This document discusses drugs that affect the central nervous system, specifically morphine alkaloids. It provides information on morphine, codeine, thebaine, apomorphine, oxycodone, and oxymorphone, including their molecular formulas and brief histories. It also discusses the chemistry, structure-activity relationships, mechanisms of action, and uses of morphine alkaloids. The presentation was given by Aswini Sasidharan of the Department of Pharmaceutical Chemistry at Grace College of Pharmacy in Palakkad.
Alkaloids are a group of naturally occurring chemical compounds that mostly contain basic nitrogen atoms.
The term alkaloid was coined by Meissner, a German pharmacist, in 1819.
Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms.
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions.
Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).
Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.
Many alkaloids dissolve poorly in water but readily dissolve in organic solvents.
Most alkaloids have a bitter taste or are poisonous when ingested.
Penicillin, one of the first and still one of the most widely used antibiotic agents, is derived from the penicillium mold. In 1928 Scottish bacteriologist alexander fleming in a contaminated green mold penicillium notatum. He isolated the mold, grew it in a fluid medium, and found that it produced a substance capable of killing many of the common bacteria that infect humans. Australian pathologist howard florey and British biochemist ernst Boris chain isolated and purified penicillin in the late 1930s, and by 1941 an injectable form of the drug was available for therapeutic use.
Penicillin's are beta lactam antibiotics and characterized by three fundamental structural requirements
The fused beta-lactam and thiazolidine ring structure.
free carboxylic acid group.
And one or more substituted acylamino side chain.
Penam nucleus: 7-oxo-l-thia-4-azabicyclo [3.2.0] heptane
Absolute configuration: 3-S, 5-R, 6-R.
Instrumental methods of characterization:
FTIR
MASS
C13-NMR
1H-NMR
FTIR: -
Penicillin G molecule and its IR spectra in D2 O and in DMSO. Spectra are characterized by the presence of three intense bands.
β- lactam CO stretching observe at 1761 cm-1 in D2O and 1762 cm-1 in DMSO solution.
Amide group is observe at 1640 cm-1 in D2O and 1674 cm-1 in DMSO solution.
Asymmetric stretching of carboxylate group is observe at 1601 cm-1 in D20 and 1615 cm-1 in DMSO solution.
A large red shift of amide , out of the frequency window, is observed upon proton exchange in DMSO.
Collision-Induced Dissociation (CID) technique
MASS:-
A high-resolution, hybrid tandem mass spectrometer was used to obtain CID spectra. The CID spectra were acquired by:
Mass selecting the precursor ions using the first mass spectrometer.
Injecting the ions into the first quadrupole (collision cell) where they undergo CID.
Mass-analyzing the fragment ions produced using the second quadrupole.
Argon was used as the collision gas, and the pressure in the collision cell was adjusted to attenuate the precursor ion intensity to 20-50% of the original intensity. The collision energy of the ions ranged from 160 to 180 eV. The mass spectra shown abundant fragmentations at m/z 160 and m/z 176 that were reported to arise from cleavage of the β-lactam ring.
protonated benzyl penicillin exhibits abundant fragment ions at m/z 160, m/z 176, m/z 217, m/z 128, and m/z 289. The most abundant CID fragment at m/z 160 and the molecular ion peak was observed at m/z 334.
C13-NMR: -
The four sp3 ring carbons give rise to resonances in the decreasing chemical shift order C-3, C-5, C-2 and C-6.
Chemical shift for C-2 is 64.9 ppm and the substituents attached with it are α-methyl 27.0 ppm and β-methyl 31.4 ppm. Chemical shift for C-3 is 73.6 ppm and 174.5 ppm for carboxylate functions (reflecting the smaller de-shielding influence of COOH over that of COO-). The chemic shift for C-5 is 67.2 ppm. The chemic shift for C-6 is 58.4 ppm.
The lactam group shows its chemical shift at 175.0 ppm
Amino group
synthesis of hetero-cyclic drugs which act as anti-malarial drugs where you get all information about synthesis, preparation, properties, uses of drugs.
Alkaloids are a group of naturally occurring chemical compounds that mostly contain basic nitrogen atoms.
The term alkaloid was coined by Meissner, a German pharmacist, in 1819.
Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms.
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions.
Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).
Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.
Many alkaloids dissolve poorly in water but readily dissolve in organic solvents.
Most alkaloids have a bitter taste or are poisonous when ingested.
Penicillin, one of the first and still one of the most widely used antibiotic agents, is derived from the penicillium mold. In 1928 Scottish bacteriologist alexander fleming in a contaminated green mold penicillium notatum. He isolated the mold, grew it in a fluid medium, and found that it produced a substance capable of killing many of the common bacteria that infect humans. Australian pathologist howard florey and British biochemist ernst Boris chain isolated and purified penicillin in the late 1930s, and by 1941 an injectable form of the drug was available for therapeutic use.
Penicillin's are beta lactam antibiotics and characterized by three fundamental structural requirements
The fused beta-lactam and thiazolidine ring structure.
free carboxylic acid group.
And one or more substituted acylamino side chain.
Penam nucleus: 7-oxo-l-thia-4-azabicyclo [3.2.0] heptane
Absolute configuration: 3-S, 5-R, 6-R.
Instrumental methods of characterization:
FTIR
MASS
C13-NMR
1H-NMR
FTIR: -
Penicillin G molecule and its IR spectra in D2 O and in DMSO. Spectra are characterized by the presence of three intense bands.
β- lactam CO stretching observe at 1761 cm-1 in D2O and 1762 cm-1 in DMSO solution.
Amide group is observe at 1640 cm-1 in D2O and 1674 cm-1 in DMSO solution.
Asymmetric stretching of carboxylate group is observe at 1601 cm-1 in D20 and 1615 cm-1 in DMSO solution.
A large red shift of amide , out of the frequency window, is observed upon proton exchange in DMSO.
Collision-Induced Dissociation (CID) technique
MASS:-
A high-resolution, hybrid tandem mass spectrometer was used to obtain CID spectra. The CID spectra were acquired by:
Mass selecting the precursor ions using the first mass spectrometer.
Injecting the ions into the first quadrupole (collision cell) where they undergo CID.
Mass-analyzing the fragment ions produced using the second quadrupole.
Argon was used as the collision gas, and the pressure in the collision cell was adjusted to attenuate the precursor ion intensity to 20-50% of the original intensity. The collision energy of the ions ranged from 160 to 180 eV. The mass spectra shown abundant fragmentations at m/z 160 and m/z 176 that were reported to arise from cleavage of the β-lactam ring.
protonated benzyl penicillin exhibits abundant fragment ions at m/z 160, m/z 176, m/z 217, m/z 128, and m/z 289. The most abundant CID fragment at m/z 160 and the molecular ion peak was observed at m/z 334.
C13-NMR: -
The four sp3 ring carbons give rise to resonances in the decreasing chemical shift order C-3, C-5, C-2 and C-6.
Chemical shift for C-2 is 64.9 ppm and the substituents attached with it are α-methyl 27.0 ppm and β-methyl 31.4 ppm. Chemical shift for C-3 is 73.6 ppm and 174.5 ppm for carboxylate functions (reflecting the smaller de-shielding influence of COOH over that of COO-). The chemic shift for C-5 is 67.2 ppm. The chemic shift for C-6 is 58.4 ppm.
The lactam group shows its chemical shift at 175.0 ppm
Amino group
synthesis of hetero-cyclic drugs which act as anti-malarial drugs where you get all information about synthesis, preparation, properties, uses of drugs.
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MORPHINE ALKALOIDS
1. Drugs Affecting
the Central Nervous System
Presented by,
ASWINI SASIDHARAN
DEPT. OF PHARMACEUTICAL CHEMISTRY
GRACE COLLEGE OF PHARMACY, PALAKKAD
2. Morphine Alkaloids
•Drugs acting on the CNS.
•Natural opium alkaloids.
•Dried extract obtained from the capsule of poppy plant
known as papaverum somniferum.
6. History
•Morphine was isolated from opium.
•By the German Chemist F W A Serturner in 1804.
•It has the power to reduce the level of physical
distress.
9. History
•First isolated by French chemist Pierre-Jean Robiquet
in 1832.
•Codein is extracted directly from opium, but mostly
from morphine & another opium derivatives.
11. History
•Thebaine (paramorphine), also known as Codeine
methyl enol ether.
•It is an opiate alkaloid.
•Name comes from the Greek word “Theber” an ancient
city in Upper Egypt.
13. History
•The use of apomorphine was suggested by Weil in
France in 1884, although seemingly not pursued until
1951.
•Clinical use was reported in 1970.
14. CHEMISTRY
A
B
C
D
E
•5 Membered ring structure.
•Ring A - Aromatic ring.
•Ring B - Cyclohexane ring.
•Ring C - Cyclohexene ring.
•Ring D - Pyridine ring.
•Ring E- Tetrahydro Furan Ring.
•3 Rings (A,B, & C) lies in the same plane.
•2 Rings (D & E) are perpenticular to the
plane.
•Tertiary Nitrogen, Alcoholic & Phenolic
hydroxyl group, Ether bridge.
15. SAR
•The presence of OH group at C-3 position
will enhances the activity.
Eg; Morphine.
•The removal of ether bridge from the
compound increases the potency.
•The modification in the OH group at C-6
position yields ester or ether, that increases
the activity of the compound.
Eg; Thebaine.
Ether bridge
16. •Oxidation & Reduction at 7th & 8th
position (C=C), increases the activity of
the compound.
•Masking the phenol group will decreases
the activity.
•Modification in N-CH3 to N-CH at C-9,
decreases the activty.
•Modification in N-CH3 to CH2-CH2-
C6H5, increases the activity.
•Removal of double bond (C7-C8),
enhances the potency of the drug.
MORPHINE
18. Uses
•Relieve moderate to severe pain (Analgesics).
•Relieve stuffy nose (Decongestants).
•Used for the pain relief in: Myocardial Infarction.
Long bone fracture.
Postoperative Patients.
Terminal stages of cancer.
Pulmonary embolism.
19. REFERENCES
1. Natural products chemistry- sources, separation & structure by Raymond Cooper &
George Nicola, Pageno; 91-95.
2.Textbook of medicinal chemistry, volume I by V Alagarsamy, Pageno; 247-252.
3.Wilson and Gisvolds Textbook of organic Medicinal Pharmaceutical chemistry, 12 th
Edition by John M Beale & John H Block, Pageno; 783-785.
4. Essential’s of pharmacology, 7th Edition by K D Thripathi.
