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Merck

SML1967

N6-(4-Hydroxybenzyl) adenine riboside

≥98% (HPLC)

Synonym(s):

N-[(4-Hydroxyphenyl)methyl]adenosine, N6-(4-Hydroxybenzyl)-adenosine, NHBA, T1-11

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About This Item

Empirical Formula (Hill Notation):
C17H19N5O5
CAS Number:
110505-75-4
Molecular Weight:
373.36
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD18641957
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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InChI

1S/C17H19N5O5/c23-6-11-13(25)14(26)17(27-11)22-8-21-12-15(19-7-20-16(12)22)18-5-9-1-3-10(24)4-2-9/h1-4,7-8,11,13-14,17,23-26H,5-6H2,(H,18,19,20)/t11-,13-,14-,17-/m1/s1

SMILES string

OC[C@H]1O[C@@H](N2C=NC3=C2N=CN=C3NCC4=CC=C(O)C=C4)[C@H](O)[C@@H]1O

InChI key

UGVIXKXYLBAZND-LSCFUAHRSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

N6-(4-Hydroxybenzyl) adenine riboside (NHBA) is an orally available and brain penetrant active active ingredient of Gastrodia elata rhizomes used for the treatment of insomnia. N6-(4-Hydroxybenzyl) adenine riboside is an adenosine A2A receptor and the equilibrative nucleoside transporter 1 (ENT1) agonist. It exhibits sedative and hypnotic effects by binding to adenosine A1 and A2A receptors in mice. N6-(4-Hydroxybenzyl) adenine riboside exerted a therapeutic effect on HD transgenic mouse by decreasing protein level of polyglutamine-expanded huntingtin in the striatum.
Orally available and brain penetrant active adenosine A2A receptors and the equilibrative nucleoside transporter 1 (ENT1) agonist

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

SML1967-25MG: + SML1967-BULK: + SML1967-5MG: + SML1967-VAR:

jan

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Certificates of Analysis (COA)

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Nai-Kuei Huang et al.
PloS one, 6(6), e20934-e20934 (2011-06-30)
Huntington's disease (HD) is a neurodegenerative disease caused by a CAG trinucleotide expansion in the Huntingtin (Htt) gene. The expanded CAG repeats are translated into polyglutamine (polyQ), causing aberrant functions as well as aggregate formation of mutant Htt. Effective treatments
Jhih-Bin Chen et al.
ChemMedChem, 6(8), 1390-1400 (2011-06-22)
A novel compound, N⁶-(4-hydroxybenzyl)adenosine, isolated from Gastrodia elata and which has been shown to be a potential therapeutic agent for preventing and treating neurodegenerative disease, was found to target both the adenosine A(2A) receptor (A(2A) R) and the equilibrative nucleoside
An-Hsun Chou et al.
Neuropharmacology, 99, 308-317 (2015-08-10)
More studies are required to develop therapeutic agents for treating spinocerebellar ataxia type 3 (SCA3), which is caused by mutant polyglutamine-expanded ataxin-3 and is the most prevalent subtype of spinocerebellar ataxias. T1-11 [N6-(4-Hydroxybenzyl) adenosine], isolated from a Chinese medicinal herb

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