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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Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons. | 1999 Jun |
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Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans. | 2001 Feb 10 |
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Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model. | 2001 Feb 15 |
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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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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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PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA. | 2001 May-Jun |
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Application of SERS spectroscopy to the identification of (3,4-methylenedioxy)amphetamine in forensic samples utilizing matrix stabilized silver halides. | 2001 Nov |
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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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Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues. | 2001 Sep |
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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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Drugs of abuse monitoring in blood for control of driving under the influence of drugs. | 2002 Apr |
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Analysis of illicit amphetamine seizures by capillary zone electrophoresis. | 2002 Dec 6 |
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[Screening and detection of amphetamine derivatives in biological stains]. | 2002 Jul-Aug |
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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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Altered states: the clinical effects of Ecstasy. | 2003 Apr |
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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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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 |
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[Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives]. | 2003 May |
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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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The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity. | 2004 Apr |
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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 |
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The Epping Jaundice outbreak: mortality after 38 years of follow-up. | 2004 Nov |
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Identification of synthetic precursors of amphetamine-like drugs using Raman spectroscopy and ab initio calculations: beta-Methyl-beta-nitrostyrene derivatives. | 2004 Nov |
|
Effectiveness of multiple internal standards: deuterated analogues of methylenedioxymethamphetamine, methylenedioxyamphetamine, methamphetamine, and amphetamine. | 2004 Nov-Dec |
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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 |
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Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine). | 2004 Sep |
|
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
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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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WIKIPEDIA |
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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7593
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100000082947
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4764-17-4
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CHEMBL6731
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C80152
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SUB10891MIG
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ENANTIOMER -> RACEMATE |
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PLASMA
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ACTIVE MOIETY |
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