Details of the Drug

General Information of Drug (ID: DMYVU47)

Drug Name
METHYLENEDIOXYMETHAMPHETAMINE
Synonyms
3,4-Methylenedioxymethamphetamine; MDMA; 3,4-methylenedioxymethamphetamine; Ecstasy; Methylenedioxymethamphetamine; 42542-10-9; N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE; DL-(3,4-Methylenedioxy)methamphetamine; (RS)-3,4-(methylenedioxy)methamphetamine; Midomafetamine; MDMA (unspecified); N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine; HSDB 6929; 1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine; CHEBI:1391; DEA No 7405; (+-)-(3,4-Methylenedioxy)methamphetamine; (+-)-N-Methyl-3,4-(methylenedioxy)amphetamine; 1,3-Benzodioxole-5-ethanamine, N,alpha-dimethyl-
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 193.24
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Elimination
The drug is excreted via renal []
Half-life
The concentration or amount of drug in body reduced by one-half in 6C10 [2]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C11H15NO2
IUPAC Name
1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
Canonical SMILES
CC(CC1=CC2=C(C=C1)OCO2)NC
InChI
InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
InChIKey
SHXWCVYOXRDMCX-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1615
ChEBI ID
CHEBI:1391
CAS Number
42542-10-9
UNII
KE1SEN21RM
DrugBank ID
DB01454
TTD ID
D0F5NJ
VARIDT ID
DR00433
INTEDE ID
DR1089
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 2A receptor (HTR2A) TTJQOD7 5HT2A_HUMAN Agonist [3]
5-HT 2B receptor (HTR2B) TT0K1SC 5HT2B_HUMAN Agonist [3]
5-HT 2C receptor (HTR2C) TTWJBZ5 5HT2C_HUMAN Agonist [3]
Dopamine transporter (DAT) TTVBI8W SC6A3_HUMAN Inhibitor [3]
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Inhibitor [3]
Serotonin transporter (SERT) TT3ROYC SC6A4_HUMAN Inhibitor [3]
Synaptic vesicle amine transporter (SLC18A2) TTNZRI3 VMAT2_HUMAN Antagonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [4]
Catechol O-methyltransferase (COMT) DEV3T4A COMT_HUMAN Substrate [4]
Cytochrome P450 102A1 (cyp102) DE4OGUF CPXB_BACMB Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Amine oxidase A (MAOA) OT8NIWMQ AOFA_HUMAN Gene/Protein Processing [6]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [7]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [7]
Arylamine N-acetyltransferase 2 (NAT2) OTBPDQOY ARY2_HUMAN Biotransformations [8]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [9]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [7]
Bcl-2-binding component 3, isoforms 3/4 (BBC3) OTUAXDAY BBC3B_HUMAN Gene/Protein Processing [7]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [7]
Bcl-2-like protein 11 (BCL2L11) OTNQQWFJ B2L11_HUMAN Gene/Protein Processing [7]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) 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
Synaptic vesicle amine transporter (SLC18A2) DTT SLC18A2 2.69E-02 -0.04 -0.11
Catechol O-methyltransferase (COMT) DME COMT 5.00E-03 9.63E-02 4.48E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 7.30E-01 -1.91E-02 -1.41E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4574).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents. Addiction. 2006 Sep;101(9):1241-5.
4 Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition. Ther Drug Monit. 2004 Apr;26(2):137-44.
5 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
6 Inhibition potential of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolites on the in vitro monoamine oxidase (MAO)-catalyzed deamination of the neurotransmitters serotonin and dopamine. Toxicol Lett. 2016 Jan 22;243:48-55.
7 An insight into the hepatocellular death induced by amphetamines, individually and in combination: the involvement of necrosis and apoptosis. Arch Toxicol. 2013 Dec;87(12):2165-85. doi: 10.1007/s00204-013-1082-9. Epub 2013 Jul 3.
8 N-acetyltransferase 2 genetic polymorphism modifies genotoxic and oxidative damage from new psychoactive substances. Arch Toxicol. 2023 Jan;97(1):189-199. doi: 10.1007/s00204-022-03383-2. Epub 2022 Sep 23.
9 P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. Addict Biol. 2003 Dec;8(4):413-8. doi: 10.1080/13556210310001646475.