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
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 | ( + / - ) |
DescriptionSources: https://doi.org/10.1371/journal.pone.0014074
Sources: https://doi.org/10.1371/journal.pone.0014074
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 |
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Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat. | 2001 Apr |
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[Designer drugs in Jutland]. | 2001 Apr 16 |
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Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats. | 2001 Feb 9 |
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Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine. | 2001 Jan |
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Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase. | 2001 Jul |
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An exploration of the history and controversies surrounding MDMA and MDA. | 2001 Jul-Sep |
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Quantitation of amphetamine-type compounds for which no reference compound is available: the validation of a theoretical model. | 2001 Jul-Sep |
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It's a rave new world: rave culture and illicit drug use in the young. | 2001 Jun |
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Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis. | 2001 Mar |
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Sensitive determination of methylenedioxylated amphetamines by liquid chromatography. | 2001 May |
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3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development. | 2001 May 1 |
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PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA. | 2001 May-Jun |
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Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS. | 2001 May-Jun |
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Usefulness of saliva for measurement of 3,4-methylenedioxymethamphetamine and its metabolites: correlation with plasma drug concentrations and effect of salivary pH. | 2001 Oct |
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Overdose of 2.3 grams of intravenous methamphetamine: case, analysis and patient perspective. | 2001 Oct-Dec |
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Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues. | 2001 Sep |
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Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine. | 2001 Sep 1 |
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Effects of the hallucinogen psilocybin on covert orienting of visual attention in humans. | 2002 |
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Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry. | 2002 |
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Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis. | 2002 Apr |
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Post-mortem redistribution of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") in the rabbit. Part I: experimental approach after in vivo intravenous infusion. | 2002 Aug |
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The pharmacology of the acute hyperthermic response that follows administration of 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') to rats. | 2002 Jan |
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Quantitation of amphetamine, methamphetamine, and their methylenedioxy derivatives in urine by solid-phase microextraction coupled with electrospray ionization-high-field asymmetric waveform ion mobility spectrometry-mass spectrometry. | 2002 Jul 1 |
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[Screening and detection of amphetamine derivatives in biological stains]. | 2002 Jul-Aug |
|
Rapid simultaneous determination of amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, and 3,4-methylenedioxyethylamphetamine in urine by solid-phase extraction and GC-MS: a method optimized for high-volume laboratories. | 2002 Jul-Aug |
|
Isotopic characterisation of 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymethylamphetamine (ecstasy). | 2002 Jun |
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Automated headspace solid-phase dynamic extraction for the determination of amphetamines and synthetic designer drugs in hair samples. | 2002 Jun 7 |
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Effect of 1-(3,4-methylenedioxyphenyl)-2-aminopropane and its optical isomers in PMMA-trained rats. | 2002 May |
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Simultaneous screening and detection of drugs in small blood samples and bloodstains. | 2002 May 23 |
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Rewarding effects of the optical isomers of 3,4-methylenedioxy-methylamphetamine ('Ecstasy') and 3,4-methylenedioxy-ethylamphetamine ('Eve') measured by conditioned place preference in rats. | 2002 Sep 27 |
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Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect? | 2002 Sep 27 |
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Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry. | 2003 |
|
Developmental 3,4-methylenedioxymethamphetamine (MDMA) impairs sequential and spatial but not cued learning independent of growth, litter effects or injection stress. | 2003 Apr 4 |
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P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. | 2003 Dec |
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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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Chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets seized in Hong Kong. | 2003 Nov |
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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 |
|
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 |
|
Application of ORAL.screen saliva drug test for the screening of methamphetamine, MDMA, and MDEA incorporated in hair. | 2004 Mar |
|
Amphetamines and 3,4-methylendioxymetamphetamine (MDMA): evaluation of KIMS (kinetic interaction of microparticles in solution) assay at two cut-off levels. | 2004 May |
|
Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro. | 2004 May |
|
Reference materials for analytical toxicology including doping control: freeze-dried urine samples. | 2004 May |
|
Interpretation of a 3,4-methylenedioxymethamphetamine (MDMA) blood level: discussion by means of a distribution study in two fatalities. | 2004 May 10 |
|
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 |
|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00823407
subjects will receive a single oral dose of MDA 98mg/70kg body weight
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:28:39 UTC 2023
by
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on
Thu Jul 06 22:28:39 UTC 2023
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Record UNII |
XJZ28FJ27W
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C47795
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DEA NO. |
7400
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PiHKAL
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M7104
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3,4-METHYLENEDIOXYAMPHETAMINE
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5875
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51497-09-7
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CHEMBL6731
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C80152
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SUB10891MIG
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