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Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 439957090
| verifiedrevid = 454826769
| IUPAC_name = (R)-(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone
| IUPAC_name = (''R'')-(1-((1-Methylpiperidin-2-yl)methyl)-1''H''-indol-3-yl)(naphthalen-1-yl)methanone
| image = AM-1220_structure.png
| image = AM-1220_structure.png
| width = 200
| width = 200

⚫
| CAS_number= 137642-54-7
<!--Clinical data-->
⚫
| CAS_supplemental= (racemic) <br /> 134959-64-1 ((R) enantiomer)
| ATC_prefix =
| tradename =
| ATC_suffix =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| PubChem = 9929889
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category =
⚫
| DrugBank =
| legal_AU = S9
⚫
| C=26|H=26|N=2|O=1
| legal_CA = Schedule II
| molecular_weight = 382.497 g/mol
| legal_DE = Anlage II
⚫
| smiles = O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53
| legal_UK = Class B
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| legal_US = Schedule I
| legal_NZ = Temporary Class
| legal_status =
⚫
| routes_of_administration =

<!--Pharmacokinetic data-->
⚫
| bioavailability =
⚫
| protein_bound =
⚫
| metabolism =
⚫
| elimination_half-life =
⚫
| excretion =

<!--Identifiers-->
| index2_label = (''R'')-enantiomer
| CAS_number_Ref = {{cascite|correct|??}}
⚫
| CAS_number = 137642-54-7
⚫
| CAS_supplemental = (racemic) <br /> 134959-64-1 ((''R'')-enantiomer)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 05850M72P2
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 44NQ9RBE1B
| ATC_prefix =
| ATC_suffix =
| PubChem = 9929889
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
| DrugBank =
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26231035
| ChemSpiderID = 26231035

⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
<!--Chemical data-->
⚫
| C=26 | H=26 | N=2 | O=1
⚫
| smiles = O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C26H26N2O/c1-27-16-7-6-11-20(27)17-28-18-24(22-13-4-5-15-25(22)28)26(29)23-14-8-10-19-9-2-3-12-21(19)23/h2-5,8-10,12-15,18,20H,6-7,11,16-17H2,1H3/t20-/m1/s1
| StdInChI = 1S/C26H26N2O/c1-27-16-7-6-11-20(27)17-28-18-24(22-13-4-5-15-25(22)28)26(29)23-14-8-10-19-9-2-3-12-21(19)23/h2-5,8-10,12-15,18,20H,6-7,11,16-17H2,1H3/t20-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = URKVBEKZCMUTQC-HXUWFJFHSA-N
| StdInChIKey = URKVBEKZCMUTQC-HXUWFJFHSA-N
⚫
| bioavailability =
⚫
| protein_bound =
⚫
| metabolism =
⚫
| elimination_half-life =
⚫
| excretion =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category=
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = banned under analog laws in some US states
⚫
| routes_of_administration =
}}
}}


'''AM-1220''' is a drug which acts as a potent and moderately selective [[agonist]] for the [[cannabinoid receptor]] [[Cannabinoid receptor 1|CB<sub>1</sub>]], with around 19x selectivity for CB<sub>1</sub> over the related [[Cannabinoid receptor 2|CB<sub>2</sub>]] 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 | assign1= }}</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 | pubdate = | gdate = 1991-11-26 | pridate= 1990-02-26 | inventor = Thomas E. D'Ambra et al | assign1= }}</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<sub>i</sub>]] of 0.27nM at CB<sub>1</sub> while the (S) enantiomer has a much weaker K<sub>i</sub> of 217nM.<ref>{{Cite doi|10.1016/0960-894X(95)00560-G}}</ref> 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>[http://proquest.umi.com/pqdlink?did=726066941&Fmt=7&clientId=79356&RQT=309&VName=PQD Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.]</ref><ref>{{Cite doi|10.1021/jm0502743}}</ref><ref name="US 7820144">{{Ref patent2 | country = US | number = 7820144 | status = granted | title = Receptor selective cannabimimetic aminoalkylindoles | pubdate = | gdate = 2010-10-26 | pridate= 2007-01-05 | inventor = Alexandros Makriyannis et al | assign1= }}</ref>
'''AM-1220''' is a drug that acts as a potent and moderately selective [[agonist]] for the [[cannabinoid receptor]] [[Cannabinoid receptor 1|CB<sub>1</sub>]], with around 19 times selectivity for CB<sub>1</sub> over the related [[Cannabinoid receptor 2|CB<sub>2</sub>]] 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<sub>i</sub>]] of 0.27&nbsp;nM at CB<sub>1</sub> while the (''S'')-enantiomer has a much weaker K<sub>i</sub> 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==
⚫
[[Image:AM1220heterocycles.png|300px|thumb|left|Related 1-(N-methylpyrrolidin-2-ylmethyl) and 1-(N-methylmorpholin-3-ylmethyl) derivatives]]{{clear-left}}
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]]
⚫
==See also==

==Legal status==
=== [[United States]] ===
in the [[United States]] of America all CB<sub>1</sub> 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 ==
* [[A-834,735]]
* [[A-834,735]]
* [[AM-1221]]
* [[AM-1221]]
⚫
* [[AM-1241]]
* [[AM-1248]]
* [[AM-1248]]
⚫
* [[AM-2201]]
* [[AM-2233]]
* [[AM-2233]]
* [[Cannabipiperidiethanone]]


==References==
== References ==
{{reflist}}
<references/>


{{Cannabinoids}}
{{Cannabinoids}}


⚫
[[Category:Cannabinoids]]
[[Category:Naphthoylindoles]]
[[Category:Naphthoylindoles]]
[[Category:AM cannabinoids]]
[[Category:AM cannabinoids]]
[[Category:Aminoalkylindoles]]
[[Category:Aminoalkylindoles]]
[[Category:Piperidines]]
[[Category:Piperidines]]
⚫
[[Category:Designer drugs]]

[[Category:CB1 receptor agonists]]

[[Category:CB2 receptor agonists]]
{{cannabinoid-stub}}

Latest revision as of 07:54, 29 May 2022

AM-1220
Legal status
Legal status
Identifiers
  • (R)-(1-((1-Methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H26N2O
Molar mass382.507 g·mol−1
3D model (JSmol)
  • O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53
  • InChI=1S/C26H26N2O/c1-27-16-7-6-11-20(27)17-28-18-24(22-13-4-5-15-25(22)28)26(29)23-14-8-10-19-9-2-3-12-21(19)23/h2-5,8-10,12-15,18,20H,6-7,11,16-17H2,1H3/t20-/m1/s1 checkY
  • Key:URKVBEKZCMUTQC-HXUWFJFHSA-N checkY
  (verify)

AM-1220 is a drug that acts as a potent and moderately selective agonist for the cannabinoid receptor CB1, 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[edit]

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

Legal status[edit]

United States[edit]

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.[8]

United Kingdom[edit]

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[edit]

As of October 2015, AM-1220 is a controlled substance in China.[9]

See also[edit]

References[edit]

  1. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  2. ^ US patent 5068234, D'Ambra TE, et al., "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26 
  3. ^ D'ambra, T. (1996). "C-Attached aminoalkylindoles: potent cannabinoid mimetics". Bioorganic & Medicinal Chemistry Letters. 6 (1): 17–22. doi:10.1016/0960-894X(95)00560-G.
  4. ^ Deng H (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut. ProQuest 304624325.
  5. ^ 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. PMID 16134948.
  6. ^ US patent 7820144, Makriyannis A, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26 
  7. ^ Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)
  8. ^ 21 U.S.C. § 812: Schedules of controlled substances
  9. ^ "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.
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