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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

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 ( + / - )

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
Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat.
2001 Apr
[Designer drugs in Jutland].
2001 Apr 16
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.
2001 Feb 9
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.
2001 Jan
Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase.
2001 Jul
An exploration of the history and controversies surrounding MDMA and MDA.
2001 Jul-Sep
Quantitation of amphetamine-type compounds for which no reference compound is available: the validation of a theoretical model.
2001 Jul-Sep
It's a rave new world: rave culture and illicit drug use in the young.
2001 Jun
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.
2001 Mar
Sensitive determination of methylenedioxylated amphetamines by liquid chromatography.
2001 May
3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development.
2001 May 1
PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA.
2001 May-Jun
Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS.
2001 May-Jun
Usefulness of saliva for measurement of 3,4-methylenedioxymethamphetamine and its metabolites: correlation with plasma drug concentrations and effect of salivary pH.
2001 Oct
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
Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine.
2001 Sep 1
Effects of the hallucinogen psilocybin on covert orienting of visual attention in humans.
2002
Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry.
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
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
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
Simultaneous screening and detection of drugs in small blood samples and bloodstains.
2002 May 23
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
Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry.
2003
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
Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study.
2003 Jul-Aug
Usefulness of sweat testing for the detection of MDMA after a single-dose administration.
2003 Jul-Aug
Chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets seized in Hong Kong.
2003 Nov
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
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
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
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
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 Thu Jul 06 22:28:39 UTC 2023
Edited
by admin
on Thu Jul 06 22:28:39 UTC 2023
Record UNII
XJZ28FJ27W
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
DEA NO. 7400
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
WIKIPEDIA PiHKAL
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
Code System Code Type Description
MERCK INDEX
M7104
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
3,4-METHYLENEDIOXYAMPHETAMINE
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
INN
5875
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
FDA UNII
XJZ28FJ27W
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
DRUG BANK
DB01509
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
CAS
51497-09-7
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
SUPERSEDED
HSDB
7593
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
SMS_ID
100000082947
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
CAS
4764-17-4
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL6731
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID40859958
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
PUBCHEM
1614
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
NCI_THESAURUS
C80152
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
EVMPD
SUB10891MIG
Created by admin on Thu Jul 06 22:28:41 UTC 2023 , Edited by admin on Thu Jul 06 22:28:41 UTC 2023
PRIMARY
Related Record Type Details
DERIVATIVE -> PARENT
PRECURSOR->PARENT
PRECURSOR->PARENT
DERIVATIVE -> PARENT
PRECURSOR->PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PRECURSOR->PARENT
PRECURSOR->PARENT
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PARENT -> METABOLITE
PARENT -> METABOLITE
PLASMA
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ACTIVE MOIETY