13450-58-3

Basic information

• Product Name: nornicotine
• Synonyms: 3-((2S)PYRROLIDIN-2-YL)PYRIDINE hydrochloride
• CAS NO: 13450-58-3
• Molecular Formula: C9H12N2
• Molecular Weight: 148.20
• Mol File: 13450-58-3.mol

Chemical Properties

• CAS DataBase Reference: nornicotine(CAS DataBase Reference)
• NIST Chemistry Reference: nornicotine(13450-58-3)
• EPA Substance Registry System: nornicotine(13450-58-3)

Safety Data

• Hazardous Substances Data: 13450-58-3(Hazardous Substances Data)

Upstream product

• 532-12-7 Myosmine 
• 17708-87-1 5-(pyridin-3-yl)pyrrolidin-2-one 
• 125198-33-6 3-(1-Hydroxy-2-pyrrolidinyl)pyridine 
• 138084-62-5 2,2,5,5-tetrametyl-1-aza-2,5-disilacyclopentane-1-propyl magnesium bromide 
• 95091-91-1 N-methoxy-N-methylpyridine-3-carboxamide 
• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 34562-98-6 N-Nicotinoyl-γ-aminobuttersaeure-ethylester 
• 1125-96-8 myosmine 
• 1076199-53-5 2-pyridin-3-ylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 5746-86-1 rac-nornicotine 
• 54-11-5 nicotin 
• 32752-52-6 1-(N-methyl)-1,5-pentanediamine 

Downstream Products

• 3000-81-5 N'-formylnornicotine 
• 69980-24-1 rac-N-[methyl-d3]nicotine 
• 5979-94-2 N-acetylnornicotine 
• 5979-92-0 N'-ethyl-S-nornicotine 
• 5979-93-1 3-((S)-1-allyl-pyrrolidin-2-yl)-pyridine 
• 16543-55-8 N'-Nitrosonornicotine 
• 54-11-5 nicotin 
• 25162-00-9 D-nicotine 
• 69730-90-1 (S)-2-pyridin-3-yl-pyrrolidine-1-carboxylic acid ethyl ester 

Relevant articles and documents

Enantioselective Synthesis of Nicotine via an Iodine-Mediated Hofmann-L?ffler Reaction

An iodine-mediated Hofmann-L?ffler reaction has been developed that enables the first enantioselective synthesis of nicotine based on this synthetic methodology. The effect of the free pyridine core on the involved electrophilic iodine reagents was explored in detail. The final synthesis proceeds under moderate reaction conditions that tolerate the free pyridine core. The same synthetic sequence is also applicable to a number of derivatives with higher substituted pyridine cores, including bipyridine derivatives.

The biosynthesis of [5'-14C]cotinine and other radiolabeled nicotine metabolites

The present study describes the biosynthesis and isolation of the major radiolabeled nicotine metabolites formed using phenobarbitone (PB)-induced rabbit hepatic homogenates (10,000 g fraction). The optimal incubation and extraction methods for cotinine formation from non-labeled nicotine were established. The biosynthesis and isolation of [5'-14C]cotinine and other radiolabeled metabolites such as [2'-14C]nornicotine and [4-14C]-(3-pyridyl)-4-oxobutyric acid, from commercially available [2'-14C]nicotine, were carried out using the developed methods. Cotinine was isolated using preparative silica gel TLC, whereas the other metabolites were obtained using a cation-exchange HPLC method. This study showed that in addition to the two major metabolites (i.e. cotinine and nornicotine), 4-(3-pyridyl)-4-oxo-butyric acid, 3-hydroxycotinine, norcotinine, nicotine-1'-N-oxide and cotinine-1-N-oxide were also formed when PB-induced rabbit hepatic homogenates were used. Two further metabolites of unknown structure were detected. However, the isolation and further purification were only carried out on cotinine, nornicotine and 4-(3-pyridyl)-4-oxo-butyric acid.

A short and efficient synthesis of unnatural (R)-nicotine

A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd.

ABILITY OF A NICOTIANA PLUMBAGINIFOLIA CELL SUSPENSION TO DEMETHYLATE NICOTINE INTO NORNICOTINE

A cell suspension of Nicotiana plumbaginifolia which does not accumulate tobacco alkaloids was found to keep the ability to demethylate nicotine into nornicotine.The highest bioconversion yield was 53.2 percent.The influence of some environmental factors upon the reaction has been studied.In particular, it appears that light enhances the catalytic activity of the cells which leads to the hypothesis that this metabolic step of tobacco alkaloids is bound to photodependent systems.

Preparation method of chiral nicotine synthesized by chiral tert-butyl sulfinamide

The preparation method comprises the following steps: 3 - pyridine formaldehyde and chiral tert-butyl sulfinamide are subjected to condensation reaction under the action of titanate. Further, magnesium bromide reacts with (1, 3 - dioxan -2 -ethyl) magnesium bromide. Cyclization is carried out under acidic conditions. Finally, by reduction and amine methylation, chiral nicotine is obtained. The method has the advantages of short reaction route, easily available and cheap raw materials, high yield of chiral nicotine generated by reaction, high ee-value and reduced production cost of chiral nicotine.

Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels?Alder/Substitution Reaction

An enantioselective domino process for the synthesis of substituted 1,2-dihydronaphthalenes has been developed by the combination of chiral amines and a bidentate Lewis acid in an orthogonal catalysis. This new method is based on an inverse electron-demand Diels?Alder and a subsequent group exchange reaction. An enamine is generated in situ from an aldehyde and a chiral secondary amine catalyst that reacts with phthalazine, activated by the coordination to a bidentate Lewis acid catalyst. The absolute configuration of the product is controlled by chiral information provided by the amine. The formed ortho-quinodimethane intermediate is then transformed via a group exchange reaction with thiols. The new method shows a broad scope and tolerates a wide range of functional groups with enantiomeric ratios up to 91 : 9. All-in-all, this enantioselective synthesis tool provides an easy access to complex 1,2-dihydronaphthalenes starting from readily available phthalazine, aldehydes and thiols in a combinatorial way.

Preparation method of nicotine and intermediate thereof

The invention relates to a preparation method of nicotine and an intermediate thereof, wherein the intermediate has a structure as shown in a formula (II), X1, X2 and X3 are respectively and independently CR2R3, R1 is a C1-6 alkyl group, and R2 and R3 are each independently H or a C1-6 alkyl group. According to the invention, the preparation method of the nicotine and the intermediate thereof has the advantages of simple operation, mild reaction conditions, easily available raw materials, and high conversion rate, can effectively reduce the production cost of the nicotine, and has the potential of industrial production, and each reaction can be directly post-fed through simple post-treatment basically.

Synthesis method of nicotine

The invention belongs to the technical field of nicotine synthesis, and particularly relates to a synthesis method of nicotine. The invention discloses a synthesis method of nicotine. The synthesis method comprises the following steps: S1, synthesizing 1-(1-butenyl)-3-nicotyl-2-pyrrolidone, namely reacting 1-(1-butenyl)-pyrrolidone with nicotine ethyl ester under the condition of NaH catalysis by using an N,N-dimethyl formamide solution carrier to obtain the 1-(1-butenyl)-3-nicotyl-2-pyrrolidone; S2, synthesizing 3-cyclopentenyl amino-pyridine, namely concentrating the 1-(1-butenyl) 3-nicotinyl-2-pyrrolidone obtained in the step S1 under a certain condition, so as to obtain the 3-cyclopentenyl amino-pyridine, S3, synthesis of a nicotine precursor: introducing hydrogen into 3-cyclopentenyl amino-pyridine under the action of a Pd/C catalyst to obtain the nicotine precursor; and S4, synthesizing nicotine, namely obtaining nicotine from the nicotine precursor obtained in S3 under the action of formaldehyde and formic acid, wherein the chemical formulas are shown in specification.

Method for synthesizing chiral nicotine from butyrolactone

The invention discloses a method for synthesizing chiral nicotine from butyrolactone. The fumarates and γ - butyrolactone are condensed under the action of a basic catalyst to yield 4 - chloro -1 - (3 - pyridine) -1 -butanone by reaction with hydrochloric acid and reacted with a chlorination reagent to produce (- B -) S (-4 -1 -dichlorobutyl) pyridine which is reacted with an amine reagent under basic conditions to give (-3 -) -1 -methyl nicotine and (S)-3 - nicotinic acetylbutanolamines obtained by the reaction with the aminating reagent under an alkaline condition to produce a chiral hydroxy S S group - (1) S- methylnicotine or a (4 -) S nicotinic acid. The application can determine whether a methylation reaction is needed according to the type of amination reagent. The yield of (S)- nicotine was high.

Synthesis method of (R, S-) nicotine

The invention belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of (R, S-) nicotine. The method comprises the following steps: (1) taking methyl nicotinate and N-butenyl pyrrolidone as raw materials, and preparing N-butenyl-3-benzoyl-1-pyrrolidone through a condensation reaction; (2) after the reaction is finished, carrying out hydrolysis reaction, cooling, adjusting the pH value to be alkaline, extracting, separating out an organic phase, concentrating and distilling to obtain an enamine intermediate; and (3) carrying out a reduction reaction on the enamine intermediate under illumination with the wavelength of 200-400nm by using a metal oxide or a complex as a reduction catalyst to obtain the target product (R, S-) nicotine. According to the method, use of the metal catalyst is innovatively proposed, reaction is initiated by illumination with specific wavelength to prepare the (R, S-) nicotine, and the method is simple and convenient to operate, high in yield, low in cost and suitable for industrial large-scale production.