Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2161 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(Cc1ccc2c(c1)OCO2)N
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 | 179.2161 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
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 |
|---|---|---|
| Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine. | 2001 Sep 1 |
|
| Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry. | 2002 |
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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 |
|
| The pharmacology of the acute hyperthermic response that follows administration of 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') to rats. | 2002 Jan |
|
| 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 |
|
| [Screening and detection of amphetamine derivatives in biological stains]. | 2002 Jul-Aug |
|
| Automated headspace solid-phase dynamic extraction for the determination of amphetamines and synthetic designer drugs in hair samples. | 2002 Jun 7 |
|
| Enantiomer analysis of a new street drug, 3,4-methylenedioxy-N-methyl-butanamine, in rat urine. | 2002 Mar |
|
| 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 |
|
| Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect? | 2002 Sep 27 |
|
| Altered states: the clinical effects of Ecstasy. | 2003 Apr |
|
| P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. | 2003 Dec |
|
| Development and validation of a gas chromatography-mass spectrometry assay for hair analysis of amphetamine, methamphetamine and methylenedioxy derivatives. | 2003 Dec 25 |
|
| Immunohistochemical demonstration of the amphetamine derivatives 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) in human post-mortem brain tissues and the pituitary gland. | 2003 Feb |
|
| Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study. | 2003 Jul-Aug |
|
| 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 |
|
| Development of a rapid and sensitive method for the quantitation of amphetamines in human plasma and oral fluid by LC-MS-MS. | 2003 Mar |
|
| Chiral separation of 3,4-methylenedioxymeth- amphetamine and related compounds in clandestine tablets and urine samples by capillary electrophoresis/fluorescence spectroscopy. | 2003 Mar |
|
| 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 |
|
| Putting an Ecstasy test kit to the test: harm reduction or harm induction? | 2003 Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:32:56 UTC 2021
by
admin
on
Fri Jun 25 20:32:56 UTC 2021
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| Record UNII |
XJZ28FJ27W
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| Record Status |
Validated (UNII)
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| Record Version |
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C47795
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DEA NO. |
7400
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| Code System | Code | Type | Description | ||
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M7104
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PRIMARY | Merck Index | ||
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3,4-METHYLENEDIOXYAMPHETAMINE
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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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4764-17-4
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CHEMBL6731
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1614
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C80152
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SUB10891MIG
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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PARENT -> METABOLITE |
PLASMA
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ACTIVE MOIETY |
