MDA19 or MDA-19 is discontinued (DEA controlled substance). It is a selective agonist of the human peripheral cannabinoid (CB2) receptor, with an EC50 value for activation (63.4 nM) that is 14-fold lower than that for central cannabinoid (CB1) activation (EC50 = 867 nM). MDA19 exhibited a distinctive in vitro functional profile at rat CB2 receptors and behaved as a CB1/CB2 agonist in vivo, characteristics of a protean agonist. MDA19 has potential for alleviating neuropathic pain without producing adverse effects in the central nervous system.

Product information

CAS Number: 1048973-47-2

Molecular Weight: 349.43

Formula: C21H23N3O2

Synonym:

MDA19

MDA-19

Chemical Name: N-[(1-hexyl-2-hydroxy-1H-indol-3-yl)imino]benzamide

Smiles: CCCCCCN1C(O)=C(N=NC(=O)C2C=CC=CC=2)C2=CC=CC=C12

InChiKey: ICNRTDOKKSWDRL-GHVJWSGMSA-N

InChi: InChI=1S/C21H23N3O2/c1-2-3-4-10-15-24-18-14-9-8-13-17(18)19(21(24)26)22-23-20(25)16-11-6-5-7-12-16/h5-9,11-14,26H,2-4,10,15H2,1H3/b23-22+

Technical Data

Appearance: Solid Power

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

Solubility: DMSO : 14.29 mg/mL (40.90 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

MDA19 displayed 4-fold-higher affinity at the human CB(2) than at the human CB1 receptor (K(i) = 43.3 +/- 10.3 vs 162.4 +/- 7.6 nM) and nearly 70-fold-higher affinity at the rat CB2 than at the rat CB1 receptor (K(i) = 16.3 +/- 2.1 vs 1130 +/- 574 nM). In guanosine triphosphate (GTP)gamma[(35)S] functional assays, MDA19 behaved as an agonist at the human CB1 and CB2 receptors and at the rat CB1 receptor but as an inverse agonist at the rat CB2 receptor. In 3', 5'-cyclic adenosine monophosphate (cAMP) assays, MDA19 behaved as an agonist at the rat CB1 receptor and exhibited no functional activity at the rat CB(2) receptor. In extracellular signal-regulated kinases 1 and 2 activation assays.

In Vivo:

MDA19 behaved as an agonist at the rat CB2 receptor. MDA19 attenuated tactile allodynia produced by spinal nerve ligation or paclitaxel in a dose-related manner in rats and CB2(+/+) mice but not in CB2(-/-) mice, indicating that CB2 receptors mediated the effects of MDA19. MDA19 did not affect rat locomotor activity.

References:

1. Xu JJ, Diaz P, Astruc-Diaz F et al. Pharmacological characterization of a novel cannabinoid ligand, MDA19, for treatment of neuropathic pain. Anesth Analg. 2010 Jul;111(1):99-109.
2. Diaz, Philippe; Xu, Jijun; Astruc-Diaz, Fanny et al. Design and Synthesis of a Novel Series of N-Alkyl Isatin Acylhydrazone Derivatives that Act as Selective Cannabinoid Receptor 2 Agonists for the Treatment of Neuropathic Pain. Journal of Medicinal Chemistry (2008), 51(16), 4932-4947.

Products are for research use only. Not for human use.