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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
Structure of TENAMFETAMINE

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
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
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

Sample Use Guides

subjects will receive a single oral dose of MDA 98mg/70kg body weight
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:32:56 UTC 2021
Edited
by admin
on Fri Jun 25 20:32:56 UTC 2021
Record UNII
XJZ28FJ27W
Record Status Validated (UNII)
Record Version
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Name Type Language
TENAMFETAMINE
INN   MART.   WHO-DD  
INN  
Official Name English
METHYLENEDIOXYAMPHETAMINE
Systematic Name English
TENAMFETAMINE [MART.]
Common Name English
LOVE
Common Name English
(+/-)-.ALPHA.-METHYL-3,4-(METHYLENEDIOXY)PHENETHYLAMINE
Common Name English
EA-1299
Code English
METHYLENE DIOXYAMPHETAMINE
Common Name English
MDA [MI]
Common Name English
TENAMFETAMINE [WHO-DD]
Common Name English
SKF-5
Code English
MDA
MI  
Common Name English
TENAMFETAMINE [INN]
Common Name English
3,4-METHYLENEDIOXYAMPHETAMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
DEA NO. 7400
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
Code System Code Type Description
MERCK INDEX
M7104
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
3,4-METHYLENEDIOXYAMPHETAMINE
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
INN
5875
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
FDA UNII
XJZ28FJ27W
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
DRUG BANK
DB01509
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
CAS
51497-09-7
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
SUPERSEDED
HSDB
7593
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
CAS
4764-17-4
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL6731
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
PUBCHEM
1614
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
NCI_THESAURUS
C80152
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
EVMPD
SUB10891MIG
Created by admin on Fri Jun 25 20:32:56 UTC 2021 , Edited by admin on Fri Jun 25 20:32:56 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE
PARENT -> METABOLITE
PLASMA
Related Record Type Details
ACTIVE MOIETY