3,3,4-Trimethyl-1-[1-[(tetrahydro-2H-pyran-4-yl)methyl]-1H-indol-3-yl]-4-penten-1-one

Description

A-834735 is an indole-derived cannabinoid (CB) with a 3-tetramethylcyclopropylmethanone substituent. It acts as a full agonist at both the central CB₁ and peripheral CB₂ receptors in rat with K_i values of 4.6 and 0.31 nM, respectively, and EC₅₀ values of 12 and 0.21 nM, respectively.¹ A-834735 readily crosses the blood-brain barrier, dose-dependently reversing thermal hyperalgesia without adverse side effects in a rat neuropathic pain model.¹ A-834735 degradant is a common impurity observed during GC-MS analysis of samples containing A-834735. The opened ring of the degradant is presumed to be produced during heating of A-834735. This structure gives rise to a prominent fragment ion that is 15 amu greater than the base peak of A-834735. This pattern is consistent with McLafferty rearrangement of the degradant which does not occur with the parent compound.²

References

1. Chin, C.L., Tovcimak, A.E., Hradil, V.P., et al. Differential effects of cannabinoid receptor agonists on regional brain activity using pharmacological MRI Br. J. Pharmacol. 153(2),367-379(2008).
2. McLafferty, F.W. Mass spectrometric analysis. Molecular rearrangements Anal. Chem. 31(1),82-87(1959).