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M4758

Sigma-Aldrich

(±)-6-Methyl-5,6,7,8-tetrahydropterine dihydrochloride

~95% (TLC)

Synonym(s):

6-MPH4, DL-2-Amino-4-hydroxy-6-methyl-5,6,7,8-tetrahydropteridine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C7H11N5O · 2HCl
CAS Number:
69113-63-9
Molecular Weight:
254.12
Beilstein:
5648114
MDL number:
MFCD00058175
UNSPSC Code:
12352204
PubChem Substance ID:
24896941
NACRES:
NA.51

Assay

~95% (TLC)

Quality Level

200

storage temp.

−20°C

SMILES string

Cl.Cl.CC1CNc2nc(N)nc(O)c2N1

InChI

1S/C7H11N5O.2ClH/c1-3-2-9-5-4(10-3)6(13)12-7(8)11-5;;/h3,10H,2H2,1H3,(H4,8,9,11,12,13);2*1H

InChI key

MKQLORLCFAZASZ-UHFFFAOYSA-N

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Application

6-MPH4 is used to study mechanisms of nitric oxide (NO) synthase and free radical induced L-DOPA release from striatal tissue.

Biochem/physiol Actions

Synthetic cofactor for tyrosine hydrolase; also cofactor for phenylalanine and tryptophan hydroxylases; less activity than the natural cofactor, BH4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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L-Tryptophan reagent grade, ≥98% (HPLC)

Sigma-Aldrich

T0254

L-Tryptophan

M Naoi et al.
Journal of chromatography, 427(2), 229-238 (1988-06-03)
A simple assay procedure for tyrosine hydroxylase activity in crude tissue samples was devised that requires minimal sample preparation and use of high-performance liquid chromatography with coulometric electrochemical detection. After incubation of enzyme samples, such as human brain homogenates or
F García-Molina et al.
Biochimica et biophysica acta, 1794(12), 1766-1774 (2009-08-22)
There is controversy in the literature concerning the action of tetrahydropterines on the enzyme tyrosinase and on melanogenesis in general. In this study, we demonstrate that tetrahydropterines can inhibit melanogenesis in several ways: i) by non-enzymatic inhibition involving purely chemical
M Bauer et al.
Journal of neurochemistry, 82(5), 1300-1310 (2002-10-03)
Glial cell line-derived neurotrophic factor (GDNF) protects dopaminergic neurones against toxic and physical damage. In addition, GDNF promotes differentiation and structural integrity of dopaminergic neurones. Here we show that GDNF can support the function of primary dopaminergic neurones by triggering
Elizabeth A Gaskell et al.
PloS one, 4(3), e4801-e4801 (2009-03-12)
The genome of the protozoan parasite Toxoplasma gondii was found to contain two genes encoding tyrosine hydroxylase; that produces L-DOPA. The encoded enzymes metabolize phenylalanine as well as tyrosine with substrate preference for tyrosine. Thus the enzymes catabolize phenylalanine to
P Abreu-González et al.
European journal of pharmacology, 541(1-2), 33-37 (2006-06-06)
In the present study we have analyzed the effect of tetrahydrobiopterin (BH4) essential cofactor for tyrosine hydroxylase and nitric oxide synthase, on the 3,4-dihydroxyphenylalanine (L-DOPA) release from in vitro incubated striatal tissue. dl-6-methyl-5,6,7,8 tetrahydropterine (6-MPH4)-stimulated L-DOPA release in a concentration-dependent
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