(R,S)-ANATABINE Chemical Properties

Boiling point:

136

Density 

1.045±0.06 g/cm3(Predicted)

storage temp. 

Amber Vial, Refrigerator, Under Inert Atmosphere

solubility 

≤15mg/ml in DMSO;15mg/ml in dimethyl formamide

form 

solution in ethanol.

pka

8.84±0.40(Predicted)

Stability:

Hygroscopic, Light Sensitive

CAS DataBase Reference

2743-90-0

Safety Information

Risk Statements 

25-36

Safety Statements 

24/25

RIDADR 

2810

HazardClass 

IRRITANT

HS Code 

29399990

(R,S)-ANATABINE Usage And Synthesis

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.

Chemical Properties

Light Yellow Oil

Uses

A nicotine metabolite

Uses

A nicotine (N412420) metabolite.

Uses

(R,S)-Anatabine is a metabolite of Nicotine (N412420).

in vitro

anatabine dose-dependently lowered aβ1-40 and aβ1-42 levels and reduced sappβ production without any effects on sappα levels. anatabine lowered aβ production by mainly impacting the β-cleavage of app. anatabine lowered nfκb activation. anatabine inhibited bace-1 transcription and reduced bace-1 protein levels in human neuronal like shsy-5y cells. (r,s)-anatabine also dose dependently inhibits nf-κb activation [1].

in vivo

in a transgenic mouse model of alzheimer's disease, acute treatment with anatabine for 4 days significantly lowered brain soluble aβ1-40 and aβ1-42 levels [1].

References

[1] paris d, beaulieu-abdelahad d, bachmeier c, et al. anatabine lowers alzheimer's aβ production in vitro and in vivo[j]. european journal of pharmacology, 2011, 670(2): 384-391.

(R,S)-ANATABINE(2743-90-0)Related Product Information

• Neotuberostemonine
• (+/-)-ANABASINE
• 2,3'-Bipyridine
• (R,S)-ANATABINE-2,4,5,6-D4
• S-(-)-ANATABINE
• ANATABINE
• (R,S)-N-NITROSOANATABINE
• (R,S)-N-NITROSOANATABINE-2,4,5,6-D4
• 1-(3-METHYL-6-(5-METHYL-6-PHENYLPYRIDIN-3-YL)-2-PHENYL-5,6-DIHYDROPYRIDIN-1(2H)-YL)ETHANONE
• (R,S)-Anatabine-d4
• 5,5'-DIMETHYL-6,6'-DIPHENYL-1,2,3,6-TETRAHYDRO-2,3'-BIPYRIDINE
• 2-CHLORO-1-(3-METHYL-6-(5-METHYL-6-PHENYLPYRIDIN-3-YL)-2-PHENYL-5,6-DIHYDROPYRIDIN-1(2H)-YL)ETHANONE
• (R,S)-ANATABINE BITARTRATE
• (3-METHYL-6-(5-METHYL-6-PHENYLPYRIDIN-3-YL)-2-PHENYL-5,6-DIHYDROPYRIDIN-1(2H)-YL)(PHENYL)METHANONE
• (R,S)-ANATABINE