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Merck

A002

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
UNSPSC Code:
12352204
PubChem Substance ID:
329770564
MDL number:
MFCD00036808

Key Documents

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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

General description

N6-Cyclohexyladenosine belongs to the class of new generation thermolytic agents.

Biochem/physiol Actions

N6-Cyclohexyladenosine is an adenosine A1 receptor agonist. It prevents thermogenesis and other response such as shivering in response to cold. N6-Cyclohexyladenosine initiates hibernation in animals.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Modulation of conventional outflow facility by the adenosine A1 agonist N6-cyclohexyladenosine
Crosson CE, et al.
Investigative Ophthalmology & Visual Science, 46(10), 3795-3799 (2005)
Precise Control of Target Temperature Using N6-Cyclohexyladenosine and Real-Time Control of Surface Temperature
Laughlin BW, et al.
Therapeutic hypothermia and temperature management, 8(2), 108-116 (2018)
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)
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
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
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