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=CC2=C(OCO2)C=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
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 |
|---|---|---|
| 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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| 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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| Delayed rhabdomyolysis after ecstasy use. | 2001 Jan |
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| An exploration of the history and controversies surrounding MDMA and MDA. | 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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| 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 |
|
| 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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| The pharmacology of the acute hyperthermic response that follows administration of 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') to rats. | 2002 Jan |
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| Multiple 5-HT receptors are involved in the effects of acute MDMA treatment: studies on locomotor activity and responding for conditioned reinforcement. | 2002 Jul |
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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 |
|
| 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 |
|
| Automated headspace solid-phase dynamic extraction for the determination of amphetamines and synthetic designer drugs in hair samples. | 2002 Jun 7 |
|
| Hypothalamic-pituitary-thyroid axis and sympathetic nervous system involvement in hyperthermia induced by 3,4-methylenedioxymethamphetamine (Ecstasy). | 2003 Apr |
|
| Developmental 3,4-methylenedioxymethamphetamine (MDMA) impairs sequential and spatial but not cued learning independent of growth, litter effects or injection stress. | 2003 Apr 4 |
|
| 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 |
|
| Direct screening of urine for MDMA and MDA by liquid chromatography-tandem mass spectrometry. | 2003 Jan-Feb |
|
| 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 |
|
| 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 |
|
| 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro. | 2003 Jun |
|
| [Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives]. | 2003 May |
|
| 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 |
|
| Prenatal 3,4-methylenedioxymethamphetamine (ecstasy) alters exploratory behavior, reduces monoamine metabolism, and increases forebrain tyrosine hydroxylase fiber density of juvenile rats. | 2003 Sep-Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Effectiveness of multiple internal standards: deuterated analogues of methylenedioxymethamphetamine, methylenedioxyamphetamine, methamphetamine, and amphetamine. | 2004 Nov-Dec |
|
| Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine). | 2004 Sep |
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DTXSID1049017
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8929NLK7WN
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6292-91-7
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26174
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m7104
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9978
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27106
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ACTIVE MOIETY
SUBSTANCE RECORD
