AM-1220 is a drug that acts as a potent and moderately selective
agonist for the
cannabinoid receptorCB1, with around 19 times selectivity for CB1 over the related
CB2 receptor.[1] It was originally invented in the early 1990s by a team led by Thomas D'Ambra at
Sterling Winthrop,[2] 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
enantiomers with quite different potency, the (R)-enantiomer having a
Ki of 0.27 nM at CB1 while the (S)-enantiomer has a much weaker Ki of 217 nM.[3]
Related compounds
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.[4][5][6] AM-1220 was first detected as an ingredient of
synthetic cannabis smoking blends in 2010.[7]
Related 1-(N-methylpyrrolidin-2-ylmethyl) and 1-(N-methylmorpholin-3-ylmethyl) derivatives
it's illegal to supply, smuggle, distribute, transport, sell or trade the pharmaceutical drug under the
Psychoactive Substances Act 2016 which was enforced on May26th 2016.
China
As of October 2015, AM-1220 is a controlled substance in China.[9]
^Deng H (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut.
ProQuest304624325.
^Willis PG, Pavlova OA, Chefer SI, Vaupel DB, Mukhin AG, Horti AG (September 2005). "Synthesis and structure-activity relationship of a novel series of aminoalkylindoles with potential for imaging the neuronal cannabinoid receptor by positron emission tomography". Journal of Medicinal Chemistry. 48 (18): 5813–22.
doi:
10.1021/jm0502743.
PMID16134948.
^US patent 7820144, Makriyannis A, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from
the original on 1 October 2015. Retrieved 1 October 2015.