(
(−)-nicotine
A mild chemical stimulant naturally found in some plants
Also known as nicotine · 3-(N-methylpyrollidino)pyridine · Nicotine betadex · Nicotine polacrilex · Nicotine · (S)-3-(1-methylpyrrolidin-2-yl)pyridine
- Formula
- C₁₀H₁₄N₂
- Mass
- 162.1157 Da
- Melting point
- -110°F
- , -79°C
1
- Density
- 1.01 g/cm³
Overview
Chemistry
All data
247 statements · 56% with external sources · numbers in brackets are citations
- Isomeric SMILES
- CN1CCC[C@H]1C2=CC=CN=C2
1
Sources- 1.Stated in Global Substance Registration SystemRetrieved 2018-02-14
- CN1CCC[C@H]1C2=CC=CN=C2
- Found in taxon
- Lycopodium obscurum
- Lycopodium annotinum
- Duboisia myoporoides
6
Sources- 1.Stated in Alkaloid composition and atropine esterase activity in callus and differentiated tissues of Duboisia myoporoides R. BR.
- 2.Stated in Alkaloid variation within Duboisia myoporoides
- 3.Stated in Alkaloid production in cultured roots of three species of Duboisia
- 4.Stated in Growth and Alkaloid Production in Duboisia myoporoides and D.leichhardtii Root Cultures.
- 5.Stated in Effects of Oxygen on Nicotine and Tropane Alkaloid Production in Cultured RootsDuboisia myoporoides
- 6.Stated in 787. The occurrence of nicotine, anabasine, and isopelletierine in Duboisia myoporoides
- Haloxylon persicum
2
Sources- 1.Stated in GLC-Mass Spectroscopy of Distilled Alkaloids of Haloxylon Persicum1
- 2.Stated in A new source of anabasine
- Camellia sinensis
1
- Brassica oleracea
2
Sources- 1.Stated in Dietary nicotine: A source of urinary cotinine
- 2.Stated in The nicotine content of common vegetables
- Solanum melongena
2
Sources- 1.Stated in Dietary nicotine: A source of urinary cotinine
- 2.Stated in The nicotine content of common vegetables
- potato
2
Sources- 1.Stated in Dietary nicotine: A source of urinary cotinine
- 2.Stated in The nicotine content of common vegetables
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- tomato
2
Sources- 1.Stated in Dietary nicotine: A source of urinary cotinine
- 2.Stated in The nicotine content of common vegetables
- Nicotiana tabacum
8
Sources- 1.Stated in The volatile bases of cigar smoke
- 2.Stated in Toxic and carcinogenic agents in dry and moist stuff
- 3.Stated in The alkaloid contents of sixty Nicotiana species
- 4.Stated in Relationship between Agrobacterium rhizogenes transformed hairy roots and intact, uninfected nicotiana plants
- 5.Stated in Nicotine production by tissue cultures of tobacco as influenced by various culture parameters
- 6.Stated in Enhanced Recovery of Nicotine from Tobacco Waste Using Sulfuric Acid and Microemulsion Medium
- Erythroxylum coca
2
Sources- 1.Stated in Analysis of alkaloids in leaves of cultivated Erythroxylum and characterization of alkaline substances used during coca chewing
- 2.Stated in A study of the chemical composition of Erythroxylum coca var. coca leaves collected in two ecological regions of Bolivia
- Erythroxylum zambesiacum
1
- Areca catechu
1
- Argyreia mollis
- Duboisia leichhardtii
4
Sources- 1.Stated in Alkaloid production in cultured roots of three species of Duboisia
- 2.Stated in Tropane alkaloid production in cultured cells of Duboisia leichhardtii
- 3.Stated in Biosynthesis of nicotine and scopolamine in a root culture of Duboisia leichhardtii
- 4.Stated in Growth and Alkaloid Production in Duboisia myoporoides and D.leichhardtii Root Cultures.
- Duboisia hopwoodii
- Nicotiana plumbaginifolia
- Nicotiana rustica
3
Sources- 1.Stated in Relationship between Agrobacterium rhizogenes transformed hairy roots and intact, uninfected nicotiana plants
- 2.Stated in The alkaloid contents of sixty Nicotiana species
- 3.Stated in Nicotine production by tissue cultures of tobacco as influenced by various culture parameters
- Nicotiana africana
- Nicotiana umbratica
- Nicotiana velutina
- Nicotiana cavicola
- Nicotiana acaulis
1
- Nicotiana acuminata
1
- Nicotiana alata
- Nicotiana ameghinoi
1
- Nicotiana amplexicaulis
1
- Nicotiana arentsii
1
- Nicotiana benavidesii
1
- Nicotiana benthamiana
1
- Nicotiana bonariensis
1
- Nicotiana clevelandii
1
- Nicotiana cordifolia
1
- Nicotiana corymbosa
1
- Nicotiana debneyi
1
- Nicotiana excelsior
1
- Nicotiana exigua
1
- Nicotiana suaveolens
1
- Nicotiana forgetiana
1
- Nicotiana fragrans
1
- Nicotiana glauca
1
- Nicotiana glutinosa
- Nicotiana goodspeedii
1
- Nicotiana gossei
1
- Nicotiana rosulata
1
- Nicotiana kawakamii
1
- Nicotiana knightiana
1
- Nicotiana langsdorffii
1
- Nicotiana linearis
1
- Nicotiana longibracteata
1
- Nicotiana longiflora
1
- Nicotiana maritima
1
- Nicotiana megalosiphon
1
- Nicotiana miersii
1
- Nicotiana nesophila
1
- Nicotiana stocktonii
1
- Nicotiana noctiflora
1
- Nicotiana nudicaulis
1
- Nicotiana otophora
1
- Nicotiana paniculata
1
- Vapor pressure
- 0.08 millimetre of mercury temperature: 68°F
- Immediately dangerous to life or health
- 5 milligram per cubic metre
- Lower flammable limit
- 0.7 volume percent
- Upper flammable limit
- 4 volume percent
- Time-weighted average exposure limit
- 0.5 milligram per cubic metre applies to jurisdiction: United States · runtime: 10 h · route of administration: skin absorption
- Stereoisomer of
- (+)-nicotine criterion used: absolute configuration
- Subject has role
- nicotinic agonist
1
- Ganglionic Stimulants
1
- developmental toxicant(since 1990)
1
Sources- 1.Stated in California Proposition 65 list of chemicalsoehha.ca.gov/chemicals/nicotineRetrieved 2020-03-18
- nicotinic agonist
- Canonical SMILES
- N=1C=CC=C(C1)C2N(C)CCC2
- Legal status (medicine)
- boxed warning
1
Sources- 1.“FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.”nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
- boxed warning
- Substance control status
- Schedule 7 (Australia) applies to jurisdiction: Australia
On other databases
68 identifiers linking (−)-nicotine across the web's reference databases
- ABC News topic IDnicotine
- Article ID in the Lithuanian Universal Encyclopedia Onlinenikotinas
- CA PROP 65 IDnicotine
- CAMEO Chemicals ID4032
- Cannabis Database ID005499
- CAS Registry Number54-11-5
- ChEBI ID17688
- ChEMBL IDCHEMBL3
- ChemSpider ID80863
- DrugBank IDDB00184
- DrugCentral ID1920
- DSSTOX compound identifierDTXCID50930
- DSSTox substance IDDTXSID1020930
- EC number200-193-3
- ECHA Substance Infocard ID100.000.177
- Encyclopædia Britannica Online IDscience/nicotine
- Freebase ID/m/09jrx
- Great Russian Encyclopedia portal IDnikotin-eca638
- Guide to Pharmacology Ligand ID2585
- HCIS ID3216
- HSDB ID1107
- Human Metabolome Database IDHMDB0001934
- ICSC ID0519
- IEDB Epitope ID1597626
- InChIInChI=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
- InChIKeySNICXCGAKADSCV-JTQLQIEISA-N
- J9U entity ID987007531422205171
- JSTOR topic ID (archived)nicotine-dependence
- KEGG IDC00745
- KNApSAcK IDC00002057
- Lex IDnikotin
- Library of Congress Authorities IDsh85091817
- MassBank accession IDMSBNK-Eawag-EQ300801
- MeSH descriptor IDD009538
- MeSH tree codeD03.132.760.570
- Microsoft Academic ID (discontinued)2779547902
- NCI Thesaurus IDC691
- NDF-RT IDN0000148163
- NL CR AUT IDph1308230
- NSC number5065
- Online PWN Encyclopedia ID3947755
- OpenAlex IDC2779547902
- OSHA Occupational Chemical Database ID396
- PACTOLS thesaurus IDpcrtbRoB6J1AY7
- PDB ligand IDNCT
- PesticideInfo chemical IDPRI4478
- PM20 ware ID143611
- Probes And Drugs IDPD003076
- PubChem CID89594
- Quora topic IDNicotine
- Reaxys registry number82108
- Römpp online IDRD-14-01147
- RxNorm CUI7407
- SPLASHsplash10-03di-0900000000-720fe01876c739a30be0
- SureChEMBL ID20192
- UK Parliament thesaurus ID494177
- UM-BBD compound IDc0468
- UniChem compound ID310474
- UNII6M3C89ZY6R
- UNSPSC code51212202
- Vikidia article IDfr:Nicotine
- WikiKids IDNicotine
- WikiSkripta article ID50920
- WordNet 3.1 Synset ID14738978-n
- Yale LUX IDconcept/c06a3346-4feb-489f-8405-cda85dbb068a
- YSO ID4846
- Zhihu topic ID19656586
- ZVG number41410