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CODEINE

Codeine is a narcotic analgesic classified as an opiate. It has a molecular weight of 299.4g/mol and appears as a colourless to white crystalline solid with a melting point of 157.5°C. Codeine is soluble in water and its mechanism of action reduces intestinal motility through local and central mechanisms. It is synthesized by methylation of morphine's 3-hydroxy group. Side effects include respiratory depression, drowsiness, nausea, vomiting, constipation, and potential cardiac and respiratory arrest.

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49 views2 pages

CODEINE

Codeine is a narcotic analgesic classified as an opiate. It has a molecular weight of 299.4g/mol and appears as a colourless to white crystalline solid with a melting point of 157.5°C. Codeine is soluble in water and its mechanism of action reduces intestinal motility through local and central mechanisms. It is synthesized by methylation of morphine's 3-hydroxy group. Side effects include respiratory depression, drowsiness, nausea, vomiting, constipation, and potential cardiac and respiratory arrest.

Uploaded by

Dr_GS
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Codeine

IUPAC nomenclature
7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol.
Classification
• Narcotic analgesics, Antitussives, Anti-diarrhoea

Physiochemical Properties

1 Molecular weight 299.4g/mol

2 Physical appearance Colourless to white crystalline solid

3 Melting point 157.5°C

4 Solubility Soluble in water

5 Presence of ring Piperidine, tetrahydrofuran, cyclohexene,


phenyl

Mechanism of Action
• Codeine phosphate reduces intestinal motility through both a local and possibly
central mechanism of action. Codeine and its salt are absorbed from the gastro-
intestinal tract and onset of analgesic action occurs 30 to 45 minutes after
administration, when given orally
Structure Activity Relationship
SAR for Opiates can be summarized as follows:
• Replacement of phenolic hydroxyl into –OCH3/-OC2H5 will
make the drug less analgesic
• Replacement of alcoholic hydroxyl with –OCH3 makes the
compound 5 times more active.
• Replacement of alcoholic hydroxyl with -OC2H5 makes the
compound 2.4 times more active than morphine.
• Replacement of alcoholic hydroxyl with –OCOCH3 will also
activates the compound by 4.2 times.
• Replacement of alcoholic hydroxyl with ketone group inactivates the compound
and makes it lesser active.
• On replacement of the methyl group from tertiary nitrogen by hydrogen atom,
activity decreases.
• On replacement of N-CH3 by NCH2CH2Ph, activity increases by 14 times.
• When the methyl group of tertiary nitrogen replaced by N-
allyl/methallyl/propyl, the compound so formed acts like the Morphine
antagonist.
• When the methyl group of tertiary nitrogen replaced by N(CH3)2 Cl–, compound
have curare action and it do not possess any analgesic activity.
Method of synthesis
Codeine is synthesized by methylation of the 3-hydroxy group of the morphine ring by
trimethylphenylammonium ethoxide.

Side Effects
• Respiratory depression, Circulatory depression, Respiratory arrest
• Cardiac arrest, Drowsiness, Nausea, Vomiting, Sweating
• Shortness of breath, Sedation, Dizziness, Constipation

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