| Revision as of 07:45, 10 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[...← Previous edit |
Latest revision as of 23:34, 21 July 2024 edit undoMeodipt (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers35,718 edits →See also |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 451605470 |
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| verifiedrevid = 454835077 |
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| IUPAC_name = 1--3-(adamant-1-oyl)indole |
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| IUPAC_name = 1--3-(adamant-1-oyl)indole |
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| image = AM-1248_structure.png |
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| image = AM-1248_structure.png |
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| width = 200 |
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| width = 150 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA = Schedule II |
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| legal_DE = NpSG |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_UK = Class B |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_NZ = Temporary Class |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = |
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| CAS_number = 335160-66-2 |
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| ATC_prefix = |
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| ATC_prefix = |
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| ATC_suffix = |
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| ATC_suffix = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8469262 |
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| UNII = 5EX9HEF4HK |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=26 | H=34 | N=2 | O=1 |
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| C=26 | H=34 | N=2 | O=1 |
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| molecular_weight = 390.561 g/mol |
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| smiles = CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5 |
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| smiles = CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C26H34N2O/c1-27-9-5-4-6-21(27)16-28-17-23(22-7-2-3-8-24(22)28)25(29)26-13-18-10-19(14-26)12-20(11-18)15-26/h2-3,7-8,17-21H,4-6,9-16H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JRECAXBHMULNJQ-UHFFFAOYSA-N |
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}} |
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}} |
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'''AM-1248''' is a drug which acts as a moderately potent ] for both the ]s ] and ], but with some dispute between sources over its exact potency and selectivity.<!-- although note Ki values often cannot be compared directly between literature sources if the assay conditions are different --> Replacing the 3-(1-naphthoyl) group found in many indole derived cannabinoid ligands, with an ]] group, generally confers significant CB<sub>2</sub> selectivity,<ref>{{Cite doi|10.1021/jm901214q}}</ref> but reasonable CB<sub>1</sub> affinity and selectivity is retained when an N-methylpiperidin-2-ylmethyl substitution is used at the indole 1-position.<ref name="US 7820144">{{Ref patent2 | country = US | number = 7820144 | status = granted | title = Receptor selective cannabimimetic aminoalkylindoles | pubdate = 2007-01-05 | gdate = 2010-10-26 | pridate= | inventor = Makriyannis A, Deng H | assign1= }}</ref><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> The related compound ] was identified as having been sold as a ] ] in Hungary in 2011, along with another synthetic cannabinoid ].<ref name="pmid21813254">{{cite journal |author=Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J |title=Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary |journal=Forensic Science International |volume= |issue= |pages= |year=2011 |month=August |pmid=21813254 |doi=10.1016/j.forsciint.2011.07.011 |url=}}</ref> |
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'''AM-1248''' is a drug that acts as a moderately potent ] for both the ]s ] and ], but with some dispute between sources over its exact potency and selectivity.<!-- although note Ki values often cannot be compared directly between literature sources if the assay conditions are different --> Replacing the 3-(1-naphthoyl) group found in many indole derived cannabinoid ligands, with an ]] group, generally confers significant CB<sub>2</sub> selectivity,<ref>{{cite journal | vauthors = Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD | display-authors = 6 | title = Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity | journal = Journal of Medicinal Chemistry | volume = 53 | issue = 1 | pages = 295–315 | date = January 2010 | pmid = 19921781 | doi = 10.1021/jm901214q }} |
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</ref> but reasonable CB<sub>1</sub> affinity and selectivity is retained when an N-methylpiperidin-2-ylmethyl substitution is used at the indole 1-position.<ref name="US 7820144">{{Ref patent2 |country= US |number= 7820144 |status= granted |title= Receptor selective cannabimimetic aminoalkylindoles |pubdate= 2007-01-05 |gdate= 2010-10-26 |inventor=], Deng H }}</ref><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> The related compound ] was identified as having been sold as a ] ] in Hungary in 2011, along with another synthetic cannabinoid ].<ref name="pmid21813254">{{cite journal | vauthors = Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J | title = Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary | journal = Forensic Science International | volume = 214 | issue = 1–3 | pages = 27–32 | date = January 2012 | pmid = 21813254 | doi = 10.1016/j.forsciint.2011.07.011 }}</ref> |
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==See also== |
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==Legality== |
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Sweden's public health agency suggested to classify AM-1248 as hazardous substance on June 1, 2015.<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/juni/23-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara | title=23 nya ämnen kan klassas som narkotika eller hälsofarlig vara | access-date=29 June 2015}}</ref> |
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As of October 2015 AM-1248 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=Chinese | 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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==References== |
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== References == |
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{{reflist}} |
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{{Cannabinoids}} |
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{{Cannabinoids}} |
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{{cannabinoid-stub}} |
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{{cannabinoid-stub}} |