2743-90-0 Usage
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
Different sources of media describe the Uses of 2743-90-0 differently. You can refer to the following data:
1. A nicotine (N412420) metabolite.
2. (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.
Check Digit Verification of cas no
The CAS Registry Mumber 2743-90-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,4 and 3 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2743-90:
(6*2)+(5*7)+(4*4)+(3*3)+(2*9)+(1*0)=90
90 % 10 = 0
So 2743-90-0 is a valid CAS Registry Number.
2743-90-0Relevant articles and documents
A Practical and Efficient Synthesis of (±)-Anatabine
Rossi, Federico V.,Ballini, Roberto,Barboni, Luciano,Allegrini, Pietro,Palmieri, Alessandro
, p. 1921 - 1925 (2018/02/19)
A new efficient synthesis of racemic anatabine is reported. The title target was obtained in an excellent overall yield of 70%, by a five-step synthesis, using cheap reagents and mild reaction conditions.
Toward Pyridine-Heterocycle Patterns through Prins and Aza-Prins Cyclisations: Application to a Short Synthesis of (±)-Anabasine
Colin, Olivier,Greck, Christine,Prim, Damien,Thomassigny, Christine
, p. 7000 - 7005 (2016/02/19)
The formation of pyridine-containing bisheterocycles through a Prins-type cyclisation is described. Pyridine-tetrahydropyran and pyridine-piperidine conjugates could be efficiently obtained using various carbaldehydes including dicarbaldehydes, and either homoallylic alcohols or a homoallylic amine. Selective partial or complete hydrogenation led to new bisheterocycle combinations. A two-step sequence involving an aza-Prins cylisation allowed us to prepare the alkaloid anabasine.
From building block to natural products: A short synthesis and complete NMR spectroscopic characterization of (±)-anatabine and (±)-anabasine
Saloranta, Tiina,Leino, Reko
, p. 4619 - 4621 (2011/09/21)
A short and straightforward synthesis of the racemic tobacco alkaloids anatabine and anabasine in five and six steps, respectively, from 3-pyridinecarboxaldehyde utilizing Barbier-type Zn-mediated allylation and ring-closing olefin metathesis, as the key steps, is reported. Additionally, a complete NMR spectroscopic analysis of the final products is carried out and full assignment of the NMR spectra of anatabine and anabasine with accurate coupling constants is accomplished and reported here for the first time.
