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M6403

Sigma-Aldrich

(±)-3,4-Methylenedioxymethamphetamine hydrochloride

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Synonym(s):
(±)-MDMA hydrochloride, DL-3,4-Methylenedioxymethamphetamine, DL-MDMA hydrochloride, Ecstasy, XTC hydrochloride
Empirical Formula (Hill Notation):
C11H15NO2 · HCl
CAS Number:
Molecular Weight:
229.70
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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 IIA (Portugal)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

solubility

H2O: soluble

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

SMILES string

Cl[H].CNC(C)Cc1ccc2OCOc2c1

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

InChI key

LUWHVONVCYWRMZ-UHFFFAOYSA-N

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Biochem/physiol Actions

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

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Methamphetamine hydrochloride United States Pharmacopeia (USP) Reference Standard

USP

1399001

Methamphetamine hydrochloride

(±)-MDEA solution 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

M-065

(±)-MDEA solution

M I Colado et al.
British journal of pharmacology, 126(4), 911-924 (1999-04-08)
1. We investigated whether dopamine plays a role in the neurodegeneration of 5-hydroxytryptamine (5-HT) nerve endings occurring in Dark Agouti rat brain after 3,4-methylenedioxymethamphetamine (MDMA or 'ecstasy') administration. 2. Haloperidol (2 mg kg(-1) i.p.) injected 5 min prior and 55
G A Ricaurte et al.
Neuropsychobiology, 42(1), 5-10 (2000-06-27)
The popular recreational drug, (+/-)3, 4-methylenedioxymethamphetamine (MDMA; 'Ecstasy') is a potent and selective brain serotonin (5-HT) neurotoxin in animals. MDMA-induced 5-HT neurotoxicity can be demonstrated using a variety of neurochemical, neuroanatomical and, more recently, functional measures of 5-HT neurons. Although
A Lavelle et al.
British journal of pharmacology, 128(5), 975-980 (1999-11-11)
1. We have investigated the effects of methylenedioxymethamphetamine (MDMA, 'ecstasy') on peripheral noradrenergic neurotransmission in the rat. 2. In rat atrial slices pre-incubated with [3H]-noradrenaline and in the presence of desipramine (1 micronM) to prevent effects of MDMA on basal
M M Iravani et al.
Synapse (New York, N.Y.), 36(4), 275-285 (2000-05-20)
We examined the effects of pressure ejected 3, 4-methylenedioxymethamphetamine (MDMA) from a micropipette on direct chemically stimulated release, and on electrically stimulated serotonin (5-HT) or dopamine (DA) release in the caudate putamen (CPu), nucleus accumbens (NAc), substantia nigra pars reticulata
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

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