WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 510212
CAS#: 868273-06-7
Description: ORG-27569 is a drug which acts as a potent and selective allosteric modulator of the cannabinoid CB1 receptor. Studies in vitro suggest that it binds to a regulatory site on the CB1 receptor target, causing a conformational change that increases the binding affinity of CB1 agonists such as CP 55,940, while decreasing the binding affinity of CB1 antagonists or inverse agonists such as rimonabant. However while Org 27569 increases the ability of CB1 agonists to bind to the receptor, it decreases their efficacy at stimulating second messenger signalling once bound, and so in practice behaves as an insurmountable antagonist of CB1 receptor function. (source: http://en.wikipedia.org/wiki/Org_27569).
MedKoo Cat#: 510212
Name: ORG-27569
CAS#: 868273-06-7
Chemical Formula: C24H28ClN3O
Exact Mass: 409.19209
Molecular Weight: 409.95
Elemental Analysis: C, 70.31; H, 6.88; Cl, 8.65; N, 10.25; O, 3.90
Synonym: ORG27569; ORG-27569; ORG 27569.
IUPAC/Chemical Name: 5-chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide
InChi Key: AHFZDNYNXFMRFQ-UHFFFAOYSA-N
InChi Code: InChI=1S/C24H28ClN3O/c1-2-20-21-16-18(25)8-11-22(21)27-23(20)24(29)26-13-12-17-6-9-19(10-7-17)28-14-4-3-5-15-28/h6-11,16,27H,2-5,12-15H2,1H3,(H,26,29)
SMILES Code: O=C(C(N1)=C(CC)C2=C1C=CC(Cl)=C2)NCCC3=CC=C(N4CCCCC4)C=C3
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, not in water
Shelf Life: >5 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: 2934.99.9001
The following data is based on the product molecular weight 409.95 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 |
1: Baillie GL, Horswill JG, Anavi-Goffer S, Reggio PH, Bolognini D, Abood ME, McAllister S, Strange PG, Stephens GJ, Pertwee RG, Ross RA. CB(1) receptor allosteric modulators display both agonist and signaling pathway specificity. Mol Pharmacol. 2013 Feb;83(2):322-38. doi: 10.1124/mol.112.080879. Epub 2012 Nov 15. PubMed PMID: 23160940; PubMed Central PMCID: PMC3558808.
2: Fay JF, Farrens DL. A key agonist-induced conformational change in the cannabinoid receptor CB1 is blocked by the allosteric ligand Org 27569. J Biol Chem. 2012 Sep 28;287(40):33873-82. Epub 2012 Jul 30. PubMed PMID: 22846992; PubMed Central PMCID: PMC3460482.
3: Erdozain AM, Diez-Alarcia R, Meana JJ, Callado LF. The inverse agonist effect of rimonabant on G protein activation is not mediated by the cannabinoid CB1 receptor: evidence from postmortem human brain. Biochem Pharmacol. 2012 Jan 15;83(2):260-8. doi: 10.1016/j.bcp.2011.10.018. Epub 2011 Nov 7. PubMed PMID: 22093909.
4: Price MR, Baillie GL, Thomas A, Stevenson LA, Easson M, Goodwin R, McLean A, McIntosh L, Goodwin G, Walker G, Westwood P, Marrs J, Thomson F, Cowley P, Christopoulos A, Pertwee RG, Ross RA. Allosteric modulation of the cannabinoid CB1 receptor. Mol Pharmacol. 2005 Nov;68(5):1484-95. Epub 2005 Aug 19. PubMed PMID: 16113085.
