(S)-nicotine (CHEBI:17688)

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CHEBI:17688 - (S)-nicotine

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ChEBI Name	(S)-nicotine

ChEBI ID	CHEBI:17688

ChEBI ASCII Name	(S)-nicotine

Definition	A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44268, CHEBI:14653, CHEBI:25536, CHEBI:7562

Supplier Information	ChemicalBook:CB5293753, eMolecules:501591, ZINC000000391812

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Molfile

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NCT - Ideal conformer

Mrv1927 02132314453D

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Time for openFile(NCT - Ideal conformer

Mrv1927 02132314453D

26 27 0 0 0 0 999 V2000

-0.6730 1.1480 -2.4250 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.6330 0.8820 -1.1340 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0180 -0.2630 -0.6670 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5510 -1.1420 -1.5760 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4840 -0.8320 -2.9250 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1420 0.3350 -3.3170 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6150 0.5860 1.5560 N 0 0 1 0 0 0 0 0 0 0 0 0

0.0280 -0.5560 0.8100 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.4030 -0.6620 1.3920 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.1930 -0.3360 2.8880 C 0 0 2 0 0 0 0 0 0 0 0 0

0.1280 0.4510 2.9460 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0660 0.3650 1.5940 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0790 1.5720 -0.4330 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0350 -2.0470 -1.2400 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9170 -1.4930 -3.6610 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1980 0.5850 -4.3660 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5900 -1.4700 1.0020 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7950 -1.6710 1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0630 0.0680 0.9260 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1110 -1.2550 3.4680 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0150 0.2750 3.2610 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8590 -0.0920 3.5440 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0450 1.4380 3.3750 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2700 -0.6600 1.9020 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4860 0.5360 0.6020 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5210 1.0550 2.3050 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 6 1 0 0 0 0

2 3 1 0 0 0 0

2 13 1 0 0 0 0

3 4 2 0 0 0 0

3 8 1 0 0 0 0

4 5 1 0 0 0 0

4 14 1 0 0 0 0

5 6 2 0 0 0 0

5 15 1 0 0 0 0

6 16 1 0 0 0 0

7 8 1 0 0 0 0

7 11 1 0 0 0 0

7 12 1 0 0 0 0

8 9 1 0 0 0 0

8 17 1 6 0 0 0

9 10 1 0 0 0 0

9 18 1 0 0 0 0

9 19 1 0 0 0 0

10 11 1 0 0 0 0

10 20 1 0 0 0 0

10 21 1 0 0 0 0

11 22 1 0 0 0 0

11 23 1 0 0 0 0

12 24 1 0 0 0 0

12 25 1 0 0 0 0

12 26 1 0 0 0 0

M END): 15 ms

reading 26 atoms

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26 atoms created

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Molfile expand

Wikipedia	License
Nicotine is a naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and Duboisia hopwoodii) and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used for smoking cessation to relieve withdrawal symptoms. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs), except at two nicotinic receptor subunits (nAChRα9 and nAChRα10) where it acts as a receptor antagonist. Nicotine constitutes approximately 0.6–3.0% of the dry weight of tobacco. Nicotine is also present at ppb concentrations in edible plants in the family Solanaceae, including potatoes, tomatoes, and eggplants, though sources disagree on whether this has any biological significance to human consumers. It functions as an antiherbivore toxin; consequently, nicotine was widely used as an insecticide in the past, and neonicotinoids (structurally similar to nicotine), such as imidacloprid, are some of the most effective and widely used insecticides. Nicotine is highly addictive. Slow-release forms (gums and patches, when used correctly) can be less addictive and help in quitting. Animal research suggests that monoamine oxidase inhibitors present in tobacco smoke may enhance nicotine's addictive properties. An average cigarette yields about 2 mg of absorbed nicotine. The estimated lower dose limit for fatal outcomes is 500–1,000 mg of ingested nicotine for an adult (6.5–13 mg/kg). Nicotine addiction involves drug-reinforced behavior, compulsive use, and relapse following abstinence. Nicotine dependence involves tolerance, sensitization, physical dependence, and psychological dependence, which can cause distress. Nicotine withdrawal symptoms include depression, stress, anxiety, irritability, difficulty concentrating, and sleep disturbances. Mild nicotine withdrawal symptoms are measurable in unrestricted smokers, who experience normal moods only as their blood nicotine levels peak, with each cigarette. On quitting, withdrawal symptoms worsen sharply, then gradually improve to a normal state. Nicotine use as a tool for quitting smoking has a good safety history. Animal studies suggest that nicotine may adversely affect cognitive development in adolescence, but the relevance of these findings to human brain development is disputed. At low amounts, it has a mild analgesic effect. According to the International Agency for Research on Cancer, "nicotine is not generally considered to be a carcinogen". The Surgeon General of the United States indicates that evidence is inadequate to infer the presence or absence of a causal relationship between exposure to nicotine and risk for cancer. Nicotine has been shown to produce birth defects in humans and is considered a teratogen. The median lethal dose of nicotine in humans is unknown. High doses are known to cause nicotine poisoning, organ failure, and death through paralysis of respiratory muscles, though serious or fatal overdoses are rare.
Read full article at Wikipedia

Formula

C10H14N2

Net Charge

Average Mass

162.236

Monoisotopic Mass

162.11570

InChI

InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1

InChIKey

SNICXCGAKADSCV-JTQLQIEISA-N

SMILES

[H][C@]1(CCCN1C)C1=CC=CN=C1

Metabolite of Species	Details
Nicotiana tabacum (NCBI:txid4097)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	teratogenic agent A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect. immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. mitogen A chemical substance that encourages a cell to commence cell division, triggering mitosis. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. neurotoxin A poison that interferes with the functions of the nervous system. nicotinic acetylcholine receptor agonist An agonist that selectively binds to and activates a nicotinic acetylcholine receptor. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	biomarker A substance used as an indicator of a biological state. immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. peripheral nervous system drug A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system. psychotropic drug A loosely defined grouping of drugs that have effects on psychological function. anxiolytic drug Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. nicotinic acetylcholine receptor agonist An agonist that selectively binds to and activates a nicotinic acetylcholine receptor. phytogenic insecticide An insecticide compound naturally occurring in plants.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(S)-nicotine (CHEBI:17688) has role anxiolytic drug (CHEBI:35474) (S)-nicotine (CHEBI:17688) has role biomarker (CHEBI:59163) (S)-nicotine (CHEBI:17688) has role immunomodulator (CHEBI:50846) (S)-nicotine (CHEBI:17688) has role mitogen (CHEBI:52290) (S)-nicotine (CHEBI:17688) has role neurotoxin (CHEBI:50910) (S)-nicotine (CHEBI:17688) has role nicotinic acetylcholine receptor agonist (CHEBI:47958) (S)-nicotine (CHEBI:17688) has role peripheral nervous system drug (CHEBI:49110) (S)-nicotine (CHEBI:17688) has role phytogenic insecticide (CHEBI:22917) (S)-nicotine (CHEBI:17688) has role plant metabolite (CHEBI:76924) (S)-nicotine (CHEBI:17688) has role psychotropic drug (CHEBI:35471) (S)-nicotine (CHEBI:17688) has role teratogenic agent (CHEBI:50905) (S)-nicotine (CHEBI:17688) has role xenobiotic (CHEBI:35703) (S)-nicotine (CHEBI:17688) is a 3-(1-methylpyrrolidin-2-yl)pyridine (CHEBI:138000) (S)-nicotine (CHEBI:17688) is conjugate base of (S)-nicotinium(1+) (CHEBI:59806) (S)-nicotine (CHEBI:17688) is enantiomer of (R)-nicotine (CHEBI:39162)

Incoming	(S)-6-hydroxynicotine (CHEBI:17532) has functional parent (S)-nicotine (CHEBI:17688) (S)-nicotine 1-N-oxide (CHEBI:132572) has functional parent (S)-nicotine (CHEBI:17688) (S)-nicotine N^1'-oxide (CHEBI:142659) has functional parent (S)-nicotine (CHEBI:17688) (S)-nicotinium N-α-D-glucosiduronate (CHEBI:63860) has functional parent (S)-nicotine (CHEBI:17688) nicotine (CHEBI:18723) has part (S)-nicotine (CHEBI:17688) (S)-nicotinium(1+) (CHEBI:59806) is conjugate acid of (S)-nicotine (CHEBI:17688) (R)-nicotine (CHEBI:39162) is enantiomer of (S)-nicotine (CHEBI:17688)

IUPAC Name

3-[(2S)-1-methylpyrrolidin-2-yl]pyridine

Synonyms	Sources
(−)-nicotine	ChemIDplus
(-)-3-(1-Methyl-2-pyrrolidyl)pyridine	HMDB
(-)-3-(N-Methylpyrrolidino)pyridine	HMDB
(R)-3-(1-Methyl-2-pyrrolidinyl)pyridine	HMDB
(S)-(−)-nicotine	NIST Chemistry WebBook
(S)-3-(1-methylpyrrolidin-2-yl)pyridine	KEGG COMPOUND
(S)-3-(N-methylpyrrolidin-2-yl)pyridine	IUBMB
(S)-Nicotine	KEGG COMPOUND
(S)-nicotine	ChemIDplus
1-Methyl-2-(3-pyridyl)pyrrolidine	HMDB
3-(1-Methyl-2-pyrollidinyl)pyridine	HMDB
3-(1-Methylpyrrolidin-2-yl)pyridine	HMDB
3-(2-(N-methylpyrrolidinyl))pyridine	NIST Chemistry WebBook
3-(N-methylpyrollidino)pyridine	NIST Chemistry WebBook
L(−)-nicotine	IUBMB
L-3-(1-Methyl-2-pyrrolidyl)pyridine	HMDB
L-Nicotine	HMDB
Nicotine	KEGG COMPOUND
Nicotine	HMDB

Manual Xrefs	Databases
1920	DrugCentral
485	BPDB
C00002057	KNApSAcK
C00745	KEGG COMPOUND
D03365	KEGG DRUG
DB00184	DrugBank
HMDB0001934	HMDB
LSM-2093	LINCS
NCT	PDBeChem
Nicotine	Wikipedia
NICOTINE	MetaCyc
View more database links

Registry Numbers	Types	Sources
3604351	Beilstein Registry Number	Beilstein
54-11-5	CAS Registry Number	KEGG COMPOUND
54-11-5	CAS Registry Number	ChemIDplus
54-11-5	CAS Registry Number	NIST Chemistry WebBook
82109	Reaxys Registry Number	Reaxys

Citations

Last Modified

13 February 2023

CHEBI:17688 - (S)-nicotine

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