NP-MRD: Showing NP-Card for Nicotine (NP0000237)

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Record Information

Version

2.0

Created at

2006-05-18 08:53:59 UTC

Updated at

2025-02-11 15:48:48 UTC

NP-MRD ID

NP0000237

Natural Product DOI

https://doi.org/10.57994/2894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nicotine

Description

Nicotine is an alkaloid found in the nightshade family of plants (Solanaceae), predominantly in tobacco and in lower quantities in tomato, potato, eggplant (aubergine), and green pepper. Nicotine alkaloids are also found in the leaves of the coca plant. Nicotine constitutes 0.3 To 5% of the tobacco plant by dry weight, with biosynthesis taking place in the root and accumulation in the leaves. It is a potent neurotoxin with particular specificity to insects; therefore nicotine was widely used as an insecticide in the past and nicotine derivatives such as imidacloprid continue to be widely used. It has been noted that the majority of people diagnosed with schizophrenia smoke tobacco. Estimates for the number of schizophrenics that smoke range from 75% to 90%. It was recently argued that the increased level of smoking in schizophrenia may be due to a desire to self-medicate with nicotine. More recent research has found the reverse: It is a risk factor without long-term benefit, used only for its short-term effects. However, research on nicotine as administered through a patch or gum is ongoing. As nicotine enters the body, it is distributed quickly through the bloodstream and can cross the blood-brain barrier. On average, it takes about seven seconds for the substance to reach the brain. The half-life of nicotine in the body is around 2 hours. The amount of nicotine inhaled with tobacco smoke is a fraction of the amount contained in the tobacco leaves (most of the substance is destroyed by the heat). The amount of nicotine absorbed by the body from smoking depends on many factors, including the type of tobacco, whether the smoke is inhaled, and whether a filter is used. For chewing tobacco, often called dip, snuff, or sinus, which is held in the mouth between the lip and gum, the amount released into the body tends to be much greater than smoked tobacco. The currently available literature indicates that nicotine, on its own, does not promote the development of cancer in healthy tissue and has no mutagenic properties. Its teratogenic properties have not yet been adequately researched, and while the likelihood of birth defects caused by nicotine is believed to be very small or nonexistent, nicotine replacement product manufacturers recommend consultation with a physician before using a nicotine patch or nicotine gum while pregnant or nursing. However, nicotine and the increased acetylcholinic activity it causes have been shown to impede apoptosis, which is one of the methods by which the body destroys unwanted cells (programmed cell death). Since apoptosis helps to remove mutated or damaged cells that may eventually become cancerous, the inhibitory actions of nicotine create a more favourable environment for cancer to develop. Thus, nicotine plays an indirect role in carcinogenesis. It is also important to note that its addictive properties are often the primary motivating factor for tobacco smoking, contributing to the proliferation of cancer. Nicotine is a highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. Nicotine is a hygroscopic, oily liquid that is miscible with water in its base form. As a nitrogenous base, nicotine forms salts with acids that are usually solid and water soluble. Nicotine easily penetrates the skin. As shown by the physical data, free base nicotine will burn at a temperature below its boiling point, and its vapours will combust at 95 °C in the air despite a low vapour pressure. Because of this, most nicotine is burned when a cigarette is smoked; however, enough is inhaled to provide the desired effects. Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible for the euphoric and addictive properties of nicotine. Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing an influx of sodium which causes depolarization of the cell and activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar. Cotinine is a byproduct of the metabolism of nicotine which remains in the blood for up to 48 hours and can be used as an indicator of a person's exposure to smoke. In high doses, nicotine will cause a blocking of the nicotinic acetylcholine receptor, which is the reason for its toxicity and its effectiveness as an insecticide. In lower concentrations, the substance acts as a stimulant in mammals and is one of the main factors responsible for the dependence-forming and energy-boosting properties of tobacco smoking.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    0.2355    1.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349    0.6620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3142    0.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -0.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567   -1.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140   -0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8893   -1.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -1.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7433    0.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924    1.3733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    0.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9150    1.2960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8154    2.7832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    2.7636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7096    1.4607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9127    2.3555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9622   -1.5768    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2579    0.4087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514   -2.7558    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1311   -2.4235    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0893   -2.2269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -2.9625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3925   -2.2128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1957    0.6777    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    2.2913    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6  2  1  0
 12  7  1  0
  1 13  1  6
  1 14  1  0
  1 15  1  0
  3 16  1  1
  3 17  1  0
  4 18  1  6
  4 19  1  0
  5 20  1  1
  5 21  1  0
  6 22  1  1
  8 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
M  END
> <DATABASE_ID>
NP0000237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC[C@H]1C1=CN=CC=C1

> <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

> <FORMULA>
C10H14N2

> <MOLECULAR_WEIGHT>
162.2316

> <EXACT_MASS>
162.115698458

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.589098097139342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
1.1625346926666664

> <ALOGPS_LOGS>
-0.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.57718555213823

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
49.655

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nicoderm CQ

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -4.102  -1.684   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.058  -5.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.914  -4.074   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.392  -4.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.770   1.334   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -3.072  -2.828   0.000  0.00  0.00           N+0
CONECT    1   12                                                            
CONECT    2    4    6                                                       
CONECT    3    5    7                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    9   11                                                       
CONECT    9    4    8   10                                                  
CONECT   10    5    9   12                                                  
CONECT   11    6    8                                                       
CONECT   12    1    7   10                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Value	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

Chemical Formula

C₁₀H₁₄N₂

Average Mass

162.2316 Da

Monoisotopic Mass

162.11570 Da

IUPAC Name

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

Traditional Name

nicoderm CQ

CAS Registry Number

54-11-5

SMILES

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

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CDCl₃, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-21	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Acacia concinna	KNApSAcK Database	22123792
Acacia rigidula Benth.	KNApSAcK Database	22123792
Areca catechu	KNApSAcK Database	22123792
Argyreia mollis	KNApSAcK Database	22123792
Asclepias syriaca	KNApSAcK Database	22123792
Brassica oleracea	LOTUS Database	35616633
Corydalis yanhusuo	KNApSAcK Database	22123792
Cyphanthera anthocercidea	KNApSAcK Database	22123792
Cyphanthera tasmanica Miers	LOTUS Database	35616633
Dendrolycopodium obscurum	LOTUS Database	35616633
Duboisia hopwoodii	LOTUS Database	35616633
Duboisia leichhardtii	LOTUS Database	35616633
Duboisia myoporoides	LOTUS Database	35616633
Equisetum arvense	KNApSAcK Database	22123792
Erythroxylum coca	LOTUS Database	35616633
Erythroxylum cuneatum	LOTUS Database	35616633
Erythroxylum zambesiacum	LOTUS Database	35616633
Haloxylon persicum	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Lycopodium spp.	KNApSAcK Database	22123792
Nicotiana acaulis	KNApSAcK Database	22123792
Nicotiana acuminata	KNApSAcK Database	22123792
Nicotiana africana	KNApSAcK Database	22123792
Nicotiana alata	KNApSAcK Database	22123792
Nicotiana ameghinoi	KNApSAcK Database	22123792
Nicotiana amplexicaulis	KNApSAcK Database	22123792
Nicotiana arentsii	KNApSAcK Database	22123792
Nicotiana attenuata	KNApSAcK Database	22123792
Nicotiana benavidesii	KNApSAcK Database	22123792
Nicotiana benthamiana	KNApSAcK Database	22123792
Nicotiana bigelovii	KNApSAcK Database	22123792
Nicotiana bonariensis	KNApSAcK Database	22123792
Nicotiana cavicola	KNApSAcK Database	22123792
Nicotiana clevelandii	KNApSAcK Database	22123792
Nicotiana cordifolia	KNApSAcK Database	22123792
Nicotiana corymbosa	KNApSAcK Database	22123792
Nicotiana debneyi	KNApSAcK Database	22123792
Nicotiana excelsior	KNApSAcK Database	22123792
Nicotiana exigua	KNApSAcK Database	22123792
Nicotiana forgetiana	KNApSAcK Database	22123792
Nicotiana fragrans	KNApSAcK Database	22123792
Nicotiana glauca	KNApSAcK Database	22123792
Nicotiana glutinosa	KNApSAcK Database	22123792
Nicotiana goodspeedii	KNApSAcK Database	22123792
Nicotiana gossei	KNApSAcK Database	22123792
Nicotiana hesperis	KNApSAcK Database	22123792
Nicotiana ingulba	KNApSAcK Database	22123792
Nicotiana kawakamii	KNApSAcK Database	22123792
Nicotiana knightiana	KNApSAcK Database	22123792
Nicotiana langsdorffii	KNApSAcK Database	22123792
Nicotiana linearis	KNApSAcK Database	22123792
Nicotiana longibracteata	KNApSAcK Database	22123792
Nicotiana longiflora	KNApSAcK Database	22123792
Nicotiana maritima	KNApSAcK Database	22123792
Nicotiana megalosiphon	KNApSAcK Database	22123792
Nicotiana miersii	KNApSAcK Database	22123792
Nicotiana nesophila	KNApSAcK Database	22123792
Nicotiana noctiflora	KNApSAcK Database	22123792
Nicotiana nudicaulis	KNApSAcK Database	22123792
Nicotiana occidentalis	KNApSAcK Database	22123792
Nicotiana otophora	KNApSAcK Database	22123792
Nicotiana paniculata	KNApSAcK Database	22123792
Nicotiana pauciflora	KNApSAcK Database	22123792
Nicotiana petunioides	KNApSAcK Database	22123792
Nicotiana plumbaginifolia	KNApSAcK Database	22123792
Nicotiana raimondii	KNApSAcK Database	22123792
Nicotiana repanda	KNApSAcK Database	22123792
Nicotiana rosulata	KNApSAcK Database	22123792
Nicotiana rotundifolia	KNApSAcK Database	22123792
Nicotiana rustica	KNApSAcK Database	22123792
Nicotiana setchellii	KNApSAcK Database	22123792
Nicotiana simulans	KNApSAcK Database	22123792
Nicotiana solanifolia	KNApSAcK Database	22123792
Nicotiana sp.	KNApSAcK Database	22123792
Nicotiana spegazzinii	KNApSAcK Database	22123792
Nicotiana stocktonii	KNApSAcK Database	22123792
Nicotiana suaveolens	KNApSAcK Database	22123792
Nicotiana sylvestris	KNApSAcK Database	22123792
Nicotiana tabacum	KNApSAcK Database	22123792
Nicotiana thyrosiflora	KNApSAcK Database	22123792
Nicotiana tomentosa	KNApSAcK Database	22123792
Nicotiana tomentosiformis	KNApSAcK Database	22123792
Nicotiana trigonophylla	KNApSAcK Database	22123792
Nicotiana umbratica	LOTUS Database	35616633
Nicotiana undulata	KNApSAcK Database	22123792
Nicotiana velutina	KNApSAcK Database	22123792
Nicotiana wigandioides	KNApSAcK Database	22123792
Sedum acre	KNApSAcK Database	22123792
Senegalia berlandieri	LOTUS Database	35616633
Solanum tuberosum	LOTUS Database	35616633
Vachellia rigidula	LOTUS Database	35616633

Chemical Taxonomy

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 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-79 °C	Not Available
Boiling Point	247.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000 mg/mL	Not Available
LogP	1.17	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

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

External Links

HMDB ID

HMDB0001934

DrugBank ID

DB00184

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Nicotine

METLIN ID

1526

PubChem Compound

89594

PDB ID

Not Available

ChEBI ID

17688

Good Scents ID

rw1142371

References

General References

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Henningfield JE, Radzius A, Cooper TM, Clayton RR: Drinking coffee and carbonated beverages blocks absorption of nicotine from nicotine polacrilex gum. JAMA. 1990 Sep 26;264(12):1560-4. [PubMed:2395197 ]
Hrnciar J, Katreniakova M, Lepej J, Okapcova J: [The effects of nicotine on leptin levels in patients with android obesity]. Vnitr Lek. 1997 Sep;43(9):562-5. [PubMed:9750463 ]
LeSage MG, Keyler DE, Pentel PR: Current status of immunologic approaches to treating tobacco dependence: vaccines and nicotine-specific antibodies. AAPS J. 2006 Feb 24;8(1):E65-75. [PubMed:16584135 ]
Terry AV Jr, Hernandez CM, Hohnadel EJ, Bouchard KP, Buccafusco JJ: Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. CNS Drug Rev. 2005 Autumn;11(3):229-52. [PubMed:16389292 ]
Marchei E, Durgbanshi A, Rossi S, Garcia-Algar O, Zuccaro P, Pichini S: Determination of arecoline (areca nut alkaloid) and nicotine in hair by high-performance liquid chromatography/electrospray quadrupole mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(22):3416-8. [PubMed:16259042 ]
Maurer P, Jennings GT, Willers J, Rohner F, Lindman Y, Roubicek K, Renner WA, Muller P, Bachmann MF: A therapeutic vaccine for nicotine dependence: preclinical efficacy, and Phase I safety and immunogenicity. Eur J Immunol. 2005 Jul;35(7):2031-40. [PubMed:15971275 ]
Warner DO, Joyner MJ, Charkoudian N: Nicotine increases initial blood flow responses to local heating of human non-glabrous skin. J Physiol. 2004 Sep 15;559(Pt 3):975-84. Epub 2004 Jul 22. [PubMed:15272048 ]
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Cerny T: Anti-nicotine vaccination: where are we? Recent Results Cancer Res. 2005;166:167-75. [PubMed:15648190 ]
Nakazawa A, Shigeta M, Ozasa K: Smoking cigarettes of low nicotine yield does not reduce nicotine intake as expected: a study of nicotine dependency in Japanese males. BMC Public Health. 2004 Jul 20;4:28. [PubMed:15265231 ]
Groner JA, Hoshaw-Woodard S, Koren G, Klein J, Castile R: Screening for children's exposure to environmental tobacco smoke in a pediatric primary care setting. Arch Pediatr Adolesc Med. 2005 May;159(5):450-5. [PubMed:15867119 ]
Stepans MB, Wilhelm SL, Dolence K: Smoking hygiene: reducing infant exposure to tobacco. Biol Res Nurs. 2006 Oct;8(2):104-14. [PubMed:17003250 ]
Moriya F, Hashimoto Y: Nicotine and cotinine levels in blood and urine from forensic autopsy cases. Leg Med (Tokyo). 2004 Jul;6(3):164-9. [PubMed:15231285 ]
Chetiyanukornkul T, Toriba A, Kizu R, Kimura K, Hayakawa K: Hair analysis of nicotine and cotinine for evaluating tobacco smoke exposure by liquid chromatography-mass spectrometry. Biomed Chromatogr. 2004 Nov;18(9):655-61. [PubMed:15386502 ]
Klein J, Blanchette P, Koren G: Assessing nicotine metabolism in pregnancy--a novel approach using hair analysis. Forensic Sci Int. 2004 Oct 29;145(2-3):191-4. [PubMed:15451092 ]
Ingram JR, Routledge P, Rhodes J, Marshall RW, Buss DC, Evans BK, Feyerabend C, Thomas GA: Nicotine enemas for treatment of ulcerative colitis: a study of the pharmacokinetics and adverse events associated with three doses of nicotine. Aliment Pharmacol Ther. 2004 Oct 15;20(8):859-65. [PubMed:15479357 ]
Fallon JH, Keator DB, Mbogori J, Taylor D, Potkin SG: Gender: a major determinant of brain response to nicotine. Int J Neuropsychopharmacol. 2005 Mar;8(1):17-26. Epub 2004 Dec 6. [PubMed:15579215 ]
Metz-Favre C, Donnay C, de Blay F: [Markers of environmental tobacco smoke (ETS) exposure]. Rev Mal Respir. 2005 Feb;22(1 Pt 1):81-92. [PubMed:15968761 ]
Fontaine B: [Smoking and breastfeeding: how can we help mothers stop smoking?]. J Gynecol Obstet Biol Reprod (Paris). 2005 Apr;34 Spec No 1:3S209-12. [PubMed:15980790 ]
Dempsey D, Tutka P, Jacob P 3rd, Allen F, Schoedel K, Tyndale RF, Benowitz NL: Nicotine metabolite ratio as an index of cytochrome P450 2A6 metabolic activity. Clin Pharmacol Ther. 2004 Jul;76(1):64-72. [PubMed:15229465 ]
Miksys S, Tyndale RF: Nicotine induces brain CYP enzymes: relevance to Parkinson's disease. J Neural Transm Suppl. 2006;(70):177-80. [PubMed:17017527 ]
Katsura M, Ohkuma S: Functional proteins involved in regulation of intracellular Ca(2+) for drug development: chronic nicotine treatment upregulates L-type high voltage-gated calcium channels. J Pharmacol Sci. 2005 Mar;97(3):344-7. Epub 2005 Mar 12. [PubMed:15764844 ]
Ziegler UE, Kauczok J, Dietz UA, Reith HB, Schmidt K: Clinical correlation between the consumption of nicotine and cotinine concentrations in urine and serum by competitive enzyme-linked immunosorbent assay. Pharmacology. 2004 Dec;72(4):254-9. [PubMed:15539886 ]
Tanaka H, Tanabe N, Shoji M, Suzuki N, Katono T, Sato S, Motohashi M, Maeno M: Nicotine and lipopolysaccharide stimulate the formation of osteoclast-like cells by increasing macrophage colony-stimulating factor and prostaglandin E2 production by osteoblasts. Life Sci. 2006 Mar 6;78(15):1733-40. Epub 2005 Nov 2. [PubMed:16266722 ]
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Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. [PubMed:17129706 ]

Showing NP-Card for Nicotine (NP0000237)

MOL for NP0000237 (Nicotine)

3D MOL for NP0000237 (Nicotine)

3D SDF for NP0000237 (Nicotine)

3D-SDF for NP0000237 (Nicotine)

PDB for NP0000237 (Nicotine)

3D PDB for NP0000237 (Nicotine)

SMILES for NP0000237 (Nicotine)

INCHI for NP0000237 (Nicotine)

Structure for NP0000237 (Nicotine)

3D Structure for NP0000237 (Nicotine)