AM-1220
Encyclopedia
AM-1220 is a drug which acts as a potent and moderately selective agonist
for the cannabinoid receptor
CB1, with around 19x selectivity for CB1 over the related CB2 receptor. It was originally invented in the early 1990s by a team led by Thomas D'Ambra at Sterling Winthrop, but has subsequently been researched by many others, most notably the team led by Alexandros Makriyannis at the University of Connecticut
. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are two enantiomer
s with quite different potency, the (R) enantiomer having a Ki
of 0.27nM at CB1 while the (S) enantiomer has a much weaker Ki of 217nM. A number of related compounds are known with similar potent cannabinoid activity, with modifications such as substitution of the indole ring at the 2- or 6- positions, the naphthoyl ring substituted at the 4- position or replaced by substituted benzoyl rings or other groups, or the 1-(N-methylpiperidin-2-ylmethyl) group replaced by similar heterocyclic groups such as N-methylpyrrolidin-2-ylmethyl or N-methylmorpholin-3-ylmethyl. AM-1220 was first detected as an ingredient of synthetic cannabis smoking blends in 2010.
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
for the cannabinoid receptor
Cannabinoid receptor
The cannabinoid receptors are a class of cell membrane receptors under the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid receptors contain seven transmembrane spanning domains...
CB1, with around 19x selectivity for CB1 over the related CB2 receptor. It was originally invented in the early 1990s by a team led by Thomas D'Ambra at Sterling Winthrop, but has subsequently been researched by many others, most notably the team led by Alexandros Makriyannis at the University of Connecticut
University of Connecticut
The admission rate to the University of Connecticut is about 50% and has been steadily decreasing, with about 28,000 prospective students applying for admission to the freshman class in recent years. Approximately 40,000 prospective students tour the main campus in Storrs annually...
. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are two enantiomer
Enantiomer
In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
s with quite different potency, the (R) enantiomer having a Ki
Dissociation constant
In chemistry, biochemistry, and pharmacology, a dissociation constant is a specific type of equilibrium constant that measures the propensity of a larger object to separate reversibly into smaller components, as when a complex falls apart into its component molecules, or when a salt splits up into...
of 0.27nM at CB1 while the (S) enantiomer has a much weaker Ki of 217nM. A number of related compounds are known with similar potent cannabinoid activity, with modifications such as substitution of the indole ring at the 2- or 6- positions, the naphthoyl ring substituted at the 4- position or replaced by substituted benzoyl rings or other groups, or the 1-(N-methylpiperidin-2-ylmethyl) group replaced by similar heterocyclic groups such as N-methylpyrrolidin-2-ylmethyl or N-methylmorpholin-3-ylmethyl. AM-1220 was first detected as an ingredient of synthetic cannabis smoking blends in 2010.
See also
- A-834,735A-834,735A-834,735 is a drug developed by Abbott Laboratories which acts as a potent cannabinoid receptor full agonist at both the CB1 and CB2 receptors, with a Ki of 12nM at CB1 and 0.21nM at CB2...
- AM-1221AM-1221AM-1221 is a drug which acts as a potent and selective agonist for the cannabinoid receptor CB2, with a Ki of 0.28nM at CB2 and 52.3nM at the CB1 receptor, giving it around 180x selectivity for CB2. The 2-methyl and 6-nitro groups on the indole ring both tend to increase CB2 affinity while...
- AM-1248AM-1248AM-1248 is a drug which acts as a moderately potent agonist for both the cannabinoid receptors CB1 and CB2, but with some dispute between sources over its exact potency and selectivity...
- AM-2201AM-2201AM-2201 discovered by Chemist Tyler Merrill, is a drug which acts as a potent but unselective agonist for the cannabinoid receptor CB1, with a Ki of 1.0nM at CB1 and 2.6nM at CB2...
- AM-2233AM-2233AM-2233 is a drug which acts as a highly potent full agonist for the cannabinoid receptors, with a Ki of 1.8nM at CB1 and 2.2nM at CB2 as the active enantiomer. It was developed as a selective radioligand for the cannabinoid receptors and has been used as its 131I derivative for mapping the...
- CannabipiperidiethanoneCannabipiperidiethanoneCannabipiperidiethanone, or 1--3-indole, is a synthetic cannabinoid which has been found as an ingredient of "herbal" synthetic cannabis blends sold in Japan, alongside JWH-122 and JWH-081...