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A7232

Sigma-Aldrich

AP-18

≥98% (HPLC), solid

Synonym(s):

4-(4-Chlorophenyl)-3-methylbut-3-en-2-oxime

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About This Item

Empirical Formula (Hill Notation):
C11H12ClNO
CAS Number:
55224-94-7
Molecular Weight:
209.67
MDL number:
MFCD00102250
UNSPSC Code:
12352200
PubChem Substance ID:
329770922
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

CC(=C/c1ccc(Cl)cc1)\C(C)=N\O

InChI

1S/C11H12ClNO/c1-8(9(2)13-14)7-10-3-5-11(12)6-4-10/h3-7,14H,1-2H3/b8-7+,13-9+

InChI key

MHTJEUOFLVQMCL-NJHPPEEMSA-N

Application

AP-18 is a selective TRPA1 channel blocker. AP-18 blocks the transient receptor potential ankyrin 1 receptors and can reduce chronic pain associated with arthritis. AP-18 reduces cinnamaldehyde-induced nociception in vivo and blocks cold- and mustard oil-induced activation of mouse TRPA1 but not capsaicin-induced activation. AP-18 reverses CFA-induced mechanical hyperalgesia in mice

Biochem/physiol Actions

AP-18 is a selective TRPA1 channel blocker. Transient receptor potential A1 (TRPA1) plays a central role for chemical sensing in the pain pathway. AP-18 is a novel TRPA1 channel blocker. It reduces cinnamaldehyde-induced nociception in vivo and blocks cold- and mustard oil-induced activation of mouse TRPA1 but not capsaicin-induced activation demonstrating selectivity vs. TRPV11. AP-18 reverses CFA-induced mechanical hyperalgesia in mice.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

A7232-25MG:
A7232-VAR:
A7232-BULK:
A7232-5MG:

Certificates of Analysis (COA)

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Sichong Chen et al.
Frontiers in physiology, 11, 576209-576209 (2020-11-17)
Transient receptor potential ankyrin 1 (TRPA1) is a non-selective cation channel that is broadly expressed in sensory pathways, such as the trigeminal and vagus nerves. It is capable of detecting various irritants in inspired gasses and is activated during hypoxia.
Daisuke Sugiyama et al.
Anesthesiology, 127(4), 695-708 (2017-06-24)
H2O2 has a variety of actions in skin wounds but has been rarely studied in deep muscle tissue. Based on response to the transient receptor potential ankyrin 1 antagonists after plantar incision, we hypothesized that H2O2 exerts nociceptive effects via
Puja Saluja et al.
Antonie van Leeuwenhoek, 101(4), 733-742 (2011-12-28)
Four yeast strains (APSS 805, APSS 806, APSS 815 and AP-18) belonging to a novel Torulaspora species were isolated from coal mine soils of Singareni in Andhra Pradesh state, India. Another strain (PBA-22) was isolated from agricultural field soil from
Chen Chen et al.
Cell biology international, 34(3), 293-299 (2009-12-02)
Adipocyte lines are a useful tool for adipocyte research. Recently, a new preadipocyte line designated AP-18 was established from subcutaneous tissue of the C3H/He mouse. In this study, we further characterized AP-18 cells. Adipocyte differentiation was assessed by accumulation of
Takashi Miyamoto et al.
PloS one, 4(10), e7596-e7596 (2009-11-07)
Nitric oxide (NO) can induce acute pain in humans and plays an important role in pain sensitization caused by inflammation and injury in animal models. There is evidence that NO acts both in the central nervous system via a cyclic
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