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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
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
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

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