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469-22-7

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469-22-7 Usage

Description

Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it produces fairly potent analgesic effects mediated through the μ-opioid receptor.

Uses

(-)-Eseroline is a metabolite of physostigmine, displaying both anti-acetylcholinesterase and opiate agonist activities.

Definition

ChEBI: Eseroline is a pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physostigmine and causes neuronal cell death by a mechanism involving loss of cell ATP. It has a role as an opioid analgesic and a human xenobiotic metabolite. It is a member of phenols and a pyrroloindole.

Check Digit Verification of cas no

The CAS Registry Mumber 469-22-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 9 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 469-22:
(5*4)+(4*6)+(3*9)+(2*2)+(1*2)=77
77 % 10 = 7
So 469-22-7 is a valid CAS Registry Number.
InChI:InChI=1/C13H18N2O/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13/h4-5,8,12,16H,6-7H2,1-3H3/t12-,13+/m1/s1

469-22-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name eseroline

1.2 Other means of identification

Product number -
Other names Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS-cis)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:469-22-7 SDS

469-22-7Relevant articles and documents

Nickel-Catalyzed Enantioselective Carbamoyl Iodination: A Surrogate for Carbamoyl Iodides

Abel-Snape, Xavier,Glorius, Frank,Lautens, Mark,Marchese, Austin D.,Mirabi, Bijan,Whyte, Andrew,Wollenburg, Marco

, p. 4780 - 4785 (2020/05/19)

This work reports the enantioselective formal transfer of a carbamoyl iodide across a 1,1-disubstituted styrene using Ni-catalysis. Employing an air-stable Ni(II) precatalyst and a commercially available chiral ligand ((S)-tBuPHOX), enantioenriched 3,3-disubstituted iodooxindoles were obtained in up to 90% yield and up to 97:3 e.r. This methodology was applied to the total synthesis of (-)-esermethole and (-)-phenserine.

Synthesis of physostigmine analogues and evaluation of their anticholinesterase activities

Zhan, Zha-Jun,Bian, Hong-Ling,Wang, Jian-Wei,Shan, Wei-Guang

scheme or table, p. 1532 - 1534 (2010/06/21)

A series of physostigmine analogues were prepared and evaluated for cholinesterase inhibition activities, including acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Most of them showed potent inhibition activities against AChE, in which compound 17 especially exhibited significantly higher selectivity over BChE than phenserine, a compound currently on clinical trial. Discussion about the relationships between structure and activity of these derivatives was also presented.

An efficient O-dealkylation procedure for the synthesis of (3aS,cis)- 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl-3,4-dihydro- 2(1H)-isoquinolinecarboxylate

Gao, Zhongli,Lee, Thomas B. K.,Rauckman, Barbara S.

, p. 331 - 333 (2007/10/03)

The title compound is synthesized in high yields and purity from (-)- eserethole (2a) via a lithium bromide catalyzed hydrobromic acid O- dealkylation procedure as the key step.

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