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|LipidBank=XPR7054
|LipidBank=XPR7054
|LipidMaps=LMFA08020040
|LipidMaps=LMFA08020040
|SysName=N- (1-methyl-2-hydroxyethyl) arachidonoylamide (R)  
|SysName=N-1R-Methyl-2-hydroxyethyl- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
|Common Name=&&N- (1-methyl-2-hydroxyethyl) arachidonoylamide (R)&&
|Common Name=&&N- (R) -1-Methyl-2-hydroxyethylarachidonoylamide&&N- (R) -1-Methyl-2-hydroxyethyl- (5Z,8Z,11Z,14Z) -eicosatetraenoylamine&&
|Melting Point=colorless liquid [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]].
|Melting Point=colorless liquid [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]].
|Optical=[ alpha ]^{25}_4 = +10.9° [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Optical=[ alpha ]^{25}_4 = +10.9° [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|NMR Spectra=^1 H NMR (200 MHz, CDCl3)  delta (TMS)5.57 (m, 1H), 5.47-5.30 (m, 8H), 4.14-4.02 (m, 1H), 3.71-3.48 (m, 2H), 2.84-2.81 (m, 6H), 2.24-2.01 (m, 6H), 1.77-1.65 (m, 2H), 1.39-1.26 (m, 6H), 1.17 (d, J=3.46Hz, 3H), 0.89 (t, J=6.12Hz, 3H) [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|NMR Spectra=^1 H NMR (200 MHz, CDCl3)  delta (TMS)5.57 (m, 1H), 5.47-5.30 (m, 8H), 4.14-4.02 (m, 1H), 3.71-3.48 (m, 2H), 2.84-2.81 (m, 6H), 2.24-2.01 (m, 6H), 1.77-1.65 (m, 2H), 1.39-1.26 (m, 6H), 1.17 (d, J=3.46Hz, 3H), 0.89 (t, J=6.12Hz, 3H) [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Chromatograms=Rf 0.3(5% MeOH/CHCl3) [[Reference:Hayaishi_O:,J. Biol. Chem.,1988,263,14593|{{RelationTable/GetFirstAuthor|Reference:Hayaishi_O:,J. Biol. Chem.,1988,263,14593}}]]
|Chromatograms=Rf 0.3(5% MeOH/CHCl3) [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Source=
|Source=
|Chemical Synthesis=This compound was synthesized from arachidonic acid and (R)-(-)-2-amino-l-propanol in 69% yield. [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]
|Chemical Synthesis=This compound was synthesized from arachidonic acid and (R)-(-)-2-amino-l-propanol in 69% yield. [[Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889|{{RelationTable/GetFirstAuthor|Reference:Abadji_V:Lin_S:Taha_G:Griffin_G:Stevenson_LA:Pertwee_RG:Makriyannis_A:,J. Med. Chem.,1994,37,1889}}]]

Latest revision as of 06:48, 8 November 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR7054
LipidMaps LMFA08020040
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406AM37
N- (R) -1-Methyl-2-hydroxyethylarachidonoylamide
LBF20406AM37.png
Structural Information
N-1R-Methyl-2-hydroxyethyl- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
  • N- (R) -1-Methyl-2-hydroxyethylarachidonoylamide
  • N- (R) -1-Methyl-2-hydroxyethyl- (5Z,8Z,11Z,14Z) -eicosatetraenoylamine
Formula C23H39NO2
Exact Mass 361.298079497
Average Mass 361.5613
SMILES C(CCC(=O)N[C@@H](CO)C)C=CCC=CCC=CCC=CCCCCC
Physicochemical Information
colorless liquid Abadji_V et al..
[ α ]25
4   = +10.9° AbadjiVet al.
This compound was synthesized from arachidonic acid and (R)-(-)-2-amino-l-propanol in 69% yield. Abadji_V et al.

LBF20406AM37FT7054.gif
Seltzman_HH et al.
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra 1H NMR (200 MHz, CDCl3) δ (TMS)5.57 (m, 1H), 5.47-5.30 (m, 8H), 4.14-4.02 (m, 1H), 3.71-3.48 (m, 2H), 2.84-2.81 (m, 6H), 2.24-2.01 (m, 6H), 1.77-1.65 (m, 2H), 1.39-1.26 (m, 6H), 1.17 (d, J=3.46Hz, 3H), 0.89 (t, J=6.12Hz, 3H) AbadjiVet al.
Other Spectra
Chromatograms Rf 0.3(5% MeOH/CHCl3) AbadjiVet al.
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406AM37 See above. Abadji_V et al. 1994
n.a. LBF20406AM37 See above. Hayaishi_O 1988
n.a. LBF20406AM37 See above. Seltzman_HH et al. 1997


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