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

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
Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons.
1999 Jun
Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans.
2001 Feb 10
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.
2001 Feb 15
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.
2001 Feb 9
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
PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA.
2001 May-Jun
Application of SERS spectroscopy to the identification of (3,4-methylenedioxy)amphetamine in forensic samples utilizing matrix stabilized silver halides.
2001 Nov
Usefulness of saliva for measurement of 3,4-methylenedioxymethamphetamine and its metabolites: correlation with plasma drug concentrations and effect of salivary pH.
2001 Oct
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
Drugs of abuse monitoring in blood for control of driving under the influence of drugs.
2002 Apr
Analysis of illicit amphetamine seizures by capillary zone electrophoresis.
2002 Dec 6
[Screening and detection of amphetamine derivatives in biological stains].
2002 Jul-Aug
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
Altered states: the clinical effects of Ecstasy.
2003 Apr
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
P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine.
2003 Dec
Development and validation of a gas chromatography-mass spectrometry assay for hair analysis of amphetamine, methamphetamine and methylenedioxy derivatives.
2003 Dec 25
Is the Ecstasy-induced ipsilateral rotation in 6-hydroxydopamine unilaterally lesioned rats dopamine independent?
2003 Jul
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
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
3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro.
2003 Jun
Determination of amphetamines in human urine by headspace solid-phase microextraction and gas chromatography.
2003 Jun 5
Development of a rapid and sensitive method for the quantitation of amphetamines in human plasma and oral fluid by LC-MS-MS.
2003 Mar
[Biomimetic electrochemical synthesis of quinol-thioether conjugates: their implication in the serotonergic neurotoxicity of amphetamine derivatives].
2003 May
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
The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity.
2004 Apr
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
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
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
Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine).
2004 Sep
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 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
  • 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 Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
DEA NO. 7400
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
WIKIPEDIA PiHKAL
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
Code System Code Type Description
MERCK INDEX
m7104
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
3,4-METHYLENEDIOXYAMPHETAMINE
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
INN
5875
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
FDA UNII
XJZ28FJ27W
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
DRUG BANK
DB01509
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
CAS
51497-09-7
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
SUPERSEDED
HSDB
7593
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
SMS_ID
100000082947
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
CAS
4764-17-4
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL6731
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID40859958
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
PUBCHEM
1614
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
NCI_THESAURUS
C80152
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
EVMPD
SUB10891MIG
Created by admin on Sat Dec 16 17:03:06 GMT 2023 , Edited by admin on Sat Dec 16 17:03:06 GMT 2023
PRIMARY
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ENANTIOMER -> RACEMATE
PRECURSOR->PARENT
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