General
Preferred name
nicotine
Synonyms
NICOTINE BITARTRATE ()
(-)-Nicotine hydrogen tartrate salt ()
(-)-Nicotine ditartrate ()
(?)-Nicotine Ditartrate ()
Nicotine Ditartrate ()
Nicotinell TTS 10 ()
Nicopatch ()
Nicopass ()
Nicabate ()
Nicoderm CQ ()
Stoppers ()
Prostep ()
Nicoderm ()
NiQuitin Minis Mint ()
NiQuitin Clr ()
Nicorette Invisi ()
NiQuitin Minis Cherry ()
NiQuitin Mint ()
Stubit ()
NiQuitin Strips Mint ()
Nicotrol NS ()
Nicotinell TTS 20 ()
Nicotrol Inhaler ()
Nicotinell TTS 30 ()
Habitrol ()
Nicotrol ()
NiQuitin Minis Orange ()
Niquitin ()
Nicotinell Support ()
NiQuitin Pre-Quit ()
Nicotinell Classic ()
(-)-Nicotine Hydrogen Tartrate Salt ()
Nicotine bitartrate dihydrate ()
Nicotine (as bitartrate) ()
Nicotine acid tartrate dihydrate ()
NSC-97238 ()
Nicotine bitartrate anhydrous ()
Nicotine hydrogen-l-tartrate ()
(?)-Nicotine (tartrate) ()
(?)-Nicotine ()
P&D ID
PD003076
CAS
104062-50-2
54-11-5
65-31-6
Tags
natural product
drug
available
Approved by
FDA
First approval
1984
1991
Drug Status
approved
Drug indication
Smoking Cessation Adjunct
Nicotine dependence
Tobacco dependence
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Nicotine is a natural alkaloid of the tobacco plant. It is an addictive stimulant, which is an agonist of most nicotinic acetylcholine receptors (nAChRs) (it is an antagonist of the nAChRα9 and nAChRα10 receptor subtypes). (GtoPdb)
MOA Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine.; Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.
DESCRIPTION Potent alpha4beta4, alpha4beta2 and alpha7 nAChR agonist (Tocris Bioactive Compound Library)
DESCRIPTION Prototype nicotinic acetylcholine receptor agonist (LOPAC library)
Cell lines
2
Organisms
2
Compound Sets
26
Cayman Chemical Bioactives
29138
20887
ChEMBL Approved Drugs
CHEMBL3
CHEMBL3989563
ChEMBL Drugs
CHEMBL3
CHEMBL3989563
Concise Guide to Pharmacology 2017/18
2585
Concise Guide to Pharmacology 2019/20
2585
Concise Guide to Pharmacology 2021/22
2585
Concise Guide to Pharmacology 2023/24
2585
Drug Repurposing Hub
DrugBank
DB00184
DrugBank Approved Drugs
DB00184
DrugCentral
1920
DrugCentral Approved Drugs
1920
DrugMAP
DMWX5CO
DrugMAP Approved Drugs
DMWX5CO
Enamine BioReference Compounds
Guide to Pharmacology
2585
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL3
Mcule NIBR MoA Box Subset
MCULE-5463946437
NCATS Inxight Approved Drugs
6M3C89ZY6R
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Other bioactive compounds
The Spectrum Collection
Tocris Bioactive Compound Library
3546
External IDs
75
Properties
(calculated by RDKit )
Molecular Weight
162.12
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
0
Rotatable Bonds
1
Ring Count
2
Aromatic Ring Count
1
cLogP
1.85
TPSA
16.13
Fraction CSP3
0.5
Chiral centers
1.0
Largest ring
6.0
QED
0.63
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Selectivity
Nicotinic
Primary Target
Nicotinic Receptors (Non-selective)
MOA
AChR agonist
Agonist
AChR
Nicotinic alpha7 Partial Agonists
acetylcholine receptor agonist
Pathway
Neuroscience
Target
Nicotinic AChR
nAChR
CHAT, CHRNA10, CHRNA2, CHRNA3, CHRNA4, CHRNA5, CHRNA6, CHRNA7, CHRNA9, CHRNB2, CHRNB3, CHRNB4, CYP19A1, TBXAS1, TRPA1
Member status
member
Indication
smoking cessation
Source data