Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11N3O |
Molecular Weight | 177.2031 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=NN1CCC[C@H]1C2=CN=CC=C2
InChI
InChIKey=XKABJYQDMJTNGQ-VIFPVBQESA-N
InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2/t9-/m0/s1
N‑Nitrosonornicotine (NNN) is a nitrosamine compound. It is produced by nitrosation of nicotine during the curing, aging, processing, and smoking of tobacco. About half of the NNN originates in the unburnt tobacco, whereas the remainder is formed during burning. NNN is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. NNN induces deleterious mutations in oncogenes and tumor suppression genes by forming DNA adducts, which could be considered as tumor initiation. Meanwhile, the binding of NNN to the nicotinic acetylcholine receptor promotes tumor growth by enhancing and deregulating cell proliferation, survival, migration, and invasion, thereby creating a microenvironment for tumor growth.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
1.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Sample Use Guides
N‑Nitrosonornicotine has been tested for carcinogenicity by various routes of administration in adult mice, rats, and Syrian hamsters, and in limited experiments in mink and ferrets.
Route of Administration:
Other
Epithelial monolayers were subsequently subcultured and then treated for 1 hour with 0.25 to 1.0 ng/ml of N-nitrosonornicotine. Even though the controls and most treatment groups terminally differentiated, cells exposed to N-nitrosonornicotine continued to divide, maintained a differentiated phenotype for 8 1/2 to 10 weeks in culture, and displayed focal growth and morphologic changes suggestive of early stages in cell transformation.