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| Formula | C26H26N2O |
| Molar mass | 382.507 g·mol−1 |
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AM-1220 is a drug that acts as a potent and moderately selectiveagonist for thecannabinoid receptorCB1, with around 19 times selectivity for CB1 over the relatedCB2 receptor.[1] It was originally invented in the early 1990s by a team led by Thomas D'Ambra atSterling Winthrop,[2] but has subsequently been researched by many others, most notably the team led byAlexandros Makriyannis at theUniversity of Connecticut. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are twoenantiomers with quite different potency, the (R)-enantiomer having aKi of 0.27 nM at CB1 while the (S)-enantiomer has a much weaker Ki of 217 nM.[3]
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 asN-methylpyrrolidin-2-ylmethyl orN-methylmorpholin-3-ylmethyl.[4][5][6] AM-1220 was first detected as an ingredient ofsynthetic cannabis smoking blends in 2010.[7]
in theUnited States of America all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as AM-1220 areSchedule I Controlled Substances under theControlled Substances Act s.[8]
it's illegal to supply, smuggle, distribute, transport, sell or trade the pharmaceutical drug under thePsychoactive Substances Act 2016 which was enforced on May26th 2016.
As of October 2015, AM-1220 is a controlled substance in China.[9]
