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Eicosanoid


DATA No : XPR7031 INFORMANT : Keizo Waku

NAME : N-((S)-(+)-1-methylpropyl)arachidonoyl amide

COMMON NAME:
SYMBOL:
FORMULA: C24H41NO MOL.WT (average) : 359.588


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BIOLOGICAL ACTIVITY
Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 377.2pm55.4 (Ref. 7001)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:colorless oil (Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:d4-25= +7.08deg (C=1, EtOH) (Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1H NMR (CDCl3) d5.30-5.42 (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). (Ref. 7001)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
This compound was synthesized from arachidonoylchloride and (S)-(+)-sec-butylamine. Yield 55%. (Ref. 7001)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Bergstrom, S.
TITLE:Prostaglandins: members of a new hormonal system. These physiologically very potent compounds of ubiquitous occurrence are formed from essential fatty acids PubMed ID:4291104
JOURNAL:Science.
VOL:157 PAGE : 382-391 (1967)
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[7001]
AUTHOR:Sheskin, T., Hanus, L., Slager, J., Vogel, Z., and Mechoulam, R.
TITLE:Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor PubMed ID:9057852
JOURNAL:J Med Chem.
VOL:40 PAGE : 659-667 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.