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H3288

HEMADO

Name: HEMADO
Brand: SIGMA

≥99% (HPLC), solid

Synonym(s):

2-(1-Hexynyl)-N⁶-methyladenosine

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₂₃N₅O₄

CAS Number:

403842-38-6

Molecular Weight:

361.40

UNSPSC Code:

12352200

PubChem Substance ID:

329815194

MDL number:

MFCD06798373

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assay

≥99% (HPLC)

form

solid

color

white

solubility

DMSO: 16 mg/mL

storage temp.

2-8°C

SMILES string

CCCCC#Cc1nc(NC)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1

InChI

1S/C17H23N5O4/c1-3-4-5-6-7-11-20-15(18-2)12-16(21-11)22(9-19-12)17-14(25)13(24)10(8-23)26-17/h9-10,13-14,17,23-25H,3-5,8H2,1-2H3,(H,18,20,21)/t10-,13-,14-,17-/m1/s1

InChI key

KOCIMZNSNPOGOP-IWCJZZDYSA-N

Biochem/physiol Actions

A₃ adenosine receptor agonist

pictograms

GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

014K4604

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N(6)-alkyl-2-alkynyl derivatives of adenosine as potent and selective agonists at the human adenosine A(3) receptor and a starting point for searching A(2B) ligands.

Rosaria Volpini et al.

Journal of medicinal chemistry, 45(15), 3271-3279 (2002-07-12)

A series of N(6)-alkyl-2-alkynyl derivatives of adenosine (Ado) have been synthesized and evaluated for their affinity at human A(1), A(2A), and A(3) receptors and for their potency at A(2B) adenosine receptor subtypes. The corresponding 2-(1-alkynyl) derivatives of 5'-N-ethylcarboxamidoadenosine (NECA) and

Pharmacological characterisation of novel adenosine A3 receptor antagonists.

Kerry Barkan et al.

Scientific reports, 10(1), 20781-20781 (2020-11-29)

The adenosine A3 receptor (A3R) belongs to a family of four adenosine receptor (AR) subtypes which all play distinct roles throughout the body. A3R antagonists have been described as potential treatments for numerous diseases including asthma. Given the similarity between

Effect of a toggle switch mutation in TM6 of the human adenosine A₃ receptor on Gi protein-dependent signalling and Gi-independent receptor internalization.

Leigh A Stoddart et al.

British journal of pharmacology, 171(16), 3827-3844 (2014-04-23)

The highly conserved tryptophan (W6.48) in transmembrane domain 6 of GPCRs has been shown to play a central role in forming an active conformation in response to agonist binding. We set out to characterize the effect of this mutation on

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