2-花生四烯酸甘油

2-花生四烯酸甘油
	IUPAC名; 2-O-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoyl]glycerol
	系统名; 1,3-Dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
别名	2-AG, 2-arachidonoylglycerol
识别
CAS号	53847-30-6
PubChem	5282280
ChemSpider	4445451
SMILES	O=C(OC(CO)CO)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC;
InChI	1/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-;
InChIKey	RCRCTBLIHCHWDZ-DOFZRALJBN
ChEBI	52392
IUPHAR配体	729
性质
化学式	C23H38O4
摩尔质量	378.55 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

2-花生四烯酸甘油, 2-AG（2-Arachidonoylglycerol）^[1]^[2] ，又称为内源性大麻素，是内源性CB1配体。1995年，拉斐尔·梅舒朗及其學生與合作者在實驗室中發現了2-AG ^[3]。大麻素會激活位於神經元末端的2-AG受體，從而使神經元誤以為已經向突觸處相連的其他神經元發送了信息（神經遞質），從而錯誤地抑制神經遞質的釋放。^[4]

2-AG在中枢神经系统中有较高的表达，同时可以在乳汁中检测到。

2-AG在免疫反应中起调控作用。

参考文献

^ Stella N, Schweitzer P, Piomelli D. A second endogenous cannabinoid that modulates long-term potentiation (PDF). Nature. August 1997, 388 (6644): 773–8 [2023-11-30]. Bibcode:1997Natur.388..773S. PMID 9285589. S2CID 4422311. doi:10.1038/42015 . （原始内容存档 (PDF)于2018-07-24）.
^ Sugiura T, Kodaka T, Nakane S, et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. The Journal of Biological Chemistry. January 1999, 274 (5): 2794–801. PMID 9915812. doi:10.1074/jbc.274.5.2794 .
^ Mechoulam R, Ben-Shabat S, Hanus L, Ligumsky M, Kaminski NE, Schatz AR, Gopher A, Almog S, Martin BR, Compton DR, Pertwee RG. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochemical pharmacology (Elsevier). 1995, 50 (1): 83––90.
^ James Kalat. Biological Psychology, 14th Edition. Cengage Learning. 2023: 58.

[pmid9285589-1] Stella N, Schweitzer P, Piomelli D. A second endogenous cannabinoid that modulates long-term potentiation (PDF). Nature. August 1997, 388 (6644): 773–8 [2023-11-30]. Bibcode:1997Natur.388..773S. PMID 9285589. S2CID 4422311. doi:10.1038/42015 . （原始内容存档 (PDF)于2018-07-24）.

[pmid9915812-2] Sugiura T, Kodaka T, Nakane S, et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. The Journal of Biological Chemistry. January 1999, 274 (5): 2794–801. PMID 9915812. doi:10.1074/jbc.274.5.2794 .

[Mechoulam1995-3] Mechoulam R, Ben-Shabat S, Hanus L, Ligumsky M, Kaminski NE, Schatz AR, Gopher A, Almog S, Martin BR, Compton DR, Pertwee RG. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochemical pharmacology (Elsevier). 1995, 50 (1): 83––90.

[Kalat_biological_psychology-4] James Kalat. Biological Psychology, 14th Edition. Cengage Learning. 2023: 58.

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