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Merck
CN

H7149

(±)-6-Hydroxy-3,4-methylenedioxymethamphetamine

Synonym(s):

6-Hydroxy-MDMA

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About This Item

Empirical Formula (Hill Notation):
C11H15NO3
CAS Number:
138808-79-4
Molecular Weight:
209.24
UNSPSC Code:
12352200
PubChem Substance ID:
329815241
MDL number:
MFCD00171438

Key Documents

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InChI

1S/C11H15NO3/c1-7(12-2)3-8-4-10-11(5-9(8)13)15-6-14-10/h4-5,7,12-13H,3,6H2,1-2H3

SMILES string

CNC(C)Cc1cc2OCOc2cc1O

InChI key

RQQIIXFYTHWFKW-UHFFFAOYSA-N

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage temp.

2-8°C

Biochem/physiol Actions

A metabolite of MDMA

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class

6.1A - 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 P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
073H4010

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Lim, H.K. and Foltz, R.L.
Biomedical Mass Spectrometry, 20, 677-677 (1991)
I Elayan et al.
European journal of pharmacology, 221(2-3), 281-288 (1992-10-20)
The long-term effects of three metabolites of 3,4-methylenedioxymethamphetamine (MDMA) on the central monoaminergic systems of the rat were examined. Seven days after the intracerebroventricular administration of 0.25 and 0.5 mumol 2,4,5-trihydroxyamphetamine, hippocampal tryptophan hydroxylase (TPH) activity was reduced to 5
T Chu et al.
Biochemical pharmacology, 51(6), 789-796 (1996-03-22)
3,4-Methylenedioxymethamphetamine (MDMA) affects both dopamine and serotonin (5-HT) systems. One of its acute actions is to cause a reversible fall in steady-state brain 5-HT concentrations. To investigate the chemical basis of this acute effect, the brain levels of the parent
T M Walker et al.
Cell biology and toxicology, 15(3), 137-142 (1999-12-02)
Rat whole-brain spheroids were used to assess the intrinsic neurotoxicity of methylenedioxy-methamphetamine (MDMA, Ecstasy) and two of its metabolites, dihydroxymethamphetamine (DHMA) and 6-hydroxy-MDMA (6-OH MDMA). Exposure of brain spheroids to MDMA or the metabolite 6-OH MDMA (up to 500 micromol/L)
H K Lim et al.
Biological mass spectrometry, 20(11), 677-686 (1991-11-01)
Aromatic hydroxylation has been established as a pathway for the in vivo metabolism of 3,4-(methylenedioxy)methamphetamine (MDMA) in the rat. Hydroxylation occurred at positions 2, 5 and 6 of the 3,4-methylenedioxyphenyl ring, but is favored at the 6 position. All three

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