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Merck
CN

E100

Supelco

(−)-Eseroline fumarate salt

analytical standard, for drug analysis

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About This Item

Empirical Formula (Hill Notation):
C13H18N2O · C4H4O4
CAS Number:
70310-73-5
Molecular Weight:
334.37
MDL number:
MFCD00055202
UNSPSC Code:
41116107
PubChem Substance ID:
329798872

Key Documents

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Quality Level

100

form

solid

optical activity

[α]23/D −107.9°, c = 0.5 in methanol(lit.)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white

solubility

0.1 M HCl: soluble (Solutions should be freshly prepared.)
0.1 M NaOH: soluble (Solutions should be freshly prepared.)
H2O: soluble (Solutions should be freshly prepared.)
methanol: slightly soluble (Solutions should be freshly prepared.)

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

storage temp.

2-8°C

SMILES string

[H]\C(=C(\[H])C(O)=O)C(O)=O.[H][C@]12N(C)CC[C@@]1(C)c3cc(O)ccc3N2C

InChI

1S/C13H18N2O.C4H4O4/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13;5-3(6)1-2-4(7)8/h4-5,8,12,16H,6-7H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t12-,13+;/m1./s1

InChI key

PBZRRADJWNBPNY-XDRMOJKASA-N

Gene Information

human ... ACHE(43)

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Metabolite of physostigmine (eserine) that is cytotoxic in several neuronal cell lines; it displays both anti-acetylcholinesterase and opiate agonist activities; potent analgesic.

Disclaimer

Hygroscopic, photosensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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S Fürst et al.
European journal of pharmacology, 83(3-4), 233-241 (1982-09-24)
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 hot plate test and was reversed by naloxone. The apparent pA2 values
A Galli et al.
The Journal of pharmacy and pharmacology, 37(1), 42-48 (1985-01-01)
The protective action of eseroline--(3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3 a, 8-trimethyl-pyrrolo[2,3-b]indol-5-ol--salicylate against (DFP) diisopropyl fluorophosphate and carbamate poisoning of cholinesterases (ChEs) has been examined in-vitro with human erythrocytes and purified preparations of electric eel acetylcholinesterase (AChE) and of horse serum butyrylcholinesterase (BuChE), and in-vivo
A Galli et al.
Biochemical pharmacology, 31(7), 1233-1238 (1982-04-01)
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 of guinea-pig ileum. While eseroline is eseroline is extremely weak-acting on horse serum BuChE (Ki = 208 +/- 42 microM), it
Swapnalee Sarmah et al.
Scientific reports, 10(1), 3951-3951 (2020-03-05)
Ethanol exposure during prenatal development causes fetal alcohol spectrum disorder (FASD), the most frequent preventable birth defect and neurodevelopmental disability syndrome. The molecular targets of ethanol toxicity during development are poorly understood. Developmental stages surrounding gastrulation are very sensitive to
Ross T Fennessy et al.
Nucleic acids research, 44(15), 7189-7203 (2016-04-24)
Nucleosomes, the fundamental subunits of eukaryotic chromatin, are organized with respect to transcriptional start sites. A major challenge to the persistence of this organization is the disassembly of nucleosomes during DNA replication. Here, we use complimentary approaches to map the
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