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SML1967

Sigma-Aldrich

N6-(4-Hydroxybenzyl) adenine riboside

≥98% (HPLC)

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Synonym(s):
N-[(4-Hydroxyphenyl)methyl]adenosine, N6-(4-Hydroxybenzyl)-adenosine, NHBA, T1-11
Empirical Formula (Hill Notation):
C17H19N5O5
CAS Number:
110505-75-4
Molecular Weight:
373.36
MDL number:
MFCD18641957
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

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

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

InChI key

UGVIXKXYLBAZND-LSCFUAHRSA-N

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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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