[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine

• ChemBase ID: 1257
• Molecular Formular: C11H15NO2
• Molecular Mass: 193.2423
• Monoisotopic Mass: 193.11027873
• SMILES: O1c2cc(CC(NC)C)ccc2OC1
• Canonical SMILES: CNC(Cc1ccc2c(c1)OCO2)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: [1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine
• IUPAC Traditional name: MDMA
• Synonyms: MDMA; Ecstasy; 3,4-Methylenedioxymethamphetamine; (±)-1,3-benzodioxolyl-N-methyl-2-propanamine(±)-3,4-methylenedioxy-N-methyl-α-methyl-2-phenethylamineDL-3,4-methylenedioxy-N-methylamphetaminemethylenedioxymethamphetamine; MDMA

Database IDs

• CAS Number: 42542-10-9
• PubChem SID: 46506404; 160964717
• PubChem CID: 1615
• CHEBI ID: 1391
• CHEMBL: 43048
• Chemspider ID: 1556
• DrugBank ID: DB01454
• Unique Ingredient Identifier: KE1SEN21RM
• Wikipedia Title: MDMA

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.3648726
• LogD (pH = 7.4): -0.76064247
• Log P: 1.8600644
• Molar Refractivity: 54.2467 cm^3
• Polarizability: 21.603132 Å^3
• Polar Surface Area: 30.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.65
• LOG S: -1.78
• Solubility (Water): 3.22e+00 g/l

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral, sublingual, insufflation, inhalation (vaporization), injection, rectal
• Excretion: Renal
• Half Life: 6–10 hours (though duration of effects is typically actually 3–5 hours)
• Metabolism: Hepatic, CYP450 extensively involved, especially CYP2D6
• Legal Status: CD Lic (UK); S9 (Australia); Schedule I (US); Schedule III (Canada)
• Pregnancy Category: C

DETAILS

DrugBank - DB01454

• Drug Groups: illicit; experimental
• Description: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy. [PubChem]
• Indication: Clinical trials are now testing the therapeutic potential of MDMA for post-traumatic stress disorder (PTSD) and anxiety associated with terminal cancer. MDMA is one of the four most widely used illicit drugs in the U.S.
• Pharmacology: MDMA acts as a releasing agent of serotonin, norepinephrine, and dopamine.
• Biotransformation: Hepatic: CYP450 extensively involved, especially CYP2D6; ; MDMA is known to be metabolized by two main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. The metabolism may be primarily by cytochrome P450 (CYP450) enzymes (CYP2D6 (in humans, but CYP2D1 in mice), and CYP3A4) and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug.
• Half Life: 6–10 (though duration of effects is typically actually 3–5 hours)
• Elimination: renal
• References: Freudenmann RW, Oxler F, Bernschneider-Reif S: The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents. Addiction. 2006 Sep;101(9):1241-5. [Pubmed] ; Jayanthi LD, Ramamoorthy S: Regulation of monoamine transporters: influence of psychostimulants and therapeutic antidepressants. AAPS J. 2005 Oct 27;7(3):E728-38. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Freudenmann RW, Oxler F, Bernschneider-Reif S: The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents. Addiction. 2006 Sep;101(9):1241-5. Pubmed
• Jayanthi LD, Ramamoorthy S: Regulation of monoamine transporters: influence of psychostimulants and therapeutic antidepressants. AAPS J. 2005 Oct 27;7(3):E728-38. Pubmed