World Library  
Flag as Inappropriate
Email this Article


Article Id: WHEBN0032279166
Reproduction Date:

Title: Am-1220  
Author: World Heritage Encyclopedia
Language: English
Subject: Cannabipiperidiethanone, CP 55,940, Nabitan, Parahexyl, JWH-073
Collection: Am Cannabinoids, Aminoalkylindoles, Cannabinoids, Designer Drugs, Naphthoylindoles, Piperidines
Publisher: World Heritage Encyclopedia


Systematic (IUPAC) name
Clinical data
Legal status
  • AU: Prohibited (S9)
  • banned under analog laws in some US states, Temporary Class Drug (NZ)
CAS number  YesY (racemic)
134959-64-1 ((R) enantiomer)
ATC code ?
ChemSpider  YesY
Chemical data
Formula C26H26N2O 
Mol. mass 382.497 g/mol

AM-1220 is a drug that acts as a potent and moderately selective agonist for the cannabinoid receptor CB1, with around 19x 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 0.27nM at CB1 while the (S) enantiomer has a much weaker Ki of 217nM.[3] 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

See also


  1. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  2. ^ US patent 5068234, Thomas E. D'Ambra 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: 17–14.  
  4. ^ Hongfeng Deng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut. 
  5. ^ Willis, P. G.; Pavlova, O. A.; Chefer, S. I.; Vaupel, D. B.; Mukhin, A. G.; Horti, A. G. (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.  
  6. ^ US patent 7820144, Alexandros Makriyannis, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26 
  7. ^ Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.

Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.