ChemicalBook >> CAS DataBase List >>Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI)

Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI)

CAS No.
176199-48-7
Chemical Name:
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI)
Synonyms
LY 354740;Eglumetad;Eglumegad;LY 354740, Group II mGlu agonist;(1S,2S,5R,6S)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid;Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S...;Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid,2-amino-,(1S,2S,5R,6S)-;Bicyclo[3.1.0]hexane-2,6-dicarboxylicacid, 2-aMino-, [1S-(1a,2b,5a,6a)]-;Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI)
CBNumber:
CB61042715
Molecular Formula:
C8H11NO4
Molecular Weight:
185.18
MDL Number:
MOL File:
176199-48-7.mol
MSDS File:
SDS
Last updated:2025-04-17 18:22:24

Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) Properties

Melting point 270-271 °C
Boiling point 376.4±32.0 °C(Predicted)
Density 1.569
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility H2O : 6.33 mg/mL (34.18 mM; Need ultrasonic and warming)
form Powder
pka 2.06±0.40(Predicted)
color White to off-white
FDA UNII ONU5A67T2S
UNSPSC Code 12352200

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P280-P301+P312-P302+P352-P305+P351+P338
NFPA 704
0
2 0

Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 5.04685 LY 354740 - CAS 176199-48-7 - Calbiochem 176199-48-7 10MG $156 2022-05-15 Buy
Cayman Chemical 24215 LY354740 ≥95% 176199-48-7 1mg $33 2024-03-01 Buy
Cayman Chemical 24215 LY354740 ≥95% 176199-48-7 5mg $106 2024-03-01 Buy
Cayman Chemical 24215 LY354740 ≥95% 176199-48-7 10mg $160 2024-03-01 Buy
Tocris 3246 LY354740 ≥98%(HPLC) 176199-48-7 10 $208 2021-12-16 Buy
Product number Packaging Price Buy
5.04685 10MG $156 Buy
24215 1mg $33 Buy
24215 5mg $106 Buy
24215 10mg $160 Buy
3246 10 $208 Buy

Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) Chemical Properties,Uses,Production

Uses

LY 354740 is a highly selective and potent agonist of group II mGluR.

Uses

Treatment ofgeneral anxiety disorders and smoking cessation (metabotropic glutamate agonist).

Definition

ChEBI: Eglumetad is a L-alpha-amino acid.

Biological Activity

Highly selective and potent agonist of group II mGlu receptors (EC 50 values are 5.1 and 24.3 nM at mGlu 2 and mGlu 3 receptors respectively and > 100000 nM at mGlu 4 , mGlu 7 , mGlu 1a and mGlu 5a receptors). Displays antianxiety and antiaddictive activity in vivo . Orally and systemically active.

in vivo

Eglumegad (LY354740) (15 or 30 mg/kg, i.p.) has no effect on spatial working memory performance in Gria1 / or WT mice, and it has no effect on rewarded alternation testing with a short inter-trial interval in Gria1 / and WT mice at concentration of 30 mg/kg. Eglumegad (LY354740) (15 or 30 mg/kg, i.p.) reduces spontaneous locomotor activity in wild-type and Gria1 / mice[1]. Eglumegad (LY354740) (15 mg/kg, i.p.) dreases novelty-induced hyperlocomotion in naive GluA1-KO and pre-handled GluA1-KO males, but not in females. Eglumegad (LY354740) (15 mg/kg, i.p.) significantly reduces the increased c-Fos expression of GluA1-KO males to the level of WT males, but not in of females[3]. Eglumegad (LY354740) (10 mg/kg, i.p.) attenuates the immobilization stress-induced increase in BDNF mRNA expression in the rat mPFC[4].

IC 50

mGluR2R: 5 nM (IC50); mGluR3R: 24 nM (IC50)

storage

+4°C

188885-69-0
176199-48-7
Synthesis of Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) from Spiro[cyclohexane-1,2'-cyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole]-4'-carboxylic acid, hexahydro-5'-oxo-, ethyl ester, (3'aR,3'bR,4'S,4'aS,5'aR)-

Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) Preparation Products And Raw materials

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Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) Eglumegad Eglumetad LY 354740 (1S,2S,5R,6S)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid Bicyclo[3.1.0]hexane-2,6-dicarboxylicacid, 2-aMino-, [1S-(1a,2b,5a,6a)]- Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid,2-amino-,(1S,2S,5R,6S)- Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S... LY 354740, Group II mGlu agonist 176199-48-7 CYCLOPENTANE Glutamate