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AM-1248

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Chemical compound Pharmaceutical compound
AM-1248
Legal status
Legal status
Identifiers
IUPAC name
  • 1--3-(adamant-1-oyl)indole
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H34N2O
Molar mass390.571 g·mol
3D model (JSmol)
SMILES
  • CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5
InChI
  • 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
  • Key:JRECAXBHMULNJQ-UHFFFAOYSA-N
  (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

  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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