| Identification | Back Directory | [Name]
(R,S)-ANATABINE | [CAS]
2743-90-0 | [Synonyms]
D,L-ANATABINE
(R,S)-ANATABINE
ANATABINE, (+/-)-(RG)
1,2,3,6-TETRAHYDRO-2,3'-BIPYRIDINE
Anatabine, froM Nicotiana tabacuM L.
(+/-)-Anatabine, 3-(1,2,3,6-Tetrahydropyridin-2-yl)pyridine, 2-(Pyridin-3-yl)-1,2,3,6-tetrahydropyridine | [Molecular Formula]
C10H12N2 | [MDL Number]
MFCD00078278 | [MOL File]
2743-90-0.mol | [Molecular Weight]
160.22 |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Oil | [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) | [color ]
Light yellow to yellow | [Stability:]
Hygroscopic, Light Sensitive | [CAS DataBase Reference]
2743-90-0 |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow Oil | [Uses]
(R,S)-Anatabine is a metabolite of Nicotine (N412420). | [Uses]
A nicotine (N412420) metabolite. | [Uses]
A nicotine metabolite | [Description]
(R,S)-Anatabine is a minor alkaloid produced in plants of the Solanaceae family, including tobacco.1 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.2,3 (R,S)-Anatabine increases nicotine self-administration and locomotor activity in rats.4 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.5 | [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]. | [storage]
Store at -20°C | [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. |
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