Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H15NO2.ClH |
| Molecular Weight | 229.7036 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(Cc1ccc2c(c1)OCO2)NC.Cl
InChI
InChIKey=LUWHVONVCYWRMZ-UHFFFAOYSA-N
InChI=1S/C11H15NO2.ClH/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;1H
| Molecular Formula | C11H15NO2 |
| Molecular Weight | 193.2427 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.4609 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Methylenedioxymethamphetamine (or 3,4-methylenedioxymethamphetamine (MDMA)), a synthetic, psychoactive drug also known as ecstasy that was used as a recreational drug. This drug acts as both a stimulant and psychedelic and exerts its effects in the brain on neurons that use the chemicals serotonin, dopamine and norepinephrine to communicate with other neurons. In spite of the presence of this compound in the List of control and forbidden compounds, it was studied in psychotherapy for patients with chronic, treatment-resistant posttraumatic stress disorder. Initial results showed efficacy for the treatment approach, although further studies are needed.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q96RJ0 Gene ID: 134864.0 Gene Symbol: TAAR1 Target Organism: Homo sapiens (Human) |
|||
Target ID: Q05940 Gene ID: 6571.0 Gene Symbol: SLC18A2 Target Organism: Homo sapiens (Human) |
|||
Target ID: CHEMBL2096662 |
|||
| 405.0 nM [IC50] | |||
Target ID: CHEMBL228 |
425.0 nM [IC50] | ||
Target ID: CHEMBL238 |
1.44 µM [IC50] |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Reinforcing effects of MDMA ("ecstasy") in drug-naive and cocaine-trained rats. | 2001 |
|
| Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat. | 2001 Apr |
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| The many faces of ecstasy. | 2001 Apr |
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| Investigating the neurocognitive deficits associated with chronic drug misuse. | 2001 Apr |
|
| Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate. | 2001 Apr |
|
| Memory impairment in abstinent MDMA ("Ecstasy") users: a longitudinal investigation. | 2001 Apr 10 |
|
| [Fatal ecstasy intoxication]. | 2001 Apr 16 |
|
| Methylenedioxymethamphetamine-induced suppression of interleukin-1beta and tumour necrosis factor-alpha is not mediated by serotonin. | 2001 Apr 20 |
|
| Intravenous administration of ecstasy (3,4-methylendioxymethamphetamine) enhances cortical and striatal acetylcholine release in vivo. | 2001 Apr 27 |
|
| Ecstasy crackdown. Will the feds use a 1980s anti-crack law to destroy the rave movement? | 2001 Apr 9 |
|
| [Complications arising from occasional consumption of ecstasy]. | 2001 Aug |
|
| Studies on the neuroprotective effect of the enantiomers of AR-A008055, a compound structurally related to clomethiazole, on MDMA ("ecstasy")-induced neurodegeneration in rat brain. | 2001 Aug |
|
| Rhabdomyolysis and 3,4 methylenedioxymethamphetamine in rheumatological practice. | 2001 Aug |
|
| Ecstasy pill testing: harm minimization gone too far? | 2001 Aug |
|
| Pre-exposure to (+/-)3,4-methylenedioxy-methamphetamine (MDMA) facilitates acquisition of intravenous cocaine self-administration in rats. | 2001 Aug |
|
| On-line identification of 3,4-methylenedioxymethamphetamine in human urine by non-aqueous capillary electrophoresis-fluorescence spectroscopy at 77 K. | 2001 Aug 15 |
|
| The road to rave. | 2001 Aug 6 |
|
| [Young woman dies of water intoxication after taking one tablet of ecstasy. Today's drug panorama calls for increased vigilance in health care]. | 2001 Feb 21 |
|
| Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats. | 2001 Feb 9 |
|
| Monitoring synthetic drug markets, trends, and public health. | 2001 Jan |
|
| The relative contributions of ecstasy and cannabis to cognitive impairment. | 2001 Jan |
|
| Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine. | 2001 Jan |
|
| Dextromethorphan and ecstasy pills. | 2001 Jan 24-31 |
|
| MDMA. | 2001 Jul |
|
| Analysis of 4-methylthioamphetamine in clinical specimens. | 2001 Jul |
|
| Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase. | 2001 Jul |
|
| MDMA ("ecstasy") exhibits an anxiogenic-like activity in social encounters between male mice. | 2001 Jul |
|
| Repeated intermittent administration of psychomotor stimulant drugs alters the acquisition of Pavlovian approach behavior in rats: differential effects of cocaine, d-amphetamine and 3,4- methylenedioxymethamphetamine ("Ecstasy"). | 2001 Jul 15 |
|
| 3,4-Methylenedioxymethamphetamine (ecstasy)-induced hepatotoxicity: multidetector CT and pathology findings. | 2001 Jul-Aug |
|
| Rave on. Ecstasy use continues to grow & present new problems for EMS. | 2001 Jun |
|
| Designer drugs. Assess & manage patients intoxicated with ecstasy, GHB or rohypnol--the three most commonly abused designer drugs. | 2001 Jun |
|
| 3,4-Methylenedioxymethamphetamine (MDMA) as a unique model of serotonin receptor function and serotonin-dopamine interactions. | 2001 Jun |
|
| A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. | 2001 Jun 15 |
|
| Effects of methylenedioxymethamphetamine on noradrenaline-evoked contractions of rat right ventricle and small mesenteric artery. | 2001 Jun 22 |
|
| Spontaneous pneumomediastinum, pneumothorax and ecstasy abuse. | 2001 Mar |
|
| 3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose. | 2001 Mar |
|
| The effect of (R)-HA966 or ACEA 1021 on dexfenfluramine or (S)-MDMA-induced changes in temperature, activity, and neurotoxicity. | 2001 Mar |
|
| Subjective effects of MDMA ('Ecstasy') on human sexual function. | 2001 Mar |
|
| Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis. | 2001 Mar |
|
| Sweat testing of MDMA with the Drugwipe analytical device: a controlled study with two volunteers. | 2001 Mar |
|
| Development of a capillary electrophoresis-77 K luminescence detection system for online spectral identification. | 2001 Mar |
|
| Caveat emptor: editors beware. | 2001 Mar |
|
| [A case of acute psychotic episode after a single dose of ecstasy]. | 2001 Mar-Apr |
|
| Sensitive determination of methylenedioxylated amphetamines by liquid chromatography. | 2001 May |
|
| Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS. | 2001 May-Jun |
|
| Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues. | 2001 Sep |
|
| Drug use and life style among college undergraduates: a 30-year longitudinal study. | 2001 Sep |
|
| Effects of ecstasy (MDMA) on the brain in abstinent users: initial observations with diffusion and perfusion MR imaging. | 2001 Sep |
|
| The mechanisms involved in the long-lasting neuroprotective effect of fluoxetine against MDMA ('ecstasy')-induced degeneration of 5-HT nerve endings in rat brain. | 2001 Sep |
|
| Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine. | 2001 Sep 1 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 22:08:21 UTC 2021
by
admin
on
Fri Jun 25 22:08:21 UTC 2021
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| Record UNII |
KNB4E1K0AV
|
| Record Status |
Validated (UNII)
|
| Record Version |
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DBSALT002574
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64057-70-1
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71285
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64057-70-1
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M7106
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SUB127825
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KNB4E1K0AV
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