Stereochemistry | ABSOLUTE |
Molecular Formula | C9H12N2 |
Molecular Weight | 148.205 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CN[C@@H](C1)C2=CN=CC=C2
InChI
InChIKey=MYKUKUCHPMASKF-VIFPVBQESA-N
InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1
Molecular Formula | C9H12N2 |
Molecular Weight | 148.205 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Nornicotine is a natural alkaloid produced by plants in the genus Nicotiana and is structurally related to nicotine. Nornicotine is the direct precursor of tobacco-specific nitrosamine N'-nitrosonornicotine, which is a highly potent human carcinogen. Nornicotine is an active nicotine metabolite, which accumulates in brain to pharmacologically relevant concentrations following repeated nicotine administration to rats. Nornicotine stimulated DA release from nucleus accumbens in a nicotinic receptor-mediated manner, further supporting the hypothesis that nornicotine contributes to tobacco dependence. Nornicotine is present in Nicotiana tobaccum in both S(-) and R(+) enantiomeric forms. Nornicotine enantiomeric forms appear to differ in analgesic potency and side effects. Exposure to nornicotine results in additional activation of α7-type receptors, which may be important for effects on cognition and attention. Likewise, the effects of nornicotine on α6-containing receptors may contribute to the reinforcing effects of nicotine, and therefore, is relevant to dependence on tobacco. In contrast to nicotine, nornicotine had relatively low activity on receptors other than those containing α7 or α6 subunits. Yaupon Therapeutics was developing Nornicotine as a once a day oral drug for smoking cessation. However this development was discontinued.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
Rats: 5 mg/kg s.c. The 5 mg/kg dose was
chosen based on a previous report suggesting that this dose was behaviorally active.
Route of Administration:
Other
The effects of nornicotine on specific combinations of neuronal nicotinic acetylcholine receptor (nAChR) subunits expressed in Xenopus oocytes were studied. Of the nAChR subtypes studied, it was found that α7 receptors were very responsive to nornicotine (EC50≈ 17 uM Imax 50% compared to ACh). nAChRs containing the ligand-binding domain of the α6 subunits (in the form of an α6/α3 chimera) were also strongly responsive to nornicotine (EC50≈ 4 uM Imax50% compared to ACh).