Nicotine

Base Information

• Chemical Name: Nicotine
• CAS No.: 54-11-5
• Deprecated CAS: 13890-81-8,13890-82-9,16760-37-5,551-13-3,6912-85-2,13890-82-9,16760-37-5,551-13-3,6912-85-2
• Molecular Formula: C10H14N2
• Molecular Weight: 162.235
• Hs Code.: 29399910
• European Community (EC) Number: 200-193-3
• ICSC Number: 0519
• UN Number: 1654
• UNII: 6M3C89ZY6R
• DSSTox Substance ID: DTXSID1020930
• Nikkaji Number: J1.808.087G,J9.266E
• Wikipedia: Nicotine
• Wikidata: Q28086552
• NCI Thesaurus Code: C691
• RXCUI: 7407
• Pharos Ligand ID: U94LJPXF37BF
• Metabolomics Workbench ID: 42592
• ChEMBL ID: CHEMBL3
• Mol file: 54-11-5.mol

Synonyms:Nicotine;Nicotine Bitartrate;Nicotine Tartrate

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Nicotine

Chemical Property:

• Appearance/Colour: Yellow liquid
• Vapor Pressure: 0.0303mmHg at 25°C
• Melting Point: -80 °C
• Refractive Index: n20/D 1.5265(lit.)
• Boiling Point: 244.4 °C at 760 mmHg
• PKA: 8.02(at 25℃)
• Flash Point: 101.7 °C
• PSA: 16.13000
• Density: 1.032 g/cm³
• LogP: 1.78620
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: ethanol: 50 mg/mL
• Water Solubility.: MISCIBLE
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.115698455
• Heavy Atom Count: 12
• Complexity: 147
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): T+,N,Xn,F,Xi
• Hazard Codes: T+,N,Xn,F,Xi,T
• Statements: 25-27-51/53-36-20/21/22-11-36/37/38-39/23/24/25-23/24/25-59-48/20-40-36/38-24-20/22-63
• Safety Statements: 7-16-36/37-45-61-36-26-37/39-59

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Drug Classes: Substance Abuse Treatment Agents
• Canonical SMILES: CN1CCCC1C2=CN=CC=C2
• Isomeric SMILES: CN1CCC[C@H]1C2=CN=CC=C2
• Recent ClinicalTrials: Nicotine Treatment for Pulmonary Sarcoidosis: A Clinical Trial Pilot Study
• Recent EU Clinical Trials: An effectiveness and safety study of Varenicline for smoking cessation in hospitalized patients with psychiatric disorders.
• Recent NIPH Clinical Trials: Prospective study on factors affecting smoking cessation support for workers
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the cardiovascular system and central nervous system. This may result in convulsions and respiratory failure. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Animal tests show that this substance possibly causes toxic effects upon human reproduction.
• Description: (–)-Nicotine is an alkaloid that has been found in tobacco. It is an agonist at neuronal nicotinic acetylcholine receptors (nAChRs) and binds to α3β4 and α4β2 subunit-containing nAChRs with Ki values of 481 and 11.1 nM, respectively. Chronic exposure to (–)-nicotine results in increased expression of certain nAChRs, particularly α4β2 subunit-containing nAChRs. (–)-Nicotine has addictive properties. Formulations containing (–)-nicotine have been used as smoking cessation aids for the relief of nicotine withdrawal symptoms. Nicotine is an alkaloid obtained from the dried leaves of Nicotiana tabacum and Nicotiana rustica. Nicotine stimulates acetylcholine receptors of the postsynaptic membrane at nerve synapses resulting in depolarization of the membrane. Toxic doses cause stimulation that is rapidly followed by blockade of nerve transmission.
• Uses: Nicotine is one of the principal constituentsof tobacco. It occurs in the dried leavesof Nicotiana tabacum and Nicotiana rusticato the extent of 2–8%. Exposure risk tothis alkaloid arises from smoking, chewing,or inhaling tobacco. Nicotine and its saltsare used as insecticides and fumigants, intanning, and in medicine. Nicotine is the second most widely used recreational drug after caffeine. At low doses, nicotineacts as a stimulant to the central nervous system by activating acetylcholine receptors, specifically called nicotinic acetylcholine receptors, in the postsynaptic neurons during nerve transmission.At higher doses nicotine acts as a depressant.Nicotine in tobacco has always been used for medicinal purposes. Nicotine solutions made from soaking tobacco leaves in water have been used as pesticides for several hundred years. In modern times, numerous pharmaceutical companies have explored nicotine's use for treating diseases. Nicotine's most prevalent medicinal use is for smoking cessation in the form of alternate delivery systems such as gums and dermal patches. Nicotine is used medically for numerous conditions and its use is being explored in additional areas including pain relievers, attention deficit disorder medications and medications associated with Alzheimer's disease, Parkinson disease, colitis, herpes, and tuberculosis. Naturally-occuring isomer Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer. (S)-(-)-Nicotine is a prototype nicotinic acetylcholine receptor agonist. (S)-(-)-Nicotine is the naturally occurring isomer. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic.
• Therapeutic Function: Ganglion depressant, Smoking deterrent

Technology Process of Nicotine

There total 107 articles about Nicotine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

cotinine (486-56-6) → nicotin (54-11-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; for 1h; Heating;

DOI:10.1021/jm00182a028

Reference yield: 93.0%

3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5) → nicotin (54-11-5)

Guidance literature:

With borane-ammonia complex; 6-hydroxy-D-nicotine oxidase; for 16h; Reagent/catalyst; enantioselective reaction; Kinetics; Enzymatic reaction;

DOI:10.1002/cctc.201301008

Reference yield: 91.0%

6-Bromonicotine (96400-85-0) → nicotin (54-11-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; Schlenk technique;

DOI:10.1021/ja511422q

upstream raw materials:

formaldehyd

nornicotine

Myosmine

formyl acetic anhydride

Downstream raw materials:

(S)-5-(1-methyl-pyrrolidin-2-yl)-2-phenyl-pyridine

(S)-3-(1-methyl-pyrrolidin-2-yl)-2-phenyl-pyridine

nicotirine

1-Methylpyrrolidine

Refernces

• 1、 -. "Method for synthesizing chiral nicotine from butyrolactone". Paragraph 0057; 0060. . Retrieved 2021/11/03.
• 2、 -. "Synthesis method of nicotine". Paragraph 0039; 0057-0063; 0081-0085. . Retrieved 2021/07/10.