Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H13NO2.ClH |
| Molecular Weight | 215.677 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(N)CC1=CC=C2OCOC2=C1
InChI
InChIKey=XLAOKZDOZHZWBK-UHFFFAOYSA-N
InChI=1S/C10H13NO2.ClH/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9;/h2-3,5,7H,4,6,11H2,1H3;1H
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Serotonergic neurotoxic metabolites of ecstasy identified in rat brain. | 2005-04 |
|
| Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism. | 2004-12-01 |
|
| Effectiveness of multiple internal standards: deuterated analogues of methylenedioxymethamphetamine, methylenedioxyamphetamine, methamphetamine, and amphetamine. | 2004-11-13 |
|
| Determination of MDMA, MDEA and MDA in urine by high performance liquid chromatography with fluorescence detection. | 2004-11-05 |
|
| The Epping Jaundice outbreak: mortality after 38 years of follow-up. | 2004-11 |
|
| Identification of synthetic precursors of amphetamine-like drugs using Raman spectroscopy and ab initio calculations: beta-Methyl-beta-nitrostyrene derivatives. | 2004-11 |
|
| 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. | 2004-10 |
|
| Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity. | 2004-09-13 |
|
| 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). | 2004-09 |
|
| Use of MDA (the "love drug") and methamphetamine in Toronto by unsuspecting users of ecstasy (MDMA). | 2004-09 |
|
| Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine). | 2004-09 |
|
| Identification and characterization of metallothionein-1 and -2 gene expression in the context of (+/-)3,4-methylenedioxymethamphetamine-induced toxicity to brain dopaminergic neurons. | 2004-08-11 |
|
| Stacking and low-temperature technique in nonaqueous capillary electrophoresis for the analysis of 3,4-methylenedioxymethamphetamine. | 2004-06 |
|
| Interpretation of a 3,4-methylenedioxymethamphetamine (MDMA) blood level: discussion by means of a distribution study in two fatalities. | 2004-05-10 |
|
| Amphetamines and 3,4-methylendioxymetamphetamine (MDMA): evaluation of KIMS (kinetic interaction of microparticles in solution) assay at two cut-off levels. | 2004-05 |
|
| Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro. | 2004-05 |
|
| Reference materials for analytical toxicology including doping control: freeze-dried urine samples. | 2004-05 |
|
| Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity. | 2004-05 |
|
| Development and validation of a high-performance liquid chromatography-mass spectrometry assay for determination of amphetamine, methamphetamine, and methylenedioxy derivatives in meconium. | 2004-04-01 |
|
| The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity. | 2004-04 |
|
| 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. | 2004-04 |
|
| Application of ORAL.screen saliva drug test for the screening of methamphetamine, MDMA, and MDEA incorporated in hair. | 2004-03 |
|
| Mixed-mode solid-phase extraction procedures for the determination of MDMA and metabolites in urine using LC-MS, LC-UV, or GC-NPD. | 2004-02-28 |
|
| 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. | 2004-01 |
|
| Hepatotoxicity of 3,4-methylenedioxyamphetamine and alpha-methyldopamine in isolated rat hepatocytes: formation of glutathione conjugates. | 2004-01 |
|
| Surface-activated chemical ionization ion trap mass spectrometry in the analysis of amphetamines in diluted urine samples. | 2004 |
|
| The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA). | 2004 |
|
| Development and validation of a gas chromatography-mass spectrometry assay for hair analysis of amphetamine, methamphetamine and methylenedioxy derivatives. | 2003-12-25 |
|
| 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. | 2003-12-13 |
|
| P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. | 2003-12 |
|
| Chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets seized in Hong Kong. | 2003-11 |
|
| Synthesis, in vitro formation, and behavioural effects of glutathione regioisomers of alpha-methyldopamine with relevance to MDA and MDMA (ecstasy). | 2003-10-17 |
|
| Putting an Ecstasy test kit to the test: harm reduction or harm induction? | 2003-10 |
|
| Identification of some N-hydroxylated metabolites of (+/-)-3,4-methylenedioxymethamphetamine in horse urine by gas chromatography-mass spectrometry. | 2003-10 |
|
| Death rates from ecstasy (MDMA, MDA) and polydrug use in England and Wales 1996-2002. | 2003-10 |
|
| Prenatal 3,4-methylenedioxymethamphetamine (ecstasy) alters exploratory behavior, reduces monoamine metabolism, and increases forebrain tyrosine hydroxylase fiber density of juvenile rats. | 2003-09-16 |
|
| Actions of amphetamine derivatives and cathinone at the noradrenaline transporter. | 2003-08-22 |
|
| Enantioselective quantitation of the ecstasy compound (R)- and (S)-N-ethyl-3,4-methylenedioxyamphetamine and its major metabolites in human plasma and urine. | 2003-08-15 |
|
| Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study. | 2003-08-12 |
|
| Usefulness of sweat testing for the detection of MDMA after a single-dose administration. | 2003-08-12 |
|
| 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. | 2003-08-12 |
|
| Methylenendioxyamphetamine produces serotonin nerve terminal loss and diminished behavioural and neurochemical responses to the antidepressant fluoxetine. | 2003-08 |
|
| Confirmation of amphetamine, methamphetamine, MDA and MDMA in urine samples using disk solid-phase extraction and gas chromatography-mass spectrometry after immunoassay screening. | 2003-07-25 |
|
| Is the Ecstasy-induced ipsilateral rotation in 6-hydroxydopamine unilaterally lesioned rats dopamine independent? | 2003-07 |
|
| Determination of amphetamines in human urine by headspace solid-phase microextraction and gas chromatography. | 2003-06-05 |
|
| 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. | 2003-06 |
|
| 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro. | 2003-06 |
|
| [Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives]. | 2003-05 |
|
| Altered states: the clinical effects of Ecstasy. | 2003-04 |
|
| Development of a rapid and sensitive method for the quantitation of amphetamines in human plasma and oral fluid by LC-MS-MS. | 2003-03 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:08:17 GMT 2025
by
admin
on
Mon Mar 31 18:08:17 GMT 2025
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| Record UNII |
8929NLK7WN
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID1049017
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8929NLK7WN
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6292-91-7
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m7104
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9978
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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PARENT -> SALT/SOLVATE |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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