BAY-59-3074 | CAS#406205-74-1 | Cannabinoid Receptor Agonist

MedKoo Cat#: 524385 | Name: BAY-59-3074

Description:

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

BAY-59-3074 is a novel cannabinoid CB1/CB2 receptor partial agonist with analgesic properties. It displays anti-hyperalgesic and antiallodynic properties in rat models of chronic neuropathic and inflammatory pain.

Chemical Structure

BAY-59-3074

CAS#406205-74-1

Theoretical Analysis

MedKoo Cat#: 524385

Name: BAY-59-3074

CAS#: 406205-74-1

Chemical Formula: C21H21FN8O

Exact Mass: 420.1822

Molecular Weight: 420.44

Elemental Analysis: C, 59.99; H, 5.03; F, 4.52; N, 26.65; O, 3.81

Price and Availability

Size	Price	Availability
50mg	USD 550.00	2 Weeks
100mg	USD 850.00	2 Weeks
200mg	USD 1,350.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 5,850.00	2 Weeks

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Synonym

BAY-59-3074; BAY 59-3074; BAY59-3074; BAY-593074; BAY 593074; BAY593074;

IUPAC/Chemical Name

1-Butanesulfonic acid, 4,4,4-trifluoro-, 3-(2-cyano-3-(trifluoromethyl)phenoxy)phenyl ester

InChi Key

LWUSZIVDPJPVBW-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H13F6NO4S/c19-17(20,21)8-3-9-30(26,27)29-13-5-1-4-12(10-13)28-16-7-2-6-15(14(16)11-25)18(22,23)24/h1-2,4-7,10H,3,8-9H2

SMILES Code

O=S(CCCC(F)(F)F)(OC1=CC=CC(OC2=CC=CC(C(F)(F)F)=C2C#N)=C1)=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

Soluble in DMSO, not in water

Shelf Life

>2 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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bay 59-3074 is a cannabinoid CB1/CB2 receptor partial agonist with Ki values of 48.3 and 45.5 nM at human CB1 and CB2 receptors, respectively.

In vitro activity:

TBD

In vivo activity:

BAY 59-3074 (0.3-3 mg/kg, p.o.) induced antihyperalgesic and antiallodynic effects against thermal or mechanical stimuli in rat models of chronic neuropathic (chronic constriction injury, spared nerve injury, tibial nerve injury, and spinal nerve ligation models) and inflammatory pain (carrageenan and complete Freund's adjuvant models). Antiallodynic efficacy of BAY 59-3074 (1 mg/kg, p.o.) in the spared nerve injury model was maintained after 2 weeks of daily administration. However, tolerance developed rapidly (within 5 days) for cannabinoid-related side effects, which occur at doses above 1 mg/kg (e.g., hypothermia). Uptitration from 1 to 32 mg/kg p.o. (doubling of daily dose every 4th day) prevented the occurrence of such side effects, whereas antihyperalgesic and antiallodynic efficacy was maintained/increased. No withdrawal symptoms were seen after abrupt withdrawal following 14 daily applications of 1 to 10 mg/kg p.o. It is concluded that BAY 59-3074 may offer a valuable therapeutic approach to treat diverse chronic pain conditions. Reference: J Pharmacol Exp Ther. 2004 Aug;310(2):620-32. https://jpet.aspetjournals.org/content/310/2/620.long

	Solvent	mg/mL	mM
Solubility
	DMSO	56.8	135.05
	Ethanol	68.2	162.14

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 420.44 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. De Vry J, Denzer D, Reissmueller E, Eijckenboom M, Heil M, Meier H, Mauler F. 3-[2-cyano-3-(trifluoromethyl)phenoxy]phenyl-4,4,4-trifluoro-1-butanesulfonate (BAY 59-3074): a novel cannabinoid Cb1/Cb2 receptor partial agonist with antihyperalgesic and antiallodynic effects. J Pharmacol Exp Ther. 2004 Aug;310(2):620-32. doi: 10.1124/jpet.103.062836. Epub 2004 May 12. PMID: 15140913.

In vitro protocol:

TBD

In vivo protocol:

1: Teng H, Thakur GA, Makriyannis A. Conformationally constrained analogs of BAY 59-3074 as novel cannabinoid receptor ligands. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5999-6002. doi: 10.1016/j.bmcl.2011.07.017. Epub 2011 Jul 23. PubMed PMID: 21880487; PubMed Central PMCID: PMC3693451. 2: De Vry J, Jentzsch KR. Discriminative stimulus effects of the structurally novel cannabinoid CB1/CB2 receptor partial agonist BAY 59-3074 in the rat. Eur J Pharmacol. 2004 Nov 28;505(1-3):127-33. PubMed PMID: 15556145. 3: De Vry J, Denzer D, Reissmueller E, Eijckenboom M, Heil M, Meier H, Mauler F. 3-[2-cyano-3-(trifluoromethyl)phenoxy]phenyl-4,4,4-trifluoro-1-butanesulfonate (BAY 59-3074): a novel cannabinoid Cb1/Cb2 receptor partial agonist with antihyperalgesic and antiallodynic effects. J Pharmacol Exp Ther. 2004 Aug;310(2):620-32. Epub 2004 May 12. PubMed PMID: 15140913.