AM-1220: Difference between revisions

{{Short description|Chemical compound}}

| verifiedrevid = 454826769

| IUPAC_name = (''R'')-(1-((1-Methylpiperidin-2-yl)methyl)-1''H''-indol-3-yl)(naphthalen-1-yl)methanone

| legal_AU = S9

| legal_CA = Schedule II

| legal_DE = Anlage II

| legal_UK = Class B

| legal_US = Schedule I

| legal_NZ = Temporary Class

| legal_status =

| routes_of_administration =

| excretion =

| index2_label = (''R'')-enantiomer

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_supplemental = (racemic) <br /> 134959-64-1 ((''R'')-enantiomer)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 05850M72P2

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 44NQ9RBE1B

'''AM-1220''' is a drug that acts as a potent and moderately selective [[agonist]] for the [[cannabinoid receptor]] [[Cannabinoid receptor 1|CB₁]], with around 19 times selectivity for CB₁ over the related [[Cannabinoid receptor 2|CB₂]] receptor.<ref name="WO 2001 28557 A1">{{Ref patent2 |country= WO |number= 200128557 |status= granted |title= Cannabimimetic indole derivatives |pubdate= 2001-04-26 |gdate= 2001-06-07 |pridate= 1999-10-18 |inventor= Makriyannis A, Deng H }}</ref> It was originally invented in the early 1990s by a team led by Thomas D'Ambra at [[Sterling Winthrop]],<ref name="US 5068234">{{Ref patent2 |country= US |number= 5068234 |status= granted |title= 3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles |gdate= 1991-11-26 |pridate= 1990-02-26 |inventor= D'Ambra TE, ''et al.'' }}</ref> 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 [[Dissociation constant|K_i]] of 0.27&nbsp;nM at CB₁ while the (''S'')-enantiomer has a much weaker K_i of 217&nbsp;nM.<ref>{{Cite journal | last1 = D'ambra | first1 = T. | doi = 10.1016/0960-894X(95)00560-G | title = C-Attached aminoalkylindoles: potent cannabinoid mimetics | journal = Bioorganic & Medicinal Chemistry Letters | volume = 6 | pages = 17–22| year = 1996 | issue=1}}</ref>

==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.<ref name=liganDesign>{{Cite thesis |type=PhD. Dissertation |title=Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs | vauthors = Deng H |year=2000 |publisher=University of Connecticut |id={{ProQuest|304624325}} }}</ref><ref>{{cite journal | vauthors = Willis PG, Pavlova OA, Chefer SI, Vaupel DB, Mukhin AG, Horti AG | title = Synthesis and structure-activity relationship of a novel series of aminoalkylindoles with potential for imaging the neuronal cannabinoid receptor by positron emission tomography | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 18 | pages = 5813–22 | date = September 2005 | pmid = 16134948 | doi = 10.1021/jm0502743 }}</ref><ref name="US 7820144">{{Ref patent2 |country= US |number= 7820144 |status= granted |title= Receptor selective cannabimimetic aminoalkylindoles |gdate= 2010-10-26 |pridate= 2007-01-05 |inventor= Makriyannis A, ''et al.'' }}</ref> AM-1220 was first detected as an ingredient of [[synthetic cannabis]] smoking blends in 2010.<ref>[http://www.drugs.ie/downloadDocs/HS_ID_Poster_714-823.pdf Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)]</ref>

[[Image:AM1220heterocycles.png|300px|thumb|none|Related 1-(''N''-methylpyrrolidin-2-ylmethyl) and 1-(''N''-methylmorpholin-3-ylmethyl) derivatives]]

==Legal status==

=== [[United States]] ===

in the [[United States]] 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]] s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>

=== [[United Kingdom]] ===

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.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

== See also ==

* [[Cannabipiperidiethanone]]

== References ==

{{reflist}}

[[Category:Designer drugs]]

[[Category:CB1 receptor agonists]]

[[Category:CB2 receptor agonists]]