MORPHINE

1. STRUCTURAL ELUCIDATION OF
MORPHINE

2. INTRODUCTION
 Morphine is derived from dried extract from the capsules of poppy plant
known as papaver somniferum.
 It is a colourless prismatic substance having M.P: 247ºc.
 Mol.formula:- C17H19NO3
 Mol.wt:- 285.4
 It is slightly soluble in water,ether,chloroform but soluble in alcohol & alkali
solution.
 Phenanthrene(opium) alkaloid.
 closely related compouds are codein,thebaine.

3. MOA & PHARMACOLOGICAL ACTIONS
 Analgesics
 Sedative
 Papillary Constriction
 Antitussive property
 Respiratory depression
 Heat regulation
 Delayed Gatric emptying time & decrease peristaltic
movement

4. ADVERSE REACTIONS
 Acute morphine poisoning
 Nausea
 Vomitting
 Constipation
 Skin rashes

5. CONTRA-INDICATION
 Infants & Elder people
 Brochial Asthama
 Head Injury
 Acute Abdominal pain
 Hypothyroidism

6. USES
 Analgesic.
 Used as pre-anesthetic medication.
 Producing Sleep & Sedation.
 Used as Anti-tussive.
 For treatment of Diarrhoea.

7. SAR OF MORPHINE

9. STRUCTURAL ELUCIDATION
 Spectral properties:-
1.UV Spectra:-
Solvent λmax(nm) A(1%,1cm)
Ethanol 286 59.44
0.1N NaOH 250 175
Solution 298 75.6

10. 2.IR Spectrum:-
Frequency cm-1 Assignment
3480,3350 Free OH
3210 Bonded OH
2940,2920 CH (stretch)
2840 CH3-NH
1650 C7= C8 (Alkene)
1605 C=C (Aromtic)
1250,1090 C4-O-C5
760 Monosubstituted
aromatics.

11. 3.NMR Spectra
Group CHEMICAL SHIFT (PPM)
H2 (aromatic)
H1 (aromatic)
H7
H8
H5
H9
H14
N-CH3
2H10
S=siglet,
d=doublet,
Morphine HCL
6.76 (d)
6.68 (d)
5.75 (d)
5.40 (d)
5.06 (d)
4.37 (m)
4.20 (d)
3.00 (s)
2.16
m=multiplet,
q=quartet
Morphine
6.42 (Abq)
4.63 (d)
2.30 (s)

12. 4.Mass Spectum
m/e Relative Intensity %
285
286
284
268
216
215
174
171
162
161
153
152
131
129
123
127
124
116
115
100.0(base)
26.1 M+1
17.2 M-1
13.3
11.1
33.3
18.9
11.1
5.8
11.0
13.3
22.2
24.4
14.4
31
27.8
43.3
16.6
74
m/e Relative Intensity %
109
103
94
91
82
81
77
70
65
60
59
58
57
56
55
54
53
52
51
22.2
16.7
26.7
21.7
22.2
42.
32.2
46.6
22.2
12.2
50
28.9
46.6
23.3
80
16.6
47.8
1.5
35.6

13. REFERENCES
 www.Sciencedirect.com
 “Organic Chemistry of Natural Product”- by Gurudep
Chatwal,Vol-1
 “Organic Chemistry of Natural Product”- by
O.P.Agarwal,Vol-1
 Elementary Organic Spectroscopy by Y.R Sharma
pg.no:256-276
 www.slideshare.com
 www.authorstream.com

14. Any question ?????

15. Thank you…..