Methanandamide

Methanandamide
Names
	IUPAC name (5Z,8Z,11Z,14Z)-N-[(1R)-2-hydroxy-1-methylethyl]icosa-5,8,11,14-tetraenamide
	Other names AM-356; Arachidonyl-1'-hydroxy-2'-propylamide
Identifiers
CAS Number	157182-49-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL120526 ;
ChemSpider	4881984 ;
IUPHAR/BPS	2506;
PubChem CID	6321351;
	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/s1 Key: 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/s1 Key: SQKRUBZPTNJQEM-FQPARAGTBH;
	SMILES O=C(N[C@H](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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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).

References

^ 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.

[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.

[1]

Names

IUPAC name (5Z,8Z,11Z,14Z)-N-[(1R)-2-hydroxy-1-methylethyl]icosa-5,8,11,14-tetraenamide
Other names AM-356; Arachidonyl-1'-hydroxy-2'-propylamide
Identifiers
CAS Number	157182-49-5
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL120526
ChemSpider	4881984
IUPHAR/BPS	2506
PubChem CID	6321351
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/s1 Key: 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/s1 Key: SQKRUBZPTNJQEM-FQPARAGTBH
SMILES O=C(N[C@H](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⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).