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 |
|---|---|---|
| Serotonergic neurotoxicity of methylenedioxyamphetamine and methylenedioxymetamphetamine. | 2001 |
|
| 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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| Overdose of 2.3 grams of intravenous methamphetamine: case, analysis and patient perspective. | 2001 Oct-Dec |
|
| Effects of the hallucinogen psilocybin on covert orienting of visual attention in humans. | 2002 |
|
| Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis. | 2002 Apr |
|
| Drugs of abuse monitoring in blood for control of driving under the influence of drugs. | 2002 Apr |
|
| Post-mortem redistribution of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") in the rabbit. Part I: experimental approach after in vivo intravenous infusion. | 2002 Aug |
|
| Analysis of illicit amphetamine seizures by capillary zone electrophoresis. | 2002 Dec 6 |
|
| The pharmacology of the acute hyperthermic response that follows administration of 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') to rats. | 2002 Jan |
|
| Multiple 5-HT receptors are involved in the effects of acute MDMA treatment: studies on locomotor activity and responding for conditioned reinforcement. | 2002 Jul |
|
| 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 |
|
| Distribution study of 3,4-methylenedioxymethamphetamine and 3,4-methylenedioxyamphetamine in a fatal overdose. | 2002 Mar |
|
| Enantiomer analysis of a new street drug, 3,4-methylenedioxy-N-methyl-butanamine, in rat urine. | 2002 Mar |
|
| Effect of 1-(3,4-methylenedioxyphenyl)-2-aminopropane and its optical isomers in PMMA-trained rats. | 2002 May |
|
| Simultaneous screening and detection of drugs in small blood samples and bloodstains. | 2002 May 23 |
|
| Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry. | 2003 |
|
| Hypothalamic-pituitary-thyroid axis and sympathetic nervous system involvement in hyperthermia induced by 3,4-methylenedioxymethamphetamine (Ecstasy). | 2003 Apr |
|
| Methylenendioxyamphetamine produces serotonin nerve terminal loss and diminished behavioural and neurochemical responses to the antidepressant fluoxetine. | 2003 Aug |
|
| 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 |
|
| Actions of amphetamine derivatives and cathinone at the noradrenaline transporter. | 2003 Aug 22 |
|
| 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 |
|
| Direct screening of urine for MDMA and MDA by liquid chromatography-tandem mass spectrometry. | 2003 Jan-Feb |
|
| Is the Ecstasy-induced ipsilateral rotation in 6-hydroxydopamine unilaterally lesioned rats dopamine independent? | 2003 Jul |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism. | 2004 Dec 1 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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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C47795
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DEA NO. |
7400
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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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ACTIVE MOIETY |
