Ogerin | CAS#1309198-71-7 | GPR68 PAM

Ogerin
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 563604

CAS#: 1309198-71-7

Description: Ogerin is a selective GPR68 PAM, suppressing recall in fear conditioning in wild-type but not in GPR68-knockout mice.

Chemical Structure

Ogerin

CAS# 1309198-71-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 563604
Name: Ogerin
CAS#: 1309198-71-7
Chemical Formula: C17H17N5O
Exact Mass: 307.14
Molecular Weight: 307.357
Elemental Analysis: C, 66.43; H, 5.58; N, 22.79; O, 5.21

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 260
25mg	USD 620
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Ogerin; ZINC67740571; ZINC-67740571; ZINC 67740571;

IUPAC/Chemical Name: {2-[4-amino-6-(benzylamino)-1,3,5-triazin-2-yl]phenyl}methanol

InChi Key: MDGIEDNDSFMSLP-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H17N5O/c18-16-20-15(14-9-5-4-8-13(14)11-23)21-17(22-16)19-10-12-6-2-1-3-7-12/h1-9,23H,10-11H2,(H3,18,19,20,21,22)

SMILES Code: OCC1=CC=CC=C1C2=NC(N)=NC(NCC3=CC=CC=C3)=N2

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: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Ogerin is a selective GPR68 positive aliasing modulator (PAM) (pEC50=6.83) with a moderate antagonistic effect on A2A (Ki=220 nM).
In vitro activity:	Ogerin is a positive allosteric modulator (PAM) of GPR68, inducing a leftward shift of the dose response curve to proton induced signaling. Using PHLFs derived from patients with both non-fibrotic and IPF diagnoses, this study shows that Ogerin inhibits, and partially reverses TGF-β induced myofibroblast differentiation in a dose dependent manner. This occurs at the transcriptional level without inhibition of canonical TGF-β induced SMAD signaling. Ogerin induces PKA dependent CREB phosphorylation, a marker of Gαs pathway activation. The ability of Ogerin to inhibit both basal and TGF-β induced collagen gene transcription, and induction of Gαs signaling is enhanced at an acidic pH (pH 6.8). Reference: PLoS One. 2022 Jul 28;17(7):e0271608. https://pubmed.ncbi.nlm.nih.gov/35901086/
In vivo activity:	In WT mice, ogerin attenuated contextual-based fear memory without effects on cue-based memory (Figure 4c–d). Crucially, administration of ogerin had no effect on memory retrieval in GPR68 KO mice (Figure 4c–d), indicating that ogerin’s in vivo effects are GPR68-dependent. Furthermore, the less active ogerin isomer, ZINC32547799, had no measurable effect on learning and memory in wild-type mice (Figure 4c–d and Extended Data Fig 8d–h). Ogerin’s effects thus support a role for GPR68 in hippocampal-associated memory. Reference: Nature. 2015 Nov 26;527(7579):477-83. https://pubmed.ncbi.nlm.nih.gov/26550826/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	110.2	358.68
	Ethanol	6.2	20.00

Preparing Stock Solutions

The following data is based on the product molecular weight 307.36 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.

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. Greenwald E, Posner C, Bharath A, Lyons A, Salmerón C, Sriram K, Wiley SZ, Insel PA, Zhang J. GPCR Signaling Measurement and Drug Profiling with an Automated Live-Cell Microscopy System. ACS Sens. 2023 Jan 27;8(1):19-27. doi: 10.1021/acssensors.2c01341. Epub 2023 Jan 5. PMID: 36602887; PMCID: PMC9994309. 2. Bell TJ, Nagel DJ, Woeller CF, Kottmann RM. Ogerin mediated inhibition of TGF-β(1) induced myofibroblast differentiation is potentiated by acidic pH. PLoS One. 2022 Jul 28;17(7):e0271608. doi: 10.1371/journal.pone.0271608. PMID: 35901086; PMCID: PMC9333254. 3. Huang XP, Karpiak J, Kroeze WK, Zhu H, Chen X, Moy SS, Saddoris KA, Nikolova VD, Farrell MS, Wang S, Mangano TJ, Deshpande DA, Jiang A, Penn RB, Jin J, Koller BH, Kenakin T, Shoichet BK, Roth BL. Allosteric ligands for the pharmacologically dark receptors GPR68 and GPR65. Nature. 2015 Nov 26;527(7579):477-83. doi: 10.1038/nature15699. Epub 2015 Nov 9. PMID: 26550826; PMCID: PMC4796946.
In vitro protocol:	1. Greenwald E, Posner C, Bharath A, Lyons A, Salmerón C, Sriram K, Wiley SZ, Insel PA, Zhang J. GPCR Signaling Measurement and Drug Profiling with an Automated Live-Cell Microscopy System. ACS Sens. 2023 Jan 27;8(1):19-27. doi: 10.1021/acssensors.2c01341. Epub 2023 Jan 5. PMID: 36602887; PMCID: PMC9994309. 2. Bell TJ, Nagel DJ, Woeller CF, Kottmann RM. Ogerin mediated inhibition of TGF-β(1) induced myofibroblast differentiation is potentiated by acidic pH. PLoS One. 2022 Jul 28;17(7):e0271608. doi: 10.1371/journal.pone.0271608. PMID: 35901086; PMCID: PMC9333254.
In vivo protocol:	1. Huang XP, Karpiak J, Kroeze WK, Zhu H, Chen X, Moy SS, Saddoris KA, Nikolova VD, Farrell MS, Wang S, Mangano TJ, Deshpande DA, Jiang A, Penn RB, Jin J, Koller BH, Kenakin T, Shoichet BK, Roth BL. Allosteric ligands for the pharmacologically dark receptors GPR68 and GPR65. Nature. 2015 Nov 26;527(7579):477-83. doi: 10.1038/nature15699. Epub 2015 Nov 9. PMID: 26550826; PMCID: PMC4796946.

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1: McAleer JP, Fan J, Roar B, Primerano DA, Denvir J. Cytokine Regulation in Human CD4 T Cells by the Aryl Hydrocarbon Receptor and Gq-Coupled Receptors. Sci Rep. 2018 Jul 19;8(1):10954. doi: 10.1038/s41598-018-29262-4. PubMed PMID: 30026493; PubMed Central PMCID: PMC6053392.

2: Huang XP, Karpiak J, Kroeze WK, Zhu H, Chen X, Moy SS, Saddoris KA, Nikolova VD, Farrell MS, Wang S, Mangano TJ, Deshpande DA, Jiang A, Penn RB, Jin J, Koller BH, Kenakin T, Shoichet BK, Roth BL. Allosteric ligands for the pharmacologically dark receptors GPR68 and GPR65. Nature. 2015 Nov 26;527(7579):477-83. doi: 10.1038/nature15699. Epub 2015 Nov 9. PubMed PMID: 26550826; PubMed Central PMCID: PMC4796946.

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