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54-11-5 molecular structure
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3-(1-methylpyrrolidin-2-yl)pyridine

ChemBase ID: 69
Molecular Formular: C10H14N2
Molecular Mass: 162.23156
Monoisotopic Mass: 162.11569846
SMILES and InChIs

SMILES:
N1(C(CCC1)c1cccnc1)C
Canonical SMILES:
CN1CCCC1c1cccnc1
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
InChIKey:
SNICXCGAKADSCV-UHFFFAOYSA-N

Cite this record

CBID:69 http://www.chembase.cn/molecule-69.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-(1-methylpyrrolidin-2-yl)pyridine
IUPAC Traditional name
nicotine
Brand Name
Black Leaf
Black Leaf 40
Campbell's Nico-Soap
Commit
Destruxol Orchid Spray
Emo-Nik
Flux Maag
Fumetobac
Habitrol
Mach-Nic
Niagara P.A. Dust
Nic-Sal
Nico-Dust
Nico-Fume
Nicocide
Nicoderm
Nicoderm Cq
Nicorette
Nicorette Plus
Nicotin
Nicotina
Nicotine Polacrilex
Nicotrol
Nicotrol Inhaler
Nicotrol Ns
Nikotin
Nikotyna
Ortho N-4 Dust
Ortho N-5 Dust
Prostep
Tendust
Synonyms
L-Nicotine
Nicotine Alkaloid
Nicotine
L-1-Methyl-2-[3-pyridyl]pyrrolidine
(-)-NICOTINE FREE BASE
3-(1-Methyl-2-pyrrolidinyl)pyridine
(±)-Nicotine
(±)-3-(1-Methyl-2-pyrrolidinyl)pyridine
(R,S)-Nicotine
1-Methyl-2-(3-pyridyl)pyrrolidine
3-(1-methylpyrrolidin-2-yl)pyridine
(±)-Nicotine
DL-Nicotine
rac-Nicotine
CAS Number
54-11-5
22083-74-5
EC Number
200-193-3
MDL Number
MFCD00065370
Beilstein Number
82108
PubChem SID
46506924
160963532
24897418
PubChem CID
942

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -1.9628259  LogD (pH = 7.4) -0.31012845 
Log P 1.1625347  Molar Refractivity 49.655 cm3
Polarizability 19.449343 Å3 Polar Surface Area 16.13 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 0.87  LOG S -0.24 
Solubility (Water) 9.33e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 g/mL expand Show data source
Chloroform expand Show data source
Ethanol expand Show data source
ethanol: soluble50 mg/mL expand Show data source
Methanol expand Show data source
Apperance
Clear Colourless to Light Yellow Oil expand Show data source
yellow liquid expand Show data source
Melting Point
-79 °C expand Show data source
Boiling Point
247 °C at 745 mmHg (partial decomposition) expand Show data source
67°C/0.5 mm expand Show data source
Flash Point
101 °C expand Show data source
101°C expand Show data source
213.8 °F expand Show data source
214 °F expand Show data source
Auto Ignition Point
244 °C (471 °F) expand Show data source
Density
1.0097 at 20 °C (water = 1) expand Show data source
1.02 g/mL at 25 °C(lit.) expand Show data source
Vapor Pressure
0.0425 mm Hg at 20 °C expand Show data source
Vapor Density
5.6 (air = 1) expand Show data source
Optical Rotation
[α]25/D 0°(lit.) expand Show data source
Hydrophobicity(logP)
0.883 expand Show data source
1.1 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C), Desiccate, Store Under Nitrogen, Protect from light expand Show data source
RTECS
QS5250000 expand Show data source
QS5257500 expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
1654 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
25-27-51/53 expand Show data source
R:25-27-51/53 expand Show data source
Safety Statements
36/37-45-61 expand Show data source
S:45-61-36/37 expand Show data source
EU Classification
T1 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
151 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H310-H411 expand Show data source
GHS Precautionary statements
P273-P280-P301 + P310-P302 + P350-P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1654 6.1/PG 2 expand Show data source
Gene Information
human ... CHRNA2(1135), CHRNA3(1136), CHRNA4(1137)rat ... Chrna3(25101), Chrna4(25590), Chrna7(25302) expand Show data source
Purity
≥99% (TLC) expand Show data source
≥99.0% (TLC) expand Show data source
95% expand Show data source
98-100% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C10H14N2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank TRC TRC Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02190671 external link
Free Base
Purity: 98-100% (~ 6.22M)
Clear light yellow liquid
DrugBank - DB00184 external link
Item Information
Drug Groups approved
Description Nicotine is 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. [PubChem]
Indication For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.
Pharmacology Nicotine, the primary alkaloid in tobacco products binds stereo-selectively to nicotinic-cholinergic receptors on autonomic ganglia, the adrenal medulla, neuromuscular junctions and in the brain. Nicotine exerts two effects, a stimulant effect exerted at the locus ceruleus and a reward effect in the limbic system. Itranvenous administration of nicotine causes release of acetylcholine, norepinephrine, dopamine, serotonine, vasopressin, beta-endorphin and ACTH. Nicotine is a highly addictive substance. Nicotine also induces peripheral vasoconstriction, tachycardia and elevated blood pressure. Nicotine inhalers and patches are used to treat smoking withdrawl syndrome. Nicotine is classified as a stimulant of autonomic ganglia.
Toxicity Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD50= 24 mg/kg (orally in mice).
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic, cotinine is the primary metabolite.
Absorption Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.
Half Life Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours
Protein Binding Less than 5%
Elimination About 10% of the nicotine absorbed is excreted unchanged in the urine.
Distribution * 2 to 3 L/kg
Clearance * 1.2 L/min [healthy adult smoker]
References
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]
de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. [Pubmed]
de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. [Pubmed]
Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - N412420 external link
Nicotine is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment o
Sigma Aldrich - N0267 external link
Biochem/physiol Actions
Prototype nicotinic acetylcholine receptor agonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N0267.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N0267.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. Pubmed
  • • de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. Pubmed
  • • Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. Pubmed
  • • Ferretti, G., et al.: J. Med. Chem., 45, 4724 (2002)
  • • Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2002)
  • • Ramunno, A., et al.: Bioorg. Med. Chem. Lett., 15, 3237 (2002)
  • • Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2002)
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PATENTS

PATENTS

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INTERNET

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