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42542-10-9 molecular structure
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[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 and InChIs

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

Cite this record

CBID:1257 http://www.chembase.cn/molecule-1257.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -1.3648726  LogD (pH = 7.4) -0.76064247 
Log P 1.8600644  Molar Refractivity 54.2467 cm3
Polarizability 21.603132 Å3 Polar Surface Area 30.49 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 1.65  LOG S -1.78 
Solubility (Water) 3.22e+00 g/l 

PROPERTIES

PROPERTIES

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

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01454 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

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