General Information of the Compound
Compound ID
CP0228182
Compound Name
(+/-)2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine
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Synonyms
1,3-Benzodioxole-5-ethanamine, alpha-methyl-
1-(1,3-benzodioxol-5-yl)propan-2-amine
3,4-Methylenedioxy-amphetamine
3,4-methylenedioxyamphetamine
4764-17-4
5-19-08-00417 (Beilstein Handbook Reference)
AI3-24882
ALPHA-METHYL-3,4-(METHYLENEDIOXY)PHENETHYLAMINE
BRN 0150196
CHEMBL6731
DEA No. 7400
MDA (pharmaceutical)
METHYLENEDIOXYAMPHETAMINE
Methylenedioxyamphetamine
NGBBVGZWCFBOGO-UHFFFAOYSA-N
Phenethylamine, alp
Tenamfetamina [Spanish]
Tenamfetamine
Tenamfetamine [INN]
Tenamfetaminum [Latin]
alpha-Methyl-1,3-benzodioxole-5-ethanamine
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Structure
Formula
C10H13NO2
Molecular Weight
179.219
Canonical SMILES
CC(N)Cc1ccc2OCOc2c1
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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
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InChIKey
NGBBVGZWCFBOGO-UHFFFAOYSA-N
CAS
4764-17-4
Physicochemical Property
logP
1.305
Rotatable Bonds
2
Heavy Atom Count
13
Polar Areas
44.48
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Complexity
13

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 1614
SID: 14748325
ChEMBL ID
CHEMBL6731
DrugBank ID
DB01509
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00884, Sodium-dependent dopamine transporter
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  2
1
IC50 = 6165.95 nM
   TI
   LI
   LO
   TS
2
Ki = 2425 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 890 nM
Protein ID: PT01026, Sodium-dependent noradrenaline transporter
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  2
1
IC50 = 3162.28 nM
   TI
   LI
   LO
   TS
2
Ki = 704 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 266 nM
Protein ID: PT00871, Sodium-dependent serotonin transporter
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  3
1
IC50 = 900 nM
   TI
   LI
   LO
   TS
2
IC50 = 6760.83 nM
   TI
   LI
   LO
   TS
3
Ki = 2306 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 478 nM
Protein ID: PT00891, Sodium-dependent serotonin transporter
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
IC50 = 996 nM
   TI
   LI
   LO
   TS
Cell Viability or Cytotoxicity Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000004 SH-SY5Y Homo sapiens (Human)  1
1
EC50 > 10000000 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( METHYLENEDIOXYAMPHETAMINE )
Drug Name METHYLENEDIOXYAMPHETAMINE
Target(s)
Serotonin transporter (SERT)
Inhibitor
Norepinephrine transporter (NET)
Inhibitor
Dopamine transporter (DAT)
Inhibitor