Clozapine Clozapine may decrease the stimulatory activities of MMDA. Approved Codeine MMDA may increase the analgesic activities of Codeine. Approved, Illicit Cyamemazine Cyamemazine may decrease the stimulatory activities of MMDA. Approved Cyclizine MMDA may decrease the sedative activities of Cyclizine. Approved Cyproheptadine MMDA may decrease the sedative activities of Cyproheptadine. Approved Dapiprazole Dapiprazole may decrease the stimulatory activities of MMDA. Approved Desipramine Desipramine may increase the stimulatory activities of MMDA. Approved, Investigational Desloratadine MMDA may decrease the sedative activities of Desloratadine. Approved, Investigational Dexbrompheniramine MMDA may decrease the sedative activities of Dexbrompheniramine. Approved Dexchlorpheniramine MMDA may decrease the sedative activities of Dexchlorpheniramine. Experimental, Investigational Dexchlorpheniramine maleate MMDA may decrease the sedative activities of Dexchlorpheniramine maleate. Approved Dextromoramide MMDA may increase the analgesic activities of Dextromoramide. Experimental, Illicit Dextropropoxyphene MMDA may increase the analgesic activities of Dextropropoxyphene. Approved, Illicit, Investigational, Withdrawn Dezocine MMDA may increase the analgesic activities of Dezocine. Approved, Investigational Dibenzepin Dibenzepin may increase the stimulatory activities of MMDA. Experimental Diclofenamide Diclofenamide may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Investigational Dihydrocodeine MMDA may increase the analgesic activities of Dihydrocodeine. Approved, Illicit Dihydroetorphine MMDA may increase the analgesic activities of Dihydroetorphine. Experimental, Illicit Dihydromorphine MMDA may increase the analgesic activities of Dihydromorphine. Experimental, Illicit Dimenhydrinate MMDA may decrease the sedative activities of Dimenhydrinate. Approved Dimetacrine Dimetacrine may increase the stimulatory activities of MMDA. Approved, Withdrawn Dimetindene MMDA may decrease the sedative activities of Dimetindene. Approved, Investigational Dimetotiazine MMDA may decrease the sedative activities of Dimetotiazine. Approved Diphenhydramine MMDA may decrease the sedative activities of Diphenhydramine. Approved, Investigational Diphenoxylate MMDA may increase the analgesic activities of Diphenoxylate. Approved, Illicit Diphenylpyraline MMDA may decrease the sedative activities of Diphenylpyraline. Approved, Investigational Dixyrazine Dixyrazine may decrease the stimulatory activities of MMDA. Experimental Dosulepin Dosulepin may increase the stimulatory activities of MMDA. Approved Doxepin MMDA may decrease the sedative activities of Doxepin. Approved, Investigational Doxylamine MMDA may decrease the sedative activities of Doxylamine. Approved, Vet Approved DPDPE MMDA may increase the analgesic activities of DPDPE. Experimental Droperidol Droperidol may decrease the stimulatory activities of MMDA. Approved, Vet Approved Ebastine MMDA may decrease the sedative activities of Ebastine. Approved, Investigational Ecopipam Ecopipam may decrease the stimulatory activities of MMDA. Investigational Emedastine MMDA may decrease the sedative activities of Emedastine. Approved Epinastine MMDA may decrease the sedative activities of Epinastine. Approved, Investigational Escitalopram MMDA may decrease the sedative activities of Escitalopram. Approved, Investigational Esmirtazapine MMDA may decrease the sedative activities of Esmirtazapine. Investigational Ethopropazine MMDA may decrease the sedative activities of Ethopropazine. Approved Ethosuximide MMDA can cause a decrease in the absorption of Ethosuximide resulting in a reduced serum concentration and potentially a decrease in efficacy. Approved Ethoxzolamide Ethoxzolamide may decrease the excretion rate of MMDA which could result in a higher serum level. Withdrawn Ethylmorphine MMDA may increase the analgesic activities of Ethylmorphine. Approved, Illicit Etoperidone MMDA may decrease the sedative activities of Etoperidone. Withdrawn Etorphine MMDA may increase the analgesic activities of Etorphine. Illicit, Vet Approved Famotidine MMDA may decrease the sedative activities of Famotidine. Approved Fencamfamine Fencamfamine may decrease the stimulatory activities of MMDA. Approved, Illicit, Withdrawn Fentanyl MMDA may increase the analgesic activities of Fentanyl. Approved, Illicit, Investigational, Vet Approved Fexofenadine MMDA may decrease the sedative activities of Fexofenadine. Approved, Investigational Fluanisone Fluanisone may decrease the stimulatory activities of MMDA. Experimental Flunarizine MMDA may decrease the sedative activities of Flunarizine. Approved Flupentixol Flupentixol may decrease the stimulatory activities of MMDA. Approved, Investigational, Withdrawn Fluphenazine Fluphenazine may decrease the stimulatory activities of MMDA. Approved Fluspirilene Fluspirilene may decrease the stimulatory activities of MMDA. Approved, Investigational Furazolidone Furazolidone may increase the hypertensive activities of MMDA. Approved, Investigational, Vet Approved Glutamic Acid The serum concentration of MMDA can be decreased when it is combined with Glutamic Acid. Approved, Nutraceutical Guanethidine The serum concentration of MMDA can be decreased when it is combined with Guanethidine. Approved Haloperidol Haloperidol may decrease the stimulatory activities of MMDA. Approved Harmaline The risk or severity of adverse effects can be increased when MMDA is combined with Harmaline. Experimental Heroin MMDA may increase the analgesic activities of Heroin. Approved, Illicit, Investigational Hydracarbazine The risk or severity of adverse effects can be increased when MMDA is combined with Hydracarbazine. Experimental Hydrocodone MMDA may increase the analgesic activities of Hydrocodone. Approved, Illicit Hydromorphone MMDA may increase the analgesic activities of Hydromorphone. Approved, Illicit Hydrotalcite Hydrotalcite may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Experimental, Investigational Hydroxyzine MMDA may decrease the sedative activities of Hydroxyzine. Approved Iloperidone Iloperidone may decrease the stimulatory activities of MMDA. Approved Imipramine Imipramine may increase the stimulatory activities of MMDA. Approved Ioflupane I-123 MMDA may decrease effectiveness of Ioflupane I-123 as a diagnostic agent. Approved Iprindole Iprindole may increase the stimulatory activities of MMDA. Experimental Iproclozide The risk or severity of adverse effects can be increased when MMDA is combined with Iproclozide. Withdrawn Iproniazid Iproniazid may increase the hypertensive activities of MMDA. Withdrawn Isocarboxazid Isocarboxazid may increase the hypertensive activities of MMDA. Approved Isothipendyl MMDA may decrease the sedative activities of Isothipendyl. Approved Ketobemidone MMDA may increase the analgesic activities of Ketobemidone. Approved, Investigational Ketotifen MMDA may decrease the sedative activities of Ketotifen. Approved Lafutidine MMDA may decrease the sedative activities of Lafutidine. Investigational Lavoltidine MMDA may decrease the sedative activities of Lavoltidine. Investigational Levocabastine MMDA may decrease the sedative activities of Levocabastine. Approved, Investigational Levocetirizine MMDA may decrease the sedative activities of Levocetirizine. Approved Levomethadyl Acetate MMDA may increase the analgesic activities of Levomethadyl Acetate. Approved, Investigational Levorphanol MMDA may increase the analgesic activities of Levorphanol. Approved Lithium Lithium may decrease the stimulatory activities of MMDA. Approved Lodoxamide MMDA may decrease the sedative activities of Lodoxamide. Approved Lofentanil MMDA may increase the analgesic activities of Lofentanil. Illicit Lofepramine Lofepramine may increase the stimulatory activities of MMDA. Experimental Loratadine MMDA may decrease the sedative activities of Loratadine. Approved, Investigational Lorpiprazole MMDA may decrease the sedative activities of Lorpiprazole. Approved Loxapine Loxapine may decrease the stimulatory activities of MMDA. Approved Lurasidone Lurasidone may decrease the stimulatory activities of MMDA. Approved, Investigational Magaldrate Magaldrate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Withdrawn Magnesium carbonate Magnesium carbonate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Investigational Magnesium hydroxide Magnesium hydroxide may decrease the excretion rate of MMDA which could result in a higher serum level. Approved, Investigational Magnesium oxide Magnesium oxide may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Magnesium peroxide Magnesium peroxide may decrease the excretion rate of MMDA which could result in a higher serum level. Experimental Magnesium silicate Magnesium silicate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Magnesium Trisilicate Magnesium Trisilicate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Maprotiline MMDA may decrease the sedative activities of Maprotiline. Approved, Investigational Mebanazine The risk or severity of adverse effects can be increased when MMDA is combined with Mebanazine. Withdrawn Meclizine MMDA may decrease the sedative activities of Meclizine. Approved Melitracen Melitracen may increase the stimulatory activities of MMDA. Experimental, Investigational Melperone Melperone may decrease the stimulatory activities of MMDA. Approved, Investigational Meptazinol MMDA may increase the analgesic activities of Meptazinol. Experimental Mepyramine MMDA may decrease the sedative activities of Mepyramine. Approved, Vet Approved Mequitazine MMDA may decrease the sedative activities of Mequitazine. Approved Mesoridazine Mesoridazine may decrease the stimulatory activities of MMDA. Approved, Investigational Methadone MMDA may increase the analgesic activities of Methadone. Approved Methadyl Acetate MMDA may increase the analgesic activities of Methadyl Acetate. Approved, Illicit Methantheline MMDA may decrease the sedative activities of Methantheline. Approved, Investigational Methapyrilene MMDA may decrease the sedative activities of Methapyrilene. Withdrawn Methazolamide Methazolamide may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Methdilazine MMDA may decrease the sedative activities of Methdilazine. Approved Methenamine The serum concentration of MMDA can be decreased when it is combined with Methenamine. Approved, Vet Approved Methotrimeprazine Methotrimeprazine may decrease the stimulatory activities of MMDA. Approved, Investigational Methylene blue The risk or severity of adverse effects can be increased when MMDA is combined with Methylene blue. Approved, Investigational Metiamide MMDA may decrease the sedative activities of Metiamide. Experimental Mianserin MMDA may decrease the sedative activities of Mianserin. Approved, Investigational Minaprine Minaprine may increase the hypertensive activities of MMDA. Approved Mirtazapine MMDA may decrease the sedative activities of Mirtazapine. Approved Mizolastine MMDA may decrease the sedative activities of Mizolastine. Investigational Moclobemide Moclobemide may increase the hypertensive activities of MMDA. Approved, Investigational Molindone Molindone may decrease the stimulatory activities of MMDA. Approved Moperone Moperone may decrease the stimulatory activities of MMDA. Experimental Morphine MMDA may increase the analgesic activities of Morphine. Approved, Investigational Mosapramine Mosapramine may decrease the stimulatory activities of MMDA. Experimental Nalbuphine MMDA may increase the analgesic activities of Nalbuphine. Approved Nialamide Nialamide may increase the hypertensive activities of MMDA. Withdrawn Nicomorphine MMDA may increase the analgesic activities of Nicomorphine. Experimental Nizatidine MMDA may decrease the sedative activities of Nizatidine. Approved Normethadone MMDA may increase the analgesic activities of Normethadone. Approved, Illicit Nortriptyline Nortriptyline may increase the stimulatory activities of MMDA. Approved Octamoxin The risk or severity of adverse effects can be increased when MMDA is combined with Octamoxin. Withdrawn Olanzapine Olanzapine may decrease the stimulatory activities of MMDA. Approved, Investigational Olopatadine MMDA may decrease the sedative activities of Olopatadine. Approved Ondansetron Ondansetron may decrease the stimulatory activities of MMDA. Approved Opipramol Opipramol may increase the stimulatory activities of MMDA. Investigational Opium MMDA may increase the analgesic activities of Opium. Approved, Illicit Orphenadrine MMDA may decrease the sedative activities of Orphenadrine. Approved Osanetant Osanetant may decrease the stimulatory activities of MMDA. Investigational Oxatomide MMDA may decrease the sedative activities of Oxatomide. Investigational Oxycodone MMDA may increase the analgesic activities of Oxycodone. Approved, Illicit, Investigational Oxymorphone MMDA may increase the analgesic activities of Oxymorphone. Approved, Investigational, Vet Approved Oxypertine Oxypertine may decrease the stimulatory activities of MMDA. Experimental Ozagrel MMDA may decrease the sedative activities of Ozagrel. Investigational Paliperidone Paliperidone may decrease the stimulatory activities of MMDA. Approved Pargyline Pargyline may increase the hypertensive activities of MMDA. Approved Pemirolast MMDA may decrease the sedative activities of Pemirolast. Approved, Investigational Penfluridol Penfluridol may decrease the stimulatory activities of MMDA. Experimental Pentazocine MMDA may increase the analgesic activities of Pentazocine. Approved, Vet Approved Perazine Perazine may decrease the stimulatory activities of MMDA. Approved, Investigational Perospirone Perospirone may decrease the stimulatory activities of MMDA. Approved Perphenazine Perphenazine may decrease the stimulatory activities of MMDA. Approved Pethidine MMDA may increase the analgesic activities of Pethidine. Approved Phenazocine MMDA may increase the analgesic activities of Phenazocine. Experimental Phenelzine Phenelzine may increase the hypertensive activities of MMDA. Approved Phenindamine MMDA may decrease the sedative activities of Phenindamine. Approved Pheniprazine The risk or severity of adverse effects can be increased when MMDA is combined with Pheniprazine. Withdrawn Pheniramine MMDA may decrease the sedative activities of Pheniramine. Approved Phenobarbital The serum concentration of Phenobarbital can be decreased when it is combined with MMDA. Approved, Investigational Phenoperidine MMDA may increase the analgesic activities of Phenoperidine. Experimental Phenoxypropazine The risk or severity of adverse effects can be increased when MMDA is combined with Phenoxypropazine. Withdrawn Phenytoin The serum concentration of Phenytoin can be decreased when it is combined with MMDA. Approved, Vet Approved Pimozide Pimozide may decrease the stimulatory activities of MMDA. Approved Pipamperone Pipamperone may decrease the stimulatory activities of MMDA. Approved, Investigational Pipotiazine Pipotiazine may decrease the stimulatory activities of MMDA. Approved, Investigational Piritramide MMDA may increase the analgesic activities of Piritramide. Approved, Investigational Pirlindole Pirlindole may increase the hypertensive activities of MMDA. Approved Pitolisant MMDA may decrease the sedative activities of Pitolisant. Approved, Investigational Pivhydrazine The risk or severity of adverse effects can be increased when MMDA is combined with Pivhydrazine. Withdrawn Pizotifen MMDA may decrease the sedative activities of Pizotifen. Approved Procaine The risk or severity of adverse effects can be increased when MMDA is combined with Procaine. Approved, Investigational, Vet Approved Procarbazine The risk or severity of adverse effects can be increased when MMDA is combined with Procarbazine. Approved, Investigational Prochlorperazine Prochlorperazine may decrease the stimulatory activities of MMDA. Approved, Vet Approved Promazine Promazine may decrease the stimulatory activities of MMDA. Approved, Vet Approved Promethazine MMDA may decrease the sedative activities of Promethazine. Approved, Investigational Propericiazine Propericiazine may decrease the stimulatory activities of MMDA. Approved, Investigational Propiomazine MMDA may decrease the sedative activities of Propiomazine. Approved Prothipendyl Prothipendyl may decrease the stimulatory activities of MMDA. Investigational Protriptyline Protriptyline may increase the stimulatory activities of MMDA. Approved Quetiapine Quetiapine may decrease the stimulatory activities of MMDA. Approved Quifenadine MMDA may decrease the sedative activities of Quifenadine. Experimental Raclopride Raclopride may decrease the stimulatory activities of MMDA. Investigational Ranitidine MMDA may decrease the sedative activities of Ranitidine. Approved Rasagiline Rasagiline may increase the hypertensive activities of MMDA. Approved Remifentanil MMDA may increase the analgesic activities of Remifentanil. Approved Remoxipride Remoxipride may decrease the stimulatory activities of MMDA. Approved, Withdrawn Reserpine Reserpine may decrease the stimulatory activities of MMDA. Approved, Investigational Risperidone Risperidone may decrease the stimulatory activities of MMDA. Approved, Investigational Ritanserin Ritanserin may decrease the stimulatory activities of MMDA. Investigational Roxatidine acetate MMDA may decrease the sedative activities of Roxatidine acetate. Approved, Investigational Rupatadine MMDA may decrease the sedative activities of Rupatadine. Approved Safrazine The risk or severity of adverse effects can be increased when MMDA is combined with Safrazine. Withdrawn Selegiline The risk or severity of adverse effects can be increased when MMDA is combined with Selegiline. Approved, Investigational, Vet Approved Sertindole Sertindole may decrease the stimulatory activities of MMDA. Approved, Investigational, Withdrawn Sodium bicarbonate Sodium bicarbonate may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Sufentanil MMDA may increase the analgesic activities of Sufentanil. Approved, Investigational Sulpiride Sulpiride may decrease the stimulatory activities of MMDA. Approved, Investigational Sultopride Sultopride may decrease the stimulatory activities of MMDA. Experimental Tapentadol MMDA may increase the analgesic activities of Tapentadol. Approved Terfenadine MMDA may decrease the sedative activities of Terfenadine. Approved, Withdrawn Tesmilifene MMDA may decrease the sedative activities of Tesmilifene. Investigational Tetrahydropalmatine Tetrahydropalmatine may decrease the stimulatory activities of MMDA. Investigational Thiopropazate Thiopropazate may decrease the stimulatory activities of MMDA. Experimental Thioproperazine Thioproperazine may decrease the stimulatory activities of MMDA. Approved Thioridazine Thioridazine may decrease the stimulatory activities of MMDA. Approved, Withdrawn Thiothixene Thiothixene may decrease the stimulatory activities of MMDA. Approved Thonzylamine MMDA may decrease the sedative activities of Thonzylamine. Approved Tianeptine Tianeptine may increase the stimulatory activities of MMDA. Approved, Investigational Tiapride Tiapride may decrease the stimulatory activities of MMDA. Approved, Investigational Tilidine MMDA may increase the analgesic activities of Tilidine. Experimental Toloxatone Toloxatone may increase the hypertensive activities of MMDA. Approved Tramadol MMDA may increase the analgesic activities of Tramadol. Approved, Investigational Tranilast MMDA may decrease the sedative activities of Tranilast. Approved, Investigational Tranylcypromine Tranylcypromine may increase the hypertensive activities of MMDA. Approved, Investigational Trazodone MMDA may decrease the sedative activities of Trazodone. Approved, Investigational Trifluoperazine Trifluoperazine may decrease the stimulatory activities of MMDA. Approved, Investigational Trifluperidol Trifluperidol may decrease the stimulatory activities of MMDA. Experimental Triflupromazine Triflupromazine may decrease the stimulatory activities of MMDA. Approved, Vet Approved Trimipramine Trimipramine may increase the stimulatory activities of MMDA. Approved Tripelennamine MMDA may decrease the sedative activities of Tripelennamine. Approved, Vet Approved Triprolidine MMDA may decrease the sedative activities of Triprolidine. Approved Tritoqualine MMDA may decrease the sedative activities of Tritoqualine. Approved Tromethamine Tromethamine may decrease the excretion rate of MMDA which could result in a higher serum level. Approved Veralipride Veralipride may decrease the stimulatory activities of MMDA. Experimental Vitamin C The serum concentration of MMDA can be decreased when it is combined with Vitamin C. Approved, Nutraceutical Ziprasidone Ziprasidone may decrease the stimulatory activities of MMDA. Approved Zotepine Zotepine may decrease the stimulatory activities of MMDA. Approved, Investigational, Withdrawn Zuclopenthixol Zuclopenthixol may decrease the stimulatory activities of MMDA. Approved, Investigational - Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- PubChem Compound
- 26175
- PubChem Substance
- 46506802
- ChemSpider
- 24386
- ChEMBL
- CHEMBL126506
- Wikipedia
- MMDA_%28psychedelic%29
Clinical Trials
Pharmacoeconomics
- Manufacturers
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- Packagers
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- Dosage forms
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- Prices
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Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.71 mg/mL ALOGPS logP 1.07 ALOGPS logP 1.27 ChemAxon logS -1.9 ALOGPS pKa (Strongest Basic) 9.99 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 53.71 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 55.94 m3·mol-1 ChemAxon Polarizability 22.38 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9972 Blood Brain Barrier + 0.9147 Caco-2 permeable + 0.6269 P-glycoprotein substrate Non-substrate 0.6271 P-glycoprotein inhibitor I Non-inhibitor 0.8586 P-glycoprotein inhibitor II Non-inhibitor 0.9336 Renal organic cation transporter Non-inhibitor 0.7891 CYP450 2C9 substrate Non-substrate 0.8935 CYP450 2D6 substrate Non-substrate 0.6434 CYP450 3A4 substrate Non-substrate 0.5519 CYP450 1A2 substrate Inhibitor 0.7772 CYP450 2C9 inhibitor Non-inhibitor 0.7849 CYP450 2D6 inhibitor Inhibitor 0.7001 CYP450 2C19 inhibitor Non-inhibitor 0.5393 CYP450 3A4 inhibitor Inhibitor 0.5469 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6085 Ames test Non AMES toxic 0.5878 Carcinogenicity Non-carcinogens 0.9168 Biodegradation Not ready biodegradable 0.7228 Rat acute toxicity 2.5346 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9776 hERG inhibition (predictor II) Non-inhibitor 0.957
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzodioxoles
- Sub Class
- Not Available
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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
- 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 June 02, 2018 06:49