AM-1220

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]

AM-1220
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H26N2O
Molar mass382.507 g·mol−1
3D model (JSmol)
  (verify)

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]

Related 1-(N-methylpyrrolidin-2-ylmethyl) and 1-(N-methylmorpholin-3-ylmethyl) derivatives

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as AM-1220 are Schedule I Controlled Substances.[8]

As of October 2015, AM-1220 is a controlled substance in China.[9]

See also

References
  1. WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
  2. US patent 5068234, D'Ambra TE, et al., "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26
  3. 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.
  4. Deng H (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut. ProQuest 304624325.
  5. 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.
  6. US patent 7820144, Makriyannis A, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26
  7. Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)
  8. 21 U.S.C. § 812: Schedules of controlled substances
  9. "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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.