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Merck
CN

C9901

N6-Cyclohexyladenosine

Synonym(s):

CHA

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About This Item

Empirical Formula (Hill Notation):
C16H23N5O4
CAS Number:
36396-99-3
Molecular Weight:
349.38
NACRES:
NA.77
PubChem Substance ID:
24278351
UNSPSC Code:
12352204
MDL number:
MFCD00036808

Key Documents

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InChI key

SZBULDQSDUXAPJ-XNIJJKJLSA-N

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

form

powder

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... ADORA1(134)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
13121210
128M4197V
018M4040V
077M4081V
13170617

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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
Domenico Tupone et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(36), 14512-14525 (2013-09-06)
Since central activation of A1 adenosine receptors (A1ARs) plays an important role in the induction of the hypothermic and hypometabolic torpid state in hibernating mammals, we investigated the potential for the A1AR agonist N6-cyclohexyladenosine to induce a hypothermic, torpor-like state
Matthew Edward Pamenter et al.
Brain research, 1213, 27-34 (2008-05-06)
Adenosine is a defensive metabolite that is critical to anoxic neuronal survival in the freshwater turtle. Channel arrest of the N-methyl-d-aspartate receptor (NMDAR) is a hallmark of the turtle's remarkable anoxia tolerance and adenosine A1 receptor (A1R)-mediated depression of normoxic
Kelly R Lobato et al.
Progress in neuro-psychopharmacology & biological psychiatry, 32(4), 994-999 (2008-02-22)
It was previously shown that the acute administration of zinc chloride elicits an antidepressant-like effect in the mouse forced swimming test (FST). We have also shown that the activation of adenosine A(1) and A(2A) receptors produces an antidepressant-like effect in
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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