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A002

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:

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

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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.

replaced by

Product No.
Description
Pricing

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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

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