6-IODONORDIHYDROCAPSAICIN Chemical Properties

Melting point:

106-107 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))

Boiling point:

552.9±50.0 °C(Predicted)

Density 

1.375±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

H₂O: insoluble

form 

solid

pka

8.93±0.25(Predicted)

color 

white

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

6-IODONORDIHYDROCAPSAICIN Usage And Synthesis

Uses

6-?iodonordihydrocapsaicin (6-?I-?CPS) is a weak ERα agonist. It was demonstrated to induce luciferase gene expression.

Definition

ChEBI: N-[(4-hydroxy-2-iodo-5-methoxyphenyl)methyl]nonanamide is a member of phenols and a member of methoxybenzenes.

Biological Activity

the vanilloid trpv1 receptor, also known as vr1 receptor, belongs to the large family of ‘transient receptor potential’ (trp). trpv1 functions as a molecular integrator of nociceptive stimuli, including heat, protons and plant toxins, and is most abundant in peripheral sensory fibers of the c and ad type. 6-iodo-nordihydrocapsaicin is a potent trpv1 antagonist.

in vitro

using human recombinant trpv1, 6-iodonordihydrocapsaicin (ic50=10 nm against 100 nm capsaicin) was about four times more potent than the prototypical trpv1 antagonist, capsazepine [1].

in vivo

6-iodonordihydrocapsaicin was tested against capsaicin also on native trpv1 in: (i) rat dorsal root ganglion neurons in culture; (ii) guinea-pig urinary bladder; and (iii) guinea-pig bronchi. in all cases, except for the guineapig bronchi, the compound was significantly more potent than capsazepine as a trpv1 antagonist [1].

IC 50

10 nm against 100 nm capsaicin

References

[1] appendino g, harrison s, de petrocellis l, daddario n, bianchi f, schiano moriello a, trevisani m, benvenuti f, geppetti p, di marzo v. halogenation of a capsaicin analogue leads to novel vanilloid trpv1 receptor antagonists. br j pharmacol. 2003 aug;139(8):1417-24.

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