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=CC2=C(OCO2)C=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
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
Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons.
1999 Jun
Serotonergic neurotoxicity of methylenedioxyamphetamine and methylenedioxymetamphetamine.
2001
[Designer drugs in Jutland].
2001 Apr 16
Stability study of the designer drugs "MDA, MDMA and MDEA" in water, serum, whole blood, and urine under various storage temperatures.
2001 Dec 15
Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans.
2001 Feb 10
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.
2001 Feb 9
An exploration of the history and controversies surrounding MDMA and MDA.
2001 Jul-Sep
3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development.
2001 May 1
Application of SERS spectroscopy to the identification of (3,4-methylenedioxy)amphetamine in forensic samples utilizing matrix stabilized silver halides.
2001 Nov
Overdose of 2.3 grams of intravenous methamphetamine: case, analysis and patient perspective.
2001 Oct-Dec
Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues.
2001 Sep
Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry.
2002
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
Effect of 1-(3,4-methylenedioxyphenyl)-2-aminopropane and its optical isomers in PMMA-trained rats.
2002 May
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
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
Actions of amphetamine derivatives and cathinone at the noradrenaline transporter.
2003 Aug 22
P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine.
2003 Dec
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
Usefulness of sweat testing for the detection of MDMA after a single-dose administration.
2003 Jul-Aug
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 Jul-Aug
[Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives].
2003 May
Putting an Ecstasy test kit to the test: harm reduction or harm induction?
2003 Oct
Surface-activated chemical ionization ion trap mass spectrometry in the analysis of amphetamines in diluted urine samples.
2004
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
Amphetamines and 3,4-methylendioxymetamphetamine (MDMA): evaluation of KIMS (kinetic interaction of microparticles in solution) assay at two cut-off levels.
2004 May
The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA).
2004 Summer
Patents

Sample Use Guides

subjects will receive a single oral dose of MDA 98mg/70kg body weight
Route of Administration: Oral
Name Type Language
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
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 Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
DEA NO. 7400
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
WIKIPEDIA PiHKAL
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
Code System Code Type Description
MERCK INDEX
m7104
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
3,4-METHYLENEDIOXYAMPHETAMINE
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
INN
5875
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
FDA UNII
XJZ28FJ27W
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
DRUG BANK
DB01509
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
CAS
51497-09-7
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
SUPERSEDED
HSDB
7593
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
SMS_ID
100000082947
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
CAS
4764-17-4
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
ChEMBL
CHEMBL6731
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
EPA CompTox
DTXSID40859958
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
PUBCHEM
1614
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
NCI_THESAURUS
C80152
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY
EVMPD
SUB10891MIG
Created by admin on Sat Dec 16 17:03:06 UTC 2023 , Edited by admin on Sat Dec 16 17:03:06 UTC 2023
PRIMARY