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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:47:32 UTC

HMDB ID

HMDB0001497

Secondary Accession Numbers

HMDB01497

Metabolite Identification

Common Name

Nicotine-1'-N-oxide

Description

Nicotine-1'-N-oxide 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. In humans, nicotine-1'-N-oxide is involved in the nicotine metabolism pathway. Nicotine-1'-N-oxide has been detected, but not quantified in, several different foods, such as black chokeberries (Photinia melanocarpa), garden onions (Allium cepa), barleys (Hordeum vulgare), gooseberries (Ribes uva-crispa), and highbush blueberries (Vaccinium corymbosum). This could make nicotine-1'-N-oxide a potential biomarker for the consumption of these foods. Nicotine-1'-N-oxide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Nicotine-1'-N-oxide.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.484 -23.733   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.903 -28.808   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.006 -22.588   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.903 -27.268   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.482 -24.053   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.236 -29.578   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.466 -22.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.570 -27.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.236 -26.498   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.236 -24.958   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      24.570 -28.808   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      21.991 -24.053   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0      20.960 -25.197   0.000  0.00  0.00           O-1
CONECT    1   12                                                            
CONECT    2    4    6                                                       
CONECT    3    7    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8   11    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    5    9   12                                                  
CONECT   11    6    8                                                       
CONECT   12    1    7   10   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0001497
HETATM    1  C1  UNL     1      -1.505   1.321   0.892  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.400   0.305  -0.108  1.00  0.00           N1+
HETATM    3  O1  UNL     1      -1.656   0.753  -1.364  1.00  0.00           O1-
HETATM    4  C2  UNL     1      -2.423  -0.733   0.124  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.955  -1.787  -0.885  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.452  -1.542  -1.060  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.213  -0.488  -0.001  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.062   0.196  -0.096  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.073  -0.094   0.798  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.298   0.556   0.714  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.548   1.507  -0.256  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.547   1.771  -1.115  1.00  0.00           N  
HETATM   13  C10 UNL     1       1.340   1.149  -1.053  1.00  0.00           C  
HETATM   14  H1  UNL     1      -0.523   1.423   1.437  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.677   2.306   0.413  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.296   1.125   1.653  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.407  -1.098   1.149  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.404  -0.385  -0.238  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.457  -1.662  -1.859  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.161  -2.801  -0.510  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.109  -2.474  -0.851  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.217  -1.182  -2.081  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.277  -1.024   0.977  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.889  -0.847   1.575  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.094   0.329   1.417  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.513   1.998  -0.298  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.551   1.377  -1.754  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4    7
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8   23
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13
CONECT   13   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olate	ChEBI
3-(1-Methyl-1-oxidopyrrolidin-2-yl)pyridine	ChEBI
Nicotine 1-N-oxide	ChEBI
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acid	Generator
(1's,2's)-Nicotine-n'-oxide	HMDB
(2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridine	HMDB
1'-Oxide nicotine	HMDB
1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxide	HMDB
3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine	HMDB
N-Oxide 3-(1-methyl-2-pyrrolidinyl)pyridine	HMDB
N-Oxide-(1-methyl-2-pyrrolidinyl)pyridine	HMDB
Nicotine 1'-oxide	HMDB
Nicotine n'-oxide	HMDB
Nicotine N(1')-oxide	HMDB
Nicotine-1'-oxide	HMDB, MeSH
Nicotine 1-N-oxide, (R)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, dihydrochloride, (S)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, (1S-cis)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, (1S-trans)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, (2S)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, 14C-labeled CPD	MeSH, HMDB
Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, (1R-cis)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, (1R-trans)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, (S)-isomer	MeSH, HMDB
Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomer	MeSH, HMDB

Chemical Formula

C₁₀H₁₄N₂O

Average Molecular Weight

178.231

Monoisotopic Molecular Weight

178.11061308

IUPAC Name

1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate

Traditional Name

nicotine 1-N-oxide

CAS Registry Number

63551-14-4

SMILES

C[N+]1([O-])CCCC1C1=CN=CC=C1

InChI Identifier

InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3

InChI Key

RWFBQHICRCUQJJ-UHFFFAOYSA-N

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
N-alkylpyrrolidine
Trialkyl amine oxide
Heteroaromatic compound
Pyrrolidine
Azacycle
N-oxide
Trisubstituted n-oxide
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organic nitrogen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrrolidine N-oxide (CHEBI:30734 )
a small molecule (CPD-2743 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-79 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL	Not Available
LogP	1.17	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	0.038	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	4.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.7 m³·mol⁻¹	ChemAxon
Polarizability	19.19 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.418	31661259
DarkChem	[M-H]-	137.418	31661259
AllCCS	[M+H]+	138.384	32859911
AllCCS	[M-H]-	149.488	32859911
DeepCCS	[M+H]+	133.022	30932474
DeepCCS	[M-H]-	130.626	30932474
DeepCCS	[M-2H]-	164.777	30932474
DeepCCS	[M+Na]+	139.265	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	142.6	32859911
AllCCS	[M+Na]+	143.8	32859911
AllCCS	[M-H]-	149.5	32859911
AllCCS	[M+Na-2H]-	150.3	32859911
AllCCS	[M+HCOO]-	151.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nicotine-1'-N-oxide	C[N+]1([O-])CCCC1C1=CN=CC=C1	2069.1	Standard polar	33892256
Nicotine-1'-N-oxide	C[N+]1([O-])CCCC1C1=CN=CC=C1	1348.4	Standard non polar	33892256
Nicotine-1'-N-oxide	C[N+]1([O-])CCCC1C1=CN=CC=C1	1494.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotine-1'-N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f96-8900000000-b2b7dd335c3a05aa57bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotine-1'-N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotine-1'-N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotine-1'-N-oxide 6V, Positive-QTOF	splash10-00pi-0900000000-43724ee9d877fcb632a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Positive-QTOF	splash10-004i-0900000000-c5515911fcd12c368c31	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Positive-QTOF	splash10-004l-5900000000-c464534b639004ad3b54	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Positive-QTOF	splash10-0uec-9300000000-2a2d1afce79d8998d3b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Negative-QTOF	splash10-004i-0900000000-4f451a2d6c2540a25c95	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Negative-QTOF	splash10-004i-0900000000-7b621173e20fa3dd7ce0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Negative-QTOF	splash10-0fb9-7900000000-1d685bcb46ea923561a3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Negative-QTOF	splash10-004i-0900000000-403f45bf7fa583376662	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Negative-QTOF	splash10-004i-0900000000-403f45bf7fa583376662	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Negative-QTOF	splash10-004i-9000000000-c2850ce6846335b0374d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Positive-QTOF	splash10-004i-0900000000-d33bcccb60db843c9005	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Positive-QTOF	splash10-03di-1900000000-c1bca04af770521cb894	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Positive-QTOF	splash10-0059-9500000000-d593bd18e59fdd3ed294	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Brain
Epidermis
Fibroblasts
Hair
Kidney
Liver
Lung
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Nicotine Action Pathway		Not Available
Nicotine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022656

KNApSAcK ID

Not Available

Chemspider ID

396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

409

PDB ID

Not Available

ChEBI ID

30734

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Urakawa N, Nagata T, Kudo K, Kimura K, Imamura T: Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry. Int J Legal Med. 1994;106(5):232-6. [PubMed:8068568 ]
Lerman C, Tyndale R, Patterson F, Wileyto EP, Shields PG, Pinto A, Benowitz N: Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation. Clin Pharmacol Ther. 2006 Jun;79(6):600-8. Epub 2006 May 11. [PubMed:16765148 ]
Court JA, Johnson M, Religa D, Keverne J, Kalaria R, Jaros E, McKeith IG, Perry R, Naslund J, Perry EK: Attenuation of Abeta deposition in the entorhinal cortex of normal elderly individuals associated with tobacco smoking. Neuropathol Appl Neurobiol. 2005 Oct;31(5):522-35. [PubMed:16150123 ]
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 ]
Fang Y, Svoboda KK: Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. J Cell Biochem. 2005 Aug 15;95(6):1108-19. [PubMed:15962330 ]
Eliasson B, Smith U, Lonnroth P: No acute effects of smoking and nicotine nasal spray on lipolysis measured by subcutaneous microdialysis. Eur J Clin Invest. 1997 Jun;27(6):503-9. [PubMed:9229231 ]
Tsurutani J, Castillo SS, Brognard J, Granville CA, Zhang C, Gills JJ, Sayyah J, Dennis PA: Tobacco components stimulate Akt-dependent proliferation and NFkappaB-dependent survival in lung cancer cells. Carcinogenesis. 2005 Jul;26(7):1182-95. Epub 2005 Mar 24. [PubMed:15790591 ]
Ramachandran J, Rubenstein D, Bluestein D, Jesty J: Activation of platelets exposed to shear stress in the presence of smoke extracts of low-nicotine and zero-nicotine cigarettes: the protective effect of nicotine. Nicotine Tob Res. 2004 Oct;6(5):835-41. [PubMed:15700919 ]
Miller VM, Lewis DA, Rud KS, Offord KP, Croghan IT, Hurt RD: Plasma nitric oxide before and after smoking cessation with nicotine nasal spray. J Clin Pharmacol. 1998 Jan;38(1):22-7. [PubMed:9597555 ]
Hureiki J, Laqueille X: [The Tuaregs addiction to tea, to smokeless tobacco and to milk: ethnological and clinical approach]. Encephale. 2003 Jan-Feb;29(1):42-8. [PubMed:12640326 ]
Bonci A, Bernardi G, Grillner P, Mercuri NB: The dopamine-containing neuron: maestro or simple musician in the orchestra of addiction? Trends Pharmacol Sci. 2003 Apr;24(4):172-7. [PubMed:12707003 ]
Nadler JL, Velasco JS, Horton R: Cigarette smoking inhibits prostacyclin formation. Lancet. 1983 Jun 4;1(8336):1248-50. [PubMed:6134041 ]
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 ]
Reddy A, Sood A, Rust PF, Busby JE, Varn E, Mathur RS, Mathur S: The effect of nicotine on in vitro sperm motion characteristics. J Assist Reprod Genet. 1995 Mar;12(3):217-23. [PubMed:8520189 ]
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Showing metabocard for Nicotine-1'-N-oxide (HMDB0001497)

MOL for HMDB0001497 (Nicotine-1'-N-oxide)

3D MOL for HMDB0001497 (Nicotine-1'-N-oxide)

3D SDF for HMDB0001497 (Nicotine-1'-N-oxide)

3D-SDF for HMDB0001497 (Nicotine-1'-N-oxide)

PDB for HMDB0001497 (Nicotine-1'-N-oxide)

3D PDB for HMDB0001497 (Nicotine-1'-N-oxide)

SMILES for HMDB0001497 (Nicotine-1'-N-oxide)

INCHI for HMDB0001497 (Nicotine-1'-N-oxide)

Structure for HMDB0001497 (Nicotine-1'-N-oxide)

3D Structure for HMDB0001497 (Nicotine-1'-N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra