53912-89-3

Basic information

• Product Name: (+)-Anabasinehydrochloride
• Synonyms: (S)-3-(Piperidin-2-yl)pyridine hydrochloride;(+)-Anabasine.HCl;(S)-(+)-3-(2-Piperidinyl)pyridine hydrochloride;alpha-Piperidyl-beta-pyridine hydrochloride;Anabaside hydrochloride;Anabasin chloride;Anabasin hydrochloride;Anabasine monohydrochloride
• CAS NO: 53912-89-3
• Molecular Formula: C₁₀H₁₄N₂*ClH
• Molecular Weight: 198.72
• Product Categories: Acetylcholine receptor
• Mol File: 53912-89-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220-222 °C
• Boiling Point: 271°Cat760mmHg
• Flash Point: 9℃
• Appearance: White to off-white solid.
• Density: 1.014g/cm³
• Vapor Pressure: 0.00662mmHg at 25°C
• Storage Temp.: Desiccate at RT
• CAS DataBase Reference: (+)-Anabasinehydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Anabasinehydrochloride(53912-89-3)
• EPA Substance Registry System: (+)-Anabasinehydrochloride(53912-89-3)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 53912-89-3(Hazardous Substances Data)

Usage

Uses

(+)-Anabasine Hydrochloride is a hydrochloride analog of (S)-Anabasine (A637170), which is a nicotinic receptor agonist.

Biological Activity

High affinity neuronal nicotinic ACh receptor partial agonist (K i values are 0.058, 0.26 and 7.2 μ M for rat α 7, rat α 4 β 2 and fish skeletal muscle nAChRs respectively). Also stimulates Ca 2+ -dependent catecholamine release from rat adrenomedullary cells in vitro .

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

Upstream product

• 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 
• 494-52-0 Anabasine 
• 121675-93-2 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-((S)-4-oxo-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl)-tetrahydro-pyran-3-yl ester 
• 121675-97-6 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)-5,6-didehydro-piperidin-4-one 
• 121675-84-1 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-tetrahydro-pyran-4-yl ester 
• 500-22-1 3-pyridinecarboxaldehyde 
• 122294-65-9 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-((S)-7-pyridin-3-yl-1,4-dithia-8-aza-spiro[4.5]dec-8-yl)-tetrahydro-pyran-3-yl ester 

Downstream Products

• 40179-50-8 (2S)-N-4'-nitrobenzoyl-2-(3-pyridyl)-4-piperidine 
• 1446339-46-3 (S)-3-{1-[2-(4-allyl-2-methoxyphenoxy)ethyl]piperidin-2-yl}pyridine oxalate 
• 1446339-48-5 (S)-3-{1-[4-(4-allyl-2-methoxyphenoxy)butyl]piperidin-2-yl}pyridine oxalate 
• 1446339-53-2 (S)-3-{1-[2-(4-acetyl-2-methoxyphenoxy)ethyl]piperidin-2-yl}pyridine oxalate 
• 1446339-55-4 (S)-3-{1-[3-(4-acetyl-2-methoxyphenoxy)propyl]piperidin-2-yl}pyridine oxalate 
• 1446339-57-6 (S)-3-{1-[4-(4-acetyl-2-methoxyphenoxy)butyl]piperidin-2-yl}pyridine oxalate 
• 34074-28-7 1,2-bis(4-formylphenoxy)ethane 
• 1446339-59-8 (S)-3-{1-[2-(4-formylphenoxy)ethyl]piperidin-2-yl}pyridine oxalate 
• 1446339-61-2 (S)-3-{1-[2-(2-methoxy-4-formylphenoxy)ethyl]piperidin-2-yl}pyridine oxalate 
• 1446339-63-4 (S)-3-(1-{2-[2-(2-methoxyphenoxy)ethoxy]ethyl}piperidin-2-yl)pyridine oxalate 
• 1446339-65-6 (S)-3-(1-{2-[2-(3-methoxyphenoxy)ethoxy]ethyl}piperidin-2-yl)pyridine oxalate 
• 1446339-06-5 (S)-3-[1-(2-phenoxyethyl)piperidin-2-yl]pyridine oxalate 
• 1446339-09-8 (S)-3-{1-[2-(2-isopropyl-5-methylphenoxy)ethyl]piperidin-2-yl}pyridine oxalate 
• 1446339-12-3 (S)-3-{1-[3-(2-isopropyl-5-methylphenoxy)propyl]piperidin-2-yl}pyridine oxalate 

Relevant articles and documents

Spectroscopy and crystal structure of anabasine salts

The anabasinium hydrochloride, hydriodide and perchlorate were characterized by IR and NMR spectroscopy as well as by X-ray diffraction. Anabasinium hydrochloride crystallizes with three independent ionic pairs in the asymmetric part of the orthorhombic unit cell, while anabasinium hydriodide and perchlorate crystals, being isostructural, are hexagonal and contain only one symmetry independent ionic pair. Despite these differences in the crystal data, both types of crystals display very similar helical solid-state patterns. The reported results combined with the CSD searches indicate an inherent tendency of anabasinium salts to crystallize with multiple asymmetric units, and to form folded arrangements in crystals. In the solid state the anabasinium cations predominantly adopt either synperiplanar or antiperiplanar conformations with respect to the mutual orientation of C*-H and pyridine C-C(N) bonds, with deformations towards, respectively, (+) synclinal or (+) anticlinal rotamers.

Kohlenhydrate als chirale Matrices: Stereoselektive Tandem-Mannich-Michael-Reaktionen zur Synthese von Piperidin-Alkaloiden

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