AFCDB: 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

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

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

Showing 1 to 10 of 14 entries

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
addictive			DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anorectic	50780	An agent which regulates the physiologic mechanisms that control the appetite and food intake.	DUKE
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti feedant			DUKE
anti fumitory			DUKE
anxiolytic	35474	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.	CHEBI
autonomic nervous system paralytic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
autonomic nervous system stimulant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cardiovascular	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE

Showing 1 to 10 of 22 entries

Enzymes

Not Available

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Files

MSDS

show

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).

Nicotine (FDB003968)

Structure for FDB003968 (Nicotine)