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Key Documents

SML0865

Sigma-Aldrich

AA92593

≥98% (HPLC)

Synonym(s):

1-(4-Methoxy-3-methyl-benzenesulfonyl)-piperidine, 1-[(4-Methoxy-3-methylphenyl)sulfonyl]-piperidine, Cy1001

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About This Item

Empirical Formula (Hill Notation):
C13H19NO3S
CAS Number:
457961-34-1
Molecular Weight:
269.36
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

InChI

1S/C13H19NO3S/c1-11-10-12(6-7-13(11)17-2)18(15,16)14-8-4-3-5-9-14/h6-7,10H,3-5,8-9H2,1-2H3

InChI key

HDTKLZINZGEPFG-UHFFFAOYSA-N

Application

AA92593 has been used as a selective melanopsin inhibitor.

Biochem/physiol Actions

AA92593 blocks melanopsin activity and stimulates α-melanocyte-stimulating hormone (α-MSH) expression and induces melanin distribution in the melanophores, which darkens the embryo.
AA92593 is an opsinamide, a potent antagonist of melanopsin-mediated phototransduction with an IC50 of 665 nM in a Ca2+ flux assay in CHO cells expressing melanopsin (Opn4) and selectivity > 10 μM at 74 common biological targets. AA41612 is believed to act by competing for binding to melanopsin. AA41612 inhibited mouse pupillary light reflex and light aversion in vivo. AA92593 and similar compounds might be useful in alleviating the photophobia associated with migraine.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Presence of melanopsin in human crystalline lens epithelial cells and its role in melatonin synthesis.
Alkozi H A, et al.
Experimental Eye Research, 154, 168-176 (2017)
Melanopsin photoreception in the eye regulates light?induced skin colour changes through the production of α?MSH in the pituitary gland.
Bertolesi G E
Pigment Cell & Melanoma Research, 28(8), 559-571 (2015)
Wei Zheng et al.
Optometry and vision science : official publication of the American Academy of Optometry, 97(7), 489-495 (2020-07-23)
Investigation of the mechanism and the role of melanopsin in lens-induced myopia is necessary to find out potential targets in the prevention of myopia development. We aimed to study the effect and mechanism of retinal melanopsin on lens-induced myopia in

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