Details of the Drug

General Information of Drug (ID: DMP204G)

Drug Name

METHYLENEDIOXYAMPHETAMINE

Synonyms

Tenamfetamine; 3,4-methylenedioxyamphetamine; Methylenedioxyamphetamine; 4764-17-4; 3,4-Methylenedioxy-amphetamine; MDA (pharmaceutical); Tenamfetamine [INN]; Tenamfetaminum [Latin]; Tenamfetamina [Spanish]; 1-(1,3-benzodioxol-5-yl)propan-2-amine; BRN 0150196; DEA No. 7400; AI3-24882; alpha-Methyl-1,3-benzodioxole-5-ethanamine; 1,3-Benzodioxole-5-ethanamine, alpha-methyl-; CHEMBL6731; ALPHA-METHYL-3,4-(METHYLENEDIOXY)PHENETHYLAMINE; NGBBVGZWCFBOGO-UHFFFAOYSA-N; 5-19-08-00417 (Beilstein Handbook Reference); Phenethylamine, alp

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

179.22

Logarithm of the Partition Coefficient (xlogp)

1.6

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C10H13NO2
IUPAC Name: 1-(1,3-benzodioxol-5-yl)propan-2-amine
Canonical SMILES: CC(CC1=CC2=C(C=C1)OCO2)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
InChIKey: NGBBVGZWCFBOGO-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 1614
ChEBI ID: CHEBI:166520
CAS Number: 4764-17-4
DrugBank ID: DB01509
TTD ID: D02TMK
VARIDT ID: DR00861

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine transporter (DAT)	TTVBI8W	SC6A3_HUMAN	Inhibitor	[1]
Norepinephrine transporter (NET)	TTAWNKZ	SC6A2_HUMAN	Inhibitor	[1]
Serotonin transporter (SERT)	TT3ROYC	SC6A4_HUMAN	Inhibitor	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[3]
Prostaglandin G/H synthase 1 (PTGS1)	OTHCRLEC	PGH1_HUMAN	Drug Response	[4]
Prostaglandin G/H synthase 2 (PTGS2)	OT75U9M4	PGH2_HUMAN	Drug Response	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine transporter (DAT)	DTT	SLC6A3	1.08E-03	-3.08	-1.99
Serotonin transporter (SERT)	DTT	SLC6A4	8.76E-01	7.18E-05	6.19E-04

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioampheta... Bioorg Med Chem. 2010 Jun 1;18(11):4009-31.
2	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents. Eur J Med Chem. 2009 Dec;44(12):4862-88.
3	Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein. Toxicol Lett. 2013 Feb 27;217(2):137-42. doi: 10.1016/j.toxlet.2012.12.012. Epub 2012 Dec 27.
4	Human prostaglandin H synthase (hPHS)-1 and hPHS-2 in amphetamine analog bioactivation, DNA oxidation, and cytotoxicity. Toxicol Sci. 2011 Mar;120(1):154-62.