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|LipidBank=XPR7030
|LipidBank=XPR7030
|LipidMaps=LMFA08020016
|LipidMaps=LMFA08020016
|SysName=N- ( (R) - (-) -1-methylpropyl) arachidonoyl amide
|SysName=N- (l-1R-Methylpropyl)- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
|Common Name=&&N- ( (R) - (-) -1-methylpropyl) arachidonoyl amide&&
|Common Name=&&N- ( (R) - (-) -1-Methylpropyl)arachidonoylamide&&N- ( (R) - (-) -1-Methylpropyl)- (5Z,8Z,11Z,14Z) -eicosatetraenoylamine&&
|Melting Point=colorless oil [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Melting Point=colorless oil [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Reflactive=dX<sub>4</sub><sup>25</sup>= -7.08°(c=l,EtOH)[[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Optical=[ alpha ]^{25}_4 = -7.08°(c=l,EtOH)[[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H NMR (CDCl3) <FONT FACE="Symbol">d</FONT>5.30-5.42 (m, 8H), 5.20 (br s, lH), 3.86-4.00 (m, lH), 2.75-2.86 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.80 (m, 2H), 1.22-1.50 (m, 8H), 1.10 (d, J=7.5Hz, 3H),0.82-0.92 (m, 6H). [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|NMR Spectra=^1 H NMR (CDCl3) delta 5.30-5.42 (m, 8H), 5.20 (br s, lH), 3.86-4.00 (m, lH), 2.75-2.86 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.80 (m, 2H), 1.22-1.50 (m, 8H), 1.10 (d, J=7.5Hz, 3H),0.82-0.92 (m, 6H). [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Source=
|Source=
|Chemical Synthesis=This compound was synthesized from arachidonoyl chloride and (R)-(-)-sec-butylamine.Yield 63 % [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Chemical Synthesis=This compound was synthesized from arachidonoyl chloride and (R)-(-)-sec-butylamine.Yield 63 % [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
|Metabolism=
|Metabolism=
|Biological Activity=Binding to the brain cannabinoid receptor (CBl),Ki(nM)= 239.9±63.8 [[Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659|{{RelationTable/GetFirstAuthor|Reference:Sheskin_T:Hanus_L:Slager_J:Vogel_Z:Mechoulam_R:,J. Med. Chem.,1997,40,659}}]]
}}
}}


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{{Lipid/Footer}}

Latest revision as of 04:42, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR7030
LipidMaps LMFA08020016
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406AM14
N- ( (R) - (-) -1-Methylpropyl)arachidonoylamide
LBF20406AM14.png
Structural Information
N- (l-1R-Methylpropyl)- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
  • N- ( (R) - (-) -1-Methylpropyl)arachidonoylamide
  • N- ( (R) - (-) -1-Methylpropyl)- (5Z,8Z,11Z,14Z) -eicosatetraenoylamine
Formula C24H41NO
Exact Mass 359.318814939
Average Mass 359.58847999999995
SMILES C(=CCCCC(=O)N[C@@H](CC)C)CC=CCC=CCC=CCCCCC
Physicochemical Information
colorless oil Sheskin_T et al.
[ α ]25
4   = -7.08°(c=l,EtOH) SheskinTet al.
This compound was synthesized from arachidonoyl chloride and (R)-(-)-sec-butylamine.Yield 63 % Sheskin_T et al.
Binding to the brain cannabinoid receptor (CBl),Ki(nM)= 239.9±63.8 Sheskin_T et al.
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra 1H NMR (CDCl3) δ 5.30-5.42 (m, 8H), 5.20 (br s, lH), 3.86-4.00 (m, lH), 2.75-2.86 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.80 (m, 2H), 1.22-1.50 (m, 8H), 1.10 (d, J=7.5Hz, 3H),0.82-0.92 (m, 6H). SheskinTet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406AM14 See above. Sheskin_T et al. 1997


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