71719-06-7

Basic information

• Product Name: 3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE
• Synonyms: 5-BROMO-3-(2-PYRROLIDINYL)PYRIDINE;3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE;3-BROMO-5-PYRROLIDIN-2-YL-PYRIDINE;(S)-3-bromo-5-(pyrrolidin-2-yl)pyridine hydrochloride;(R,S)-3-BroMo Nornicotine
• CAS NO: 71719-06-7
• Molecular Formula: C₉H₁₁BrN₂
• Molecular Weight: 227.1
• EINECS: 200-258-5
• Product Categories: Heterocycles;Nicotine Derivatives;Aromatics;Chiral Reagents;Mutagenesis Research Chemicals
• Mol File: 71719-06-7.mol

Chemical Properties

• Boiling Point: 295.4°C at 760 mmHg
• Flash Point: 132.5°C
• Appearance: /
• Density: 1.434g/cm³
• Vapor Pressure: 0.00153mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.56±0.10(Predicted)
• CAS DataBase Reference: 3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE(71719-06-7)
• EPA Substance Registry System: 3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE(71719-06-7)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 71719-06-7(Hazardous Substances Data)

Usage

Uses

Used in Immunoassays:
3-Bromo-5-(2-pyrrolidinyl)pyridine is used as haptens in immunoassays for the detection of specific antibodies. Its structural similarity to Nornicotine allows it to bind to antibodies that target this compound, enabling the development of sensitive and specific immunoassays for various applications.
Used in Pharmaceutical Research:
As a Nornicotine analog, 3-Bromo-5-(2-pyrrolidinyl)pyridine can be used in pharmaceutical research to study the effects of Nornicotine and develop potential therapeutic agents targeting the nicotine receptors. This can lead to the discovery of new drugs for the treatment of nicotine addiction and related disorders.
Used in Chemical Synthesis:
3-Bromo-5-(2-pyrrolidinyl)pyridine can also be used as a starting material or intermediate in the synthesis of various chemical compounds. Its unique structure allows for further functionalization and modification, making it a versatile building block for the development of new molecules with potential applications in various industries.

InChI:InChI=1/C9H11BrN2/c10-8-4-7(5-11-6-8)9-2-1-3-12-9/h4-6,9,12H,1-3H2

Upstream product

• 64319-85-3 3-bromo-5-(4,5-dihydro-3H-pyrrol-2-yl)-pyridine 
• 20826-04-4 5-bromo-3-pyridinecarboxylic acid 
• 20986-40-7 ethyl 5-bromo-3-pyridinecarboxylate 
• 201292-62-8 3-(5-Bromo-pyridine-3-carbonyl)-1-vinyl-pyrrolidin-2-one 
• 201610-91-5 5-bromo-3-(2-pyrrolin-1-yl)pyridine 

Downstream Products

• 83023-58-9 (S)-5-bromo-3-(1H-2-pyrrolidinyl)pyridine 
• 83023-56-7 3-bromo-5-(pyrrolidin-2-yl)pyridine 
• 71719-09-0 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine 
• 5746-86-1 rac-nornicotine 
• 263888-13-7 (2'R)-N'-[(1R,2S,5R)-Menthoxycarbonyl]-5-bromonornicotine 
• 263888-14-8 (2'S)-N'-[(1R,2S,5R)-Menthoxycarbonyl]-5-bromonornicotine 
• 350820-80-3 rac-2-(3-pyridinyl)-1-pyrrolidinebutanoic acid phenylmethyl ester 
• 179120-51-5 SIB-1765F 
• 494-97-3 nornicotine 
• 7076-23-5 (+)-nornicotine 

Relevant articles and documents

Prescreening of Nicotine Hapten Linkers in Vitro To Select Hapten-Conjugate Vaccine Candidates for Pharmacokinetic Evaluation in Vivo

Since the demonstration of nicotine vaccines as a possible therapeutic intervention for the effects of tobacco smoke, extensive effort has been made to enhance nicotine specific immunity. Linker modifications of nicotine haptens have been a focal point for improving the immunogenicity of nicotine, in which the evaluation of these modifications usually relies on in vivo animal models, such as mice, rats or nonhuman primates. Here, we present two in vitro screening strategies to estimate and predict the immunogenic potential of our newly designed nicotine haptens. One utilizes a competition enzyme-linked immunoabsorbent assay (ELISA) to profile the interactions of nicotine haptens or hapten-protein conjugates with nicotine specific antibodies, both polyclonal and monoclonal. Another relies on computational modeling of the interactions between haptens and amino acid residues near the conjugation site of the carrier protein to infer linker-carrier protein conjugation effect on antinicotine antibody response. Using these two in vitro methods, we ranked the haptens with different linkers for their potential as viable vaccine candidates. The ELISA-based hapten ranking was in an agreement with the results obtained by in vivo nicotine pharmacokinetic analysis. A correlation was found between the average binding affinity (IC50) of the haptens to an anti-Nic monoclonal antibody and the average brain nicotine concentration in the immunized mice. The computational modeling of hapten and carrier protein interactions helps exclude conjugates with strong linker-carrier conjugation effects and low in vivo efficacy. The simplicity of these in vitro screening strategies should facilitate the selection and development of more effective nicotine conjugate vaccines. In addition, these data highlight a previously under-appreciated contribution of linkers and hapten-protein conjugations to conjugate vaccine immunogenicity by virtue of their inclusion in the epitope that binds and activates B cells.

METHODS OF RATIONAL NICOTINE HAPTEN DESIGN AND USES THEREOF

Provided herein are methods for rational design of nicotine haptens. More particularly, provided herein are methods for designing, selecting, and synthesizing nicotine haptens and nicotine hapten conjugates. Also provided herein are novel nicotine haptens and methods for using nicotine haptens to treat nicotine addiction.

COMPOUNDS AND METHODS FOR THE DIAGNOSIS AND TREATMENT OF AMYLOID ASSOCIATED DISEASES

The invention is in general directed to compounds, such as tannic acid, nicotine, nicotine derivatives and pyrrolidine derivatives of nicotine, and methods for diagnosing, preventing or alleviating the symptoms of amyloid-associated diseases, for example, neuronal diseases, such as, for example, Alzheimer's disease, compounds and methods for inhibiting ion channel activity of beta amyloid, and methods of diagnostic imaging of A/3 fibrils.

An immunotherapeutic program for the treatment of nicotine addiction: Hapten design and synthesis

People continue to smoke and use tobacco products despite well-established hazardous consequences. The most contributing factor is the addictive nature of nicotine. There is no highly effective treatment for the problem of nicotine dependence. Immunotherapy offers an alternative to conventional approaches. The chemistry necessary for a comprehensive immunopharmacological program is presented. Haptens for the generation of antibodies specific for naturally occurring (S)-nicotine, (S)- and (R)-nornicotine, and the metabolite (S)-cotinine were prepared with high optical purity. Preliminary data for antinicotine antibodies are reported.

A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (S)-(-)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)

An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholinegated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis(trimethylsilyl)amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5-bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new heteroaryl-alkyne cross-coupling protocol for the introduction of the ethyne moiety in (S)-2. The preparation of enantiomerically pure (S)-2 was accomplished via a combination of enantioselective reduction of imine 5 and crystallization of enantiomerically enriched 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (7) as the dibenzoyl-L-tartaric acid salt.

MODULATORS OF ACETYLCHOLINE RECEPTORS

The present invention provides a class of pyridine compounds which are modulators of acetylcholine receptors, i.e., compounds which displace acetylcholine receptor ligands from their binding sites. Invention compounds may act as agonists, partial agonists

MODULATORS OF ACETYLCHOLINE RECEPTORS

The present invention provides a class of pyridine compounds which are modulators of acetylcholine receptors, i.e., compounds which displace acetylcholine receptor ligands from their binding sites. Invention compounds may act as agonists, partial agonists

METHODS FOR THE PREPARATION OF MODULATORS OF ACETYLCHOLINE RECEPTORS

In accordance with the present invention, there is provided a class of pyridine compounds which are modulators of acetylcholine receptors. The compounds of the invention displace acetylcholine receptor ligands from their binding sites. Invention compounds

Modulators of acetylcholine receptors

In accordance with the present invention, there is provided a class of pyridine compounds which are modulators of acetylcholine receptors. The compounds of the invention displace acetylcholine receptor ligands from their binding sites. Invention compounds

MODULATORS OF ACETYLCHOLINE RECEPTORS

gIn accordance with the present invention, there is provided a class of pyridine compounds which are modulators of acetylcholine receptors. The compounds of the invention displace acetylcholine receptor ligands from their binding sites. Invention compound