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Merck
CN

T4425

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride

≥98% (HPLC), powder

Synonym(s):

(6R)-BH4

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About This Item

Empirical Formula (Hill Notation):
C9H15N5O3 · 2HCl
CAS Number:
69056-38-8
Molecular Weight:
314.17
UNSPSC Code:
12352200
PubChem Substance ID:
24277922
NACRES:
NA.77
MDL number:
MFCD00891665

Key Documents

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Product Name

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride,

SMILES string

Cl.Cl.C[C@H](O)[C@H](O)[C@H]1CNC2=C(N1)C(=O)NC(N)=N2

InChI

1S/C9H15N5O3.2ClH/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7;;/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17);2*1H/t3-,4+,6-;;/m0../s1

InChI key

RKSUYBCOVNCALL-NTVURLEBSA-N

solubility

water, oxygen free: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

−20°C

Quality Level

200

Gene Information

human ... PAH(5053)

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Application

(6R)-BH4 has been used as a buffer component for assaying tyrosine hydroxylase enzyme activity in mouse brain tissues. (6R)-BH4 has also been identified as an activator compound from a LOPAC library screen using a fluorogenic α-glucosidase assay.

Biochem/physiol Actions

Lack of tetrahydrobiopterin may cause hyperphenylalaninemia. Diseases like, Parkinson′s, autism, depression and Alzheimer′s shows low concentration of tetrahydrobiopterin in the cerebrospinal fluid. This coenzyme participates in dopamine (DA) synthesis.

Features and Benefits

This compound is featured on the Dopamine, Norepinephrine and Epinephrine Synthesis and Nitric Oxide Synthases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Tetrahydrobiopterin is a natural cofactor for phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase, nitric oxide synthase and alkylglycerol monooxygenase.

Preparation Note

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride ((6R)-BH4 ) is soluble in oxygen free water at 19.60 - 20.40 mg/ml and yields a clear to slightly hazy, colorless to faint yellow solution.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000469924
0000469924
0000401299
0000409697
0000401299

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Rebecca Ebenhoch et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(50), 31838-31849 (2020-11-25)
Guanosine triphosphate (GTP) cyclohydrolase I (GCH1) catalyzes the conversion of GTP to dihydroneopterin triphosphate (H2NTP), the initiating step in the biosynthesis of tetrahydrobiopterin (BH4). Besides other roles, BH4 functions as cofactor in neurotransmitter biosynthesis. The BH4 biosynthetic pathway and GCH1
Pteridines
Colette DS, et al.
reference module in biomedical sciences (2018)
Translational Medicine Strategies in Drug Development for Mood Disorders
Handbook of Biologically Active Peptides (2019)
Keun-Sung Lee et al.
The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology, 17(1), 89-97 (2013-02-27)
Developing an animal model for a specific disease is very important in the understanding of the underlying mechanism of the disease and allows testing of newly developed new drugs before human application. However, which of the plethora of experimental animal
Ailing Fu et al.
Brain research, 1352, 208-213 (2010-07-06)
Glial-derived neurotrophic factor (GDNF) is a trophic factor for the nigra-striatal tract in experimental Parkinson's disease (PD). The neurotrophin must be administered by intra-cerebral injection, because GDNF does not cross the blood-brain barrier (BBB). In the present study, GDNF was
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血清素合成及代谢

血清素（5-羟色胺）主要存在于三种主要细胞类型中：i）中杻神经系统（CNS）和肠肌间神经丛中的血清素能神经元，ii）胃肠道粘膜中的肠嗜铬细胞，和iii）血小板。血清素的代谢主要通过外部线粒体膜酶单胺氧化酶（MAO）进行，它以两种分子亚型存在，分别称为MAO-A和MAO-B。

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