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Key Documents

C9901

Sigma-Aldrich

N6-Cyclohexyladenosine

Synonym(s):

CHA

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About This Item

Empirical Formula (Hill Notation):
C16H23N5O4
CAS Number:
Molecular Weight:
349.38
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

form

powder

Quality Level

storage temp.

2-8°C

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCCC4)ncnc23

InChI

1S/C16H23N5O4/c22-6-10-12(23)13(24)16(25-10)21-8-19-11-14(17-7-18-15(11)21)20-9-4-2-1-3-5-9/h7-10,12-13,16,22-24H,1-6H2,(H,17,18,20)/t10-,12-,13-,16-/m1/s1

InChI key

SZBULDQSDUXAPJ-XNIJJKJLSA-N

Gene Information

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Biochem/physiol Actions

Selective A1 adenosine receptor agonist.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

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Enbo Zhan et al.
American journal of physiology. Heart and circulatory physiology, 301(3), H1183-H1189 (2011-07-12)
All four adenosine receptor subtypes have been shown to play a role in cardioprotection, and there is evidence that all four subtypes may be expressed in cardiomyocytes. There is also increasing evidence that optimal adenosine cardioprotection requires the activation of
José Luis Albasanz et al.
The European journal of neuroscience, 26(12), 3501-3508 (2007-12-07)
The adenosine A(1) receptor (A(1)R)-adenylyl cyclase (AC) pathway was studied in post-mortem human frontal and occipital cortex from Pick's disease (PiD) cases and age-matched nondemented controls. In frontal cortex, the main brain area affected in PiD, A(1)Rs, determined by radioligand
M N Galardo et al.
Molecular and cellular endocrinology, 330(1-2), 49-58 (2010-08-21)
This work evaluates adenosine effects on Sertoli cell functions, which are different to those resulting from occupancy of purinergic receptors. The effects of adenosine and N(6)-cyclohexyladenosine (CHA) - an A(1) receptor agonist resistant to cellular uptake - on Sertoli cell
Seiji Miyazawa et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 295(3), R991-R996 (2008-07-04)
Body temperature drops dramatically during hibernation, but the heart retains the ability to contract and is resistant to induction of arrhythmia. Although adaptive changes in the heart prior to hibernation may be involved in the cold-resistant property, it remains unclear
Gerard J Marek
Neuropharmacology, 56(8), 1082-1087 (2009-03-28)
Modulation of glutamatergic neurotransmission by metabotropic glutamate2/3 (mGlu2/3) receptor agonists effectively treats seemingly diverse neuropsychiatric illness such as generalized anxiety disorder and schizophrenia. Activation of adenosine A(1) heteroceptors, like mGlu2 autoreceptors, decreases glutamate release in the medial prefrontal cortex (mPFC)

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