Home Amines 176199-48-7
176199-48-7,MFCD04113018
Catalog No.:AA0024DS

176199-48-7 | Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)-

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥95%
in stock  
$48.00   $33.00
- +
5mg
≥95%
in stock  
$152.00   $106.00
- +
10mg
≥95%
in stock  
$229.00   $160.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0024DS
Chemical Name:
Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)-
CAS Number:
176199-48-7
Molecular Formula:
C8H11NO4
Molecular Weight:
185.1772
MDL Number:
MFCD04113018
SMILES:
OC(=O)[C@H]1[C@H]2[C@@H]1[C@](CC2)(N)C(=O)O
Properties
Properties
 
Form:
Solid  
Storage:
Light sensitive;Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
290  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
-3.2  

Downstream Synthesis Route

[1]TetrahedronAsymmetry,2010,vol.21,p.1486-1493

[2]TetrahedronAsymmetry,1997,vol.8,p.511-514

[1]TetrahedronLetters,1998,vol.39,p.9305-9308

[1]TetrahedronLetters,2003,vol.44,p.5431-5434

[1]TetrahedronLetters,2005,vol.46,p.7299-7302

67-56-1    176199-48-7   
(1S,2S,5R,6S)-2-aminobicyclo3.1.0hexane-2,6-dicarboxylicaciddimethylesterhydrochloride 

[1]TetrahedronLetters,2005,vol.46,p.7299-7302

[2]JournalofMedicinalChemistry,2005,vol.48,p.5305-5320

Literature

Title: An allosteric modulator of metabotropic glutamate receptors (mGluR₂), (+)-TFMPIP, inhibits restraint stress-induced phasic glutamate release in rat prefrontal cortex.

Journal: Journal of neurochemistry 20120801

Title: Positive allosteric modulation reveals a specific role for mGlu2 receptors in sensory processing in the thalamus.

Journal: The Journal of physiology 20120215

Title: Structural determinants of allosteric antagonism at metabotropic glutamate receptor 2: mechanistic studies with new potent negative allosteric modulators.

Journal: British journal of pharmacology 20110901

Title: Group II mGluR agonist LY354740 and NAAG peptidase inhibitor effects on prepulse inhibition in PCP and D-amphetamine models of schizophrenia.

Journal: Psychopharmacology 20110701

Title: Hippocampal CA3 calcineurin activity participates in depressive-like behavior in rats.

Journal: Journal of neurochemistry 20110601

Title: Density of metabotropic glutamate receptors 2 and 3 (mGluR2/3) in the dorsolateral prefrontal cortex does not differ with schizophrenia diagnosis but decreases with age.

Journal: Schizophrenia research 20110501

Title: Orally active glutamate carboxypeptidase II inhibitor 2-MPPA attenuates dizocilpine-induced prepulse inhibition deficits in mice.

Journal: Brain research 20110131

Title: Absence of direct effects on the dopamine D2 receptor by mGluR2/3-selective receptor agonists LY 354,740 and LY 379,268.

Journal: Synapse (New York, N.Y.) 20110101

Title: Progress in the developement of positive allosteric modulators of the metabotropic glutamate receptor 2.

Journal: Current medicinal chemistry 20110101

Title: Synthesis and characterization of 1,3-dihydro-benzo[b][1,4]diazepin-2-one derivatives: Part 4. In vivo active potent and selective non-competitive metabotropic glutamate receptor 2/3 antagonists.

Journal: Bioorganic & medicinal chemistry letters 20101201

Title: Impact of metabotropic glutamate 2/3 receptor stimulation on activated dopamine release and locomotion.

Journal: Psychopharmacology 20100901

Title: The intestinal absorption of a prodrug of the mGlu2/3 receptor agonist LY354740 is mediated by PEPT1: in situ rat intestinal perfusion studies.

Journal: Journal of pharmaceutical sciences 20100301

Title: In vitro and in vivo evidence for a lack of interaction with dopamine D2 receptors by the metabotropic glutamate 2/3 receptor agonists 1S,2S,5R,6S-2-aminobicyclo[3.1.0]hexane-2,6-bicaroxylate monohydrate (LY354740) and (-)-2-oxa-4-aminobicyclo[3.1.0] Hexane-4,6-dicarboxylic acid (LY379268).

Journal: The Journal of pharmacology and experimental therapeutics 20091201

Title: Comparison of the mGlu(5) receptor positive allosteric modulator ADX47273 and the mGlu(2/3) receptor agonist LY354740 in tests for antipsychotic-like activity.

Journal: European journal of pharmacology 20091125

Title: Mutagenesis and molecular modeling of the orthosteric binding site of the mGlu2 receptor determining interactions of the group II receptor antagonist (3)H-HYDIA.

Journal: ChemMedChem 20090701

Title: Effects of a metabotropic glutamate receptor group II agonist LY354740 in animal models of positive schizophrenia symptoms and cognition.

Journal: Behavioural pharmacology 20090201

Title: Modulation of group II metabotropic glutamate receptor (mGlu2) elicits common changes in rat and mice sleep-wake architecture.

Journal: European journal of pharmacology 20090128

Title: Transepithelial transport of the group II metabotropic glutamate 2/3 receptor agonist (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylate (LY354740) and its prodrug (1S,2S,5R,6S)-2-[(2'S)-(2'-amino)propionyl]aminobicyclo[3.1.0]hexane-2,6-dicarboxylate (LY544344).

Journal: Drug metabolism and disposition: the biological fate of chemicals 20090101

Title: Efficacy and tolerability of an mGlu2/3 agonist in the treatment of generalized anxiety disorder.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20080601

Title: Dopamine partial agonist actions of the glutamate receptor agonists LY 354,740 and LY 379,268.

Journal: Synapse (New York, N.Y.) 20080201

Title: Asymmetric synthesis and receptor pharmacology of the group II mGlu receptor ligand (1S,2R,3R,5R,6S)-2-amino-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid-HYDIA.

Journal: ChemMedChem 20080201

Title: Glutamate agonists for schizophrenia stimulate dopamine D2High receptors.

Journal: Schizophrenia research 20080201

Title: Synthesis and characterization of 8-ethynyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one derivatives: part 2. New potent non-competitive metabotropic glutamate receptor 2/3 antagonists.

Journal: Bioorganic & medicinal chemistry letters 20080201

Title: Defensive-like behaviors induced by ultrasound: further pharmacological characterization in Lister-hooded rats.

Journal: Psychopharmacology 20071001

Title: Pharmacokinetics, metabolism, and excretion of the intestinal peptide transporter 1 (SLC15A1)-targeted prodrug (1S,2S,5R,6S)-2-[(2'S)-(2-amino)propionyl]aminobicyclo[3.1.0.]hexen-2,6-dicarboxylic acid (LY544344) in rats and dogs: assessment of first-pass bioactivation and dose linearity.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20071001

Title: Stimulation of the metabotropic glutamate 2/3 receptor attenuates social novelty discrimination deficits induced by neonatal phencyclidine treatment.

Journal: Psychopharmacology 20070701

Title: Pharmacological and pharmacokinetic properties of a structurally novel, potent, and selective metabotropic glutamate 2/3 receptor agonist: in vitro characterization of agonist (-)-(1R,4S,5S,6S)-4-amino-2-sulfonylbicyclo[3.1.0]-hexane-4,6-dicarboxylic acid (LY404039).

Journal: The Journal of pharmacology and experimental therapeutics 20070401

Title: Synthesis and metabotropic glutamate receptor activity of S-oxidized variants of (-)-4-amino-2-thiabicyclo-[3.1.0]hexane-4,6-dicarboxylate: identification of potent, selective, and orally bioavailable agonists for mGlu2/3 receptors.

Journal: Journal of medicinal chemistry 20070125

Title: Unitary IPSPs enhance hilar mossy cell gain in the rat hippocampus.

Journal: The Journal of physiology 20070115

Title: Group III metabotropic glutamate receptor agonists selectively suppress excitatory synaptic currents in the rat prefrontal cortex induced by 5-hydroxytryptamine2A receptor activation.

Journal: The Journal of pharmacology and experimental therapeutics 20070101

Title: Modulation of GABAergic inhibition in the rat superior colliculus by a presynaptic group II metabotropic glutamate receptor.

Journal: The Journal of physiology 20061201

Title: Differential changes of group II and group III mGluR function in central amygdala neurons in a model of arthritic pain.

Journal: Journal of neurophysiology 20061001

Title: Subchronic administration of LY354740 does not modify ketamine-evoked behavior and neuronal activity in rats.

Journal: European journal of pharmacology 20060821

Title: 5-Hydroxytryptamine2A (5-HT2A) receptor regulation in rat prefrontal cortex: interaction of a phenethylamine hallucinogen and the metabotropic glutamate2/3 receptor agonist LY354740.

Journal: Neuroscience letters 20060807

Title: Synthesis, in vitro pharmacology, and structure-activity relationships of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as mGluR2 antagonists.

Journal: Bioorganic & medicinal chemistry 20060515

Title: The mGlu2/3 receptor agonist LY354740 suppresses immobilization stress-induced increase in rat prefrontal cortical BDNF mRNA expression.

Journal: Neuroscience letters 20060508

Title: Modulation of amphetamine-induced dopamine release by group II metabotropic glutamate receptor agonist LY354740 in non-human primates studied with positron emission tomography.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20060501

Title: Improved bioavailability of the mGlu2/3 receptor agonist LY354740 using a prodrug strategy: in vivo pharmacology of LY544344.

Journal: The Journal of pharmacology and experimental therapeutics 20060201

Title: Group-II metabotropic glutamate receptors negatively modulate NMDA transmission at striatal cholinergic terminals: role of P/Q-type high voltage activated Ca++ channels and endogenous dopamine.

Journal: Molecular and cellular neurosciences 20060201

Title: Assessment of neuroprotective effects of glutamate modulation on glaucoma-related retinal ganglion cell apoptosis in vivo.

Journal: Investigative ophthalmology & visual science 20060201

Title: A metabotropic glutamate 2/3 receptor antagonist, MGS0039, increases extracellular dopamine levels in the nucleus accumbens shell.

Journal: Neuroscience letters 20060130

Title: Enhanced group II mGluR-mediated inhibition of pain-related synaptic plasticity in the amygdala.

Journal: Molecular pain 20060101

Title: Asymmetric sulfonium ylide mediated cyclopropanation: stereocontrolled synthesis of (+)-LY354740.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20051223

Title: Metabotropic glutamate II receptor agonists in panic disorder: a double blind clinical trial with LY354740.

Journal: International clinical psychopharmacology 20051101

Title: LY-544344. Eli Lilly.

Journal: IDrugs : the investigational drugs journal 20050901

Title: Dipeptides as effective prodrugs of the unnatural amino acid (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740), a selective group II metabotropic glutamate receptor agonist.

Journal: Journal of medicinal chemistry 20050811

Title: Distribution and abundance of metabotropic glutamate receptor subtype 2 in rat brain revealed by [3H]LY354740 binding in vitro and quantitative radioautography: correlation with the sites of synthesis, expression, and agonist stimulation of [35S]GTPgammas binding.

Journal: The Journal of comparative neurology 20050620

Title: 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.

Journal: Journal of medicinal chemistry 20050519

Title: Preliminary evidence of attenuation of the disruptive effects of the NMDA glutamate receptor antagonist, ketamine, on working memory by pretreatment with the group II metabotropic glutamate receptor agonist, LY354740, in healthy human subjects.

Journal: Psychopharmacology 20050401

Title: Anxiolytic-like activity of the mGLU2/3 receptor agonist LY354740 in the elevated plus maze test is disrupted in metabotropic glutamate receptor 2 and 3 knock-out mice.

Journal: Psychopharmacology 20050401

Title: Effects of a metabotropic glutamate(2/3) receptor agonist (LY544344/LY354740) on panic anxiety induced by cholecystokinin tetrapeptide in healthy humans: preliminary results.

Journal: Psychopharmacology 20050401

Title: Group II and III mGluRs-mediated presynaptic inhibition of EPSCs recorded from hippocampal interneurons of CA1 stratum lacunosum moleculare.

Journal: Neuropharmacology 20050101

Title: Comparison of c-Fos induction in the brain by the mGlu2/3 receptor antagonist LY341495 and agonist LY354740: evidence for widespread endogenous tone at brain mGlu2/3 receptors in vivo.

Journal: Neuropharmacology 20050101

Title: Distinct properties of presynaptic group II and III metabotropic glutamate receptor-mediated inhibition of perforant pathway-CA1 EPSCs.

Journal: The European journal of neuroscience 20040501

Title: The mGlu2/3 receptor agonist, LY354740, blocks immobilization-induced increases in noradrenaline and dopamine release in the rat medial prefrontal cortex.

Journal: Journal of neurochemistry 20040101

Title: Group II metabotropic and alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionate (AMPA)/kainate glutamate receptors regulate the deficit in brain reward function associated with nicotine withdrawal in rats.

Journal: The Journal of pharmacology and experimental therapeutics 20030901

Title: Functional calcium coupling with the human metabotropic glutamate receptor subtypes 2 and 4 by stable co-expression with a calcium pathway facilitating G-protein chimera in Chinese hamster ovary cells.

Journal: Biochemical pharmacology 20030901

Title: LY354740, an mGlu2/3 receptor agonist as a novel approach to treat anxiety/stress.

Journal: Stress (Amsterdam, Netherlands) 20030901

Title: Antipsychotic action of selective group II metabotropic glutamate receptor agonist MGS0008 and MGS0028 on conditioned avoidance responses in the rat.

Journal: Life sciences 20030815

Title: Anxiolytic effects of a novel group II metabotropic glutamate receptor agonist (LY354740) in the fear-potentiated startle paradigm in humans.

Journal: Psychopharmacology 20030801

Title: Psychiatric drugs. Excited by glutamate.

Journal: Science (New York, N.Y.) 20030620

Title: Group II metabotropic glutamate receptor modulation of DOI-induced c-fos mRNA and excitatory responses in the cerebral cortex.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030101

Title: LY-354740 (Eli Lilly).

Journal: IDrugs : the investigational drugs journal 20030101

Title: The mGluR5 antagonist MPEP, but not the mGluR2/3 agonist LY314582, augments PCP effects on prepulse inhibition and locomotor activity.

Journal: Neuropharmacology 20021201

Title: Modulation of DOI-induced increases in cortical BDNF expression by group II mGlu receptors.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: Group II mGlu receptor agonists inhibit behavioural and electrophysiological effects of DOI in mice.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: The anxiolytic action of mGlu2/3 receptor agonist, LY354740, in the fear-potentiated startle model in rats is mechanistically distinct from diazepam.

Journal: Pharmacology, biochemistry, and behavior 20020901

Title: (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-methylcyclopropyl) glycine is a potent and selective metabotropic group 2 receptor agonist with anxiolytic properties.

Journal: Journal of medicinal chemistry 20020815

Title: Dopamine modulates the function of group II and group III metabotropic glutamate receptors in the substantia nigra pars reticulata.

Journal: The Journal of pharmacology and experimental therapeutics 20020801

Title: Common and selective molecular determinants involved in metabotopic glutamate receptor agonist activity.

Journal: Journal of medicinal chemistry 20020718

Title: Role of p/q-Ca2+ channels in metabotropic glutamate receptor 2/3-dependent presynaptic long-term depression at nucleus accumbens synapses.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020601

Title: Stereoselective synthesis of 2-amino-3-fluoro bicyclo[3.1.0]hexane-2,6-dicarboxylic acid.

Journal: Bioorganic & medicinal chemistry 20020201

Title: Nicotine potentiation of brain stimulation reward reversed by DH beta E and SCH 23390, but not by eticlopride, LY 314582 or MPEP in rats.

Journal: Psychopharmacology 20020201

Title: Pharmacological and endocrinological characterisation of stress-induced hyperthermia in singly housed mice using classical and candidate anxiolytics (LY314582, MPEP and NKP608).

Journal: European journal of pharmacology 20020125

Title: The disposition, metabolism, and pharmacokinetics of a selective metabotropic glutamate receptor agonist in rats and dogs.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020101

Title: The role of striatal metabotropic glutamate receptors in Parkinson's disease.

Journal: Amino acids 20020101

Title: Identification of essential residues involved in the glutamate binding pocket of the group II metabotropic glutamate receptor.

Journal: Molecular pharmacology 20011101

Title: The antianxiety-like effects of antagonists of group I and agonists of group II and III metabotropic glutamate receptors after intrahippocampal administration.

Journal: Psychopharmacology 20011001

Title: Changes in rat serum corticosterone after treatment with metabotropic glutamate receptor agonists or antagonists.

Journal: Journal of neuroendocrinology 20010801

Title: Presynaptic group II mGluR inhibition of short-term depression in the medial perforant path of the dentate gyrus in vitro.

Journal: Journal of neurophysiology 20010601

Title: Interactions between LY354740, a group II metabotropic agonist and the GABA(A)-benzodiazepine receptor complex in the rat elevated plus-maze.

Journal: Journal of psychopharmacology (Oxford, England) 20010601

Title: Pharmacology and neuroprotective actions of mGlu receptor ligands.

Journal: Developmental medicine and child neurology. Supplement 20010301

Title: Amygdala regulation of nucleus accumbens dopamine output is governed by the prefrontal cortex.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20010115

Title: Activation of group II metabotropic glutamate receptors results in long-term potentiation following preconditioning stimulation in the dentate gyrus.

Journal: Neuroscience 20010101

Title: A major role for thalamocortical afferents in serotonergic hallucinogen receptor function in the rat neocortex.

Journal: Neuroscience 20010101

Title: Synthesis, SARs, and pharmacological characterization of 2-amino-3 or 6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent, selective, and orally active group II metabotropic glutamate receptor agonists.

Journal: Journal of medicinal chemistry 20001214

Title: Cocaine and kindling alter the sensitivity of group II and III metabotropic glutamate receptors in the central amygdala.

Journal: Journal of neurophysiology 20000801

Title: Characterization of [(3)H]-LY354740 binding to rat mGlu2 and mGlu3 receptors expressed in CHO cells using semliki forest virus vectors.

Journal: Neuropharmacology 20000724

Title: The role of metabotropic glutamate receptor (mGluR) ligands in parkinsonian muscle rigidity.

Journal: Amino acids 20000101

Title: Potential anti-anxiety, anti-addictive effects of LY 354740, a selective group II glutamate metabotropic receptors agonist in animal models.

Journal: Neuropharmacology 19991201

Title: [3H]-LY341495 as a novel antagonist radioligand for group II metabotropic glutamate (mGlu) receptors: characterization of binding to membranes of mGlu receptor subtype expressing cells.

Journal: Neuropharmacology 19991001

Title: Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.

Journal: Brain research. Molecular brain research 19990420

Title: Synthesis, pharmacological characterization, and molecular modeling of heterobicyclic amino acids related to (+)-2-aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid (LY354740): identification of two new potent, selective, and systemically active agonists for group II metabotropic glutamate receptors.

Journal: Journal of medicinal chemistry 19990325

Title: LY354740, a group II metabotropic glutamate receptor agonist with potential antiparkinsonian properties in rats.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19981001

Title: Characterization of [3H]-(2S,2'R,3'R)-2-(2',3'-dicarboxy-cyclopropyl)glycine ([3H]-DCG IV) binding to metabotropic mGlu2 receptor-transfected cell membranes.

Journal: British journal of pharmacology 19980201

Title: A novel orally active group 2 metabotropic glutamate receptor agonist: LY354740.

Journal: Neuroreport 19970414

Title: LY354740 is a potent and highly selective group II metabotropic glutamate receptor agonist in cells expressing human glutamate receptors.

Journal: Neuropharmacology 19970101

Title: Boerner T, et al. The group II metabotropic glutamate receptor agonist LY354740 and the D2 receptor antagonist haloperidol reduce locomotor hyperactivity but fail to rescue spatial working memory in GluA1 knockout mice. Eur J Neurosci. 2017 Apr;45(7):912-

Title: Orlando R, et al. Levels of the Rab GDP dissociation inhibitor (GDI) are altered in the prenatal restrain stress mouse model of schizophrenia and are differentially regulated by the mGlu2/3 receptor agonists, LY379268 and LY354740. Neuropharmacology. 2014

Title: Procaccini C, et al. Reversal of novelty-induced hyperlocomotion and hippocampal c-Fos expression in GluA1 knockout male mice by the mGluR2/3 agonist LY354740. Neuroscience. 2013 Oct 10;250:189-200

Title: Lee Y, et al. The mGlu2/3 receptor agonist LY354740 suppresses immobilization stress-induced increase in rat prefrontal cortical BDNF mRNA expression. Neurosci Lett. 2006 May 8;398(3):328-32.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:176199-48-7 Molecular Formula|176199-48-7 MDL|176199-48-7 SMILES|176199-48-7 Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)-