Varenicline tartrate

Iupac Name：(2R,3R)-2,3-dihydroxybutanedioic acid;5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

CAS No.: 375815-87-5

Molecular Weight：361.354

Modify Date.: 2022-11-22 20:09

Introduction: Nicotinic a4? acetylcholine receptor partial agonist. Aid in smoking cessation. View more+

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1. Names and Identifiers

1.1 Name: Varenicline tartrate
1.2 Synonyms: (1R,12S)-5,8-Diaza-14-azoniatetracyclo[10.3.1.0.0]hexadeca-2(11),3,5,7,9-pentaen-(2R,3R)-3-carboxy-2,3-dihydroxypropanoat (1R,12S)-5,8-Diaza-14-azoniatetracyclo[10.3.1.0.0]hexadeca-2(11),3,5,7,9-pentaene (2R,3R)-3-carboxy-2,3-dihydroxypropanoate (2R,3R)-3-carboxy-2,3-dihydroxypropanoate de (1R,12S)-5,8-diaza-14-azoniatétracyclo[10.3.1.0.0]hexadéca-2(11),3,5,7,9-pentaène ,10-Methano-6H-pyrazino[2,3-h][3]benzazepine, 7,8,9,10-tetrahydro- 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine (2R,3R)-2,3- dihydroxybutanedioate 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine tartrate Champix Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-, compd. with (6R,10S)-7,8,9,10-tetrahydro-6,10-methano-6H-azepino[4,5-g]quinoxaline (1:1) Champix Chantix CP 526555-18 CS-291 Varenicline Tartarate Varenicline tartrate for research

1.3 CAS No.: 375815-87-5

1.4 CID: 9906942

1.5 EINECS(EC#): 638-780-5

1.6 Molecular Formula: C17H19N3O6 (isomer)

1.7 Inchi: InChI=1S/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.1/s1

1.8 InChkey: TWYFGYXQSYOKLK-LREBCSMRSA-N

1.9 Canonical Smiles: C1C2CNCC1C3=CC4=NC=CN=C4C=C23.C(C(C(=O)O)O)(C(=O)O)O

1.10 Isomers Smiles: C1C2CNCC1C3=CC4=NC=CN=C4C=C23.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

2. Properties

2.1 Melting point: 206-208°C

2.1 Boiling point: 400.6 °C at 760 mmHg

2.1 Flash Point: 400.6 °C at 760 mmHg

2.1 Precise Quality: 243.10500

2.1 PSA: 23.79000

2.1 logP: 4.49528

2.1 Solubility: DMSO: >5mg/mL

2.2 Appearance: white to beige

2.3 Storage: Desiccate at RT

2.4 Chemical Properties: Tan Solid

2.5 Color/Form: Powder

2.6 Water Solubility: DMSO: >5mg/mL

2.7 StorageTemp: room temp

3. Use and Manufacturing

3.1 Definition: ChEBI: A tartrate salt obtained by reaction of varenicline with one equivalent of (R,R)-tartaric acid. A partial agonist for nicotinic cholinergic receptors, it is used as an aid to giving up smoking.

3.2 Usage: Nicotinic a4? acetylcholine receptor partial agonist. Aid in smoking cessation.

4. Safety and Handling

4.1 Symbol: GHS02, GHS06, GHS08

4.1 Hazard Codes: Xn,N,T,F

4.1 Signal Word: Danger

4.1 Risk Statements: 22-50-39/23/24/25-23/24/25-11

4.1 Safety Statements: 22-57-45-36/37-16-7

4.1 Hazard Declaration: H225-H301 + H311 + H331-H370

4.1 RIDADR: UN 3077 9 / PGIII

4.1 Caution Statement: P210-P260-P280-P301 + P310-P311

4.1 WGK Germany: 3

4.1 Specification

The?systematic name of?Varenicline tartrate 7,8,9,10-tetrahydro-6H-6,10-methanoazepino[4,5-g]quinoxaline 2,3-dihydroxybutanedioate (1:1) . With the?CAS registry number 375815-87-5, it is also named as?6,10-Methano-6H-pyrazino(2,3-h)(3)benzazepine, 7,8,9,10-tetrahydro-, (2R,3R)-2,3-dihydroxybutanedioate (1:1) ; CP 526555-18 ; Champix ; Chantix ; UNII-82269ASB48 .

The?Varenicline tartrate is?tan solid. It?is a drug for the treatment of nicotine addiction which was developed by a pharmaceutical company in?United States.?In 2006, the drug is approved?by U.S. Food and Drug Administration?(FDA), which is?the first new prescription smoking cessation drugs in the?last 10 years.?The most common side effects?are including nausea, abnormal dreams, constipation, flatulence and vomiting.

The product is 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 .

The other characteristics of this product can be summarized as:?(1)#H bond acceptors: 3 ; (2)#H bond donors: 1 ; (3)Enthalpy of Vaporization: 65.15 kJ/mol ; (4)Vapour Pressure: 1.25E-06 mmHg at 25°C ; (5)Rotatable Bond Count: 3 ; (6)Exact Mass: 361.127385 ; (7)MonoIsotopic Mass: 361.127385 ; (8)Topological Polar Surface Area: 153 ; (9)Heavy Atom Count: 26 ; (10)Complexity: 388.

People can use the following data to convert to the molecule structure.?SMILES: O=C(O)[C@@H](O)[C@H](O)C(=O)O.n1c2cc3c(cc2ncc1)C4CNCC3C4;?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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

375815-87-5Total: 1 Synthesis Route

249296-44-4 86 Suppliers

87-69-4 580 Suppliers

375815-87-5 113 Suppliers

Literatures:
Medichem, S.A. Patent: US2012/4239 A1, 2012 ; Location in patent: Page/Page column 12 ;
Yield: ~64%

7. Precursor and Product

precursor:

87-69-4

249296-44-4

8. Other Information

8.0 Mesh: Drugs that bind to and activate nicotinic cholinergic receptors (RECEPTORS, NICOTINIC). Nicotinic agonists act at postganglionic nicotinic receptors, at neuroeffector junctions in the peripheral nervous system, and at nicotinic receptors in the central nervous system. Agents that function as neuromuscular depolarizing blocking agents are included here because they activate nicotinic receptors, although they are used clinically to block nicotinic transmission. (See all compounds classified as Nicotinic Agonists.)|Substances that facilitate the cessation of tobacco smoking. (See all compounds classified as Smoking Cessation Agents.)

8.1 Mesh Entry Terms: 6,7,8,9-tetrahydro-6,10-methano-6H-pyrazino(2,3-h)benzazepine

8.2 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

8.3 Target: Value

8.4 Chemical Properties: Tan Solid

8.5 Uses: Nicotinic a4? acetylcholine receptor partial agonist. Aid in smoking cessation.

8.6 Uses: Nicotinic α4β2 acetylcholine receptor partial agonist. Aid in smoking cessation.

8.7 Uses: Varenicline tartrate is a prescription medication used to treat smoking addiction. Varenicline is a nicotinic receptor partial agonist. In this respect, it is similar to cytisine and different from the nicotinic antagonist, bupropion, and nicotine replacement ther

8.8 Definition: ChEBI: A tartrate salt obtained by reaction of varenicline with one equivalent of (R,R)-tartaric acid. A partial agonist for nicotinic cholinergic receptors, it is used as an aid to giving up smoking.

8.9 Brand name: Chantix (Pfizer).

8.10 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 .

8.11 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.

9. Computational chemical data

Molecular Weight: 361.354g/mol
Molecular Formula: C₁₇H₁₉N₃O₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 361.12738533
Monoisotopic Mass: 361.12738533
Complexity: 388
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 9
Topological Polar Surface Area: 153
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 2
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7OAAAAAAAAAAAAAAAAAAAAYAAAAA8WIAABYAAAGCx8AAAHgAQCAAADRzhngY8yLLIEgCoAzT3TAKCgCQxEiAI2KF4dJgJcPbAkZGUYAhlsADJyAdTgMAOiAAAQAAQACAQAACAACAAQQAACAAAAA==

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