()-Eseroline fumarate salt

Names

[ Name ]:
()-Eseroline fumarate salt

[Synonym ]:
(-)-Eseroline fumarate salt
(u2212)-Eseroline fumarate salt
E100_FLUKA

Biological Activity

[Description]:

(-)-Eseroline fumarate is a metabolic of Physostigmine (HY-N6608), an AChE inhibitor. (-)-Eseroline fumarate elicits a leakage of lactic acid dehydrogenase (LDH) from cancer cells. (-)-Eseroline fumarate also induces the release of adenine nucleotides and 5-hydroxytryptamine (5-HT) from neuronal cells, thus induce cell death. (-)-Eseroline fumarate inhibits the electrically evoked twitches of the mouse vas deferens and of the guinea-pig ileum[1][2].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[In Vitro]

(-)-Eseroline fumarate (0.5 mM; 0-25 hr) 时间依赖性地诱导小鼠神经母细胞瘤 N1E-115、大鼠胶质瘤 C6 和神经母细胞癌-胶质瘤杂交 NG 108-15 中的 LDH 泄露[1]。

[In Vivo]

(-)-Eseroline fumarate (盐酸; 10 mg/kg; 静脉注射; 单剂量) 诱导成年杂种猫的大脑皮层释放5-HT[2]。 (-)-Eseroline fumarate (水杨酸; 9 mg/kg; 皮下注射; 单剂量) 在小鼠甩尾试验中显示出镇痛的作用，并强烈地降低 Physostigmine (HY-N6608) 的抗伤害作用[3]。

[References]

[1]. Somani SM, et al. Eseroline, a metabolite of physostigmine, induces neuronal cell death. Toxicol Appl Pharmacol. 1990 Oct;106(1):28-37.

[2]. Bartolini A, et al. Eseroline: a new antinociceptive agent derived from physostigmine with opiate receptor agonist properties. Experimental in vivo and in vitro studies on cats and rodents. Neurosci Lett. 1981 Sep 1;25(2):179-83.

[3]. Harris LS, et al. Narcotic-antagonist analgesics: interactions with cholinergic systems. J Pharmacol Exp Ther. 1969 Sep;169(1):17-22.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₇H₂₂N₂O₅

[ Molecular Weight ]:
334.36700

[ Exact Mass ]:
334.15300

[ PSA ]:
101.31000

[ LogP ]:
1.47600

[ Appearance of Characters ]:
white

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
0.1 M HCl: soluble (Solutions should be freshly prepared.)

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Articles

Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine.

Biochem. Pharmacol. 31 , 1233, (1982)

The action of eseroline--(3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indo l-5-ol--salicylate was tested on preparations of ChE from different sources and on the longitudinal muscle...

Direct evidence that eseroline possesses morphine-like effects.

Eur. J. Pharmacol. 83 , 232, (1982)

The opiate-like effects of eseroline, a physostigmine derivative, were studied in different tests. The antinociceptive effect of eseroline given s.c. and intracerebrally could be detected in the rat h...

Eseroline, a metabolite of physostigmine, induces neuronal cell death.

Toxicol. Appl. Pharmacol. 106 , 28, (1990)

The toxic effects of physostigmine, an anticholinesterase drug, and its metabolite eseroline were investigated in three neuronal cell culture systems, mouse neuroblastoma N1E-115, rat glioma C6, and n...