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Methanandamide

From Wikipedia, the free encyclopedia
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 mass361.570 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Methanandamide (AM-356) is asynthetically created stablechiralanalog ofanandamide.[1] Its effects have been observed to act on thecannabinoid receptors (specifically onCB1 receptors, which are part of thecentral nervous system) found in different organisms such as mammals, fish, and certain invertebrates (e.g.Hydra).

References

[edit]
  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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