Nicotine derivatives of medical significance such as niacinamide which acts as enzyme cofactor vitamin. Methyl nicotinate is a bronchial vasodilator

Nicotine has pharmacological properties that can increase

Blood Pressure and Heart Rate (Wolf, 1994)

تذكير: الخصائص الكيميائية وتفاعل النيكوتين.

ويعرض النيكوتين آثارا إيجابية وسلبية على جسم الإنسان يمكن تفسيرها بخصائصها الكيميائية.

واحدة من السمات الكيميائية للاهتمام من النيكوتين هو حقيقة أنه ثنائي القاعدة: النيكوتين يحتوي على كل من بيريدين وحلقة بيروليدين التي عمودي على بعضها البعض. ذرات النيتروجين الموجودة على هذه الحلقات لها بكا مختلفة مما أدى إلى تفاعلات المنافسة بين الحلقتين. مما يدل على تفاعل أكبر من النيتروجين بيروليدين: يكا من N-1 هو 3.04 و يكا من N-1 'هو 7.84.

Reminder: chemical properties and nicotine reaction.

It presents nicotine positive and negative effects on the human body can be explained by the chemical characteristics.

One of the interesting features of the chemical nicotine is the fact that it is a dual base: nicotine contains both pyridine ring that pyrrolidine perpendicular to each other. Nitrogen atoms on these rings have different BCAA which led to the interactions of competition between the two rings. Which shows greater nitrogen pyrrolidine reaction: Wicca from N-1 is 3.04 and Wicca of N-1 'is 7.84

Nicotine derivatives of medical significance such as niacinamide which acts as enzyme cofactor vitamin. Methyl nicotinate is a bronchial vasodilator.

in addition, Nicotine is frequently used for its performance-enhancing effects on cognition, alertness, and focus. Review noted that stimulation of the α4β2 nicotinic receptor is responsible for certain improvements in attentional performance; among the nicotinic receptor subtypes, nicotine has the highest binding affinity at the α4β2 receptor (ki=1 nM), which is also the biological target that mediates nicotine's addictive properties

Niacinamide, aka nicotinamide, is a dietary supplement used to improve a patient's health condition and stimulate normal growth. There is a similarity ( nicotine ) in their containment and two security functions

Research interests in the synthesis, characterization and biological activity of nicotine derivatives

Our approach to the synthesis of nicotine analogues.

A plethora of nicotine derivatives have been synthesized and display interesting biological properties. However, their synthesis is often low yielding because of the necessity to resolve the racemic material produced. We decided to investigate the regioselective synthesis of nicotine derivatives using natural (S)-nicotine as a starting material. Avoiding the use of a resolution to obtain enantiopure material will reduce both the length and the cost of the synthesis of these derivatives.

Previous work on the synthesis of nicotine derivatives.

The various uses of nicotine as a potential drug and as an insecticide make it a valuable subject of studies for chemists. Rondahl conducted an early study on the structure-activity relationship of nicotine analogues in 1977. He prepared racemic 5-bromo and 5-chloronicotines according to the same procedure used by Leete to prepare 5-fluoronicotine

Concerning Biological activities.

Initial tests were conducted on adult yellow fever mosquitoes. Some nicotine derivatives have been shown to have greater nicotine activity and activity similar to malathion, an insecticide currently used to control adult mosquitoes.

Apparently, a large fat-loving group in C-4 of nicotinoids increases insect activity of nicotine, which is the opposite of central nervous system activity: the replacement of nicotine derivatives C-4 shows less or no activity. These new nicotine derivatives can have selective activity, meaning they can be developed as insecticides that reduced mammalian toxicity. There is a need to test more vehicles to determine the more detailed trajectory.

. Many organic compounds of interest in biological and pharmaceutical fields

contain heterocycles. Although several analogs of nicotine have been reported in the literature, there has been no report as far as we knew, of derivatives with a heteroaromatic rings. Palladium chemistry was utilized for installation of heteroaromatic rings at C-4, C-5 and C-6 positions of (S) -nicotine pyridine ring.

One of the contemporary challenges is to synthesize nicotine derivatives that would display the same beneficial effects of nicotine at lower toxicity

Via the N-oxide.

Nicotine N-oxide was recently treated with 10 equivalents of phosphorus oxychloride to give a mixture of 2-chloro and 6-chloro nicotines in low yield. Addition of 3.4 equivalents of diisopropylamine eliminated the formation of the 2-chloronicotine, yielding 38% of 6-chloronicotine .

Synthesis of Nicotine Derivatives via Reductive Disilylation of (S)-Nicotine: Proo fof Optical Purity.In 1970, Sulzbach reported the reductive disilylation of pyridine with alkali metals and trimethylsilyl chloride.

syntheses of 5-halonicotines :

In the last decade, asymmetric syntheses of (S)-nicotine and nicotine derivatives substituted on the pyridine ring have been achieved. Glennon and co-workers reported the synthesis of C-4 substituted derivatives of (S)-nicotine [15] .

[15]. Leete, E.; Bodmen, G. B.; Manuel, M. F. Phytochemistry,1971, 10,2687-2692

Substitution at C-6 : Nicotine N-oxide was recently treated with 10 equivalents of phosphorus oxychloride to give a mixture of 2-chloro and 6-chloro nicotines in low yield . Addition of 3.4 equivalents of diisopropylamine eliminated the formation of the 2-chloronicotine, yielding 38% of 6-chloronicotine .

Development of nicotine N-oxide methodology. As discussed in the literature review,

nicotine-N,N'-dioxide has been known since Taylor and Boyer first discussed properties and synthesis in 1953. The N-monooxide or nicotine N-oxide was said to be highly unstable and sensitive to vacuum distillation, impeding purification, NMR characterization, and synthetic uses. The picric acid salts of nicotine oxides were studied by NMR. Also, the archaic preparation used antiquated reagents requiring lengthy reaction times .

Synthesis of the 4-furanyldihydronicotine employees a Grignard which is made by lithiation of furan followed by addition of magnesium dibromide etherate The reaction is very sensitive to moisture and all reagents must be freshly distilled, and it also requires precise order of addition and carefully monitored reaction temperatures to yield the product .

Nicotine is commercially obtained from tobacco scraps and is used as an insecticide and as a veterinary vermifuge.

Nitric acid or other oxidizing agents convert it to nicotinic acid, or niacin, which is used as a food supplement.

Nicotine derivatives are primarily used in smoking cessation products. The most common medication derived from nicotine is:

Nicotine Replacement Therapy (NRT): This includes products like nicotine gum, patches, lozenges, inhalers, and nasal sprays. These products deliver controlled doses of nicotine to help reduce withdrawal symptoms and cravings in individuals trying to quit smoking.

Aside from NRT, nicotine derivatives have also been explored for potential therapeutic uses in conditions like ADHD (Attention Deficit Hyperactivity Disorder) and Alzheimer's disease, but these are still in experimental stages and not widely used as medications.