Nicotine

Details

• Internal ID: 42b00310-59b7-4ba1-8f01-0e508339886b
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyrrolidinylpyridines
• IUPAC Name: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• SMILES (Canonical): CN1CCCC1C2=CN=CC=C2
• SMILES (Isomeric): CN1CCC[C@H]1C2=CN=CC=C2
• 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/t10-/m0/s1
• InChI Key: SNICXCGAKADSCV-JTQLQIEISA-N
• Popularity: 58,392 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23 g/mol
• Exact Mass: 162.115698455 g/mol
• Topological Polar Surface Area (TPSA): 16.10 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• L-Nicotine
• 54-11-5
• (-)-Nicotine
• (S)-Nicotine
• (S)-3-(1-methylpyrrolidin-2-yl)pyridine
• Habitrol
• Nicotrol
• (S)-(-)-Nicotine
• Nicoderm
• 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• Fumetobac
• Micotine
• Nicocide
• Nicotin
• Prostep
• Tendust
• Black leaf
• Nico-dust
• Nicoderm Cq
• Nicotine alkaloid
• Emo-nik
• Nico-Fume
• Mach-Nic
• Nic-Sal
• Nicotine polacrilex
• Flux MAAG
• Nicotina
• Nikotyna
• Ortho N-4 dust
• Ortho N-5 dust
• XL All Insecticide
• Niagara P.A. dust
• Destruxol orchid spray
• Nikotin [German]
• Nikotyna [Polish]
• L(-)-nicotine
• Nicotina [Italian]
• Black Leaf 40
• 3-(N-Methylpyrollidino)pyridine
• 3-(N-Methylpyrrolidino)pyridine
• Nicabate
• Nicorette
• Nicotinum
• Niquitin
• Tabazur
• Exodus
• L-3-(1-Methyl-2-pyrrolidyl)pyridine
• Caswell No. 597
• Ortho N-4 and N-5 dusts
• Nicotrol Inhaler
• (-)-3-(1-Methyl-2-pyrrolidyl)pyridine
• Nicotrol NS
• (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine
• Nicotine [USAN]
• RCRA waste number P075
• NSC 5065
• Nikotin
• ENT 3,424
• beta-Pyridyl-alpha-N-methylpyrrolidine
• 3-(2-(N-methylpyrrolidinyl))pyridine
• CCRIS 1637
• Nicotine [BSI:ISO]
• 1-Methyl-2-(3-pyridyl)pyrrolidine
• beta-Pyridyl-alpha-N-methyl pyrrolidine
• fumeto bac
• Nictoine patch
• Nicoderm Patch
• Nicotine Patch
• HSDB 1107
• Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)-
• 3-((2S)-1-methylpyrrolidin-2-yl)pyridine
• EINECS 200-193-3
• UNII-6M3C89ZY6R
• nicotine s(-)
• (-)-3-(N-Methylpyrrolidino)pyridine
• 3-(1-Methyl-2-pyrollidinyl)pyridine
• Habitrol (TN)
• Nicotine (USP)
• Nicotine [ISO]
• Transdermal Nicotine
• EPA Pesticide Chemical Code 056702
• 6M3C89ZY6R
• Pyrrolidine, 1-methyl-2-(3-pyridal)-
• DTXSID1020930
• CHEBI:17688
• (S)-3-(N-methylpyrrolidin-2-yl)pyridine
• AI3-03424
• 3-(1-Methyl-2-pyrrolidinyl)pyridine
• Nicotine [USP:BAN]
• nicotine replacement patch
• Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl)
• Tetrahydronicotyrine, DL-
• UN1654
• RCRA waste no. P075
• S-(-)-Nicotine
• DTXCID50930
• Nicotine [UN1654] [Poison]
• EC 200-193-3
• Pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)-
• Pyridine, 3-[(2S)-1-methyl-2-pyrrolidinyl]-
• NICOTINE COMPONENT OF COMMIT
• NSC-5065
• 3-(1-Methyl-2-pyrrolidyl)pyridine
• 1-Methyl-2-(3-pyridiyl)pyrrolidine
• NICOTINE COMPONENT OF NICORETTE
• 104062-50-2
• Pyrrolidine, 1-methyl-2-(3-pyridyl)-
• NICOTINE (MART.)
• NICOTINE [MART.]
• Nicotine [for single use]
• NICOTINE-L (BASE)
• (2S) 3-(1-Methyl-pyrrolidin-2-yl)-pyridine
• destruxol
• Pyridine, 3-(1-methyl-2-pyrrolidinyl)-,(S)-
• 3-((2S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE
• (-)-1-Methyl-2-(3-pyridyl)pyrrolidine
• NICOTINE (EP MONOGRAPH)
• NICOTINE [EP MONOGRAPH]
• NICOTINE (USP MONOGRAPH)
• NICOTINE [USP MONOGRAPH]
• Nicotine-D salicylate
• CAS-54-11-5
• DL-tetrahydronicotyrine
• SMR000059074
• 3-[(2s)-1-methyl-2-pyrrolidinyl]pyridine
• methyl-2-pyrrolidinyl)pyridine
• MFCD00006369
• CHEBI:18723
• delta-Nicotine
• Nicorette gum
• Nicotine betadex
• 1-methyl-2-(3-pyridal)-pyrrolidene
• Nicorette (TN)
• MACHNIC
• a-N-methylpyrrolidine
• Campbell's nico-soap
• Caswell No 597
• 3-N-methylpyrrolidine
• R)-(+)-nicotine
• a -N-methylpyrrolidine
• TEN DUST
• CHEMBL3
• NIAGARA PA DUST
• 1uw6
• TA-NIC
• NIC (CHRIS Code)
• NICOTINE [HSDB]
• alpha-N-methylpyrrolidine
• NICOTINE [MI]
• Nicotine vaccine, Xenova
• Nicotine [UN1654]
• NICOTINE [VANDF]
• NICOTINUM [HPUS]
• (S)-(-)--nicotine
• bmse000105
• D05QIM
• D0T8GD
• NICOTINE [WHO-DD]
• NICOTINE, (LIQUID)
• Nicotine polacrilex [USAN]
• Vaccine (nicotine), Xenova
• S-()-Nicotine-pyridine-d4
• SCHEMBL20192
• MLS001055457
• MLS001335905
• BIDD:GT0599
• NICOTINE [ORANGE BOOK]
• GTPL2585
• BDBM82070
• Nicotine abuse therapy, ImmuLogic
• HMS2230H17
• HMS3259E16
• Nicotine [UN1654] [Poison]
• HY-B0638
• Nicotine 10 microg/mL in Methanol
• Tox21_201814
• Tox21_300174
• NA1654
• Nicotine 100 microg/mL in Methanol
• PDSP1_000113
• PDSP1_000465
• PDSP2_000463
• PDSP2_000555
• 1-methyl-2-(3-pyridal)-Pyrrolidine
• (S)-(-)-NICOTINE, 3-[(2S)-1-METHYL-2-PYRROLIDINYL] PYRIDINE
• AKOS016843798
• Nicotine 1000 microg/mL in Methanol
• 3-(1-methyl-2-pyrrolidinyl)-Pyridine
• CCG-204892
• CS-3999
• DB00184
• NC00577
• SB12751
• SDCCGMLS-0066911.P001
• SDCCGSBI-0050785.P004
• USEPA/OPP Pesticide Code: 056702
• NCGC00090693-01
• NCGC00090693-02
• NCGC00090693-03
• NCGC00090693-04
• NCGC00090693-05
• NCGC00090693-06
• NCGC00090693-07
• NCGC00090693-08
• NCGC00090693-09
• NCGC00254095-01
• NCGC00259363-01
• (-)-Nicotine, >=99% (GC), liquid
• NICOTINE COMPOUND, LIQUID, N.O.S.
• SBI-0050785.P003
• CAS_29790-52-1
• N0079
• NICOTINE PREPARATION, LIQUID, N.O.S.
• C00745
• D03365
• EN300-304948
• P10017
• Piridina, 3-[(2S)-1-metil-2-pirrolidinil]-
• PYRROLIDENE, 1-METHYL-2-(3-PYRIDAL)-
• (-)-.beta.-Pyridyl-.alpha.-N-methylpyrrolidine
• AB00694322_12
• (-)-Nicotine, PESTANAL(R), analytical standard
• 3-[(1R)-1beta-Methylpyrrolidine-2alpha-yl]pyridine
• J-500021
• SR-05000001762-5
• BRD-K05395900-322-02-1
• BRD-K05395900-322-04-7
• Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl), (S)-
• Q28086552
• PYRIDINE, 3-(TETRAHYDRO-1-METHYL PYRROL-2-YL)
• Z1198150037
• 434F7990-3240-4A43-ACEC-E6CC1E495FA0
• Nicotine; (Pyridine, (S)-3-(1-methyl-2-pyrrolidinyl)-)
• (S)-(-)-NICOTINE; 3-[(2S)-1-METHYL-2-PYRROLIDINYL] PYRIDINE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.9426	94.26%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.4196	41.96%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.9603	96.03%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8806	88.06%
P-glycoprotein inhibitior	-	0.9957	99.57%
P-glycoprotein substrate	-	0.7747	77.47%
CYP3A4 substrate	-	0.5825	58.25%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	+	0.6763	67.63%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8433	84.33%
CYP2C19 inhibition	-	0.8543	85.43%
CYP2D6 inhibition	-	0.8838	88.38%
CYP1A2 inhibition	-	0.6347	63.47%
CYP2C8 inhibition	-	0.8418	84.18%
CYP inhibitory promiscuity	-	0.7589	75.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7042	70.42%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8658	86.58%
Skin irritation	+	0.8032	80.32%
Skin corrosion	-	0.5826	58.26%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5145	51.45%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.8770	87.70%
skin sensitisation	-	0.9436	94.36%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8018	80.18%
Acute Oral Toxicity (c)	II	0.7410	74.10%
Estrogen receptor binding	-	0.9297	92.97%
Androgen receptor binding	-	0.9392	93.92%
Thyroid receptor binding	-	0.8383	83.83%
Glucocorticoid receptor binding	-	0.6638	66.38%
Aromatase binding	-	0.8745	87.45%
PPAR gamma	-	0.8154	81.54%
Honey bee toxicity	-	0.9726	97.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.8400	84.00%
Fish aquatic toxicity	+	0.6563	65.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM; 15848.9 nM; 39810.7 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL5282	P11509	Cytochrome P450 2A6	579428.7 nM	IC50	PMID: 19110342
CHEMBL1293224	P10636	Microtubule-associated protein tau	22387.2 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1882	P43681	Neuronal acetylcholine receptor protein alpha-4 subunit	6600 nM; 4700 nM	EC50; EC50	PMID: 19552432; PMID: 19232492
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	21000 nM; 7600 nM	IC50; IC50	PMID: 11312774; PMID: 23561269
CHEMBL3068	P32297	Neuronal acetylcholine receptor subunit alpha-3	45 nM; 45 nM	IC50; IC50	via Super-PRED; PMID: 11312774
CHEMBL2109233	P17787	Neuronal acetylcholine receptor; alpha3/alpha6/beta2/beta3	84.8 nM	IC50	via Super-PRED
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	0.045 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	4.5 nM	Potency	via Super-PRED
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	17000 nM	EC50	PMID: 20356305
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	141.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.88%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.14%	91.49%
CHEMBL2581	P07339	Cathepsin D	91.83%	98.95%
CHEMBL5203	P33316	dUTP pyrophosphatase	91.60%	99.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.16%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.63%	93.65%
CHEMBL1907599	P05556	Integrin alpha-4/beta-1	84.56%	92.86%
CHEMBL1902	P62942	FK506-binding protein 1A	84.53%	97.05%
CHEMBL3920	Q04759	Protein kinase C theta	83.36%	97.69%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.98%	96.00%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	81.90%	98.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.19%	97.09%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.77%	96.25%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.61%	91.43%

Plants that contains it

• Areca catechu
• Argyreia mollis
• Asclepias syriaca
• Cyphanthera tasmanica
• Duboisia hopwoodii
• Duboisia leichhardtii
• Duboisia myoporoides
• Ephedra intermedia
• Equisetum arvense
• Erythroxylum coca
• Erythroxylum cuneatum
• Erythroxylum zambesiacum
• Euonymus alatus
• Garcinia lucida
• Haloxylon persicum
• Laurus nobilis
• Meconopsis punicea
• Nicotiana africana
• Nicotiana alata
• Nicotiana attenuata
• Nicotiana glutinosa
• Nicotiana plumbaginifolia
• Nicotiana tabacum
• Papaver bracteatum
• Piper nigrum
• Senegalia berlandieri
• Solanum tuberosum
• Vachellia rigidula
• Virola calophylla

Cross-Links

• PubChem: 89594
• NPASS: NPC182570
• ChEMBL: CHEMBL3
• LOTUS: LTS0184620
• wikiData: Q28086552