Pharmaceutical and Medicinal Organic Chemistry Laboratory (Finals)
Post-lab: Experiment 7 – Chloroform
Instructor: Ms. Shane Valerie G. Bautista, RPh || Transcribed by: Anne Bernadette Lingad
Chloroform (CHCl3)
Toxicity of Chloroform
• Metabolites of chloroform include phosgene,
carbene and chlorine, all of which may contribute to
its cytotoxic activity.
• Prolonged administration of chloroform as an
anaesthetic can cause toxemia.
• Chloroform may also cause delayed-onset damage
to the liver, heart and kidneys.
• Inhalation:
IUPAC Name- Chloroform o 40,000 ppm – death
o 1,500 to 30,000 – anesthesia
Systematic Name- Trichloromethane o <1,500 ppm – dizziness, headache,
tiredness
Other Names:
• Oral:
• Methyl trichloride o Fatal oral dose: 10mL
• Formyl Trichloride
Signs and Symptoms on the Acute Toxicity of
• Methane trichloride
Chloroform include:
• TCM
• Freon 20 • Headache
• R-20 • Altered consciousness
• UN 1888 • Convulsions
• Respiratory paralysis
• Disturbances of the ANS: dizziness, nausea, and
Chloroform vomiting
❖ Colorless, highly volatile, sweetly – scented liquid.
❖ Halogenated compound which is well known for its Synthesis of Chloroform
historical use as an anesthetic.
1. Chloroform may be prepared by the
❖ Considered as somewhat hazardous.
❖ Half as dense as water and of about the same viscosity. chlorination of methane.
❖ Has a heavy, burning sweetness of taste (about 40x as
sweet as cane sugar).
❖ Almost immiscible in water.
❖ Freely miscible with organic solvents.
❖ An important solvent for gums, resins, fats, elements
such as sulfur and iodine, and a wide variety of organic
compounds.
Uses of Chloroform
Industry:
➢ Solvent in producing dyes and pesticides
➢ Used for plant extraction
o Extract morphine from poppies
o Scopolamine from Datura plants
➢ As a reagent in organic synthesis.
2. By the action of iron and acid on carbon
Medicine: tetrachloride. This is the principal industrial
method in current use.
• Inhalational anesthetic agent
o MOA: inhibiting the TRPC5* calcium ion
channels predominant in the brain.
o TRPC = Transient Receptor Potential
Channels
3. Chloroform may be prepared by the chlorination
of Ethanol.
4. Chloroform may be prepared by the chlorination
of Acetone.
Chemical Tests of Chloroform
• Inflammability of chloroform: (+) not flammable
• Oxidation of chloroform: (+) Leafy odor of the gas
o (+) oxidizing agent
o Exposure to light and air
• Reaction with alcoholic silver nitrate:
o (+) pure chloroform does not give white
precipitate with alcoholic silver nitrate
Phosgene
• Smells like freshly cut hay or grass
• Low conc – new moon hay
• High conc – unpleasant strong smell
Uses
• For plastics and pesticides
• Choking agent in WWII
Dangerous concentration of phosgene may cause
• Pulmonary edema, coughing, burning sensation
in the throat and eyes, blurred vision
Answers to the Manual Questions:
✓ A: Chloroform should be protected from light
- Phosgene product of metabolism of
chloroform can occur in the presence of
oxygen and ultraviolet light.
- CHCl3 + [O] → COCl2 + HCl
- The chemical was named by combining the
Greek words ‘phos’ (meaning light) and
genesis (birth).
✓ A: Sodium bicarbonate may be used to neutralize
liquid spills of phosgene. Gaseous spills may be
mitigated with ammonia.
Pharmaceutical and Medicinal Organic Chemistry Laboratory (Finals)
Post-lab: Exercise 8 – Benzamide
Instructor: Ms. Shane Valerie G. Bautista, RPh || Transcribed by: Anne Bernadette Lingad
Benzamide (C7H7NO)
❖ It has a benzene ring and a amide functional group
❖ Amide functional group = RCO(NH2)
Synonyms
✓ Benzoic acid amide
✓ Phenyl carboxamide
✓ Benzoylamide
✓ Benzamid (German)
✓ Benzamida (Spanish)
General Facts
• Derivative of benzoic acid
• White powder, slightly soluble in water, ethanol and carbon tetrachloride
• Simplest carboxylic amide
Synthesis of Benzamide
+ NH3 → or Benzoyl chloride + Ammonia = Benzamide
Chemical Tests
• Hydrolysis using alkali
➢ (+) red → blue color of litmus paper
• Acid hydrolysis
➢ (+) blue → red color of litmus paper
• Action of Nitrous acid
➢ (+) yellow effervescence at the side of the tubes
