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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyMMDA
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
Structure for MMDA (DB01442)
- Synonyms
- (+-)-MMDA
- 3-Methoxy-4,5-methylenedioxyphenylisopropylamine
- 3-Methoxy-alpha-methyl-4,5-methylenedioxyphenethylamine
- 3-methoxy-methylenedioxyamphetamine
- 5-Methoxy-3,4-methylenedioxyamphetamine
- External IDs
- DEA No. 7401
- Categories
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Amphetamines
- Antidepressive Agents
- Central Nervous System Depressants
- Ethylamines
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Phenethylamines
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Agonists
- Serotonin Agents
- Serotonin Receptor Agonists
- Sympathomimetics
- 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
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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 agonistHumans ASodium-dependent dopamine transporter negative modulatorHumans ASodium-dependent serotonin transporter negative modulatorHumans ASodium-dependent noradrenaline transporter negative modulatorHumans ASynaptic vesicular amine transporter inhibitorHumans AChromaffin granule amine transporter inhibitorHumans AAmine oxidase [flavin-containing] A inhibitorHumans AAmine oxidase [flavin-containing] B inhibitorHumans - 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 (R)-warfarin The risk or severity of adverse effects can be increased when MMDA is combined with (R)-warfarin. (S)-Warfarin The risk or severity of adverse effects can be increased when MMDA is combined with (S)-Warfarin. 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid The risk or severity of hypertension can be increased when MMDA is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid. 1-benzylimidazole The therapeutic efficacy of 1-benzylimidazole can be decreased when used in combination with MMDA. 3-isobutyl-1-methyl-7H-xanthine The risk or severity of adverse effects can be increased when MMDA is combined with 3-isobutyl-1-methyl-7H-xanthine. 3,5-diiodothyropropionic acid The risk or severity of adverse effects can be increased when MMDA is combined with 3,5-diiodothyropropionic acid. 4-hydroxycoumarin The risk or severity of adverse effects can be increased when MMDA is combined with 4-hydroxycoumarin. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when MMDA is combined with 4-Methoxyamphetamine. 6-O-benzylguanine The risk or severity of adverse effects can be increased when MMDA is combined with 6-O-benzylguanine. 7-Deazaguanine The risk or severity of adverse effects can be increased when MMDA is combined with 7-Deazaguanine. - 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
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
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
- Humans
- 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
- Humans
- 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
- Humans
- 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
- Humans
- 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
- Humans
- 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
- Humans
- 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
- Humans
- 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
- Humans
- 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 December 14, 2018 05:37