NICOTINE
(-)-NICOTINE is classified as super toxic. Probable oral lethal dose in humans is less than 5 mg/kg or a taste (less than 7 drops) for a 70 kg (150 lbs.) person. It may be assumed that ingestion of 40-60 mg of nicotine is lethal to humans. There is fundamental difference between acute toxicity from use of nicotine as insecticide or from ingestion, and chronic toxicity that may be caused by prolonged exposure to small doses as occurs in smoking. Maternal smoking during pregnancy is associated with increased risk of spontaneous abortion, low birth weight and still-birth. Nicotine was found as a co-carcinogen in animals.
An alkaloid produced from tobacco. Colorless, oily liquid, combustible, highly toxic. When heated to decomposition (-)-NICOTINE(54-11-5) emits very toxic fumes of carbon monoxide and oxides of nitrogen [Lewis, 3rd ed., 1993, p. 919].
Properties of Nicotine
| Formula | C10H14N2 |
| Molecular Weight | 162,234 g.mol-1 |
| Melting point | -7,9 ° C |
| Boiling point | 247 ° C |
| Rotatory index (S) |
aD = -168 at 20° C
|
| Density | d=1,010 |
| Refractive index | n=1,530 |
| Comments | Pale yellow to dark brown liquid with a slight, fishy odor when warm. Insecticide. |
1D 1H(+/-) Nicotine
2D [1H,1H]-TOCSY(+/-) Nicotine
1D 13C(+/-) Nicotine
1D DEPT90(+/-) Nicotine
1D DEPT135(+/-) Nicotine
2D [1H,13C]-HSQC(+/-) Nicotine
IR analysis
On this spectrum, we can notice several peaks, which characterise the different chemical functions of nicotine:
· Around 3400 cm-1, we can see the large peak of water (it deals with a liquid film).· Between 2970 and 2780 cm-1 : C-H stretching.
· The peak at 1677 cm-1 : aromatic C=N double bond stretching.
· The peak at 1691 cm-1 : aromatic C=C double bond stretching.
· The peaks at 717 cm-1 and 904 cm-1 correspond to the out of plane bending of the C-H bond of the monosubstituted pyridinic cycle.
Mass spectrum analysis
We can notice the molecular peak at 162 m/z. However, the biggest peak is at 84 m/z. It corresponds to the fragmentation of nicotine. It deals with the pyrrolidine cycle, which has this molecular weight. During the electronic bombardment, the nicotine was split between the two cycles.
1H-RMN analysis in CDCl3 (400MHz)
Assignment
|
Chemical shift (ppm)
|
A
|
8,543
|
B
|
8,487
|
C
|
7,711
|
D
|
7,255
|
E
|
3,237
|
F
|
3,087
|
G
|
2,307
|
J
|
2,200
|
K
|
2,160
|
L
|
1,958
|
M
|
1,820
|
N
|
1,725
|
Done with C-H COSY
| |
13C-RMN analysis in CDCl3
| Assignment | Chemical shift (ppm) | Integration |
| 1 | 149,45 | 750 |
| 2 |
148,51
| 783 |
| 3 | 138,80 | 517 |
| 4 | 134,86 | 917 |
| 5 | 123,54 | 894 |
| 6 | 68,83 | 1000 |
| 7 | 56,96 | 844 |
| 8 | 40,32 | 783 |
| 9 | 35,23 | 833 |
| 10 | 22,60 | 839 |
L-Nicotine
CAS:54-11-5
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