Showing Compound Nicotine (FDB003968)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:02 UTC

Update date

2019-11-26 02:59:42 UTC

Primary ID

FDB003968

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Nicotine

Description

Nicotine, also known as (S)-nicotine or habitrol, belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. Nicotine is a very strong basic compound (based on its pKa). Nicotine is a bitter tasting compound. Nicotine has been detected, but not quantified in, several different foods, such as common persimmons, fox grapes, citrus, winter squash, and macadamia nuts. This could make nicotine a potential biomarker for the consumption of these foods.

CAS Number

54-11-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-Nicotine	ChEBI
(-)-3-(1-Methyl-2-pyrrolidyl)pyridine	ChEBI
(-)-3-(N-Methylpyrrolidino)pyridine	ChEBI
(R)-3-(1-Methyl-2-pyrrolidinyl)pyridine	ChEBI
(S)-(-)-Nicotine	ChEBI
(S)-3-(1-Methylpyrrolidin-2-yl)pyridine	ChEBI
(S)-3-(N-Methylpyrrolidin-2-yl)pyridine	ChEBI
1-Methyl-2-(3-pyridyl)pyrrolidine	ChEBI
3-(1-Methyl-2-pyrollidinyl)pyridine	ChEBI
3-(1-Methylpyrrolidin-2-yl)pyridine	ChEBI
3-(2-(N-Methylpyrrolidinyl))pyridine	ChEBI
3-(N-Methylpyrollidino)pyridine	ChEBI
L(-)-Nicotine	ChEBI
L-3-(1-Methyl-2-pyrrolidyl)pyridine	ChEBI
L-Nicotine	ChEBI
(S)-Nicotine	Kegg
Habitrol	Kegg
(+)-Nicotine	HMDB
(R,S)-Nicotine	HMDB
1-Methyl-2-(3-pyridal)-pyrrolidene	HMDB
1-Methyl-2-(3-pyridal)-pyrrolidine	HMDB
1-Methyl-2-(3-pyridiyl)pyrrolidine	HMDB
2'-beta-H-Nicotine	HMDB
3-(1-Methyl-2-pyrrolidinyl)-pyridine	HMDB
3-(1-Methyl-2-pyrrolidinyl)pyridine	HMDB
3-(N-Methylpyrrolidino)pyridine	HMDB
3-N-Methylpyrrolidine	HMDB
a -N-Methylpyrrolidine	HMDB
a-N-Methylpyrrolidine	HMDB
alpha-N-Methylpyrrolidine	HMDB
beta-Pyridyl-alpha-N-methylpyrrolidine	HMDB
D-Nicotine	HMDB
delta-Nicotine	HMDB
Destruxol	HMDB
DL-Tetrahydronicotyrine	HMDB
Fumeto bac	HMDB
Methyl-2-pyrrolidinyl)pyridine	HMDB
Nicoderm	HMDB
Nicotine polacrilex	HMDB
R)-(+)-Nicotine	HMDB
Tartrate, nicotine	HMDB
Nicotine bitartrate	HMDB
Nicotine tartrate	HMDB
Bitartrate, nicotine	HMDB
Nicotine	ChEBI
(S)-3-(1-Methyl-2-pyrrolidinyl)pyridine	biospider
L -1-Methyl-2-[3-pyridyl]pyrrolidine	biospider
L-nicotine	biospider
Pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)-	biospider
Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)- (9CI)	biospider

Predicted Properties

Property	Value	Source
Water Solubility	93.3 g/L	ALOGPS
logP	0.87	ALOGPS
logP	1.16	ChemAxon
logS	-0.24	ALOGPS
pKa (Strongest Basic)	8.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.66 m³·mol⁻¹	ChemAxon
Polarizability	18.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H14N2

IUPAC name

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

InChI Identifier

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

InChI Key

SNICXCGAKADSCV-JTQLQIEISA-N

Isomeric SMILES

CN1CCC[C@H]1C1=CN=CC=C1

Average Molecular Weight

162.2316

Monoisotopic Molecular Weight

162.115698458

Classification

Description

Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyrrolidinylpyridines

Direct Parent

Pyrrolidinylpyridines

Alternative Parents

Substituents

Pyrrolidinylpyridine
Alkaloid or derivatives
Aralkylamine
N-alkylpyrrolidine
Heteroaromatic compound
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nicotine (CHEBI:17688 )
Pesticides (C00745 )
Pyridine alkaloids (C00745 )
Alkaloids (C00745 )

Ontology

Physiological effect

Health effect:

Health condition:

Dizziness

Vascular disorders:

Hypotension

Psychiatric disorders:

Confusion

General disorders and administration site conditions:

Pain

Gastrointestinal disorders:

Cardiac disorders:

Palpitations

Disposition

Route of exposure:

Parenteral:

Inhalation

Enteral:

Ingestion

Source:

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Biological location:

Organ and components:

Tissue and substructures:

Hair

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 74.04%; H 8.70%; N 17.27%	CCD
Melting Point	-79 oC
Boiling Point	Bp 730.5 246.1 °	CCD
Experimental Water Solubility	1000 mg/mL	SEIDELL,A (1941)
Experimental logP	1.17	HANSCH,C ET AL. (1995)
Experimental pKa	3.1
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a] D -166	CCD
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9400000000-47a036aa305825218fa2	2014-09-20	View Spectrum
GC-MS	Nicotine, non-derivatized, GC-MS Spectrum	splash10-001i-9500000000-f2d4835c504301f9410e	Spectrum
GC-MS	Nicotine, non-derivatized, GC-MS Spectrum	splash10-01q9-7900000000-1e2c38b5e4e7aae10d37	Spectrum
GC-MS	Nicotine, non-derivatized, GC-MS Spectrum	splash10-001i-9800000000-fe889308f7088d47c31d	Spectrum
GC-MS	Nicotine, non-derivatized, GC-MS Spectrum	splash10-001i-9500000000-f2d4835c504301f9410e	Spectrum
Predicted GC-MS	Nicotine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-4900000000-6d65165a4417a6129eeb	Spectrum
Predicted GC-MS	Nicotine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-3e7377f36ca2547f4885	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-2900000000-a505fff3a4028a6f0d52	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00lr-7900000000-b91a12a16d7688e8679d	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-01q9-7900000000-10d401d7ffa1c2cdbd9f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-0900000000-440798524836a27b78b4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-01q9-0900000000-926940dd7f4851dbd73b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00lr-0900000000-6bccc06d40ab273cf972	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0159-2900000000-f7512c405bb662e040a6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-7900000000-f1781566be5aee88f6ef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-0900000000-09e9b29571abf3a52e44	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-16cdb5f23105be4a892b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-720fe01876c739a30be0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-85a813588b57acf531fe	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-93a3dae1577f4f2dda53	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-1900000000-cb6f8cec40dd9ed35d00	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00lr-1900000000-1443b1cf22d2de281898	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-440798524836a27b78b4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01q9-0900000000-926940dd7f4851dbd73b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00lr-0900000000-6bccc06d40ab273cf972	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-bf73c660c9fef052a3e2	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-317ad58e8bc4c3092420	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9400000000-ea4895202e26a55d8a9b	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ed813017157d07798ea2	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1900000000-02ba66ba693d048f19ab	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-442e757e1da476d883af	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17688

Phenol-Explorer ID

Not Available

DrugBank ID

DB00184

HMDB ID

HMDB01934

CRC / DFC (Dictionary of Food Compounds) ID

BCM12-J:BCM12-J

EAFUS ID

Not Available

Dr. Duke ID

NICOTINE

BIGG ID

Not Available

KNApSAcK ID

C00002057

HET ID

NCT

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Nicotine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Addictive		A substance causing physical or psychological dependency, often triggering compulsive use despite negative effects. Its biological role involves activating the brain's reward system, releasing feel-good chemicals like dopamine. Therapeutically, understanding addictive substances informs treatment of addiction disorders. Key medical uses include managing pain, although caution is advised due to the risk of dependency.	DUKE
Analgesic	35480	An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
Anorectic	50780	An agent that suppresses appetite, reducing food intake. It plays a biological role in regulating hunger and satiety. Therapeutically, anorectics are used to treat obesity and weight-related disorders, aiding in weight loss and management. Key medical uses include short-term treatment of exogenous obesity and managing weight in patients with type 2 diabetes or other weight-related health issues.	DUKE
Autonomic nervous system paralytic	52217	An agent that disrupts autonomic nervous system function, blocking involuntary actions. Therapeutically, it reduces excessive sympathetic activity, commonly used in managing hypertension, cardiac arrhythmias, and perioperative tachycardia and hypertension.	DUKE
Autonomic nervous system stimulant	52217	An agent that enhances the activity of the autonomic nervous system, regulating involuntary functions. Therapeutically, it increases heart rate, blood pressure, and respiration. Key medical uses include treating hypotension, bradycardia, and neurogenic shock, as well as aiding in anesthesia and critical care.	DUKE
Anti estrogenic	35222	An agent that blocks or reduces estrogen's effects, used to treat hormone-sensitive cancers, such as breast cancer, and manage conditions like endometriosis and uterine fibroids, by inhibiting estrogen's biological role in promoting cell growth.	DUKE
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti-fumitory		An agent that inhibits the activity of fumitory, a plant-based toxin. Therapeutically, it reduces inflammation and oxidative stress, with applications in managing respiratory and gastrointestinal disorders, and potentially treating conditions like asthma and irritable bowel syndrome.	DUKE
Cardiovascular	38070	A system that transports blood, oxygen, and nutrients throughout the body, playing a crucial role in overall health. Therapeutically, cardiovascular agents manage conditions like hypertension, heart failure, and atherosclerosis, with key medical uses including regulating blood pressure, preventing blood clots, and improving cardiac function.	DUKE
Cholinergic	38323	An agent that stimulates the parasympathetic nervous system by mimicking acetylcholine, enhancing muscle contraction, and regulating various bodily functions. Therapeutically, it treats conditions like glaucoma, myasthenia gravis, and Alzheimer's disease, improving muscle tone, cognition, and eye pressure.	DUKE
Copaminigenic	48560	An agent that enhances dopamine production, playing a role in mood regulation and motor control. Therapeutically, it has applications in managing depression, anxiety, and Parkinson's disease, with key medical uses including treating mood disorders and neurodegenerative diseases.	DUKE
Ectoparasiticide	38956	An agent that kills or repels external parasites, reducing infestations. Therapeutically, it's used to treat conditions like scabies, lice, and mite infestations, providing relief from itching and skin irritation. Key medical uses include topical treatments for parasitic skin infections and prevention of parasite-borne diseases.	DUKE
Epinephrininergic		An agent that mimics or enhances the effects of epinephrine, a neurotransmitter involved in the body's "fight or flight" response. It plays a biological role in regulating heart rate, blood pressure, and energy metabolism. Therapeutically, epinephrininergic agents are used to treat conditions such as asthma, anaphylaxis, and cardiac arrest, and have key medical uses in emergency medicine and critical care.	DUKE
Herbicide	24527	A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.	DUKE
Hyperglycemic	76916	An agent that increases blood glucose levels, often used to treat hypoglycemia (low blood sugar) and as a diagnostic tool to assess pancreatic function.	DUKE
Insecticide	24852	An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.	DUKE
Nematistat		An agent that disorients, paralyzes, or confuses nematodes, preventing root infestation, with potential therapeutic applications in agriculture and key medical uses in managing parasitic nematode infections.	DUKE
Neurotoxic	50910	A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Serotoninergic	48278	An agent that modulates serotonin activity, regulating mood, appetite, and sleep. It has therapeutic applications in treating depression, anxiety, and mood disorders, with key medical uses including antidepressants, anxiolytics, and anti-migraine medications.	DUKE
Tranquilizer		An agent that induces relaxation and reduces anxiety, used therapeutically to manage anxiety disorders, insomnia, and restlessness, promoting calmness and sedation in individuals.	DUKE
Anxiolytic	35474	An agent that reduces anxiety symptoms, commonly used in managing anxiety disorders, such as generalized anxiety disorder and panic disorder, by modulating neurotransmitters like GABA, promoting relaxation and calming effects.	CHEBI

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Nicotine Pathway	SMP00431	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).