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
• Article Data: 20

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

Description

(-)-Anabasine, also known as the (S)-enantiomer of anabasine, is a pale yellow oil with chemical properties that make it a potent nicotinic receptor agonist. It is a naturally occurring alkaloid found in various plant species, including Nicotiana glauca, Anabasis aphylla L., Chenopodiaceae, and Solanaceae.

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

• 1966-44-5 rac-N-methylanabasine 
• 154874-91-6 tert-butyl 2-(pyridine-3-yl)piperidine-1-carboxylate 
• 337974-58-0 (2S)-N-[(1S)-1-phenylethyl]-2-(3-pyridyl)-4-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 
• 13078-04-1 anabasine 
• 581-49-7 anatabine 
• 1270360-24-1 C₁₀H₁₃BrN₂ 
• 1643933-28-1 (S)-1-[(S)-2-(methoxymethyl)pyrrolidin-1-yl]-6-(pyridin-3-yl)piperidin-2-one 
• 1643933-38-3 (S)-1-[2-(methoxymethyl)pyrrolidin-1-yl]-6-(pyridin-3-yl)-3,4-dihydropyridin-2(1H)-one 
• 1643933-44-1 C₁₇H₂₉BN₂O₄ 
• 1394905-55-5 1-((S)-2-methoxymethylpyrrolidin-1-yl)-piperidine-2,6-dione 
• 108-55-4 glutaric anhydride, 
• 91842-86-3 (S)-2,3,4,5-tetrahydro-1H-[2,3']bipyridyl-6-one 
• 1296689-65-0 C₂₃H₂₆N₂O₂ 

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 
• 53912-89-3 (2S)-2-(3-pyridyl)piperidine hydrochloride 
• 20377-52-0 (S)-(-)-anabasine hydroiodide 
• 1065040-46-1 (2S)-1-{3-[4-(N-acetylamino)-3-(methoxycarbonyl)phenyl]prop-2-ynyl}-2-(3-pyridyl)piperidine 
• 1380335-62-5 (S)-2-(pyridin-3-yl)piperidinium bis(2-phenethyl)thioselenophosphinate 

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.

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.

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.