623579-03-3

Basic information

• Product Name: (2S,3R)-rel-1-Methyl-2-(3-pyridinyl)-3-pyrrolidinemethanamine
• Synonyms: (2S,3R)-rel-1-Methyl-2-(3-pyridinyl)-3-pyrrolidinemethanamine;rac-trans 3’-Aminomethyl Nicotine;rac-trans 3a€-Aminomethyl Nicotine
• CAS NO: 623579-03-3
• Molecular Formula: C11H17N3
• Molecular Weight: 191.27278
• Product Categories: Amines;Heterocycles;Nicotine Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 623579-03-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• CAS DataBase Reference: (2S,3R)-rel-1-Methyl-2-(3-pyridinyl)-3-pyrrolidinemethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-rel-1-Methyl-2-(3-pyridinyl)-3-pyrrolidinemethanamine(623579-03-3)
• EPA Substance Registry System: (2S,3R)-rel-1-Methyl-2-(3-pyridinyl)-3-pyrrolidinemethanamine(623579-03-3)

Safety Data

• Hazardous Substances Data: 623579-03-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R)-rel-1-Methyl-2-(3-pyridinyl)-3-pyrrolidinemethanamine is used as a nicotine conjugate for the therapy of nicotine addiction. As a conjugate, it can potentially help in reducing the cravings for nicotine and aid in the treatment of nicotine addiction by providing a controlled release of nicotine or by acting as a partial agonist at the nicotine receptors.
Used in Chemical Industry:
(2S,3R)-rel-1-Methyl-2-(3-pyridinyl)-3-pyrrolidinemethanamine, being a yellow oil, can be utilized as a starting material or intermediate in the synthesis of various other organic compounds. Its unique structure and functional groups can be further modified or used in the development of new molecules with specific applications in the chemical industry.

Upstream product

• 939437-34-0 (±)-trans-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxamide 

Downstream Products

• 272124-60-4 (-)-((2S,3R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-3-yl)methanamine 

Relevant articles and documents

A conjugate vaccine using enantiopure hapten imparts superior nicotine-binding capacity

A leading nicotine conjugate vaccine was only efficacious for one-third of clinical trial participants, likely due in part to its use of racemic nicotine hapten, (±)-3′-AmNic. Immunization of male Wistar rats with (+)-, (-)-, or (±)-3′-AmNicSucTT and subsequent antibody immunoassays suggest that a vaccine using enantiopure (-)-3′-AmNic hapten imparts superior capacity to bind (-)-nicotine. Future nicotine vaccine clinical candidates must incorporate this design consideration (i.e., hapten enantiopurity) in order to maximize efficacy.

ENANTIOPURE HAPTENS FOR NICOTINE VACCINE DEVELOPMENT

The invention provides chiral haptens (-)-3'-AmNic and (-)-N4N for use in generating antibodies in a patient specific for (-)-nicotine. The haptens can be conjugated to suitable carrier proteins and administered as an antigenic mixture, optionally comprising adjuvant(s), to a patient suffering from nicotine or tobacco addiction or habituation.