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Identification
Name3,4-Methylenedioxyamphetamine
Accession NumberDB01509
TypeSmall Molecule
GroupsExperimental, Illicit
Description

An amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
TenamfetamineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number4764-17-4
WeightAverage: 179.2157
Monoisotopic: 179.094628665
Chemical FormulaC10H13NO2
InChI KeyNGBBVGZWCFBOGO-UHFFFAOYSA-N
InChI
InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
IUPAC Name
1-(2H-1,3-benzodioxol-5-yl)propan-2-amine
SMILES
CC(N)CC1=CC2=C(OCO2)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Aralkylamine
  • Benzenoid
  • Oxacycle
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9668
Caco-2 permeable+0.6011
P-glycoprotein substrateNon-substrate0.7169
P-glycoprotein inhibitor INon-inhibitor0.9117
P-glycoprotein inhibitor IINon-inhibitor0.9278
Renal organic cation transporterNon-inhibitor0.801
CYP450 2C9 substrateNon-substrate0.8661
CYP450 2D6 substrateNon-substrate0.6198
CYP450 3A4 substrateNon-substrate0.6464
CYP450 1A2 substrateInhibitor0.7625
CYP450 2C9 substrateNon-inhibitor0.8247
CYP450 2D6 substrateInhibitor0.7713
CYP450 2C19 substrateNon-inhibitor0.5475
CYP450 3A4 substrateNon-inhibitor0.7028
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.6835
CarcinogenicityNon-carcinogens0.8578
BiodegradationReady biodegradable0.6509
Rat acute toxicity2.4882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9589
hERG inhibition (predictor II)Non-inhibitor0.9386
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP1.64HANSCH,C & LEO,AJ (1985)
pKa9.67 (at 25 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility2.83 mg/mLALOGPS
logP1.15ALOGPS
logP1.43ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.47 m3·mol-1ChemAxon
Polarizability19.51 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:14