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Methanandamide

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Methanandamide
Names
Preferred IUPAC name (5Z,8Z,11Z,14Z)-N-icosa-5,8,11,14-tetraenamide
Other names AM-356; Arachidonyl-1'-hydroxy-2'-propylamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
IUPHAR/BPS
PubChem CID
UNII
InChI
  • InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m1/s1Key: SQKRUBZPTNJQEM-FQPARAGTSA-N
  • InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m1/s1Key: SQKRUBZPTNJQEM-FQPARAGTBH
SMILES
  • O=C(N(C)CO)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
Chemical formula C23H39NO2
Molar mass 361.570 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Methanandamide (AM-356) is a synthetically created stable chiral analog of anandamide. Its effects have been observed to act on the cannabinoid receptors (specifically on CB1 receptors, which are part of the central nervous system) found in different organisms such as mammals, fish, and certain invertebrates (e.g. Hydra).

References

  1. Abadji V; Lin S; Taha G; Griffin G; Stevenson LA; Pertwee RG; Makriyannis A (1994). "(R)-methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability". Journal of Medicinal Chemistry. 37 (12): 1889–93. doi:10.1021/jm00038a020. PMID 8021930.


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Allosteric CBRTooltip Cannabinoid receptor ligands
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  • Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272 (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
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