852679-66-4

Basic information

• Product Name: (1S,2S,4R,5R,6S)-2-Amino-4-methylbicyclo[3.1.0]hexane-2,6-dicarboxylicacid
• Synonyms: (1S,2S,4R,5R,6S)-2-Amino-4-methylbicyclo[3.1.0]hexane-2,6-dicarboxylicacid;LY 395756
• CAS NO: 852679-66-4
• Molecular Formula: C9H13NO4
• Molecular Weight: 199.2
• Mol File: 852679-66-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Store at +4°C
• CAS DataBase Reference: (1S,2S,4R,5R,6S)-2-Amino-4-methylbicyclo[3.1.0]hexane-2,6-dicarboxylicacid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4R,5R,6S)-2-Amino-4-methylbicyclo[3.1.0]hexane-2,6-dicarboxylicacid(852679-66-4)
• EPA Substance Registry System: (1S,2S,4R,5R,6S)-2-Amino-4-methylbicyclo[3.1.0]hexane-2,6-dicarboxylicacid(852679-66-4)

Safety Data

• Hazardous Substances Data: 852679-66-4(Hazardous Substances Data)

Usage

Uses

(±)-LY 395756 is an agonist at mGlu2 receptors and an antagonist at mGlu3 receptors.

Upstream product

• 191399-80-1 (1S,2S,4S,5R,6S)-2-Amino-2-cyano-4-methyl-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 134176-18-4 (+/-)-(1S,5R,6S)-ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 1359762-15-4 di-tert-butyl (1S,2S,4R,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate 
• 1379471-57-4 di-tert-butyl (1S,2S,4S,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate 

Relevant articles and documents

Improved synthesis of C4α- and C4β-methyl analogues of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylate

An efficient and divergent synthesis of C4α- and C4β-methyl- substituted analogues of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate, which are important tools in the study of metabotropic glutamate receptor function, has been achieved. By taking advantage

Methyl substitution of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate (LY354740) determines functional activity at metabotropic glutamate receptors: Identification of a subtype selective mGlu2 receptor agonist

LY354740 (1) is a highly potent and selective agonist of metabotropic glutamate (mGlu) receptors 2 and 3. In the present study, we have prepared C3- and C4-methyl-substituted variants of rac-1, compounds 5, 9, and 13. Each of these racemic methyl-substituted analogues displaced specific binding of the mGlu2/3 receptor antagonist 3H-2S-2-amino-2-(1S,2S-2- carboxycycloprop-l-yl)-3-(xanth-9-yl)propanoic acid (3H-LY341495) from membranes expressing mGlu2 or mGlu3 receptor subtypes. Evaluation of the functional effects of this series on second messenger responses in cells expressing human mGlu2 or mGlu3 receptors revealed C3β-methyl analogue 5 to possess antagonist properties at both mGlu2 and mGlu3 receptors while C4β-methyl analogue 9 acts as a full agonist at each of these targets. Unexpectedly, we found that incorporation of a methyl substituent at the C4α-position as in analogue 13 results in a mixed mGlu2 agonist/mGlu3 antagonist pharmacological profile. All of the mGlu2 agonist and mGlu3 antagonist activity of rac-13 was found to reside in its resolved (+)-isomer.