494-52-0

Basic information

• Product Name: (-)-ANABASINE
• Synonyms: (-)-anabasin;(s)-3-(2-piperidinyl)pyridine;2-(3-pyridyl)-piperidin;3-(2-Piperidinyl)pyridine;3-(2-piperidyl)-pyridin;Anabasin;Anabazin;l-3-(2’-piperidyl)pyridine
• CAS NO: 494-52-0
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23
• EINECS: 207-791-3
• Product Categories: Aromatics Compounds;Aromatics;Chiral Reagents;Nicotine Derivatives
• Mol File: 494-52-0.mol

Chemical Properties

• Melting Point: 9°C
• Boiling Point: 270-272°C
• Flash Point: 93°C
• Appearance: White fine crystalline powder
• Density: 1,0455 g/cm3
• Vapor Pressure: 0.00662mmHg at 25°C
• Refractive Index: 1.5430
• Storage Temp.: Refrigerator
• PKA: 8.98±0.10(Predicted)
• Merck: 14,619
• BRN: 82637
• CAS DataBase Reference: (-)-ANABASINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ANABASINE(494-52-0)
• EPA Substance Registry System: (-)-ANABASINE(494-52-0)

Safety Data

• Hazard Codes: T
• Statements: 27/28-51/53-23/24/25
• Safety Statements: 28-36/37-45-61-36/37/39-28A
• RIDADR: 3140
• RTECS: BV4375000
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 494-52-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Anabasine is used as a nicotinic receptor agonist for its potential therapeutic applications in the treatment of various conditions related to the nervous system. Its agonistic properties on nicotinic receptors can be utilized to modulate neurotransmission and potentially provide relief from certain neurological disorders.
Used in Agriculture:
(-)-Anabasine is used as an insecticide due to its natural occurrence in certain plant species. It can help protect crops from pests and improve overall agricultural productivity.
Used in Metal Anticorrosive Applications:
(-)-Anabasine is also used as a metal anticorrosive agent, where it can help protect metal surfaces from corrosion and extend the lifespan of various metal components in industrial applications.

Health Hazard

The acute toxic symptoms include increasedsalivation, confusion, disturbed vision, photophobia,nausea, vomiting, diarrhea, respiratorydistress, and convulsions. It causesrespiratory muscle stimulation similar to thatcaused by lobeline. An oral lethal dose indogs is 50 mg/kg. A subcutaneous lethaldose in guinea pigs is 10 mg/kg.

Biological Activity

Anabasine ((S)-Anabasine) is an alkaloid, a component of tobacco. Anabasine is a botanical insecticide that acts as a pan-agonist of nicotinic acetylcholine receptors (nAChRs). Anabasine induces depolarization in TE671 cells endogenously expressing human myogenic nAChRs (EC50=0.7 μM).

Safety Profile

Poison by ingestion,subcutaneous, and intravenous routes. Moderately toxicby skin contact. An experimental teratogen. Insecticide.Acute and subacute toxicity: increased salivation, vertigo,confusion, disturbed vision and hearing, photophobia,cold ext

in vivo

Anabasine significantly reverses the impairment at the 0.2 mg/kg (p<0.05) and 2 mg/kg doses (p<0.025). Anabasine does not have any significant effects on response latency when administered alone. The 0.06 mg/kg Anabasine dose, in fact, significantly (p<0.05) exacerbates the dizocilpine-induced impairment. None of these Anabasine doses affects choice accuracy on their own. Individual dose comparisons show that the 0.06 mg/kg Anabasine dose plus dizocilpine (6.7±2.6) causes a significant (p<0.05) increase in non-response trials compare with dizocilpine alone (2.1±0.8).

InChI:InChI=1/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2/p+1/t10-/m0/s1

Upstream product

• 581-49-7 anatabine 
• 13078-04-1 anabasine 
• 31944-77-1 (2S)-N-benzyl-2-(3-pyridyl)-piperidine 
• 121675-95-4 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-(S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl-tetrahydro-pyran-3-yl ester 
• 314280-34-7 (S)-3,6-2H-[2,3']bipyridinyl-1-carboxylic acid 
• 337974-58-0 (2S)-N-[(1S)-1-phenylethyl]-2-(3-pyridyl)-4-piperidine 
• 40179-50-8 (2S)-N-4'-nitrobenzoyl-2-(3-pyridyl)-4-piperidine 
• 283610-12-8 (2R)-2-phenyl-2-[(2'R)-2'-(3''-pyridyl)-1-piperidinyl]-1-ethanol 
• 1966-44-5 rac-N-methylanabasine 
• 22971-46-6 5-oxo-5-(pyridin-3-yl)pentanoic acid 
• 500-22-1 3-pyridinecarboxaldehyde 
• 337974-57-9 (S)-8-((S)-1-Phenyl-ethyl)-7-pyridin-3-yl-1,4-dithia-8-aza-spiro[4.5]decane 
• 141120-47-0 benzyl-pyridin-3-ylmethylene-amine 
• 141120-60-7 (2S)-N-benzyl-2-(3-pyridyl)-4-piperidinone 

Downstream Products

• 719-84-6 (Ξ)-1-((S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridyl-1-yl)-propan-2-ol 
• 31944-77-1 (2S)-N-benzyl-2-(3-pyridyl)-piperidine 
• 56078-09-2 N-(methoxycarbonyl)anabasine 
• 581-50-0 2,3'-bipyridine 
• 13078-04-1 anabasine 
• 1133-64-8 N'-Nitrosoanabasine 
• 40179-50-8 (2S)-N-4'-nitrobenzoyl-2-(3-pyridyl)-4-piperidine 
• 59-67-6 nicotinic acid 
• 110-86-1 pyridine 
• 100-70-9 2-Cyanopyridine 
• 100-54-9 pyridine-3-carbonitrile 
• 53912-89-3 (2S)-2-(3-pyridyl)piperidine hydrochloride 
• 20377-52-0 (S)-(-)-anabasine hydroiodide 
• 6944-24-7 N-Benzoylanabasin 

Relevant articles and documents

Absolute configuration of anabasine from Messor and Aphaenogaster ants

A method has been developed to assign the absolute configuration and enantiomeric excess of anabasine based on small amounts of material (in the microgram range), by derivatization with (+)-menthylchloroformate followed by capillary GC analysis of the resulting carbamate(s). This method was applied to three samples of anabasine isolated from Messor and Aphaenogaster ants. In Messor sanctus, only (2′S)-anabasine was present, whereas in Aphaenogaster subterranea and A. miamiana (2′S)-anabasine was determined to have an ee of 78 and 24%, respectively.

Iridium-catalyzed asymmetric hydrogenation of 2-pyridyl cyclic imines: A highly enantioselective approach to nicotine derivatives

A highly efficient asymmetric hydrogenation of cyclic imines containing a pyridyl moiety was established by using iridium catalysts with chiral spiro phosphine-oxazoline ligands. This process will facilitate the development of new nicotine-related pharmaceuticals. The introduction of a substituent at the ortho position of the pyridyl ring to reduce its coordinating ability ensures the success of the hydrogenation and excellent enantioselectivity.

Nicotine and pesticide poisonous chenopodium album method for the asymmetric synthesis of alkali

The invention relates to an asymmetric synthesis method for botanical pesticide nicotine and anabasine. The low-cost and easily acquired 2,5-dibromopyridine is taken as an initial raw material and is processed in two steps, so that the hydrogenation precursor annular imine is acquired; under the induction of the chiral catalyst, iridium-phosphine oxazoline, an important hydrogenated product intermediate is acquired through high enantioselectivity; the intermediate is processed in two steps, so that L-nicotine is acquired; the intermediate is converted into L-anabasine in one step. The asymmetric hydrogenation of the annular imine containing pyridine gene is taken as the key step of the method. According to the invention, the chiral catalyst, iridium-phosphine oxazoline, is used for catalyzing the asymmetric hydrogenation and the key intermediate with ultrahigh ee value is acquired, and then the methylation and reduction bromine-removing two-step reaction is performed for converting, so that the target products, natural nicotine and anabasine, are acquired. According to the invention, the operation is stable, the purity is high and the cost is low.

Experimental and quantum-chemical studies of anabasine complexes with copper(II) and zinc(II) ions

Anabasine copper(II) and zinc(II) complexes have been studied using experimental methods and quantum-chemical studies. Preferred coordination centers and possible structures of the complexes have been determined. It has been revealed, that the main coordi

Asymmetric synthesis of 2-heteroaryl cyclic amines: Total synthesis of (-)-anabasine

A new and concise method for the synthesis of enantioenriched 2-heteroaryl cyclic amines was developed through an intramolecular chirality transfer. The influence of the nature of both ring size and heteroaryl moiety was investigated. The versatility of this reaction was demonstrated by the enantioselective synthesis of (-)-anabasine. Copyright

Development of an R-selective amine oxidase with broad substrate specificity and high enantioselectivity

Amine oxidases are useful bio-catalysts for the synthesis of enantiomerically pure 1°, 2° and 3° chiral amines. Enzymes in this class (e.g., MAO-N from Aspergillus niger) reported previously have been shown to be highly S selective. Herein we report the development of an enantiocomplementary R-selective amine oxidase based on 6-hydroxy-D-nicotine oxidase (6-HDNO) with broadened substrate scope and high enantioselectivity. The engineered 6-HDNO enzyme has been applied to the preparative deracemisation of a range of racemic amines to yield S-configured products, for example, (S)-nicotine, in high ee. Nicotine rush: An R-selective amine oxidase based on 6-hydroxy-D-nicotine oxidase (6-HDNO) with broadened substrate scope and high enantioselectivity has been developed. The engineered 6-HDNO enzyme is applied to the preparative deracemization of a range of racemic amines to yield S-configured products, for example, (S)-nicotine, in high ee.

A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

A three-component diastereoselective vinylogous Mannich-type reaction (VMR) with the silyl ketene acetal (1) was developed. Adducts from the reactions provided valuable intermediates for construction of a variety of chiral 6-alkylated piperidinone and 2-piperidine compounds. The strategy was applied in a concise synthesis (S)-anabasine.

Application of catalytic dynamic resolution of N-Boc-2-lithiopiperidine to the asymmetric synthesis of 2-aryl and 2-vinyl piperidines

The highly enantioselective synthesis of 2-aryl-and 2-vinyl-piperidines has been accomplished through a catalytic dynamic resolution (CDR) of N-Boc-2-lithiopiperidine. The method has been applied to the synthesis of both enantiomers of the tobacco alkaloid anabasine.

A straightforward synthesis of (S)-Anabasine via the catalytic, enantioselective vinylogous mukaiyama-Mannich reaction

The tobacco alkaloid (S)-anabasine was synthesized by a straightforward 4-step sequence with the catalytic enantioselective vinylogous Mannich reaction as a key step. Only 3 mol% of a structurally optimized chiral BINOL-based phosphoric acid was employed to control the absolute configuration of the natural product. Georg Thieme Verlag Stuttgart.

Hydroformylation of homoallylic azides: A rapid approach toward alkaloids

(Chemical Equation Presented) Unprecedented hydroformylation of homoallylic azides combined with useful one-pot operations provides an expeditive access to alkaloids.