(R,S)-ANATABINE

Base Information

• Chemical Name: (R,S)-ANATABINE
• CAS No.: 2743-90-0
• Molecular Formula: C10H12N2
• Molecular Weight: 160.219
• Hs Code.: 29399990
• Mol file: 2743-90-0.mol

Synonyms:(±)-1,2,3,6-Tetrahydro-2,3'-bipyridine;2-(3-Pyridyl)-1,2,3,6-tetrahydropyridine;1,2,3,6-Tetrahydro-2,3'-bipyridine;1,2,3,6-Tetrahydro-2,3'-dipyridine;D,L-Anatabine;

Chemical Property of (R,S)-ANATABINE

Chemical Property:

• Appearance/Colour: Light Yellow Oil
• Boiling Point: 269 °C at 760 mmHg
• PKA: 8.84±0.40(Predicted)
• Flash Point: 116.5 °C
• PSA: 24.92000
• Density: 1.045 g/cm³
• LogP: 2.00100
• Storage Temp.: Amber Vial, Refrigerator, Under Inert Atmosphere
• Solubility.: ≤15mg/ml in DMSO;15mg/ml in dimethyl formamide

Purity/Quality:

99% ^*data from raw suppliers

(R,S)-Anatabine ^*data from reagent suppliers

Safty Information:

• Statements: 25-36
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: (R,S)-Anatabine is a minor alkaloid produced in plants of the Solanaceae family, including tobacco. The detection of (R,S)-anatabine in urine is used as an indicator of tobacco use, particularly when nicotine-containing products (gum, patches, inhalers, and medications) are also being used. (R,S)-Anatabine increases nicotine self-administration and locomotor activity in rats. Of note, (R,S)-anatabine diminishes amyloid-β production in vitro and in vivo. (R,S)-Anatabine reduces (600 μg/ml) the transcription and protein levels of β-secretase, lowering the amount of Aβ (1-40) and Aβ (1-42) in a dose dependent manner in SHSY-5Y cells. (R,S)-Anatabine also dose dependently inhibits NF-κB activation.
• Uses: A nicotine (N412420) metabolite. (R,S)-Anatabine is a metabolite of Nicotine (N412420).

Technology Process of (R,S)-ANATABINE

There total 17 articles about (R,S)-ANATABINE 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: 72.0%

tert-butyl 3,6-dihydro-[2,3'-bipyridine]-1(2H)-carboxylate (1159977-12-4) → (+/-)-Anatabine (2743-90-0,126454-22-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 8h;

DOI:10.1055/s-0036-1591538

Reference yield: 60.0%

N-(prop-2-en-1-yl)-1-(pyridin-3-yl)but-3-en-1-amine (1332337-79-7) → (+/-)-Anatabine (2743-90-0,126454-22-6)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.06.093

Reference yield: 59.0%

→ (+/-)-Anatabine (2743-90-0,126454-22-6)

Guidance literature:

With pyridine; water; for 72h; Ambient temperature;

DOI:10.1139/v97-073

upstream raw materials:

Benzhydrylidene-((Z)-5-chloro-1-pyridin-3-yl-pent-3-enyl)-amine

3-Aminomethylpyridine

N-(diphenylmethylene)-1-(pyridin-3-yl)methanamine

(+/-)-N-methylanatabine-N-oxide

Downstream raw materials:

anabasine

tert-butyl 3,6-dihydro-[2,3'-bipyridine]-1(2H)-carboxylate

2,3'-bipyridine

Refernces

• 1、 -. "Preparation method for anatabine". Paragraph 0021; 0029; 0030; 0038; 0039; 0047; 0048. . Retrieved 2017/11/04.
• 2、 -. "METHODS OF SYNTHESIZING ANATABINE". Page/Page column 5. . Retrieved 2011/10/12.