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
• Article Data: 17

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

Description

(+)-NICOTINE-(+)-DI-P-TOLUOYL TARTRATE SYNTHETIC >99%, also known as the (R)-enantiomer of nicotine, is an unnatural isomer of nicotine. It is a colorless liquid with unique chemical properties that make it suitable for various applications across different industries.

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

• 54-11-5 nicotin 
• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 16426-44-1 4-(methylamino)-1-(3'-pyridyl)-1-butanone dihydrochloride 
• 532-12-7 Myosmine 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 2055-23-4 Pseudooxynicotine 
• 50-00-0 formaldehyd 
• 5746-86-1 rac-nornicotine 
• 326818-54-6 3-((R)-1-Azido-but-3-enyl)-pyridine 
• 7076-23-5 (+)-nornicotine 
• 144635-03-0 (S)-1-(pyridin-3-yl)but-3-en-1-ol 

Downstream Products

• 60282-15-7 R-(+)-N'-methylnicotinium ion 
• 94419-25-7 R-(+)-N-methylnicotinium ion 
• 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 
• 42459-12-1 1-methyl-5-pyridin-3-yl-pyrrolidine-2-carbonitrile 

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.

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.

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.

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.