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Nicotine

PubChem CID: 89594

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Compound Synonyms nicotine, L-Nicotine, 54-11-5, (-)-Nicotine, (S)-Nicotine, (S)-3-(1-methylpyrrolidin-2-yl)pyridine, (S)-(-)-Nicotine, Habitrol, Nicotrol, 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine, Nicoderm, Nicotine polacrilex, Fumetobac, Micotine, Nicocide, Prostep, Tendust, Nico-dust, Nicoderm Cq, Nicotine alkaloid, Emo-nik, Nico-Fume, Mach-Nic, Nic-Sal, Flux MAAG, Nicotina, Nikotyna, Ortho N-4 dust, Ortho N-5 dust, XL All Insecticide, Niagara P.A. dust, Destruxol orchid spray, L(-)-nicotine, 3-(N-Methylpyrollidino)pyridine, 3-(N-Methylpyrrolidino)pyridine, Nicabate, Nicorette, Nicotinum, Niquitin, Tabazur, L-3-(1-Methyl-2-pyrrolidyl)pyridine, Caswell No. 597, Ortho N-4 and N-5 dusts, Nicotin, (-)-3-(1-Methyl-2-pyrrolidyl)pyridine, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine, RCRA waste number P075, 1-Methyl-2-(3-pyridyl)pyrrolidine, NSC 5065, S-(-)-Nicotine, Nikotin, ENT 3,424, 3-(2-(N-methylpyrrolidinyl))pyridine, CCRIS 1637, fumeto bac, HSDB 1107, Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)-, 3-((2S)-1-methylpyrrolidin-2-yl)pyridine, EINECS 200-193-3, UNII-6M3C89ZY6R, MFCD00006369, nicotine s(-), (-)-3-(N-Methylpyrrolidino)pyridine, 3-(1-Methyl-2-pyrollidinyl)pyridine, beta-Pyridyl-alpha-N-methylpyrrolidine, EPA Pesticide Chemical Code 056702, beta-Pyridyl-alpha-N-methyl pyrrolidine, 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], Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl), Pyrrolidine, 1-methyl-2-(3-pyridyl)-, DTXCID50930, EC 200-193-3, Pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)-, NSC-5065, 1-Methyl-2-(3-pyridiyl)pyrrolidine, Nikotin [German], Nikotyna [Polish], 104062-50-2, Nicotina [Italian], Nicotine (USP:BAN), Nicotrol Inhaler, NICOTINE (MART.), NICOTINE [MART.], Nicotrol NS, Nicotine [for single use], NICOTINE-L (BASE), destruxol, Pyridine, 3-[(2S)-1-methyl-2-pyrrolidinyl]-, 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 [BSI:ISO], Exodus, Nicotine-D salicylate, CAS-54-11-5, DL-tetrahydronicotyrine, Habitrol (TN), Nicotine (USP), Nicotine [ISO], SMR000059074, (S)-(-)-Nicotine (1.0 mg/mL in Methanol), methyl-2-pyrrolidinyl)pyridine, UN1654, RCRA waste no. P075, CHEBI:18723, blip, Nicorelief, bjwc nicotine, euqate nicotine, NicoretteMint, NicotineMini, nictoine gum, delta-Nicotine, Lucy nicotine, Nicorette gum, Equate Nicotine, Leader Nicotine, Rexall Nicotine, Maxi Nicotine, Mini Nicotine, Nicotine betadex, Nicotine Mini, Nicotinum,, Careone Nicotine, Good Sense, Habitrol Lozenge, NicoretteOriginal, Sunmark Nicotine, Topcare Nicotine, 1-methyl-2-(3-pyridal)-pyrrolidene, HabitrolStep 1, HabitrolStep 2, HabitrolStep 3, Equaline Nicotine, HEB Nicotine, Nicotine polarilex, Nicotinetransdermal, Stop Smoking Aid, nicotinemint flavor, NicotineSugar Free, Care One Nicotine, DG Health nicotine, NicoretteFresh Mint, 3-(1-Methyl-2-pyrrolidyl)pyridine, Basic Care Nicotine, Good Sense Nicotine, NicoretteFruit Chill, Up and Up Nicotine, Health Mart Nicotine, MACHNIC, NICODERMCQ, Topcare Nicotine Gum, a-N-methylpyrrolidine, Campbell's nico-soap, Caswell No 597, 3-N-methylpyrrolidine, Habitrol LozengeCherry, Members Mark Nicotine, R)-(+)-nicotine, good sense nicotinemint, Harris Teeter Nicotine, a -N-methylpyrrolidine, NicoretteCinnamon Surge, TEN DUST, CHEMBL3, NIAGARA PA DUST, Signature Care Nicotine, 1uw6, exchange select nicotine, family wellness nicotine, NicoretteSpearmint Burst, Nicotine PolacrilexMINT, NicoretteWhite Ice Mint, basic care nicotine mini, NICOTINE [HSDB], up and up mini nicotine, NICOTINE (TPD), alpha-N-methylpyrrolidine, NICOTINE [MI], Nicotine [UN1654], NICOTINE [VANDF], Nicotinetransdermal system, NICOTINUM [HPUS], (S)-(-)--nicotine, foster and thrive nicotine, Nicotine COATED ice mint, Nicotine Polacrilexoriginal, Kirkland Signature Quit 2, Kirkland Signature Quit 4, bmse000105, Kirkland Signature Nicotine, Members Mark Mini Nicotine, NICOTINE [WHO-DD], (2S) 3-(1-Methyl-pyrrolidin-2-yl)-pyridine, Berkley and Jensen Nicotine, NICOTINE, (LIQUID), Nicotine polacrilex [USAN], Pyridine, 3-(1-methyl-2-pyrrolidinyl)-,(S)-, S-()-Nicotine-pyridine-d4, SCHEMBL20192, MLS001055457, MLS001335905, Nicotine Polacrilexcoated mint, BIDD:GT0599, Habitrol LozengeOriginal Flavor, NICOTINE [ORANGE BOOK], Good Neighbor Pharmacy Nicotine, GTPL2585, BDBM82070, l-Nicotine, 1mg/ml in Methanol, Nicotine Polacrilexcoated cinnamon, Nicotine Transdermal System Patch, Nicotinetransdermal system step 2, l-Nicotine, 10mg/ml in Methanol, l-Nicotine, 50mg/ml in Methanol, Nicotine PolacrilexOrigianl Flavor, Nicotine PolacrilexOriginal Flavor, Nicotine Transdermal SystemStep 1, Nicotine Transdermal SystemStep 2, Nicotine Transdermal SystemStep 3, HMS2230H17, HMS3259E16, Nicotine [UN1654] [Poison], Nicotine PolacrilexCoated Ice Mint, good neighbor pharmacy nicotine mini, HY-B0638, l-Nicotine, 100mg/ml in Methanol, Nicotine 10 microg/mL in Methanol, NICOTINE COMPONENT OF COMMIT, NICOTINETransdermal System Step 1, NICOTINETransdermal System Step 3, Good Sense NicotineStop Smoking Aid, Tox21_201814, Tox21_300174, Nicotine 100 microg/mL in Methanol, PDSP1_000113, PDSP1_000465, PDSP2_000463, PDSP2_000555, 1-methyl-2-(3-pyridal)-Pyrrolidine, AKOS016843798, Nicotac Nicotine PolacrilexCoated Mint, Nicotine 1000 microg/mL in Methanol, NICOTINE COMPONENT OF NICORETTE, 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, Nicotac Nicotine PolacrilexCoated Cinnamon, 3-[(S)-1-Methylpyrrolidin-2-yl]pyridine, NICOTINE COMPOUND, LIQUID, N.O.S., SBI-0050785.P003, CAS_29790-52-1, N0079, NS00010445, NICOTINE PREPARATION, LIQUID, N.O.S., C00745, D03365, EN300-304948, LEADER NICOTINE TRANSDERMAL SYSTEMSTEP 1, LEADER NICOTINE TRANSDERMAL SYSTEMSTEP 2, LEADER NICOTINE TRANSDERMAL SYSTEMSTEP 3, P10017, PYRROLIDENE, 1-METHYL-2-(3-PYRIDAL)-, (-)-.beta.-Pyridyl-.alpha.-N-methylpyrrolidine, AB00694322_12, (-)-Nicotine, PESTANAL(R), analytical standard, SR-05000001762-5, BRD-K05395900-322-02-1, BRD-K05395900-322-04-7, BRD-K05395900-322-05-4, Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl), (S)-, Q28086552, PYRIDINE, 3-(TETRAHYDRO-1-METHYL PYRROL-2-YL), Z1198150037, 434F7990-3240-4A43-ACEC-E6CC1E495FA0, (S)-(-)-NICOTINE, 3-[(2S)-1-METHYL-2-PYRROLIDINYL] PYRIDINE, 200-193-3
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 16.1
Hydrogen Bond Donor Count 0.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCC(C2CCCC2)CC1
Np Classifier Class Pyridine alkaloids
Deep Smiles CNCCC[C@H]5ccccnc6
Heavy Atom Count 12.0
Classyfire Class Pyridines and derivatives
Description Nicotine, also known as (S)-3-(1-methylpyrrolidin-2-yl)pyridine or (-)-nicotine, is a member of the class of compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. Nicotine is soluble (in water) and a very strong basic compound (based on its pKa). Nicotine is a bitter tasting compound and can be found in a number of food items such as mexican oregano, shea tree, pepper (capsicum), and black salsify, which makes nicotine a potential biomarker for the consumption of these food products. Nicotine can be found primarily in blood, saliva, and urine, as well as throughout most human tissues. In humans, nicotine is involved in the nicotine action pathway. Moreover, nicotine is found to be associated with smoking. Nicotine is a drug which is used for the relief of nicotine withdrawal symptoms and as an aid to smoking cessation. Beyond addiction, both short and long-term nicotine exposure have not been established as dangerous to adults, except among certain vulnerable groups. At high-enough doses, nicotine is associated with poisonings and is potentially lethal. Nicotine as a tool for quitting smoking has a good safety history. There is inadequate research to show that nicotine itself is associated with cancer in humans. Nicotine in the form of nicotine replacement products is less of a cancer risk than smoking. Nicotine is linked to possible birth defects. During pregnancy, there are risks to the child later in life for type 2 diabetes, obesity, hypertension, neurobehavioral defects, respiratory dysfunction, and infertility. The use of electronic cigarettes, which are designed to be refilled with nicotine-containing e-liquid, has raised concerns over nicotine overdoses, especially with regard to the possibility of young children ingesting the liquids . Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD<sub>50</sub>= 24 mg/kg (orally in mice) (DrugBank).
Scaffold Graph Node Level C1CNCC(C2CCCN2)C1
Classyfire Subclass Pyrrolidinylpyridines
Isotope Atom Count 0.0
Molecular Complexity 147.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 1.0
Uniprot Id P27338, P21397, P08684, P11712, P33261, P05181, P10635, P20813, P04798, Q16696, P05177, P10632, P11509, O76082, Q9H015, O15245, O15244, O75751, Q9GZZ6, Q9UGM1, Q15822, P12390, Q05941, P02714, P43681, P36544, P32297, P02718, Q05901, P10980, P12392, P49582, Q8WXA8, Q07001, P43144, Q2MKA5, P30926, Q04844, P02708, n.a., Q12809, Q99720, Q92887, P58154, P20852, P12389, O75762, P10636, P00352, P97697, P21728, Q96KQ7, P83916, Q13951, O89049, P49798, P84022, Q8WSF8, O88446, Q9R141, Q9R0W2, Q63089, Q16236, O75496, P10145, P51449, P30532, O94956, Q9NPD5, Q9Y6L6, O42275, P81908, Q8R493, Q8R4G9, P09482, P25162, A9XFY4, O70174, Q7YWJ9, P02710, P21687, Q9NUW8, Q13148, P15289, Q7RTT9, P43143, O95342, O15438, O15439, Q8BLA8, P0DTD1, P10275
Iupac Name 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
Prediction Hob 1.0
Class Pyridines and derivatives
Veber Rule True
Classyfire Superclass Organoheterocyclic compounds
Target Id NPT410, NPT424, NPT5033, NPT98, NPT240, NPT208, NPT346, NPT51, NPT94, NPT2599, NPT109
Xlogp 1.2
Superclass Alkaloids and derivatives
Subclass Pyrrolidinylpyridines
Gsk 4 400 Rule True
Molecular Formula C10H14N2
Scaffold Graph Node Bond Level c1cncc(C2CCCN2)c1
Prediction Swissadme 0.0
Inchi Key SNICXCGAKADSCV-JTQLQIEISA-N
Silicos It Class Soluble
Fcsp3 0.5
Logs 0.79
Rotatable Bond Count 1.0
State Liquid
Logd 0.748
Synonyms (-)-3-(1-Methyl-2-pyrrolidyl)pyridine, (-)-3-(N-Methylpyrrolidino)pyridine, (-)-Nicotine, (+)-Nicotine, (R,S)-Nicotine, (R)-3-(1-Methyl-2-pyrrolidinyl)pyridine, (S)-(-)-Nicotine, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine, (S)-3-(1-Methylpyrrolidin-2-yl)pyridine, (S)-3-(N-Methylpyrrolidin-2-yl)pyridine, (S)-Nicotine, 1-Methyl-2-(3-pyridal)-pyrrolidene, 1-Methyl-2-(3-pyridal)-pyrrolidine, 1-Methyl-2-(3-pyridiyl)pyrrolidine, 1-Methyl-2-(3-pyridyl)pyrrolidine, 2'-beta-H-Nicotine, 3-(1-Methyl-2-pyrollidinyl)pyridine, 3-(1-Methyl-2-pyrrolidinyl)-pyridine, 3-(1-Methyl-2-pyrrolidinyl)pyridine, 3-(1-Methylpyrrolidin-2-yl)pyridine, 3-(2-(N-Methylpyrrolidinyl))pyridine, 3-(N-Methylpyrollidino)pyridine, 3-(N-Methylpyrrolidino)pyridine, 3-N-Methylpyrrolidine, a -N-Methylpyrrolidine, a-N-Methylpyrrolidine, alpha-N-Methylpyrrolidine, beta-Pyridyl-alpha-N-methylpyrrolidine, D-Nicotine, delta-Nicotine, Destruxol, DL-Tetrahydronicotyrine, Fumeto bac, Habitrol, L -1-Methyl-2-[3-pyridyl]pyrrolidine, L-3-(1-Methyl-2-pyrrolidyl)pyridine, L-nicotine, L(-)-Nicotine, Methyl-2-pyrrolidinyl)pyridine, Nicoderm, Nicotine, Nicotine polacrilex, Pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)-, Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)- (9CI), R)-(+)-Nicotine, L-Nicotine, Tartrate, nicotine, Nicotine bitartrate, Nicotine tartrate, Bitartrate, nicotine, nicotin, nicotine, β-pyridyl-α-n-methylpyrrolidine (nicotine)
Substituent Name Nicotine, Alkaloid or derivatives, Pyrrolidinylpyridine, Aralkylamine, N-alkylpyrrolidine, Pyridine, Heteroaromatic compound, Pyrrolidine, Tertiary aliphatic amine, Tertiary amine, Azacycle, Organoheterocyclic compound, Hydrocarbon derivative, Organonitrogen compound, Amine, Aromatic heteromonocyclic compound
Esol Class Very soluble
Functional Groups CN(C)C, cnc
Compound Name Nicotine
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 162.116
Formal Charge 0.0
Monoisotopic Mass 162.116
Hydrogen Bond Acceptor Count 2.0
Molecular Weight 162.23
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 1.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteromonocyclic compounds
Lipinski Rule Of 5 True
Esol -1.8869631999999998
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
Smiles CN1CCC[C@H]1C2=CN=CC=C2
Nring 2.0
Np Classifier Biosynthetic Pathway Alkaloids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent Pyrrolidinylpyridines
Np Classifier Superclass Nicotinic acid alkaloids

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