TENAMFETAMINE

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
Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons.	1999 Jun	10336889
Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans.	2001 Feb 10	11232860
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.	2001 Feb 15	11160413
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.	2001 Feb 9	11388689
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
PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA.	2001 May-Jun	11420094
Application of SERS spectroscopy to the identification of (3,4-methylenedioxy)amphetamine in forensic samples utilizing matrix stabilized silver halides.	2001 Nov	11763093
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
Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues.	2001 Sep	11550823
Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry.	2002	11948818
Drugs of abuse monitoring in blood for control of driving under the influence of drugs.	2002 Apr	11897967
Analysis of illicit amphetamine seizures by capillary zone electrophoresis.	2002 Dec 6	12498266
[Screening and detection of amphetamine derivatives in biological stains].	2002 Jul-Aug	12365331
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
Altered states: the clinical effects of Ecstasy.	2003 Apr	12667887
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	12906896
Actions of amphetamine derivatives and cathinone at the noradrenaline transporter.	2003 Aug 22	12969746
P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine.	2003 Dec	14690877
Development and validation of a gas chromatography-mass spectrometry assay for hair analysis of amphetamine, methamphetamine and methylenedioxy derivatives.	2003 Dec 25	14643504
Is the Ecstasy-induced ipsilateral rotation in 6-hydroxydopamine unilaterally lesioned rats dopamine independent?	2003 Jul	12811632
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	12860031
Usefulness of sweat testing for the detection of MDMA after a single-dose administration.	2003 Jul-Aug	12908943
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	12908938
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	12782103
3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro.	2003 Jun	12761331
Determination of amphetamines in human urine by headspace solid-phase microextraction and gas chromatography.	2003 Jun 5	12726843
Development of a rapid and sensitive method for the quantitation of amphetamines in human plasma and oral fluid by LC-MS-MS.	2003 Mar	12670001
[Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives].	2003 May	12714929
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	14670133
The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity.	2004 Apr	15228153
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
The Epping Jaundice outbreak: mortality after 38 years of follow-up.	2004 Nov	15538614
Identification of synthetic precursors of amphetamine-like drugs using Raman spectroscopy and ab initio calculations: beta-Methyl-beta-nitrostyrene derivatives.	2004 Nov	15508041
Effectiveness of multiple internal standards: deuterated analogues of methylenedioxymethamphetamine, methylenedioxyamphetamine, methamphetamine, and amphetamine.	2004 Nov-Dec	15538959
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	15516295
Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine).	2004 Sep	15319342
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 `Sat Dec 16 17:03:05 GMT 2023` Edited by `admin` on `Sat Dec 16 17:03:05 GMT 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