AM-1248

AM-1248
Legal status
Legal status
Identifiers
  • 1-[(N-methylpiperidin-2-yl)methyl]-3-(adamant-1-oyl)indole
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H34N2O
Molar mass390.571 g·mol−1
3D model (JSmol)
  • CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5
  • InChI=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 ☒N
  • Key:JRECAXBHMULNJQ-UHFFFAOYSA-N ☒N
 ☒NcheckY (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,[1] but reasonable CB1 affinity and selectivity is retained when an N-methylpiperidin-2-ylmethyl substitution is used at the indole 1-position.[2][3] 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.[4]

Legality

Sweden's public health agency suggested to classify AM-1248 as hazardous substance on June 1, 2015.[5]

As of October 2015 AM-1248 is a controlled substance in China.[6]

See also

References

  1. ^ 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.
  2. ^ US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26 
  3. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  4. ^ 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.
  5. ^ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Retrieved 29 June 2015.
  6. ^ "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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