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M1796

Sigma-Aldrich

(±)-3,4-Methylenedioxy-N-­ethyl­amphetamine hydrochloride

≥98% (TLC)

Synonym(s):

MDEA hydrochloride, N-Ethyl-3,4-MDA hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C12H17NO2 · HCl
CAS Number:
74341-78-9
Molecular Weight:
243.73
MDL number:
MFCD01659568
UNSPSC Code:
12352116
PubChem Substance ID:
24896694
NACRES:
NA.77

Quality Level

200

Assay

≥98% (TLC)

drug control

USDEA Schedule I; Home Office Schedule 1; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IA (Portugal)

SMILES string

Cl[H].NCCc1ccc2OCOc2c1

InChI

1S/C12H17NO2.ClH/c1-3-13-9(2)6-10-4-5-11-12(7-10)15-8-14-11;/h4-5,7,9,13H,3,6,8H2,1-2H3;1H

InChI key

IBDIPBWIXJRJQM-UHFFFAOYSA-N

Biochem/physiol Actions

Psychotropic compound causing a reduction in serotonin level and in tryptophan hydroxylase activity in the brain. May cause structural damage to serotonenergic neurons.

Other Notes

CAS# 116861-63-3, which was listed previously, is for histidine-copper complex.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H336

Hazard Classifications

Acute Tox. 3 Oral - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H G Series et al.
Experimental neurology, 128(1), 50-58 (1994-07-01)
N-ethyl-3,4-methylenedioxyamphetamine (MDE) is one of a group of substituted amphetamines which have effects on several serotonergic markers such as tissue levels of serotonin and activity of tryptophan hydroxylase. In this study we have compared its effects on the rat brain
M Johnson et al.
Biochemical pharmacology, 38(23), 4333-4338 (1989-12-01)
The effect of N-ethyl-3,4-methylenedioxyamphetamine (MDE) on the central serotonergic system was studied. Within 1 hr after administration of MDE (10 mg/kg), the concentration of 5-hydroxytryptamine (5-HT) and the activity of tryptophan hydroxylase (TPH) had declined significantly in the hippocampus but
Ashley Thigpen et al.
Journal of chromatographic science, 46(10), 900-906 (2008-11-15)
Three regioisomeric 3,4-methylenedioxyphenethylamines having the same molecular weight and major mass spectral fragments of equal mass have been reported as drugs of abuse in forensic studies in recent years. These compounds are 3,4-methylenedioxy-N-ethylamphetamine (MDEA), 3,4-methylenedioxy-N-N-dimethylamphetamine (MDMMA), and N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB). The
Markus R Meyer et al.
Chemical research in toxicology, 22(6), 1205-1211 (2009-05-26)
The designer drugs R,S-3,4-methylenedioxy-methamphetamine (MDMA, Ecstasy), R,S-3,4-methylenedioxy-ethylamphetamine (MDEA, Eve), and R,S-N-methyl-benzodioxolyl-butanamine (MBDB, Eden) are chiral compounds, and their in vitro and in vivo metabolism is enantioselective with a preference for the S-enantiomer caused in part by P450-mediated demethylenation. As the
Kei Zaitsu et al.
Forensic science international, 188(1-3), 131-139 (2009-05-02)
This is the first report on identifying the specific metabolites of the new designer drugs 2-methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one (bk-MBDB) and 2-ethylamino-1-(3,4-methylenedioxyphenyl)propan-1-one (bk-MDEA) in human urine using synthesized standards. Based on GC/MS and LC/MS, we identified N-dealkylation, demethylenation followed by O-methylation, and beta-ketone
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