NICOTINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1984)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N07BA01
UNII: 6M3C89ZY6R

Structure
InChI Key SNICXCGAKADSCV-JTQLQIEISA-N
Smile CN1CCC[C@H]1c1cccnc1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H14N2
Molecular Weight 162.24
AlogP 1.85
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 16.13
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 12.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Neuronal acetylcholine receptor; alpha4/beta2 agonist PubMed PubMed PubMed PubMed PubMed PubMed PubMed PubMed PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2A Cytochrome P450 2A6
- - - 4400 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2A
- - 54000 4400 -
Enzyme Hydrolase
- - - - 1
Enzyme Isomerase
- 4800 - - -
Ion channel Ligand-gated ion channel 5HT3 receptor
- - - 71000 -
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor alpha subunit
1-9400 1-430 0-45000 1-35 100-100
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor beta subunit
1-9400 1-430 0-45000 1-35 100-100
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor delta subunit
60000 1-4 - 1480-6270 -
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor epsilon subunit
65000 - - - -
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor gamma subunit
60000 1-4 - 1480-6270 -
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor
1-9400 1-430 0-45000 1-35 100-100
Ion channel Voltage-gated ion channel Transient receptor potential channel
2000-17000 - - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- 28000-32000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 11
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Unclassified protein
- - 316-479 63-496 -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Smoking Cessation 3 D016540 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 3 D029424 ClinicalTrials
Tuberculosis 3 D014376 ClinicalTrials
Marijuana Abuse 3 D002189 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Carcinoma in Situ 2 D002278 ClinicalTrials
Substance-Related Disorders 2 D019966 ClinicalTrials
Depressive Disorder 2 D003866 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Postoperative Nausea and Vomiting 2 D020250 ClinicalTrials
Alcohol Drinking 2 D000428 ClinicalTrials
Cognitive Dysfunction 2 D060825 ClinicalTrials
Wounds and Injuries 2 D014947 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Attention Deficit Disorder with Hyperactivity 1 D001289 ClinicalTrials
Sarcoidosis 1 D012507 ClinicalTrials
Memory Disorders 1 D008569 ClinicalTrials
Aging 1 D000375 ClinicalTrials
Schizophrenia 1 D012559 ClinicalTrials
Cocaine-Related Disorders 1 D019970 ClinicalTrials

Related Entries

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache
Nervous system disorders Headache 18.0
General disorders and administration site conditions Application site reaction
Nervous system disorders Headache
Reproductive system and breast disorders Dysmenorrhoea
General disorders and administration site conditions Influenza like illness
Musculoskeletal and connective tissue disorders Back pain 6.0
Cardiac disorders Dyspnoea
Cardiac disorders Dizziness
Nervous system disorders Headache 5.4
Nervous system disorders Insomnia
Musculoskeletal and connective tissue disorders Arthralgia 5.0
Cardiac disorders Dyspnoea 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 5.0
Gastrointestinal disorders Nausea
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Flatulence 4.0
Nervous system disorders Headache
Reproductive system and breast disorders Menstrual disorder
Reproductive system and breast disorders Menstrual disorder 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Gastrointestinal disorders Nausea
Cardiac disorders Palpitations
Cardiac disorders Palpitations 4.0
Gastrointestinal disorders Tooth disorder 4.0
Gastrointestinal disorders Nausea 3.5
Nervous system disorders Headache 3.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.1
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Myalgia 3.1
Ear and labyrinth disorders Vertigo 3.1
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 3.0
Skin and subcutaneous tissue disorders Acne 3.0
Nervous system disorders Confusional state
Nervous system disorders Confusional state 3.0
Reproductive system and breast disorders Dysmenorrhoea 3.0
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Feeling abnormal 3.0
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Musculoskeletal and connective tissue disorders Myalgia 3.0
Skin and subcutaneous tissue disorders Pruritus
Gastrointestinal disorders Flatulence 2.7
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Nausea 2.4
General disorders and administration site conditions Pain 2.1
Skin and subcutaneous tissue disorders Pruritus 2.0
Skin and subcutaneous tissue disorders Dermatitis 1.9
Gastrointestinal disorders Diarrhoea 1.9
Gastrointestinal disorders Dysgeusia 1.9
General disorders and administration site conditions Oedema 1.9
Nervous system disorders Paraesthesia 1.9
Skin and subcutaneous tissue disorders Pruritus 1.9
Skin and subcutaneous tissue disorders Rash 1.9
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Dysgeusia
Gastrointestinal disorders Mouth ulceration 1.6
Gastrointestinal disorders Stomatitis 1.6
Skin and subcutaneous tissue disorders Acne 1.2
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Dyspepsia 1.2
General disorders and administration site conditions Oedema
Nervous system disorders Paraesthesia
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Rash
Gastrointestinal disorders Tongue disorder 1.2
Skin and subcutaneous tissue disorders Acne
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Gastrointestinal disorders Tooth disorder
Ear and labyrinth disorders Vertigo
Gastrointestinal disorders Mouth ulceration
Gastrointestinal disorders Stomatitis
Gastrointestinal disorders Tongue disorder

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
23.86
Injury, poisoning and procedural complications
22.05
Skin and subcutaneous tissue disorders
12.24
Psychiatric disorders
9.69
Product issues
7.02
Nervous system disorders
6.71
Gastrointestinal disorders
3.99
Cardiac disorders
2.74
Vascular disorders
2.26
Respiratory, thoracic and mediastinal disorders
2.21

Cross References

Resources Reference
CAS NUMBER 54-11-5
ChEBI 17688
ChEMBL CHEMBL3
DrugBank DB00184
DrugCentral 1920
EPA CompTox DTXSID1020930
FDA SRS 6M3C89ZY6R
Human Metabolome Database HMDB0001934
Guide to Pharmacology 2585
KEGG C00745
PDB NCT
PubChem 89594
SureChEMBL SCHEMBL20192
ZINC ZINC000000391812
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