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]
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.