Methanandamide: Difference between revisions

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
CAS Number	157182-49-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL120526 ;
ChemSpider	4881984 ;
IUPHAR/BPS	2506;
PubChem CID	6321351;
UNII	F4U8EF3PBH ;
	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). verify (what is ?) Infobox references

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Latest revision as of 19:46, 17 February 2022

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.

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[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]

@@ Line 1: / Line 1: @@
 {{Chembox
+| Verifiedfields = changed
-| verifiedrevid = 408592062
+| verifiedrevid = 461740736
 | ImageFile = Methanandamide.svg
 | ImageSize = 200px
-| IUPACName = (5''Z'',8''Z'',11''Z'',14''Z'')-''N''-[(1''R'')-2-hydroxy-1-methylethyl]icosa-5,8,11,14-tetraenamide
+| PIN = (5''Z'',8''Z'',11''Z'',14''Z'')-''N''-[(2''R'')-1-Hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
 | OtherNames = AM-356; Arachidonyl-1'-hydroxy-2'-propylamide
-| Section1 = {{Chembox Identifiers
+|Section1={{Chembox Identifiers
+| IUPHAR_ligand = 2506
-|  CASNo = 157182-49-5
-|   CASNo_Ref = {{cascite|correct|CAS}}
+| CASNo = 157182-49-5
+| CASNo_Ref = {{cascite|correct|CAS}}
+| UNII_Ref = {{fdacite|correct|FDA}}
-|  PubChem = 6321351
+| UNII = F4U8EF3PBH
-|  ChemSpiderID = 4881984
+| PubChem = 6321351
-|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 4881984
-|  SMILES = O=C(N[C@H](C)CO)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-|  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
+| SMILES = O=C(N[C@H](C)CO)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
+| 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
 | InChIKey = SQKRUBZPTNJQEM-FQPARAGTBH
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
@@ Line 19: / Line 23: @@
 | StdInChIKey = SQKRUBZPTNJQEM-FQPARAGTSA-N
 | ChEMBL = 120526
-|  ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
   }}
-| Section2 = {{Chembox Properties
+|Section2={{Chembox Properties
 | C=23 | H=39 | N=1 | O=2
-|  Appearance =
+| Appearance =
-|  Density =
+| Density =
-|  MeltingPt =
+| MeltingPt =
-|  BoilingPt =
+| BoilingPt =
-|  Solubility =
+| Solubility =
   }}
-| Section3 = {{Chembox Hazards
+|Section3={{Chembox Hazards
-|  MainHazards =
+| MainHazards =
-|  FlashPt =
+| FlashPt =
-|  Autoignition =
+| AutoignitionPt =
   }}
 }}
-'''Methanandamide''' ('''AM-356''') is a [[Organic compound#Synthetic compounds|synthetic]]ally created stable [[Chiral (chemistry)|chiral]] [[Structural analog|analog]] of [[anandamide]].<ref>{{cite journal |pmid= 8021930 |year= 1994 |last= Abadji |first= V, ''et al.'' |title= (R)-methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability |volume= 37 |issue= 12 |pages= 1889–93 |journal= Journal of Medical Chemistry |doi=10.1021/jm00038a020}}</ref>  Its effects have been observed to act on the [[cannabinoid receptor]]s (specifically on [[Cannabinoid receptor type 1|CB<sub>1</sub>]] receptors, which are part of the [[central nervous system]]) found in different organisms such as mammals, fish, and certain invertebrates (e.g. ''[[Hydra (genus)|Hydra]]'').
+'''Methanandamide''' ('''AM-356''') is a [[Organic compound#Synthetic compounds|synthetic]]ally created stable [[Chiral (chemistry)|chiral]] [[Structural analog|analog]] of [[anandamide]].<ref>{{cite journal |pmid= 8021930 |year= 1994 |author1= Abadji V|title= (''R'')-methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability |volume= 37 |issue= 12 |pages= 1889–93 |journal= Journal of Medicinal Chemistry |doi=10.1021/jm00038a020|author2= Lin S|author3=Taha G|author4=Griffin G|author5=Stevenson LA|author6=Pertwee RG|author7=Makriyannis A|authorlink7=Alexandros Makriyannis}}</ref>  Its effects have been observed to act on the [[cannabinoid receptor]]s (specifically on [[Cannabinoid receptor type 1|CB<sub>1</sub>]] receptors, which are part of the [[central nervous system]]) found in different organisms such as mammals, fish, and certain invertebrates (e.g. ''[[Hydra (genus)|Hydra]]'').
 ==References==
@@ Line 46: / Line 50: @@
 [[Category:Fatty acid amides]]
-[[Category:Cannabinoids]]
-[[Category:Alcohols]]
+[[Category:Primary alcohols]]
 [[Category:AM cannabinoids]]