TENAMFETAMINE

Investigational

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 Search

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	( + / - )

Description
Sources: https://doi.org/10.1371/journal.pone.0014074

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

Title	Date	PubMed
Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat.	2001 Apr	11371001
[Designer drugs in Jutland].	2001 Apr 16	11344661
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.	2001 Feb 9	11388689
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.	2001 Jan	11271404
Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase.	2001 Jul	11453733
An exploration of the history and controversies surrounding MDMA and MDA.	2001 Jul-Sep	11718314
Quantitation of amphetamine-type compounds for which no reference compound is available: the validation of a theoretical model.	2001 Jul-Sep	11515165
It's a rave new world: rave culture and illicit drug use in the young.	2001 Jun	11405616
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.	2001 Mar	11300514
Sensitive determination of methylenedioxylated amphetamines by liquid chromatography.	2001 May	11394297
3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development.	2001 May 1	11312307
PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA.	2001 May-Jun	11420094
Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS.	2001 May-Jun	11386639
Usefulness of saliva for measurement of 3,4-methylenedioxymethamphetamine and its metabolites: correlation with plasma drug concentrations and effect of salivary pH.	2001 Oct	11568088
Overdose of 2.3 grams of intravenous methamphetamine: case, analysis and patient perspective.	2001 Oct-Dec	11824700
Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues.	2001 Sep	11550823
Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine.	2001 Sep 1	11473798
Effects of the hallucinogen psilocybin on covert orienting of visual attention in humans.	2002	12097810
Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry.	2002	11948818
Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis.	2002 Apr	11991532
Post-mortem redistribution of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") in the rabbit. Part I: experimental approach after in vivo intravenous infusion.	2002 Aug	12185492
The pharmacology of the acute hyperthermic response that follows administration of 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') to rats.	2002 Jan	11786492
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	12141666
[Screening and detection of amphetamine derivatives in biological stains].	2002 Jul-Aug	12365331
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	12166811
Isotopic characterisation of 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymethylamphetamine (ecstasy).	2002 Jun	12146919
Automated headspace solid-phase dynamic extraction for the determination of amphetamines and synthetic designer drugs in hair samples.	2002 Jun 7	12134820
Effect of 1-(3,4-methylenedioxyphenyl)-2-aminopropane and its optical isomers in PMMA-trained rats.	2002 May	11900801
Simultaneous screening and detection of drugs in small blood samples and bloodstains.	2002 May 23	12062939
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	12270646
Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect?	2002 Sep 27	12270640
Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry.	2003	12569443
Developmental 3,4-methylenedioxymethamphetamine (MDMA) impairs sequential and spatial but not cued learning independent of growth, litter effects or injection stress.	2003 Apr 4	12644267
P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine.	2003 Dec	14690877
Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study.	2003 Jul-Aug	12908947
Usefulness of sweat testing for the detection of MDMA after a single-dose administration.	2003 Jul-Aug	12908943
Chemical profiling of 3,4-methylenedioxymethamphetamine (MDMA) tablets seized in Hong Kong.	2003 Nov	14640267
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	15306638
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.	2004 Dec 1	15498516
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	14979364
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	14987425
Application of ORAL.screen saliva drug test for the screening of methamphetamine, MDMA, and MDEA incorporated in hair.	2004 Mar	15068568
Amphetamines and 3,4-methylendioxymetamphetamine (MDMA): evaluation of KIMS (kinetic interaction of microparticles in solution) assay at two cut-off levels.	2004 May	15202792
Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro.	2004 May	15144219
Reference materials for analytical toxicology including doping control: freeze-dried urine samples.	2004 May	15116239
Interpretation of a 3,4-methylenedioxymethamphetamine (MDMA) blood level: discussion by means of a distribution study in two fatalities.	2004 May 10	15062945
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	15169827
Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity.	2004 Sep 13	15292928
The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA).	2004 Summer	15179441
Serotonergic neurotoxic metabolites of ecstasy identified in rat brain.	2005 Apr	15634943

Patents

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 `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

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Name

Type

Language

TENAMFETAMINE

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	Locators: MI Sources:

Common Name

English

tenamfetamine [INN]

Common Name

English

3,4-METHYLENEDIOXYAMPHETAMINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47795