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E8375

Eserine

Name: Eserine
Brand: SIGMA

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:

12352200

PubChem Substance ID:

24277867

Beilstein/REAXYS Number:

91230

MDL number:

MFCD00151090

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Properties

assay

≥99% (HPLC)

mp

102-104 °C (lit.)

SMILES string

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

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

Gene Information

human ... ACHE(43), APP(351), BCHE(590)
mouse ... Ache(11423), Bche(12038), Chrm1(12669)
rat ... Ache(83817), Bche(65036), Chrm2(81645)

Description

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.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) and Acetylcholine Synthesis and Metabolism pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

GHS06

signalword

Danger

hcodes

H300 + H330

pcodes

P301 + P310 + P330 - P304 + P340 + P310

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

ppe

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

Regulatory Information

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Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.

Federica Belluti et al.

Journal of medicinal chemistry, 48(13), 4444-4456 (2005-06-25)

In continuing research that led us to identify a new class of carbamate derivatives acting as potent (Rampa et al. J. Med. Chem. 1998, 41, 3976) and long-lasting (Rampa et al. J. Med. Chem. 2001, 44, 3810) acetylcholinesterase (AChE) inhibitors

Partial antagonism of propofol anaesthesia by physostigmine in rats is associated with potentiation of fast (80-200 Hz) oscillations in the thalamus.

S J Reed et al.

British journal of anaesthesia, 110(4), 646-653 (2012-12-06)

Positron emission tomography studies in human subjects show that propofol-induced unconsciousness in humans is associated with a reduction in thalamic blood flow, suggesting that anaesthesia is associated with impairment of thalamic function. A recent study showed that antagonism of propofol-induced

Cholinergic enhancement reduces functional connectivity and BOLD variability in visual extrastriate cortex during selective attention.

Emiliano Ricciardi et al.

Neuropharmacology, 64, 305-313 (2012-08-22)

Enhancing cholinergic function improves performance on various cognitive tasks and alters neural responses in task specific brain regions. We have hypothesized that the changes in neural activity observed during increased cholinergic function reflect an increase in neural efficiency that leads

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