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I-6400 5'-Iodoresiniferatoxin, >99%

[5'-IRTX]

I-6400PR

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M.W. 754.62

C₃₇H₃₉IO₉

Storage: Store at or below -20 ºC. Solubility: Soluble in DMSO or ethanol. Disposal: A LIGHT-SENSITIVE!

IRTX is an important new compound that appears to be a very potent vanilloid receptor antagonist. IRTX binds to the VR1 receptor with high affinity (Kd = 4.3 nM) but does not induce RTX- or capsaicin-like effects in Xenopus laevis oocytes expressing VR1. IRTX completely blocked capsaicin-induced currents in these cells, with an IC50 of 3.9 nM. In vivo, intrathecal IRTX was 3.5-fold more potent that morphine in blocking a pain response induced in the mouse paw by injected capsaicin. In this assay capsazepine was inactive at 3 µg/mouse, a 113-fold higher dose than the ITX ED50. IRTX's potency as a vanilloid antagonist is some 40-fold higher than that of capsazepine, a weak vanilloid antagonist having other, unrelated biological activities. Wahl, P., et al. "Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist." Mol. Pharm. 59: 9-15 (2001).

NOTE: The structure shown in FIg. 1 of Wahl et al. is incorrect; the iodine atom should be next to the free OH-group on the homovanillic acid moiety, as depicted below.

5'-IRTX has also been shown to be a pure antagonist in HEK cells expressing the human VR1, with an IC50 of 27 nM. McDonnell, M.E., et al. "Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor." Bioorg. Med. Chem. Lett. 12: 1189-1192 (2002).

NOTE: IRTX is sensitive to UV light, and prolonged exposure to daylight or fluorescent room light may cause slow degradation. Thus, although IRTX can be handled in normal room light, it is recommended that such exposure be kept to a minimum.

Pharmaceutical formulations containing this compound, and anti-inflammatory, anti-viral and anti-psoriatic uses, are covered by U.S. patents 5,643,948 and 5,955,501.

Sold for laboratory or manufacturing purposes only; not for human, veterinary, food, or household use.