3,4-Methylenedioxymethamphetamine (MDMA),[note 1] commonly kent as ecstasy (E), is a psychoactive drog uised primarily as a recreautional drog.
Quick Facts Clinical data, Pronunciation ...
MDMA |
 |
| Clinical data |
|---|
| Pronunciation | methylenedioxymethamphetamine:
|
|---|
| AHFS/Drugs.com | entry |
|---|
Dependence
liability | Pheesical: nae teepical[1]
Psychological: moderate |
|---|
Addiction
liability | Law–moderate[2][3][4] |
|---|
Routes o
admeenistration | Common: bi mooth[5]
Uncommon: snortin,[5] inhalation (vapourisation),[5] injection,[5][6] rectal |
|---|
| Drog cless | empathogen–entactogen
stimulant |
|---|
| ATC code | |
|---|
| Legal status |
|---|
| Legal status |
- AU: S9 (Prohibitit)
- CA: Schedule I
- DE: Anlage I (Controlled)
- NZ: Class B
- UK: Cless A
- US: Schedule I
- UN: Psychotropic Schedule I
|
|---|
| Pharmacokinetic data |
|---|
| Metabolism | Liver, CYP450 extensively involved, includin CYP2D6 |
|---|
| Metabolites | MDA, HMMA, HMA, DHA, MDP2P, MDOH[7] |
|---|
| Onset o action | 30–45 minutes (bi mooth)[8] |
|---|
| Biological hauf-life | (R)-MDMA: 5.8 ± 2.2 oors[9]
(S)-MDMA: 3.6 ± 0.9 oors[9] |
|---|
| Duration o action | 4–6 hours[3][8] |
|---|
| Excretion | Neer |
|---|
| Identifiers |
|---|
IUPAC name
- (RS)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
|
| Synonyms | 3,4-MDMA, ecstasy (E, X, XTC), molly, mandy[10][11] |
|---|
| CAS Nummer | |
|---|
| PubChem CID | |
|---|
| IUPHAR/BPS | |
|---|
| DrugBank | |
|---|
| ChemSpider | |
|---|
| UNII | |
|---|
| KEGG | |
|---|
| ChEBI | |
|---|
| ChEMBL | |
|---|
| PDB ligand | |
|---|
| Chemical and physical data |
|---|
| Formula | C11H15NO2 |
|---|
| Molar mass | 193.25 g·mol−1 |
|---|
| 3D model (Jmol) | |
|---|
| Chirality | Racemic mixtur |
|---|
| Bylin pynt | 105 °C (221 °F) at 0.4 mmHg (experimental) |
|---|
SMILES
CC(NC)CC1=CC=C(OCO2)C2=C1
|
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 Y Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N Y
|
| (verify) |
|---|
Close
.svg)