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Merck
CN

219312

Eserine

99%

Synonym(s):

Physostigmine

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About This Item

Empirical Formula (Hill Notation):
C15H21N3O2
CAS Number:
57-47-6
Molecular Weight:
275.35
EC Number:
200-332-8
UNSPSC Code:
12352103
MDL number:
MFCD00151090
Beilstein/REAXYS Number:
91230

Key Documents

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InChI

1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1

InChI key

PIJVFDBKTWXHHD-HIFRSBDPSA-N

SMILES string

[H][C@]12N(C)CC[C@@]1(C)c3cc(OC(=O)NC)ccc3N2C

assay

99%

optical activity

[α]25/D −116°, c = 1 in benzene

mp

102-104 °C (lit.)

Biochem/physiol Actions

Acetylcholinesterase inhibitor that crosses the blood-brain barrier and forms a carbamylated enzyme complex with acetyl cholinesterase that degrades slowly.
Acetylcholinesterase inhibitor that crosses the blood-brain barrier.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

>212.0 °F

flash_point_c

> 100 °C

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
05017HT
26507MB
18411AO
16226KA
06712BF

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Ciaran G Carolan et al.
Journal of medicinal chemistry, 53(3), 1190-1199 (2010-01-14)
Isosorbide-2-benzyl carbamate-5-benzoate is a highly potent and selective BuChE inhibitor. Meanwhile, isosorbide-2-aspirinate-5-salicylate is a highly effective aspirin prodrug that relies on the salicylate portion to interact productively with human BuChE. By integrating the salicylate group into the carbamate design, we
Weiming Luo et al.
Journal of medicinal chemistry, 48(4), 986-994 (2005-02-18)
Reductive cyclization of 5-hydroxy-3-methyl-3-methoxycarbonylmethylenebenzofuran-2(3H)-one (4) gave 5-hydroxy-3a-methyl-2,3,3a,8a-tatrahydrofuro[2,3-b]benzofuran (5) and the rearrangement product 7-hydroxy-4,5-dihydro-2,5-methano-1,3-benzodioxepine (6). Reaction of compounds 5 and 6 with different isocyanates provided two series novel carbamates (7-12) whose structures were confirmed by X-ray crystallography. These were assessed for
Ciaran G Carolan et al.
Journal of medicinal chemistry, 51(20), 6400-6409 (2008-09-27)
In this study, we report the SAR and characterization of two groups of isosorbide-based cholinesterase inhibitors. The first was based directly on the clinically used nitrate isosorbide mononitrate (ISMN) retention of the 5-nitrate group and introduction of a series of
Morwenna C Baird et al.
Journal of natural products, 72(4), 679-684 (2009-02-19)
The semisynthesis of the Stemona alkaloids (3'R)-stemofolenol (1), (3'S)-stemofolenol (2), methylstemofoline (3), and (3'S)-hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3'R-hydroxystemofoline (11) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (4). This synthesis allowed, for the first time, access to
Yvonne Schott et al.
Bioorganic & medicinal chemistry letters, 16(22), 5840-5843 (2006-09-02)
In the course of studies directed toward the discovery of novel acetyl- and butyrylcholinesterase (AChE and BChE) inhibitors for the treatment of Alzheimer's disease, we focused on beta-carbolines (BCs). 6-Oxygenated beta-carboline and beta-carbolinium derivatives based on the serotonin template were
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