Eicosanoid

DATA No : XPR7001 INFORMANT : Keizo Waku

NAME : N-Arachidonoylethanolamine

COMMON NAME	:	Anandamide(20:4, n-6)
SYMBOL	:
FORMULA	:	C₂₂H₃₇NO₂ MOL.WT (average) : 347.535

Download ChemDraw structure data

BIOLOGICAL ACTIVITY

Anandamide inhibited the specific binding of cannabinoid probe to synaptosomal membrane and produced a concentration-dependent inhibition of the electrically evoked twitch response of the mouse vas deferens, a characteristic effect of psychotropic cannabinoids. Anandamidefunctions as a natural ligand for the cannabinoid receptor (CBl). Binding to rat brain CB1, Ki(nM) = 39.

5.7(Ref. 7001)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	oil(Ref. 7001)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:	soluble in organic solvent(Ref. 7001)

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	¹H NMR spectra.The peaks attributed to double bond protons(d5.30 to 5.45, multiplet)were coupled with those of protons that have the chemical shifts of doubly allylic protons(d2.75 to 2.90, multiplet). (Ref. 7001)

MASS SPECTRA	:	CID measurement of m/z 348 MH⁺ion gave rise to the following significant fragments:m/z 287, 245 ,203, 62 (highest abundance), and 44. m/z 62 fragment ion is HOCH₂CH₂NH₂⁺. (Ref. 7001)

OTHER SPECTRA	:

CHROMATOGRAM DATA

1-Anthroyl derivatives of various types of N-acylethanolamine were separated by reverse phase HPLC (Ref. 7005)
[Chromatogram 7001]

SOURCE

Originally found in porcine brain (Ref. 7006). It was also found in rat brain (Ref. 7005)and testis(Ref. 7008)

CHEMICAL SYNTHESIS

N-Arachidonoylethanolamine was synthesized from arachidonyl chloride and ethanolamine. The product was purified by silica gel column chromatography. It was 97 % pure as judged by GC-MS. (Ref. 7001)

METABOLISM

It was biosynthesized from N-acylphosphatidylethanolamine by phospholipase D like reaction in rat brain microsomes (Ref. 7005).It was hydrolyzed by the anandamide amidohydrolase in rat brain microsomes to ethanolamine and arachidonic acid (Ref. 7007).

GENETIC INFORMATION

1. CB1(Ref. 7002) 2. CB2(Ref. 7003) 3. CB1A(Ref. 7004)

NOTE

REFERENCES

[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)

[TOP]

[7002]

AUTHOR	:	Matsuda, L. A., Lolait, S. J., Brownstein, M. J., Young, A. C., and Bonner, T. I.
TITLE	:	Structure of a cannabinoid receptor and functional expression of the cloned cDNA PubMed ID:2165569
JOURNAL	:	Nature.
VOL	:	346 PAGE : 561-564 (1990)

[TOP]

[7003]

AUTHOR	:	Munro, S., Thomas, K. L., and Abu-Shaar, M.
TITLE	:	Molecular characterization of a peripheral receptor for cannabinoids PubMed ID:7689702
JOURNAL	:	Nature.
VOL	:	365 PAGE : 61-65 (1993)

[TOP]

[7004]

AUTHOR	:	Shire, D., Carillon, C., Kaghad, M., Calandra, B., Rinaldi-Carmona, M., Le Fur, G., Caput, D., and Ferrara, P.
TITLE	:	An amino-terminal variant of the central cannabinoid receptor resulting from alternative splicing PubMed ID:7876112
JOURNAL	:	J Biol Chem.
VOL	:	270 PAGE : 3726-3731 (1995)

[TOP]

[7005]

AUTHOR	:	Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., Ishima, Y., and Waku, K.
TITLE	:	Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonoylethanolamine, an endogenous cannabinoid-receptor ligand, in rat brain microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine PubMed ID:8797835
JOURNAL	:	Eur J Biochem.
VOL	:	240 PAGE : 53-62 (1996)

[TOP]

[7006]

AUTHOR	:	Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R.
TITLE	:	Isolation and structure of a brain constituent that binds to the cannabinoid receptor PubMed ID:1470919
JOURNAL	:	Science.
VOL	:	258 PAGE : 1946-1949 (1992)

[TOP]

[7007]

AUTHOR	:	Desarnaud, F., Cadas, H., and Piomelli, D.
TITLE	:	Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization PubMed ID:7890734
JOURNAL	:	J Biol Chem.
VOL	:	270 PAGE : 6030-6035 (1995)

[TOP]

[7008]

AUTHOR	:	Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., and Waku, K.
TITLE	:	Enzymatic synthesis of anandamide, an endogenous cannabinoid receptor ligand, through N-acylphosphatidylethanolamine pathway in testis: involvement of Ca(2+)-dependent transacylase and phosphodiesterase activities PubMed ID:8573114
JOURNAL	:	Biochem Biophys Res Commun.
VOL	:	218 PAGE : 113-117 (1996)

[TOP]