Methanandamide

Methanandamide
	source ↗
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
CAS Number	157182-49-5 Y;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL120526 Y;
ChemSpider	4881984 Y;
IUPHAR/BPS	2506;
PubChem CID	6321351;
UNII	F4U8EF3PBH Y;
	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 Y Key: SQKRUBZPTNJQEM-FQPARAGTSA-N Y; 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). N verify (what is YN ?) Infobox references

Methanandamide (AM-356) is a synthetically created stable chiral analog of anandamide with improved metabolic stability.¹ Its effects have been observed to act on the cannabinoid receptors (specifically on CB₁ receptors,² which are part of the central nervous system) found in different organisms such as mammals, fish, and certain invertebrates (e.g. Hydra).³⁴⁵

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.
Childers SR. Activation of G-proteins in brain by endogenous and exogenous cannabinoids. AAPS J. 2006 Mar 10;8(1):E112-7. doi:10.1208/aapsj080113 PMID 16584117
Justinova Z, Solinas M, Tanda G, Redhi GH, Goldberg SR. The endogenous cannabinoid anandamide and its synthetic analog R(+)-methanandamide are intravenously self-administered by squirrel monkeys. J Neurosci. 2005 Jun 8;25(23):5645-50. doi:10.1523/JNEUROSCI.0951-05.2005 PMID 15944392
Alexander SPH. Methanandamide. In xPharm: The Comprehensive Pharmacology Reference. 2007; pp 1-3. ISBN 9780080552323 doi:10.1016/B978-008055232-3.62144-0
Mock ED, Gagestein B, van der Stelt M. Anandamide and other N-acylethanolamines: A class of signaling lipids with therapeutic opportunities. Prog Lipid Res. 2023 Jan;89:101194. doi:10.1016/j.plipres.2022.101194 PMID 36150527

[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.

[2] Childers SR. Activation of G-proteins in brain by endogenous and exogenous cannabinoids. AAPS J. 2006 Mar 10;8(1):E112-7. doi:10.1208/aapsj080113 PMID 16584117

[3] Justinova Z, Solinas M, Tanda G, Redhi GH, Goldberg SR. The endogenous cannabinoid anandamide and its synthetic analog R(+)-methanandamide are intravenously self-administered by squirrel monkeys. J Neurosci. 2005 Jun 8;25(23):5645-50. doi:10.1523/JNEUROSCI.0951-05.2005 PMID 15944392

[4] Alexander SPH. Methanandamide. In xPharm: The Comprehensive Pharmacology Reference. 2007; pp 1-3. ISBN 9780080552323 doi:10.1016/B978-008055232-3.62144-0

[5] Mock ED, Gagestein B, van der Stelt M. Anandamide and other N-acylethanolamines: A class of signaling lipids with therapeutic opportunities. Prog Lipid Res. 2023 Jan;89:101194. doi:10.1016/j.plipres.2022.101194 PMID 36150527

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