NICOTINE COSY

The Two-Dimensional H,H-COSY highlighting the distinct correlations of two spin systems within the molecule

1H NMR NICOTINE

13 C NMR

DEPT90







DEPT135

1H 13C HSQC





HH TOCSY







MORE.....................

Structure and properties of Nicotine

1 - Structure of the molecule

Nicotine is also called 3-(1-methyl-2-pyrrolidinyl)pyridine according to the IUPAC^a nomenclature. It is a bicyclic compound with a  pyridine cycle and a pyrrolidine cycle. The molecule possesses an asymetric carbon and so exists in two enantiomeric compounds. In nature, nicotine only exists in the S shape, which is levogyre.

Representation of the S molecule in 2D : 

Representation^b of the R molecule in 3D :

2 - 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.

3 - 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.

4 - 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.

5 - 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

 
6 - 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

http://newdrugapprovals.org/

DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO

NICOTINE .......FRIEND FOR ORGANIC SPECTROSCOPY

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

Nicotine biosynthesis