Methanandamide

Methanandamide (AM-356) is a synthetically created stable chiral analog of anandamide.[1] 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).

Methanandamide
Names
Preferred IUPAC name
(5Z,8Z,11Z,14Z)-N-[(2R)-1-Hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
Other names
AM-356; Arachidonyl-1'-hydroxy-2'-propylamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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/s1 checkY
    Key: SQKRUBZPTNJQEM-FQPARAGTSA-N checkY
  • 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/s1
    Key: SQKRUBZPTNJQEM-FQPARAGTBH
  • O=C(N[C@H](C)CO)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
C23H39NO2
Molar mass 361.570 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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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