375815-87-5

Basic information

• Product Name: Varenicline tartrate
• Synonyms: VARENICLINE TARTRATE;Varenicline tartrate for research;7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine (2R,3R)-2,3- dihydroxybutanedioate;Champix;CP 526555-18;6,10-Methano-6H-pyrazino(2,3-H)(3)benzazepine, 7,8,9,10-tetrahydro-, (2R,3R)-2,3-dihydroxybutanedioate (1:1);Unii-82269asb48;,10-Methano-6H-pyrazino[2,3-h][3]benzazepine, 7,8,9,10-tetrahydro-
• CAS NO: 375815-87-5
• Molecular Formula: C₄H₆O₆*C₁₃H₁₃N₃
• Molecular Weight: 361.34926
• EINECS: 200-659-6
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;APIs;Pfizer compounds;Chantix, Champix;Inhibitors
• Mol File: 375815-87-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 206-208°C
• Boiling Point: 400.6 °C at 760 mmHg
• Flash Point: 196.1 °C
• Appearance: white to beige/
• Vapor Pressure: 1.25E-06mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: >5mg/mL
• CAS DataBase Reference: Varenicline tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: Varenicline tartrate(375815-87-5)
• EPA Substance Registry System: Varenicline tartrate(375815-87-5)

Safety Data

• Hazard Codes: Xn,N,T,F
• Statements: 22-50-39/23/24/25-23/24/25-11
• Safety Statements: 22-57-45-36/37-16-7
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 375815-87-5(Hazardous Substances Data)

Usage

Description

Varenicline tartrate is a tartrate salt derived from the reaction of varenicline with (R,R)-tartaric acid. It functions as a partial agonist for nicotinic cholinergic receptors and is characterized by its tan solid appearance.

Uses

Used in Pharmaceutical Industry:
Varenicline tartrate is used as a prescription medication for treating smoking addiction. It acts as a nicotinic α4β2 acetylcholine receptor partial agonist, which aids in smoking cessation by reducing the pleasurable effects of smoking and decreasing withdrawal symptoms.
Used in Smoking Cessation Aids:
Varenicline tartrate is used as a smoking cessation aid to help individuals quit smoking. It works by partially activating the nicotinic a4? acetylcholine receptors, which helps to alleviate cravings and withdrawal symptoms associated with nicotine dependence.
Used in Research and Development:
Varenicline tartrate is also utilized in research and development for the study of nicotinic cholinergic receptors and their role in addiction and other related conditions. This knowledge can contribute to the development of new treatments and therapies for various nicotine-related disorders.

Biological Activity

Orally active, subtype-selective partial agonist at α 4 β 2 nicotinic receptors (K i values are 0.06, 240, 322 and 3540 nM for α 4 β 2, α 3 β 4, α 7, α 1 β γ δ receptors respectively). Reduces nicotine-evoked dopamine release in vitro and decreases nicotine self-administration in vivo .

Biochem/physiol Actions

Varenicline tartrate is a partial α4β2 nicotinic receptor agonist and α7 full agonist. Varenicline competitively binds to α4β2 receptors and partially stimulates without creating a full nicotine effect, while simultaneoudly blocking the ability of nicotine to bind to the receptors. Varenicline thus blocks the ability of nicotine to activate α4β2 receptors and stimulate the central nervous mesolimbic dopamine system, believed to be the neuronal mechanism underlying reinforcement and reward experienced upon smoking.

InChI:InChI=1/C13H13N3.C4H6O6/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1;5-1(3(7)8)2(6)4(9)10/h1-2,4-5,8-9,14H,3,6-7H2;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.0/s1

Upstream product

• 249296-44-4 varenicline 
• 87-69-4 L-Tartaric acid 
• 230615-70-0 1-(9,10-dihydro-6H-6,10-methanoazepino[4,5-g]quinoxaline-8(7H)-yl)-2,2,2,-trifluoroethanone 
• 230615-69-7 1-(7,8-diamino-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone 

Relevant articles and documents

CRYSTALLINE FORMS OF NOVEL VARENICLINE SALTS, PREPARATION METHODS THEREOF AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEREOF

The present invention refers to crystalline form of 7, 8, 9, 10 - tetrahydro - 6, 10 - methano - 6H - [3] [2, 3 a-h] pyrazole roh it cuts the person number pin new salt, and manufacturing method of including pharmaceutical compositions are disclosed. (by machine translation)

HIGHLY PURE VARENICLINE OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF SUBSTANTIALLY FREE OF METHYLVARENICLINE IMPURITY

Provided herein is an impurity of varenicline, 6-methyl-5,8,14-triazatetracyclo[l 0.3.1.02'n,04'9]hexadeca-2(l l),3,5,7,9-pentaene (methylvarenicline) impurity, and a process for the preparation and isolation thereof. Provided further herein is a highly pure varenicline or a pharmaceutically acceptable salt thereof substantially free of methylvarenicline impurity, a process for the preparation thereof, and pharmaceutical compositions comprising highly pure varenicline or a pharmaceutically acceptable salt thereof substantially free of methylvarenicline impurity.

PROCESS FOR PREPARING VARENICLINE, VARENICLINE INTERMEDIATES, AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

Provided herein is an improved, convenient, commercially viable and environmentally friendly process for the preparation of varenicline or a pharmaceutically acceptable salt thereof comprising reacting l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien- 10-yl)-2,2,2-trifluoro-ethanone with chloroacetaldehyde in the pressence of an oxygen source. Provided further herein is an improved and industrially advantageous process for the preparation of l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien-10-yl)-2,2,2- trifluoro-ethanone.