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Merck
CN

65963

(±)-3,4-Methylenedioxymethamphetamine hydrochloride

analytical standard

Synonym(s):

(±)-MDMA hydrochloride, DL-3,4-Methylenedioxymethamphetamine, DL-MDMA hydrochloride, Ecstasy, XTC hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C11H15NO2 · HCl
CAS Number:
64057-70-1
Molecular Weight:
229.70
UNSPSC Code:
41116107
MDL number:
MFCD00079444

Key Documents

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InChI key

LUWHVONVCYWRMZ-UHFFFAOYSA-N

InChI

1S/C11H15NO2.ClH/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10;/h3-4,6,8,12H,5,7H2,1-2H3;1H

SMILES string

Cl[H].CNC(C)Cc1ccc2OCOc2c1

grade

analytical standard

assay

≥98.5% (HPLC)

shelf life

limited shelf life, expiry date on the label

drug control

USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIA (Portugal)

technique(s)

HPLC: suitable, gas chromatography (GC): suitable, solid phase extraction (SPE): suitable

suitability

corresponds for H-NMR

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Hallucinogen; releases serotonin and dopamine from axon terminals; selective serotonergic neurotoxin.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301,H336

Hazard Classifications

Acute Tox. 3 Oral - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

涉药品监管产品
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Melanie Mueller et al.
The Journal of pharmacology and experimental therapeutics, 344(2), 479-488 (2012-12-05)
The neurotoxicity of (±)-3,4-methylenedioxymethamphetamine (MDMA; "Ecstasy") is influenced by temperature and varies according to species. The mechanisms underlying these two features of MDMA neurotoxicity are unknown, but differences in MDMA metabolism have recently been implicated in both. The present study
Mariana Angoa-Pérez et al.
Journal of neurochemistry, 125(1), 102-110 (2012-12-05)
Mephedrone (4-methylmethcathinone) is a β-ketoamphetamine stimulant drug of abuse with close structural and mechanistic similarities to methamphetamine. One of the most powerful actions associated with mephedrone is the ability to stimulate dopamine (DA) release and block its re-uptake through its
Clara Ros-Simó et al.
Journal of neurochemistry, 125(5), 736-746 (2013-03-26)
Ethanol and 3, 4-Methylenedioxymethamphetamine (MDMA) are popular recreational drugs widely abused by adolescents that may induce neurotoxic processes associated with behavioural alterations. Adolescent CD1 mice were subjected to ethanol intake using the drinking in the dark (DID) procedure, acute MDMA
Tove Abrahamsson et al.
Substance use & misuse, 48(4), 353-357 (2013-02-13)
The aim of the present study was to report independent correlates of ecstasy use in the Swedish general population. Data were drawn from a Swedish national household survey conducted in 2008-2009 on a random, stratified sample of 58,000 inhabitants of
Amy K Goodwin et al.
The Journal of pharmacology and experimental therapeutics, 345(3), 342-353 (2013-03-22)
(±)-3,4-Methylenedioxymethamphetamine (MDMA, "Ecstasy") is a popular drug of abuse. We aimed to characterize the behavioral effects of intragastric MDMA in a species closely related to humans and to relate behavioral effects to plasma MDMA and metabolite concentrations. Single doses of
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