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E8375

Sigma-Aldrich

Eserine

Synonym(s):

Physostigmine

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About This Item

Empirical Formula (Hill Notation):
C15H21N3O2
CAS Number:
57-47-6
Molecular Weight:
275.35
Beilstein:
91230
EC Number:
200-332-8
MDL number:
MFCD00151090
UNSPSC Code:
12352200
PubChem Substance ID:
24277867

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)

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Biochem/physiol Actions

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

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

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H330

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Irina Esterlis et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 54(1), 78-82 (2012-11-20)
In vivo estimation of β(2)-nicotinic acetylcholine receptor availability with molecular neuroimaging is complicated by competition between the endogenous neurotransmitter acetylcholine and the radioligand (123)I-3-[2(S)-2-azetidinylmethoxy]pyridine ((123)I-5-IA). We examined whether binding of (123)I-5-IA is sensitive to increases in extracellular levels of acetylcholine
Anna M Lilja et al.
PloS one, 8(1), e54887-e54887 (2013-02-06)
Neuronal dysfunction and demise together with a reduction in neurogenesis are cardinal features of Alzheimer's disease (AD) induced by a combination of oxidative stress, toxic amyloid-β peptide (Aβ) and a loss of trophic factor support. Amelioration of these was assessed
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