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
• #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: CHEMBL43048
  CAS Number: 42542-10-9
  UNII: KE1SEN21RM
  DrugBank ID: DB01454
  TTD ID: D0F5NJ
  VARIDT ID: DR00433
  INTEDE ID: DR1089
• Drug-Molecule Activity Atlas (DMA)NEW: Click to Jump to the Detailed DMA Information of This Drug
• Drug ADMET Endpoint Profile (DAE)NEW: Click to Jump to the Detailed DAE 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
Arylamine N-acetyltransferase 2 (NAT2)	OTBPDQOY	ARY2_HUMAN	Biotransformations	[6]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[7]
Bcl-2 homologous antagonist/killer (BAK1)	OTDP6ILW	BAK_HUMAN	Gene/Protein Processing	[8]
Bcl-2-binding component 3, isoforms 3/4 (BBC3)	OTUAXDAY	BBC3B_HUMAN	Gene/Protein Processing	[8]
Bcl-2-like protein 1 (BCL2L1)	OTRC5K9O	B2CL1_HUMAN	Gene/Protein Processing	[8]
Bcl-2-like protein 11 (BCL2L11)	OTNQQWFJ	B2L11_HUMAN	Gene/Protein Processing	[8]
Bcl2-associated agonist of cell death (BAD)	OT63ERYM	BAD_HUMAN	Gene/Protein Processing	[8]
BH3-interacting domain death agonist (BID)	OTOSHSHU	BID_HUMAN	Gene/Protein Processing	[8]
Sodium-dependent serotonin transporter (SLC6A4)	OT6FGDLW	SC6A4_HUMAN	Gene/Protein Processing	[9]

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

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] 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.
• [7] P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. Addict Biol. 2003 Dec;8(4):413-8. doi: 10.1080/13556210310001646475.
• [8] 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.
• [9] Pharmacological characterization of the aminorex analogs 4-MAR, 4,4'-DMAR, and 3,4-DMAR. Neurotoxicology. 2019 May;72:95-100. doi: 10.1016/j.neuro.2019.02.011. Epub 2019 Feb 15.