Perrottetinene is a naturally occurring
cannabinoid
Cannabinoids () are several structural classes of compounds found primarily in the ''Cannabis'' plant or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary psychoact ...
compound found in
liverworts
Liverworts are a group of non-vascular plant, non-vascular embryophyte, land plants forming the division Marchantiophyta (). They may also be referred to as hepatics. Like mosses and hornworts, they have a gametophyte-dominant life cycle, in wh ...
from the family
Radulaceae native to Japan, New Zealand and Costa Rica, namely ''
Cladoradula perrottetii'', ''
Radula marginata'' and ''Radula laxiramea'',
along with a number of similar compounds. Its chemical structure closely resembles that of
THC, the main active component of
marijuana
Cannabis (), commonly known as marijuana (), weed, pot, and ganja, List of slang names for cannabis, among other names, is a non-chemically uniform psychoactive drug from the ''Cannabis'' plant. Native to Central or South Asia, cannabis has ...
but with a ''cis'' rather than ''trans'' conformation and a bibenzyl tailchain instead of pentyl.
The absolute configuration of perrottetinene was established in 2008 by an enantioselective total synthesis.
Pharmacology
In 2018, a study showed that perrottetinene is mild to moderately
psychoactive through activation of the
cannabinoid receptor 1. (-)-''cis''-Perrottetinene was found to have a binding affinity of 481 nM at CB1 and 225 nM at CB2, while the unnatural (-)-''trans''-perrottetinene was found to more active with binding affinities of 127 nM at CB1 and 126 nM at CB2, both acting as
partial agonist
In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...
s. In terms of binding affinity, this study found ''cis''-perrottetinene to be over 22 times weaker than delta-9-THC. The same study also reported significantly reduced
prostaglandin D2 and
E2 brain concentrations in mice after perrottetinene administration.
Perrottetinene is structurally related to
machaeriol A and other machaeriols found in ''
Machaerium'' species.
See also
*
Cis-THC
*
CP 42,096
*
KM-233
*
AM-411
References
Cannabinoids
Benzochromenes
Hydroxyarenes
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