AA92593
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MedKoo CAT#: 555939

CAS#: 457961-34-1

Description: AA92593, also known as Cy1001, is a selective melanopsin inhibitor. AA92593 blocks melanopsin activity and stimulates α-melanocyte-stimulating hormone (α-MSH) expression and induces melanin distribution in the melanophores, which darkens the embryo.


Chemical Structure

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AA92593
CAS# 457961-34-1

Theoretical Analysis

MedKoo Cat#: 555939
Name: AA92593
CAS#: 457961-34-1
Chemical Formula: C13H19NO3S
Exact Mass: 269.1086
Molecular Weight: 269.359
Elemental Analysis: C, 57.97; H, 7.11; N, 5.20; O, 17.82; S, 11.90

Price and Availability

Size Price Availability Quantity
25.0mg USD 250.0 2 Weeks
50.0mg USD 450.0 2 Weeks
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 1950.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 4950.0 2 Weeks
5.0g USD 6950.0 2 Weeks
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Synonym: AA92593; AA-92593; AA 92593; Cy1001; Cy-1001; Cy 1001;

IUPAC/Chemical Name: 1-(4-Methoxy-3-methyl-benzenesulfonyl)-piperidine

InChi Key: O=S(N1CCCCC1)(C2=CC=C(OC)C(C)=C2)=O

InChi Code: 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

SMILES Code: O=S(N1CCCCC1)(C2=CC=C(OC)C(C)=C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: AA92593 is a selective antagonist of Melanopsin (OPN4).
In vitro activity: This study then pharmacologically inhibited melanopsin with the antagonist AA92593, shown to be specific because it competes with retinaldehyde for the melanopsin retinal binding site which is very distinct from other opsins. These data show that the increase of Per1 level induced by heat in Melan-a and B16-F10 cells was significantly reduced in the presence of the melanopsin antagonist (Fig. 3A,C) whereas Bmal1 expression was not affected (Fig. 3B,D). Surprisingly, in Melan-a cells the group incubated with the antagonist and kept at 37 °C showed a statistically significant increase of Per1 transcript when compared to DMSO-treated control group (p = 0.0478, Fig. 3A); a phenomenon that showed no statistical significance (p = 0.08) in B16-F10 cells. Reference: Sci Rep. 2017; 7: 13977. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5656685/
In vivo activity: The contents of dopamine and melatonin in the retinal neural epithelium of the guinea pigs in the control group were 1.02 ± 0.30 and 0.36 ± 0.09 ng/mg, respectively. The content of dopamine in the defocus group decreased to 0.64 ± 0.18 ng/mg (P = .008), whereas the melatonin content was 0.38 ± 0.09 ng/mg (P = .58). The intravitreal injection of AA92593 into the defocus eyes resulted in a marked increase in melatonin content in retinal neuroepithelium (0.55 ± 0.13 ng/mg; P = .01) compared with the defocus group, but had no marked effect on the dopamine content (0.61 ± 0.17 ng/mg; P > .99; Figs. 4A, B). In the defocus + AA92593 group, the melatonin content of the retinal neuroepithelium was correlated with the refractive error (Pearson correlation coefficient = −0.68, P = .006) and axial length (Pearson correlation coefficient = 0.74, P = .02; Figs. 4C, D). Reference: Optom Vis Sci. 2020 Jul;97(7):489-495. https://pubmed.ncbi.nlm.nih.gov/32697555/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 54.0 200.48

Preparing Stock Solutions

The following data is based on the product molecular weight 269.359 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Moraes MN, de Assis LVM, Magalhães-Marques KK, Poletini MO, de Lima LHRG, Castrucci AML. Melanopsin, a Canonical Light Receptor, Mediates Thermal Activation of Clock Genes. Sci Rep. 2017 Oct 25;7(1):13977. doi: 10.1038/s41598-017-13939-3. PMID: 29070825; PMCID: PMC5656685. 2. Bertolesi GE, Vazhappilly ST, Hehr CL, McFarlane S. Pharmacological induction of skin pigmentation unveils the neuroendocrine circuit regulated by light. Pigment Cell Melanoma Res. 2016 Mar;29(2):186-98. doi: 10.1111/pcmr.12442. PMID: 26582755. 3. Zheng W, Chen Y, Zhou X, Zhang X, Chen Y, Guan X, Mao J. Regulation of Retinal Melanopsin on Lens-induced Myopia in Guinea Pigs. Optom Vis Sci. 2020 Jul;97(7):489-495. doi: 10.1097/OPX.0000000000001529. PMID: 32697555. 4. Pintor J. Light-induced ATP release from the lens. Purinergic Signal. 2018 Dec;14(4):499-504. doi: 10.1007/s11302-018-9626-3. Epub 2018 Sep 20. PMID: 30238191; PMCID: PMC6298921.
In vitro protocol: 1. Moraes MN, de Assis LVM, Magalhães-Marques KK, Poletini MO, de Lima LHRG, Castrucci AML. Melanopsin, a Canonical Light Receptor, Mediates Thermal Activation of Clock Genes. Sci Rep. 2017 Oct 25;7(1):13977. doi: 10.1038/s41598-017-13939-3. PMID: 29070825; PMCID: PMC5656685. 2. Bertolesi GE, Vazhappilly ST, Hehr CL, McFarlane S. Pharmacological induction of skin pigmentation unveils the neuroendocrine circuit regulated by light. Pigment Cell Melanoma Res. 2016 Mar;29(2):186-98. doi: 10.1111/pcmr.12442. PMID: 26582755.
In vivo protocol: 1. Zheng W, Chen Y, Zhou X, Zhang X, Chen Y, Guan X, Mao J. Regulation of Retinal Melanopsin on Lens-induced Myopia in Guinea Pigs. Optom Vis Sci. 2020 Jul;97(7):489-495. doi: 10.1097/OPX.0000000000001529. PMID: 32697555. 2. Pintor J. Light-induced ATP release from the lens. Purinergic Signal. 2018 Dec;14(4):499-504. doi: 10.1007/s11302-018-9626-3. Epub 2018 Sep 20. PMID: 30238191; PMCID: PMC6298921.

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1: Zheng W, Chen Y, Zhou X, Zhang X, Chen Y, Guan X, Mao J. Regulation of Retinal Melanopsin on Lens-induced Myopia in Guinea Pigs. Optom Vis Sci. 2020 Jul;97(7):489-495. doi: 10.1097/OPX.0000000000001529. PMID: 32697555.

2: Lledó VE, Alkozi HA, Pintor J. Yellow Filter Effect on Melatonin Secretion in the Eye: Role in IOP Regulation. Curr Eye Res. 2019 Jun;44(6):614-618. doi: 10.1080/02713683.2019.1570276. Epub 2019 Jan 24. PMID: 30640554.

3: Pintor J. Light-induced ATP release from the lens. Purinergic Signal. 2018 Dec;14(4):499-504. doi: 10.1007/s11302-018-9626-3. Epub 2018 Sep 20. PMID: 30238191; PMCID: PMC6298921.

4: Moraes MN, de Assis LVM, Magalhães-Marques KK, Poletini MO, de Lima LHRG, Castrucci AML. Melanopsin, a Canonical Light Receptor, Mediates Thermal Activation of Clock Genes. Sci Rep. 2017 Oct 25;7(1):13977. doi: 10.1038/s41598-017-13939-3. PMID: 29070825; PMCID: PMC5656685.

5: Alkozi HA, Wang X, Perez de Lara MJ, Pintor J. Presence of melanopsin in human crystalline lens epithelial cells and its role in melatonin synthesis. Exp Eye Res. 2017 Jan;154:168-176. doi: 10.1016/j.exer.2016.11.019. Epub 2016 Nov 30. PMID: 27914990.

6: Bertolesi GE, Vazhappilly ST, Hehr CL, McFarlane S. Pharmacological induction of skin pigmentation unveils the neuroendocrine circuit regulated by light. Pigment Cell Melanoma Res. 2016 Mar;29(2):186-98. doi: 10.1111/pcmr.12442. PMID: 26582755.

7: Bertolesi GE, Hehr CL, McFarlane S. Melanopsin photoreception in the eye regulates light-induced skin colour changes through the production of α-MSH in the pituitary gland. Pigment Cell Melanoma Res. 2015 Sep;28(5):559-71. doi: 10.1111/pcmr.12387. Epub 2015 Jul 7. PMID: 26095528.

AA92593

25.0mg / USD 250.0