U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of TENAMFETAMINE

SMILES

CC(N)CC1=CC=C2OCOC2=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

HIDE SMILES / InChI
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 ( + / - )

Description

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

Unknown
149124
PubMed

PubMed

TitleDatePubMed
Serotonergic neurotoxic metabolites of ecstasy identified in rat brain.
2005-04
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.
2004-12-01
Effectiveness of multiple internal standards: deuterated analogues of methylenedioxymethamphetamine, methylenedioxyamphetamine, methamphetamine, and amphetamine.
2004-11-13
Determination of MDMA, MDEA and MDA in urine by high performance liquid chromatography with fluorescence detection.
2004-11-05
The Epping Jaundice outbreak: mortality after 38 years of follow-up.
2004-11
Identification of synthetic precursors of amphetamine-like drugs using Raman spectroscopy and ab initio calculations: beta-Methyl-beta-nitrostyrene derivatives.
2004-11
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.
2004-10
Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity.
2004-09-13
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).
2004-09
Use of MDA (the "love drug") and methamphetamine in Toronto by unsuspecting users of ecstasy (MDMA).
2004-09
Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine).
2004-09
Identification and characterization of metallothionein-1 and -2 gene expression in the context of (+/-)3,4-methylenedioxymethamphetamine-induced toxicity to brain dopaminergic neurons.
2004-08-11
Stacking and low-temperature technique in nonaqueous capillary electrophoresis for the analysis of 3,4-methylenedioxymethamphetamine.
2004-06
Interpretation of a 3,4-methylenedioxymethamphetamine (MDMA) blood level: discussion by means of a distribution study in two fatalities.
2004-05-10
Amphetamines and 3,4-methylendioxymetamphetamine (MDMA): evaluation of KIMS (kinetic interaction of microparticles in solution) assay at two cut-off levels.
2004-05
Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro.
2004-05
Reference materials for analytical toxicology including doping control: freeze-dried urine samples.
2004-05
Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity.
2004-05
Development and validation of a high-performance liquid chromatography-mass spectrometry assay for determination of amphetamine, methamphetamine, and methylenedioxy derivatives in meconium.
2004-04-01
The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity.
2004-04
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.
2004-04
Application of ORAL.screen saliva drug test for the screening of methamphetamine, MDMA, and MDEA incorporated in hair.
2004-03
Mixed-mode solid-phase extraction procedures for the determination of MDMA and metabolites in urine using LC-MS, LC-UV, or GC-NPD.
2004-02-28
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.
2004-01
Hepatotoxicity of 3,4-methylenedioxyamphetamine and alpha-methyldopamine in isolated rat hepatocytes: formation of glutathione conjugates.
2004-01
Surface-activated chemical ionization ion trap mass spectrometry in the analysis of amphetamines in diluted urine samples.
2004
The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA).
2004
Development and validation of a gas chromatography-mass spectrometry assay for hair analysis of amphetamine, methamphetamine and methylenedioxy derivatives.
2003-12-25
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.
2003-12-13
P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine.
2003-12
Chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets seized in Hong Kong.
2003-11
Synthesis, in vitro formation, and behavioural effects of glutathione regioisomers of alpha-methyldopamine with relevance to MDA and MDMA (ecstasy).
2003-10-17
Putting an Ecstasy test kit to the test: harm reduction or harm induction?
2003-10
Identification of some N-hydroxylated metabolites of (+/-)-3,4-methylenedioxymethamphetamine in horse urine by gas chromatography-mass spectrometry.
2003-10
Death rates from ecstasy (MDMA, MDA) and polydrug use in England and Wales 1996-2002.
2003-10
Prenatal 3,4-methylenedioxymethamphetamine (ecstasy) alters exploratory behavior, reduces monoamine metabolism, and increases forebrain tyrosine hydroxylase fiber density of juvenile rats.
2003-09-16
Actions of amphetamine derivatives and cathinone at the noradrenaline transporter.
2003-08-22
Enantioselective quantitation of the ecstasy compound (R)- and (S)-N-ethyl-3,4-methylenedioxyamphetamine and its major metabolites in human plasma and urine.
2003-08-15
Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study.
2003-08-12
Usefulness of sweat testing for the detection of MDMA after a single-dose administration.
2003-08-12
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.
2003-08-12
Methylenendioxyamphetamine produces serotonin nerve terminal loss and diminished behavioural and neurochemical responses to the antidepressant fluoxetine.
2003-08
Confirmation of amphetamine, methamphetamine, MDA and MDMA in urine samples using disk solid-phase extraction and gas chromatography-mass spectrometry after immunoassay screening.
2003-07-25
Is the Ecstasy-induced ipsilateral rotation in 6-hydroxydopamine unilaterally lesioned rats dopamine independent?
2003-07
Determination of amphetamines in human urine by headspace solid-phase microextraction and gas chromatography.
2003-06-05
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.
2003-06
3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro.
2003-06
[Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives].
2003-05
Altered states: the clinical effects of Ecstasy.
2003-04
Development of a rapid and sensitive method for the quantitation of amphetamines in human plasma and oral fluid by LC-MS-MS.
2003-03
Patents

Patents

8877802
2
WO2007016190A2
2

Sample Use Guides

In Vivo Use Guide
subjects will receive a single oral dose of MDA 98mg/70kg body weight
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:42:45 GMT 2025
Edited
by admin
on Wed Apr 02 08:42:45 GMT 2025
Record UNII
XJZ28FJ27W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MDA
MI  
Preferred Name English
TENAMFETAMINE
INN   MART.   WHO-DD  
INN  
Official Name English
TENAMFETAMINE [MART.]
Common Name English
LOVE
Common Name English
(±)-.ALPHA.-METHYL-3,4-(METHYLENEDIOXY)PHENETHYLAMINE
Systematic Name English
Tenamfetamine [WHO-DD]
Common Name English
EA-1299
Code English
METHYLENE DIOXYAMPHETAMINE
Common Name English
MDA [MI]
Common Name English
MDA (PSYCHEDELIC)
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 Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
DEA NO. 7400
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
WIKIPEDIA PiHKAL
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
Code System Code Type Description
MERCK INDEX
m7104
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
3,4-METHYLENEDIOXYAMPHETAMINE
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
INN
5875
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
FDA UNII
XJZ28FJ27W
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
DRUG BANK
DB01509
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
CAS
51497-09-7
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
SUPERSEDED
HSDB
7593
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
SMS_ID
100000082947
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
CAS
4764-17-4
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
ChEMBL
CHEMBL6731
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID40859958
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
PUBCHEM
1614
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
NCI_THESAURUS
C80152
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
EVMPD
SUB10891MIG
Created by admin on Wed Apr 02 08:42:45 GMT 2025 , Edited by admin on Wed Apr 02 08:42:45 GMT 2025
PRIMARY
Related Record Type Details
Structure of 3,4-ETHYLIDENEDIOXYAMPHETAMINE
DERIVATIVE -> PARENT
Structure of NITROETHANE
PRECURSOR->PARENT
Structure of PMK METHYL GLYCIDATE
PRECURSOR->PARENT
Structure of 6-METHYL-MDA
DERIVATIVE -> PARENT
Structure of 3,4-METHYLENEDIOXYPHENYL-2-PROPANONE
PRECURSOR->PARENT
Structure of TENAMFETAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of TENAMFETAMINE, (R)-
ENANTIOMER -> RACEMATE
Structure of TENAMFETAMINE, (S)-
ENANTIOMER -> RACEMATE
Structure of PIPERONAL
PRECURSOR->PARENT
ISOSAFROLE
PRECURSOR->PARENT
Related Record Type Details
Structure of MDE
MDE
PARENT -> METABOLITE
Structure of MIDOMAFETAMINE
PARENT -> METABOLITE
PLASMA
Related Record Type Details
Structure of TENAMFETAMINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966