7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine

Base Information

• Chemical Name: 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine
• CAS No.: 249296-44-4
• Molecular Formula: C13H13N3
• Molecular Weight: 211.266
• UNII: W6HS99O8ZO
• DSSTox Substance ID: DTXSID70891447
• Nikkaji Number: J2.192.947F
• Wikipedia: Varenicline
• Wikidata: Q411330
• NCI Thesaurus Code: C73609
• RXCUI: 591622
• Pharos Ligand ID: 3TAPHRAR5C42
• Metabolomics Workbench ID: 43474
• ChEMBL ID: CHEMBL1076903
• Mol file: 249296-44-4.mol

Synonyms:6,7,8,9-tetrahydro-6,10-methano-6H-pyrazino(2,3-h)benzazepine;Champix;Chantix;varenicline;varenicline tartrate

Chemical Property of 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine

Chemical Property:

• Vapor Pressure: 1.25E-06mmHg at 25°C
• Melting Point: 138.5 °C
• Refractive Index: 1.667
• Boiling Point: 400.6 °C at 760 mmHg
• PKA: 9.60±0.20(Predicted)
• Flash Point: 196.1 °C
• PSA: 152.87000
• Density: 1.247 g/cm³
• LogP: 0.01010
• Solubility.: Soluble in DMSO
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 211.110947427
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

99%, ^*data from raw suppliers

Varenicline >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Substance Abuse Treatment Agents
• Canonical SMILES: C1C2CNCC1C3=CC4=NC=CN=C4C=C23
• Isomeric SMILES: C1[C@@H]2CNC[C@H]1C3=CC4=NC=CN=C4C=C23
• Recent ClinicalTrials: Cannabis and Tobacco Co-use Study
• Recent EU Clinical Trials: A RANDOMIZED DOUBLE-BLIND PLACEBO-CONTROLLED MULTICENTER TRIAL ON THE EFFICACY OF VARENICLINE AND BUPROPION, IN COMBINATION AND ALONE, FOR THE TREATMENT OF ALCOHOL USE DISORDER
• Recent NIPH Clinical Trials: Effects of smoking cessation on HDL function and cardiovascular biomarkers.
• Description: Varenicline, a partial agonist of the a4b2 nicotinic receptor, is a first-in-class drug launched by Pfizer as an aid to smoking cessation treatment. Varenicline exhibits dual action by decreasing craving and withdrawal symptoms, and by decreasing the reinforcement associated with smoking. The addictive properties of nicotine are thought to be mediated in part through its action as an agonist at α4β2 neuronal nicotinic acetylcholine receptors (nAChRs). Activation of α4β2 receptors by nicotine increases the release of dopamine in the mesolimbic system, an effect that is shared by most drugs of abuse. As nicotine levels decrease, dopamine levels decline, which in turn stimulates the urge to smoke. Additionally, a reduced dopaminergic tone due to abstinence from smoking stimulates craving and the withdrawal syndrome. A partial agonist of α4β2 receptors such as varenicline is expected to elicit a moderate and sustained increase in dopamine levels to relieve craving and withdrawal symptoms. In addition, by competitively binding to a4b2 receptors and inhibiting nicotineinduced dopaminergic activation, a partial agonist could attenuate the pharmacologic reward associated with smoking.
• Uses: Varenicline is a useful medication for smoking cessation. Smoking cessation (selective nicotinic receptor modulator).
• Clinical Use: Aid to smoking cessation
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine

There total 17 articles about 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.06%

5,8,14-triazatetracyclo[10.3.1.0(2,11).0(4,9)]hexadeca-2(11).3.5,7,9-pentaene tosylate (1197286-22-8) → varenicline (249296-44-4)

Guidance literature:

With ammonia; In water; at 20 - 30 ℃; pH=9 - 10; Product distribution / selectivity;

Reference yield: 95.0%

1-(9,10-dihydro-6H-6,10-methanoazepino[4,5-g]quinoxaline-8(7H)-yl)-2,2,2,-trifluoroethanone (230615-70-0) → varenicline (249296-44-4)

Guidance literature:

With sodium carbonate; In methanol;

DOI:10.1016/j.bmcl.2005.08.035

Reference yield: 90.0%

N-benzylvarenicline → varenicline (249296-44-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 3h; under 760.051 Torr;

upstream raw materials:

1-(9,10-dihydro-6H-6,10-methanoazepino[4,5-g]quinoxaline-8(7H)-yl)-2,2,2,-trifluoroethanone

1-(4-amino-10-aza-tricyclo[6.3.1.0^2,7]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanone

5,8,14-triazatetracyclo[10.3.1.0(2,11).0(4,9)]hexadeca-2⁽¹¹⁾.3.5,7,9-pentaene tosylate

C₂₁H₂₁N₃O

Downstream raw materials:

varenicline L-tartarate

5,8,14-triazatetracyclo[10.3.1.0(2,11).0(4,9)]hexadeca-2⁽¹¹⁾.3.5,7,9-pentaene tosylate

Refernces

Metal-Free-Visible Light C-H Alkylation of Heteroaromatics via Hypervalent Iodine-Promoted Decarboxylation

10.1021/acs.orglett.8b01085

The study presents a metal-free photoredox C?H alkylation of heteroaromatics using hypervalent iodine dicarboxylates and an organic photocatalyst, 9-mesityl-10-methyl acridinium (MesAcr), under blue LED light. The method leverages readily available carboxylic acids as coupling partners and operates under mild conditions at room temperature. Key chemicals include bis(trifluoroacetoxy)iodobenzene (PIFA) as the oxidant, which helps avoid complications from forming undesired alkylated products and eliminates the need for additional trifluoroacetic acid. The study explores the scope of various carboxylic acids, which generate different alkyl radicals (primary, secondary, tertiary) under the reaction conditions, and tests a range of heteroaromatics and complex molecules, including drugs like voriconazole, varenicline, and quinine, demonstrating good functional group tolerance. Mechanistic investigations, including control experiments, photophysical studies, and DFT calculations, suggest a distinct reaction mechanism involving a chain reaction with a low quantum yield, likely due to an inefficient initiation step.

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