AM-1220: Difference between revisions
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Importing Wikidata short description: "Chemical compound" |
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| verifiedrevid = 454826769 |
| verifiedrevid = 454826769 |
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| IUPAC_name = (R)-(1-((1- |
| IUPAC_name = (''R'')-(1-((1-Methylpiperidin-2-yl)methyl)-1''H''-indol-3-yl)(naphthalen-1-yl)methanone |
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| image = AM-1220_structure.png |
| image = AM-1220_structure.png |
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| width = 200 |
| width = 200 |
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| legal_CA = Schedule II |
| legal_CA = Schedule II |
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| legal_DE = Anlage II |
| legal_DE = Anlage II |
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| legal_UK = |
| legal_UK = Class B |
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| legal_US = |
| legal_US = Schedule I |
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| legal_NZ = Temporary Class |
| legal_NZ = Temporary Class |
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| legal_status = |
| legal_status = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| index2_label = (''R'')-enantiomer |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 137642-54-7 |
| CAS_number = 137642-54-7 |
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| CAS_supplemental = (racemic) <br /> 134959-64-1 ((R) |
| CAS_supplemental = (racemic) <br /> 134959-64-1 ((''R'')-enantiomer) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 05850M72P2 |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = 44NQ9RBE1B |
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| ATC_prefix = |
| ATC_prefix = |
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| ATC_suffix = |
| ATC_suffix = |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=26 | H=26 | N=2 | O=1 |
| C=26 | H=26 | N=2 | O=1 |
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| molecular_weight = 382.497 g/mol |
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| smiles = O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53 |
| smiles = O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
}} |
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'''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 |
'''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 nM at CB<sub>1</sub> while the (''S'')-enantiomer has a much weaker K<sub>i</sub> of 217 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> |
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16134948| pmc = }}</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= Alexandros Makriyannis, ''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> |
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==Related compounds== |
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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> |
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=== [[United States]] === |
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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> |
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=== [[United Kingdom]] === |
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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. |
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== |
===China=== |
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| ⚫ | 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> |
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== See also == |
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* [[A-834,735]] |
* [[A-834,735]] |
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* [[AM-1221]] |
* [[AM-1221]] |
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* [[Cannabipiperidiethanone]] |
* [[Cannabipiperidiethanone]] |
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==References== |
== References == |
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{{reflist}} |
{{reflist}} |
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{{Cannabinoids}} |
{{Cannabinoids}} |
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[[Category:Cannabinoids]] |
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[[Category:Naphthoylindoles]] |
[[Category:Naphthoylindoles]] |
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[[Category:AM cannabinoids]] |
[[Category:AM cannabinoids]] |
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Latest revision as of 07:54, 29 May 2022
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| Chemical and physical data | |
| Formula | C26H26N2O |
| Molar mass | 382.507 g·mol−1 |
| 3D model (JSmol) | |
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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]
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]
- ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
- ^ US patent 5068234, D'Ambra TE, et al., "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26
- ^ 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.
- ^ Deng H (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut. ProQuest 304624325.
- ^ 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.
- ^ US patent 7820144, Makriyannis A, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26
- ^ Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)
- ^ : Schedules of controlled substances
- ^ "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.