2010 - Undergraduate Research, Scholarship and Creative Activity

Synthetic Analogs of Anandamide and
Tetrahydrocannabinol
Janel Gracia, Biochemistry
Mentor: Michael J. Marsella
Department of Chemistry
Tetrahydrocannabinol (THC) is the main
psychoactive component of cannabis sativa
(marijuana), and an exogenous ligand that
mimics endogenous anandamide (the ―bliss
molecule‖). THC is used for its pharmaceutical
effects, such as its use in Marinol® where it acts
as an anti-emetic; it is also targeted for CNS
disorders and pain management. The binding of
THC (a CB 1 /CB 2 ligand) to its receptor is key to
its function. Here, the objective is to synthesize
analogs of these compounds, with the goal of
developing lead compounds for treatment of
depression, anxiety, schizophrenia, certain
dementias, and other CNS disorders. These
targets include CB 1 agonists/antagonists that
mimic the desirable properties of
endocannabinoids without inducing unwanted
psychotropic effects. The key challenge is to
synthesize a common core from which many
different analogs can be produced. The present
strategy is a conversion of a CBC analog to
THC. Results to date will be presented.
oxidation. Our focus is to oxidize these
compounds in order to generate highly reactive
. + ++
and unknown P 2 and P 2 fragments
stabilized by carbenes and characterize them.
We first synthesized the imidazolium (NHC,
HCl) precursor of the free carbene according to
the literature. We then checked the product by
13 C and
1 H Nuclear Magnetic Resonance
(NMR). We generated the free NHC by
deprotonation of NHC, HCl with KOtBu and
reacted it with PCl 3 to form a NHC- PCl 3 adduct
which was then reduced using KC 8 to make
NHC- P 2 - NHC, characterized by 1 H, 13 C and 31 P
NMR. The Cyclic Voltamperometry of the
compound showed that it can undergo two one
electron reversible oxidations. According to this
analysis we will chemically carry out a one
electron oxidation to generate the corresponding
radical cation [NHC- P 2 - NHC] +. which will
be characterized by a EPR and x-ray diffraction
study. We will then oxidize NHC-P2-NHC twice
to get the diamagnetic dication [NHC- P 2 -
NHC] ++ which will be characterized by 31 P, 13 C
and 1 H NMR and x-ray diffraction. Finally we
will study the reactivity of this dication which is
predicted to contain a highly reactive
diphosphene moiety.
Synthesis of P 2
+ . and P 2 ++ Fragments
Stabilized by Nitrogen Heterocyclic Carbene
(NHC) and Cyclic Alkyl Amino Carbene
(CAAC)
Mellissa Gray, Chemistry
Contributor: Olivier Back
Mentor: Guy Bertrand
Department of Chemistry
Very recently carbenes have been used to
stabilize highly reactive transitient species based
on main group elements. Indeed, once stabilized,
conventional analysis can be used to gain more
insight into their structure, but very few
examples of stabilized cationic or radical
fragments are known. Recently, P 2 carbene
adducts containing two very electron rich
phosphorous atoms have been made by using
Childhood Trauma, Alexithymia, and
Problematic Internet Use in Young
Adulthood
(Cancelled)
Margo Gregor, Psychology
Mentor: Tuppett Yates
Department of Psychology
Over the past several years, technological
advances have rendered the internet increasingly
accessible. This growth in internet accessibility,
however, has surpassed our understanding of its
developmental effects, particularly with respect
to the potential for problematic or addictive use.
This study builds on a small literature base,
which has primarily evaluated correlates of
problematic internet use (PIU). Previous
research has linked maladaptive internet use to
increased levels of loneliness, selfconsciousness,
anxiety, depression, impulsivity,
NHC and CAAC and are then prone to
Fourth Annual UCR Symposium for Undergraduate Research, Scholarship and Creative Activity
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