LBF20406AM15: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
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|LipidBank=XPR7031
|LipidBank=XPR7031
|LipidMaps=LMFA08020017
|LipidMaps=LMFA08020017
|SysName=N- ( (S) - (+) -1-methylpropyl) arachidonoyl amide
|SysName=N- (d-1S-Methylpropyl)- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
|Melting Point=colorless oil <<0001>>
|Common Name=&&N- ( (S) - (+) -1-Methylpropyl)arachidonoylamide&&N- ( (S) - (+) -1-Methylpropyl)- (5Z,8Z,11Z,14Z) -eicosatetraenoylamine&&
|Reflactive=dX<sub>4</sub><sup>25</sup>= +7.08° (C=1, EtOH) <<0001>>
|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}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H NMR (CDCl3) <FONT FACE="Symbol">d</FONT>5.30-5.42 (m, 8H), 5.22 (br s, lH), 3.88-3.98 (m, lH), 2.75-2.90 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.76 (m, 2H), 1.22-1.50 (m, 8H), 1.12 (d, J=7.5Hz, 3H), 0.82-0.96 (m, 6H). <<7001>>
|Optical=[ alpha ]^{25}_4 = +7.08° (C=1, EtOH) [[Reference:Bergstrom_S:,Science,1967,157,382|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:,Science,1967,157,382}}]]
|NMR Spectra=^1 H NMR (CDCl3) delta 5.30-5.42 (m, 8H), 5.22 (br s, lH), 3.88-3.98 (m, lH), 2.75-2.90 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.76 (m, 2H), 1.22-1.50 (m, 8H), 1.12 (d, J=7.5Hz, 3H), 0.82-0.96 (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=
|Chemical Synthesis=This compound was synthesized from arachidonoylchloride and (S)-(+)-sec-butylamine. Yield 55%. [[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=
|Biological Activity=Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 377.2±55.4 [[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}}]]
}}
}}
{{Lipid/Footer}}

Latest revision as of 06:42, 8 November 2010

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Upper classes: LB LBF



N- ( (S) - (+) -1-Methylpropyl)arachidonoylamide
LBF20406AM15.png
Structural Information
N- (d-1S-Methylpropyl)- (cis-5,cis-8,cis-11,cis-14) -eicosatetraenoylamine
  • N- ( (S) - (+) -1-Methylpropyl)arachidonoylamide
  • N- ( (S) - (+) -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=1, EtOH) BergstromS
This compound was synthesized from arachidonoylchloride and (S)-(+)-sec-butylamine. Yield 55%. Sheskin_T et al.
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 377.2±55.4 Sheskin_T et al.
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra 1H NMR (CDCl3) δ 5.30-5.42 (m, 8H), 5.22 (br s, lH), 3.88-3.98 (m, lH), 2.75-2.90 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.76 (m, 2H), 1.22-1.50 (m, 8H), 1.12 (d, J=7.5Hz, 3H), 0.82-0.96 (m, 6H). SheskinTet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406AM15 See above. Bergstrom_S 1967
n.a. LBF20406AM15 See above. Sheskin_T et al. 1997