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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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsBenzodioxoles; Alkyl Aryl Ethers; Polyamines; Acetals; Monoalkylamines
Substituentsalkyl aryl ether; acetal; ether; polyamine; amine; primary amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9668
Caco-2 permeable + 0.6011
P-glycoprotein substrate Non-substrate 0.7169
P-glycoprotein inhibitor I Non-inhibitor 0.9117
P-glycoprotein inhibitor II Non-inhibitor 0.9278
Renal organic cation transporter Non-inhibitor 0.801
CYP450 2C9 substrate Non-substrate 0.8661
CYP450 2D6 substrate Non-substrate 0.6198
CYP450 3A4 substrate Non-substrate 0.6464
CYP450 1A2 substrate Inhibitor 0.7625
CYP450 2C9 substrate Non-inhibitor 0.8247
CYP450 2D6 substrate Inhibitor 0.7713
CYP450 2C19 substrate Non-inhibitor 0.5475
CYP450 3A4 substrate Non-inhibitor 0.7028
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5
Ames test Non AMES toxic 0.6835
Carcinogenicity Non-carcinogens 0.8578
Biodegradation Ready biodegradable 0.6509
Rat acute toxicity 2.4882 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9589
hERG inhibition (predictor II) Non-inhibitor 0.9386
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 solubility2.83e+00 g/lALOGPS
logP1.15ALOGPS
logP1.43ChemAxon
logS-1.8ALOGPS
pKa (strongest basic)10.01ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area44.48ChemAxon
rotatable bond count2ChemAxon
refractivity49.47ChemAxon
polarizability19.51ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound1614
PubChem Substance46506100
ChemSpider1555
BindingDB50005247
ChEBI100592
ChEMBL
Wikipedia3,4-Methylenedioxyamphetamine
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