Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(N)CC1=CC2=C(OCO2)C=C1
InChI
InChIKey=NGBBVGZWCFBOGO-UHFFFAOYSA-N
InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
Tenamfetamine (also known as 3,4-methylenedioxyamphetamine (or MDA)) is a hallucinogen that acts as a serotonergic 5-HT2A receptor agonist and releases monoamines by interacting with monoamine plasmalemmal transporters. Tenamfetamine had no accepted medical use and it was scheduled as a controlled substance in the US in 1970. Despite appearing in illicit drug preparations, tenamfetamine has not been studied in humans in over 30 years. In 2010 was published article where was described the action of tenamfetaminea in a clinical trial in humans. In this trial was shown that the drug had induced mystical-type experiences and, in at least some individuals, closed-eye visions. However, during that experiment were impossible to provide strong evidence for changes in the efficacy of top-down influences on perception or acutely increased occipital cortex excitation.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Altered states: the clinical effects of Ecstasy. | 2003 Apr |
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| Methylenendioxyamphetamine produces serotonin nerve terminal loss and diminished behavioural and neurochemical responses to the antidepressant fluoxetine. | 2003 Aug |
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| Enantioselective quantitation of the ecstasy compound (R)- and (S)-N-ethyl-3,4-methylenedioxyamphetamine and its major metabolites in human plasma and urine. | 2003 Aug 15 |
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| Actions of amphetamine derivatives and cathinone at the noradrenaline transporter. | 2003 Aug 22 |
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| P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. | 2003 Dec |
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| Development and validation of a gas chromatography-mass spectrometry assay for hair analysis of amphetamine, methamphetamine and methylenedioxy derivatives. | 2003 Dec 25 |
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| Is the Ecstasy-induced ipsilateral rotation in 6-hydroxydopamine unilaterally lesioned rats dopamine independent? | 2003 Jul |
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| Confirmation of amphetamine, methamphetamine, MDA and MDMA in urine samples using disk solid-phase extraction and gas chromatography-mass spectrometry after immunoassay screening. | 2003 Jul 25 |
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| Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study. | 2003 Jul-Aug |
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| Usefulness of sweat testing for the detection of MDMA after a single-dose administration. | 2003 Jul-Aug |
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| Comparison and evaluation of DRI methamphetamine, DRI ecstasy, Abuscreen ONLINE amphetamine, and a modified Abuscreen ONLINE amphetamine screening immunoassays for the detection of amphetamine (AMP), methamphetamine (MTH), 3,4-methylenedioxyamphetamine (MDA), and 3,4-methylenedioxymethamphetamine (MDMA) in human urine. | 2003 Jul-Aug |
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| Plasma levels of parent compound and metabolites after doses of either d-fenfluramine or d-3,4-methylenedioxymethamphetamine (MDMA) that produce long-term serotonergic alterations. | 2003 Jun |
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| 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro. | 2003 Jun |
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| Determination of amphetamines in human urine by headspace solid-phase microextraction and gas chromatography. | 2003 Jun 5 |
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| Development of a rapid and sensitive method for the quantitation of amphetamines in human plasma and oral fluid by LC-MS-MS. | 2003 Mar |
|
| [Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives]. | 2003 May |
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| Chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets seized in Hong Kong. | 2003 Nov |
|
| Concentrations and ratios of amphetamine, methamphetamine, MDA, MDMA, and MDEA enantiomers determined in plasma samples from clinical toxicology and driving under the influence of drugs cases by GC-NICI-MS. | 2003 Nov-Dec |
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| Putting an Ecstasy test kit to the test: harm reduction or harm induction? | 2003 Oct |
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| Identification of some N-hydroxylated metabolites of (+/-)-3,4-methylenedioxymethamphetamine in horse urine by gas chromatography-mass spectrometry. | 2003 Oct |
|
| Death rates from ecstasy (MDMA, MDA) and polydrug use in England and Wales 1996-2002. | 2003 Oct |
|
| Synthesis, in vitro formation, and behavioural effects of glutathione regioisomers of alpha-methyldopamine with relevance to MDA and MDMA (ecstasy). | 2003 Oct 17 |
|
| Prenatal 3,4-methylenedioxymethamphetamine (ecstasy) alters exploratory behavior, reduces monoamine metabolism, and increases forebrain tyrosine hydroxylase fiber density of juvenile rats. | 2003 Sep-Oct |
|
| Surface-activated chemical ionization ion trap mass spectrometry in the analysis of amphetamines in diluted urine samples. | 2004 |
|
| The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity. | 2004 Apr |
|
| High-performance liquid chromatography with fluorescence detection for the simultaneous determination of 3,4-methylenedioxymethamphetamine, methamphetamine and their metabolites in human hair using DIB-Cl as a label. | 2004 Apr |
|
| Development and validation of a high-performance liquid chromatography-mass spectrometry assay for determination of amphetamine, methamphetamine, and methylenedioxy derivatives in meconium. | 2004 Apr 1 |
|
| Identification and characterization of metallothionein-1 and -2 gene expression in the context of (+/-)3,4-methylenedioxymethamphetamine-induced toxicity to brain dopaminergic neurons. | 2004 Aug 11 |
|
| Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism. | 2004 Dec 1 |
|
| Evaluation of ephedrine, pseudoephedrine and phenylpropanolamine concentrations in human urine samples and a comparison of the specificity of DRI amphetamines and Abuscreen online (KIMS) amphetamines screening immunoassays. | 2004 Jan |
|
| Hepatotoxicity of 3,4-methylenedioxyamphetamine and alpha-methyldopamine in isolated rat hepatocytes: formation of glutathione conjugates. | 2004 Jan |
|
| Mixed-mode solid-phase extraction procedures for the determination of MDMA and metabolites in urine using LC-MS, LC-UV, or GC-NPD. | 2004 Jan-Feb |
|
| Stacking and low-temperature technique in nonaqueous capillary electrophoresis for the analysis of 3,4-methylenedioxymethamphetamine. | 2004 Jun |
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| Application of ORAL.screen saliva drug test for the screening of methamphetamine, MDMA, and MDEA incorporated in hair. | 2004 Mar |
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| Amphetamines and 3,4-methylendioxymetamphetamine (MDMA): evaluation of KIMS (kinetic interaction of microparticles in solution) assay at two cut-off levels. | 2004 May |
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| Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro. | 2004 May |
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| Reference materials for analytical toxicology including doping control: freeze-dried urine samples. | 2004 May |
|
| Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity. | 2004 May |
|
| Interpretation of a 3,4-methylenedioxymethamphetamine (MDMA) blood level: discussion by means of a distribution study in two fatalities. | 2004 May 10 |
|
| The Epping Jaundice outbreak: mortality after 38 years of follow-up. | 2004 Nov |
|
| Identification of synthetic precursors of amphetamine-like drugs using Raman spectroscopy and ab initio calculations: beta-Methyl-beta-nitrostyrene derivatives. | 2004 Nov |
|
| Determination of MDMA, MDEA and MDA in urine by high performance liquid chromatography with fluorescence detection. | 2004 Nov 5 |
|
| Effectiveness of multiple internal standards: deuterated analogues of methylenedioxymethamphetamine, methylenedioxyamphetamine, methamphetamine, and amphetamine. | 2004 Nov-Dec |
|
| Thioether metabolites of 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymethamphetamine inhibit human serotonin transporter (hSERT) function and simultaneously stimulate dopamine uptake into hSERT-expressing SK-N-MC cells. | 2004 Oct |
|
| Enantiomeric separation and quantitation of (+/-)-amphetamine, (+/-)-methamphetamine, (+/-)-MDA, (+/-)-MDMA, and (+/-)-MDEA in urine specimens by GC-EI-MS after derivatization with (R)-(-)- or (S)-(+)-alpha-methoxy-alpha-(trifluoromethy)phenylacetyl chloride (MTPA). | 2004 Sep |
|
| Use of MDA (the "love drug") and methamphetamine in Toronto by unsuspecting users of ecstasy (MDMA). | 2004 Sep |
|
| Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine). | 2004 Sep |
|
| Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity. | 2004 Sep 13 |
|
| The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA). | 2004 Summer |
|
| Serotonergic neurotoxic metabolites of ecstasy identified in rat brain. | 2005 Apr |
Patents
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47795
Created by
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DEA NO. |
7400
Created by
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WIKIPEDIA |
PiHKAL
Created by
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| Code System | Code | Type | Description | ||
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m7104
Created by
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PRIMARY | Merck Index | ||
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3,4-METHYLENEDIOXYAMPHETAMINE
Created by
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5875
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XJZ28FJ27W
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DB01509
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51497-09-7
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7593
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100000082947
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4764-17-4
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CHEMBL6731
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DTXSID40859958
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1614
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C80152
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SUB10891MIG
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ACTIVE MOIETY
PARENT (METABOLITE)
PARENT (METABOLITE)
SALT/SOLVATE (PARENT)
