AM-1220 is a drug that acts as a potent and moderately selective

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ag ...

for the

cannabinoid receptor Cannabinoid receptors, located throughout the body, are part of the endocannabinoid system a class of cell membrane receptors in the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid recep ...

CB₁, with around 19 times 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 Sterling Drug was an American global pharmaceutical company, also known as Sterling Winthrop, Inc. in its last years (after the merger with Winthrop-Stearns Inc. which itself resulted from the merger of ''Winthrop Chemical Company Inc.'' and '' ...

, but has subsequently been researched by many others, most notably the team led by

Alexandros Makriyannis Alexandros Makriyannis (born September 9, 1939) is an American biochemist and professor of Chemistry and Chemical Biology in the Department of Medicinal Chemistry at Northeastern University in Boston, Massachusetts, where he directs the Center for ...

at the

University of Connecticut The University of Connecticut (UConn) is a public land-grant research university in Storrs, Connecticut, a village in the town of Mansfield. The primary 4,400-acre (17.8 km2) campus is in Storrs, approximately a half hour's drive from H ...

. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are two

enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...

s with quite different potency, the (''R'')-enantiomer having a K_i of 0.27 nM at CB₁ while the (''S'')-enantiomer has a much weaker K_i of 217 nM.

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. AM-1220 was first detected as an ingredient of synthetic cannabis smoking blends in 2010.

Legal status

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

of America all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as AM-1220 are Schedule I Controlled Substances under the

Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States ...

United Kingdom The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom (UK) or Britain, is a country in Europe, off the north-western coast of the continental mainland. It comprises England, Scotland, Wales and ...

it's illegal to supply, smuggle, distribute, transport, sell or trade the pharmaceutical drug under the

Psychoactive Substances Act 2016 The Psychoactive Substances Act 2016 (c. 2) is an Act of the Parliament of the United Kingdom intended to restrict the production, sale and supply of a new class of psychoactive substances often referred to as "legal highs". The bill was given R ...

which was enforced on May26th 2016.

China

As of October 2015, AM-1220 is a controlled substance in China.

References

{{Cannabinoids Naphthoylindoles AM cannabinoids Aminoalkylindoles Piperidines Designer drugs CB1 receptor agonists CB2 receptor agonists

Related compounds

Legal status

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

United Kingdom The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom (UK) or Britain, is a country in Europe, off the north-western coast of the continental mainland. It comprises England, Scotland, Wales and ...

China

See also

References