25162-00-9

Basic information

• Product Name: (+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE S YNTHETIC >99%
• Synonyms: (r)-3-(1-methyl-2-pyrrolidinyl)pyridine;2’-beta-h-nicotine;d-nicotine;(+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE S YNTHETIC >99%;5-23-06-00064 (Beilstein Handbook Reference);2'bH-Nicotine (8CI);Pseudonicotine;Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (R)-
• CAS NO: 25162-00-9
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23156
• Product Categories: Nicotine Derivatives
• Mol File: 25162-00-9.mol

Chemical Properties

• Boiling Point: 60-65°C/0.1mmHg
• Flash Point: 101.7°C
• Appearance: /
• Density: 1.032g/cm³
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• PKA: 8.00±0.50(Predicted)
• CAS DataBase Reference: (+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE S YNTHETIC >99%(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE S YNTHETIC >99%(25162-00-9)
• EPA Substance Registry System: (+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE S YNTHETIC >99%(25162-00-9)

Safety Data

• Hazardous Substances Data: 25162-00-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE SYNTHETIC >99% is used as an active pharmaceutical ingredient for the development of medications targeting nicotine addiction and related conditions. Its unnatural isomer nature allows for the exploration of novel therapeutic approaches and potential benefits in treating nicotine dependence.
Used in Chemical Research:
In the field of chemical research, (+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE SYNTHETIC >99% serves as a valuable compound for studying the effects of enantiomers on biological systems. This can lead to a better understanding of the role of stereochemistry in drug action and the development of more effective and selective medications.
Used in Agrochemical Industry:
(+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE SYNTHETIC >99% can be utilized in the agrochemical industry as a component in the development of novel pesticides or insecticides. Its unique chemical properties may provide new insights into pest control strategies and contribute to the creation of more effective and environmentally friendly products.
Used in Material Science:
The colorless liquid nature of (+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE SYNTHETIC >99% makes it a potential candidate for use in material science, where it could be explored for its potential applications in the development of new materials or coatings with specific properties, such as improved chemical resistance or enhanced biological activity.

Upstream product

• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 16426-44-1 4-(methylamino)-1-(3'-pyridyl)-1-butanone dihydrochloride 
• 2055-23-4 Pseudooxynicotine 

Downstream Products

• 60282-15-7 R-(+)-N'-methylnicotinium ion 
• 94419-25-7 R-(+)-N-methylnicotinium ion 
• 42459-12-1 1-methyl-5-pyridin-3-yl-pyrrolidine-2-carbonitrile 
• 68935-27-3 nicotine di-p-toluoyl tartrate 
• 68935-25-1 l-nicotine di-(p-toluoyl)-d-tartrate 
• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 54-11-5 nicotin 
• 627870-30-8 (S)-1-(6-cyclohexyl-hexyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridmium bromide hydrobromide salt 

Relevant articles and documents

Preparation of Optically Pure (R)-(+)-Nicotine. Studies on the Microbial Degradation of Nicotinoids

(R)-(+)-Nicotine (1a) of high optical purity (average 99.6percent) has been obtained from (R,S)-nicotine by stereoselective microbial degradation of the (S)-(-)-nicotine with use of the microorganism Pseudomonas putida.Liquid culture results indicated that the organism growing on (S)-(-)-nicotine can utilize 1a but at a slower rate.Studies on related nicotinoids showed the microorganism to be primarily specific for (S)-(-)-nicotine.

Enantioselective Hydrosilylation and Hydrogenation of Alkaloid Precursors

Enantioselective hydrosilylations of the 3,4-dihydropyrrole derivatives 1a-c and 5 with in-situ catalysts consisting of 2 and optically active phosphines yield the N-silyl compounds 2a-c and 6 in up to 66.1percent ee.The N-silyl derivatives were treated with acetic formic anhydride or trifluoroacetic anhydride to give the N-formyl and N-trifluoroacetyl compounds 3a-c, 4a-c, 7, and 8.The alkaloids nicotine and macrostomine were synthesized with 63.3 and 33percent ee by reduction of the N-formyl compounds 8 and 12.Enantioselective hydrogenations of the N-formyl and N-trifluoroacetyl-2-phenylpyrrolines 14 and 15 with the same in-situ catalysts produce the cyclic amides 3a and 4a in up to 36.1percent ee.

The pyrolysis of (-)-(S)-nicotine: Racemization and decomposition

The pyrolytic behaviour of (1)-(S)-nicotine in methanol was investigated using on-line pyrolysis GC/MS to establish whether racemization to the R(+) antipode occurs and to identify other products of pyrolysis. The conditions used included pyrolysing the sample for 15 seconds in an atmosphere of 9% oxygen in nitrogen (275ml/min total flow) across the temperature range of 200°C-1000°C. A chiral Cyclodex-B analytical column (30m × 0.25mm i.d. × 0.25 μm film thickness) was used to separate the enantiomers of nicotine, although the two enantiomer peaks were not baseline resolved. The results of the experiment shows that there is no increase in (+)-(R)-nicotine levels across a wide temperature range. This suggests that the elevated levels of (+)-R-nicotine observed in tobacco smoke (compared to tobacco leaf material) are not due to the pyrolytic auto-racemization of (1)-(S)-nicotine but are a result of more complex interactions between (-)-(S)-nicotine and other smoke components. The pyrolysis of isotopically labelled nicotine established that nicotine undergoes thermal decomposition to β-nicotyrine which in turn may decompose to other products. Chirality 22:442-446, 2010.

Asymmetric preparation method of nicotine

The invention relates to a preparation method of nicotine, in particular to a preparation method of nicotine from nicotinic acid ester as a starting material through five-step reaction. The method comprises the following specific steps: (1) a condensation reaction of the nicotinate with N - methylpyrrolidinone in a suitable reaction vessel, and adding a strong acid to react to obtain 4 - methylamino -1 - (3 - pyridine) - butanone hydrochloride after the reaction is finished. (2) The amino group is protected with a suitable amino protecting reagent to give an intermediate (4). (3) The chiral alcohol intermediate (5) is obtained by asymmetric reduction. (4) The chiral alcohol intermediate can be converted into nicotine through two-step conversion. The asymmetric reduction reaction of metal catalysis is a key step of the method, so that the chiral alcohol intermediate with high optical activity can be obtained, and nicotine can be prepared through two-step conversion. The nicotine preparation method provided by the invention is simple to operate, low in cost, mild in reaction condition and suitable for industrial production.

Preparation method of nicotine with optical activity

The invention discloses a preparation method of nicotine with optical activity, which comprises the following steps: adding a nitrogen-containing or phosphorus-containing chiral ligand and a metal catalyst into an organic solvent, preparing a catalyst, sequentially adding an imine salt and a reducing agent to carry out a reduction reaction, and adding an extracting agent to extract the nicotine compound. According to the preparation method disclosed by the invention, the imine salt derivative is used as a precursor, the initial raw material cost is low, the reaction conditions are mild (for example, catalysis and reduction reactions occur in a temperature range near normal temperature), the catalyst and the reducing agent are common chemical substances, the synthesis yield and the chemicalpurity of the final product nicotine are high, and large-scale industrial production is convenient to realize.

ENANTIOMERIC SEPARATION OF RACEMIC NICOTINE BY ADDITION OF AN O,O'-DISUBSTITUTED TARTARIC ACID ENANTIOMER

The present invention relates to a method of separating racemic nicotine of Formula (l-a) as a mixture of the (R)- and (S)-enantiomers into the enantiomerically pure (S)- and (R)-nicotine represented by Formula (l-b) and (l-c), by adding a mixture of the L- and the D-enantiomer of a O,O'-disubstituted tartaric acid, wherein the molar ratio of the L- to the D-enantiomer is from 80:20 to 95:5, and obtaining the (S)-nicotine of formula (l-b), or by adding O,O'-dibenzoyl-D-tartaric acid and obtaining the (R)-nicotine of formula (l-c).

PREPARATION OF RACEMIC NICOTINE BY REACTION OF ETHYL NICOTINATE WITH N-VINYLPYRROLIDONE IN THE PRESENCE OF AN ALCOHOLATE BASE AND SUBSEQUENT PROCESS STEPS

The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.

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.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

SYNTHESIS AND RESOLUTION OF NICOTINE

The present disclosure generally relates to methods of preparing nicotine and resolving R,S nicotine to enrich the (S)(?) enantiomer. The method may comprise combining N-methyl-2-pyrrolidone or a salt thereof with a nicotinate compound in the presence of a solvent and a strong base to form 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof; and reducing the 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na2S2O4 to produce racemic nicotine or salt thereof. Resolving the racemic nicotine (or other enantiomeric mixture) may comprise combining the nicotine with (?)-O,O′-di-p-toluoyl-L-tartaric acid (L-PTTA).