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}} | |||
{{Drugbox | {{Drugbox | ||
| Verifiedfields = changed | |||
| verifiedrevid = |
| verifiedrevid = 454835077 | ||
| IUPAC_name = 1--3-(adamant-1-oyl)indole | | IUPAC_name = 1--3-(adamant-1-oyl)indole | ||
| image = AM-1248_structure.png | | image = AM-1248_structure.png | ||
| width = |
| width = 150 | ||
<!--Clinical data--> | <!--Clinical data--> | ||
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| pregnancy_category = | | pregnancy_category = | ||
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | ||
| legal_CA = |
| legal_CA = Schedule II | ||
| legal_DE = NpSG | |||
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | |||
| legal_UK = Class B | |||
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | ||
| legal_NZ = Temporary Class | |||
| legal_status = |
| legal_status = | ||
| routes_of_administration = | | routes_of_administration = | ||
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<!--Identifiers--> | <!--Identifiers--> | ||
| CAS_number_Ref = {{cascite|changed|??}} | |||
| CAS_number = | | CAS_number = 335160-66-2 | ||
| ATC_prefix = | | ATC_prefix = | ||
| ATC_suffix = | | ATC_suffix = | ||
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ||
| DrugBank = | | DrugBank = | ||
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | |||
| ChemSpiderID = 8469262 | |||
| UNII = 5EX9HEF4HK | |||
| UNII_Ref = {{fdacite|changed|FDA}} | |||
<!--Chemical data--> | <!--Chemical data--> | ||
| C=26 | H=34 | N=2 | O=1 | | C=26 | H=34 | N=2 | O=1 | ||
| molecular_weight = 390.561 g/mol | |||
| smiles = CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5 | | smiles = CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5 | ||
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} | |||
| 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 | |||
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | |||
| StdInChIKey = JRECAXBHMULNJQ-UHFFFAOYSA-N | |||
}} | }} | ||
'''AM-1248''' is a drug |
'''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 }} | ||
</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> | |||
== |
==Legality== | ||
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> | |||
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> | |||
== See also == | |||
* ] | * ] | ||
* ] | |||
* ] | |||
* ] | * ] | ||
* ] | * ] | ||
* ] | * ] | ||
* ] | |||
==References== | == References == | ||
{{reflist}} | |||
<references/> | |||
{{Cannabinoids}} | {{Cannabinoids}} | ||
⚫ | ] | ||
] | ] | ||
] | ] | ||
] | ] | ||
] | ] | ||
⚫ | ] | ||
{{cannabinoid-stub}} | {{cannabinoid-stub}} |
Latest revision as of 23:34, 21 July 2024
Chemical compound Pharmaceutical compoundLegal status | |
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IUPAC name
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UNII | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C26H34N2O |
Molar mass | 390.571 g·mol |
3D model (JSmol) | |
SMILES
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InChI
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(what is this?) (verify) |
AM-1248 is a drug that acts as a moderately potent agonist for both the cannabinoid receptors CB1 and CB2, but with some dispute between sources over its exact potency and selectivity. Replacing the 3-(1-naphthoyl) group found in many indole derived cannabinoid ligands, with an adamantoyl group, generally confers significant CB2 selectivity, but reasonable CB1 affinity and selectivity is retained when an N-methylpiperidin-2-ylmethyl substitution is used at the indole 1-position. The related compound 1-pentyl-3-(1-adamantoyl)indole was identified as having been sold as a cannabinoid designer drug in Hungary in 2011, along with another synthetic cannabinoid AM-679.
Legality
Sweden's public health agency suggested to classify AM-1248 as hazardous substance on June 1, 2015.
As of October 2015 AM-1248 is a controlled substance in China.
See also
References
- Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". Journal of Medicinal Chemistry. 53 (1): 295–315. doi:10.1021/jm901214q. PMID 19921781.
- US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26
- WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
- Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J (January 2012). "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". Forensic Science International. 214 (1–3): 27–32. doi:10.1016/j.forsciint.2011.07.011. PMID 21813254.
- "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Retrieved 29 June 2015.
- "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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