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A9719

Sigma-Aldrich

Arachidonyl-2′-chloroethylamide hydrate

≥97% (HPLC), oil

Synonym(s):

ACEA

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About This Item

Empirical Formula (Hill Notation):
C22H36ClNO · xH2O
CAS Number:
220556-69-4
Molecular Weight:
365.98 (anhydrous basis)
MDL number:
MFCD02683581
UNSPSC Code:
51111800
PubChem Substance ID:
24891489
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

oil

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated

color

brown-red

solubility

DMSO: soluble
H2O: insoluble

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCCl

InChI

1S/C22H36ClNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-

InChI key

SCJNCDSAIRBRIA-DOFZRALJSA-N

Gene Information

mouse ... Cnr1(12801) , Cnr2(12802)
rat ... Cnr1(25248)

Biochem/physiol Actions

Potent and selective neuronal CB1 cannabinoid receptor agonist.

Features and Benefits

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

Caution

Photosensitive; store under argon or nitrogen.

Storage Class Code

10 - Combustible liquids

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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Aakanksha Jain et al.
Nature communications, 9(1), 3185-3185 (2018-08-11)
Innate cytokines are critical drivers of priming and differentiation of naive CD4 T cells, but their functions in memory T cell response are largely undefined. Here we show that IL-1 acts as a licensing signal to permit effector cytokine production
Kristina B V Døssing et al.
Genes, 9(7) (2018-07-06)
Somatostatin (SST) analogues are used to control the proliferation and symptoms of neuroendocrine tumors (NETs). MicroRNAs (miRNA) are small non-coding RNAs that modulate posttranscriptional gene expression. We wanted to characterize the miRNAs operating under the control of SST to elucidate
Tamás Oláh et al.
The Journal of physiology, 594(24), 7381-7398 (2016-10-28)
Marijuana was found to cause muscle weakness, although the exact regulatory role of its receptors (CB1 cannabinoid receptor; CB1R) in the excitation-contraction coupling (ECC) of mammalian skeletal muscle remains unknown. We found that CB1R activation or its knockout did not
Chris L Baker et al.
British journal of pharmacology, 142(8), 1361-1367 (2004-07-28)
The vasoactive effects of the synthetic cannabinoid (CB) arachidonyl-2-chloroethylamide (ACEA) was tested in the knee joints of urethane-anaesthetised rats. Experiments were also performed to determine whether these vasomotor responses could be blocked by the selective CB(1) receptor antagonists AM251 (N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide)
C J Hillard et al.
The Journal of pharmacology and experimental therapeutics, 289(3), 1427-1433 (1999-05-21)
Two subtypes of the cannabinoid receptor (CB1 and CB2) are expressed in mammalian tissues. Although selective antagonists are available for each of the subtypes, most of the available cannabinoid agonists bind to both CB1 and CB2 with similar affinities. We
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