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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5733_Библиотеки_им_академика_М_И_Перельмана
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167
HYDROMORPHONE
(Dihydromorphinone)
Chemical Name: 4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one.
Molecular structure:
Physical properties:
1. Appearance and colour:
Tablets: These are typically small, round or oval-shaped, and may be white
or colored, depending on the manufacturer. They often have an imprint
identifying the medication and dosage.
Extended-Release Tablets: These are often larger than immediate-release
tablets, and may be round or oval-shaped. They might have a coating that
can be different colors, depending on the brand.
Liquid: Hydromorphone in liquid form is usually clear and colorless, but it
can sometimes have a slight yellow tint. It is typically provided in a bottle
with a dropper or dosing cup.
Injectable Solution: The injectable form of hydromorphone is a clear,
colorless to slightly yellow solution provided in ampoules or vials.
Suppositories: These are solid, torpedo-shaped forms that are designed to
dissolve at body temperature. They are usually white or off-white.
2. Melting point: 262°C (504°F).
3. Solubility:
Water: Hydromorphone is soluble in water.
Ethanol: It is slightly soluble in ethanol.
Chloroform: Hydromorphone is sparingly soluble in chloroform.
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Ether: It is practically insoluble in ether
4. Molecular Framework: Core Structure: Hydromorphone's core structure is the
morphinan ring system, which includes four interconnected rings:
A-ring: A benzene ring.
B-ring: A cyclohexane ring.
C-ring: A piperidine ring.
D-ring: A dihydrofuran ring (an ether ring fused with the piperidine ring).
5. Molecular weight: 285.343 g/mol
Chemical properties:
Chemical formula: C17H19NO3
Chemical classification: categorized under the family of phenanthrenes
Functional groups present in Hydromorphone:
- Hydroxyl group (-OH): Attached to the 3-position on the morphinan
framework.
- Ketone group (C=O): Attached to the 6-position on the morphinan
framework.
- Methyl group (CH3): Attached to the nitrogen atom at the 17-
position.
Ph of hydromorphone: The pH of hydromorphone can vary depending on
its formulation:
Injectable Solution: The pH of hydromorphone hydrochloride injection
typically ranges from 3.5 to 5.5. This acidic pH helps maintain the stability
and solubility of the drug in solution.
Oral Solution: The pH of oral hydromorphone solutions can also be slightly
acidic but can vary depending on the specific formulation and any
buffering agents used.
Physical Methods
1. Marquis Test
Reagent: Formaldehyde in sulfuric acid.
Procedure: A small amount of hydromorphone is mixed with the reagent.
Observation: A color change indicates the presence of certain alkaloids or
other substances. For hydromorphone, a purple to black color is often
observed.
2. Mecke Test
Reagent: Selenious acid in sulfuric acid.
Procedure: The test sample is mixed with the reagent.
Observation: Hydromorphone typically results in a green color change.
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3. Froehde Test
Reagent: Molybdenum oxide in sulfuric acid.
Procedure: Mix a small amount of hydromorphone with the reagent.
Observation: Hydromorphone usually produces a dark green to blue color.
4. Simon's Test
Reagent: Sodium nitroprusside in acetaldehyde and sodium carbonate.
Procedure: Mix the reagent with the sample.
Observation: The presence of secondary amines will result in a blue color.
However, this is less specific for hydromorphone.
Safety and Limitations
Safety: Always wear appropriate personal protective equipment (PPE)
such as gloves and safety glasses when handling reagents.
Limitations: These tests are presumptive and should not be used as a sole
means of identification. They can produce false positives or false negatives
and should be confirmed with more specific methods like chromatography
or mass spectrometry.
Chemical methods:
1. High-Performance Liquid Chromatography (HPLC)
Principle: Separates compounds in a mixture based on their interactions with a
stationary phase and a mobile phase.
Procedure:
Dissolve the hydromorphone sample in a suitable solvent.
Inject the sample into the HPLC system.
Use a suitable column and mobile phase to separate hydromorphone from
other components.
Detect and quantify hydromorphone using a UV detector.
Advantages: High sensitivity and specificity, capable of quantifying
hydromorphone.
2. Gas Chromatography-Mass Spectrometry (GC-MS)
Principle: Separates compounds by gas chromatography and identifies them by
mass spectrometry.
Procedure:
Derivatize hydromorphone if necessary to make it volatile.
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Inject the sample into the GC system.
Separate the components using a GC column.
Analyze the separated components with a mass spectrometer to identify
and quantify hydromorphone.
Advantages: High sensitivity, specificity, and can provide structural information.
3. Liquid Chromatography-Mass Spectrometry (LC-MS)
Principle: Combines liquid chromatography separation with mass spectrometry
detection.
Procedure:
Dissolve the hydromorphone sample in a suitable solvent.
Inject the sample into the LC system.
Separate the components using an LC column.
Detect and quantify hydromorphone using mass spectrometry.
Advantages: Highly sensitive and specific, no need for derivatization.
4. Fourier-Transform Infrared Spectroscopy (FTIR)
Principle: Measures the absorption of infrared radiation by the sample to identify
functional groups.
Procedure:
Prepare a thin film of the hydromorphone sample.
Place the sample in the FTIR spectrometer.
Record the infrared spectrum.
Compare the spectrum to known standards to identify hydromorphone.
Advantages: Non-destructive and can provide structural information.
5. Nuclear Magnetic Resonance (NMR) Spectroscopy
Principle: Uses the magnetic properties of nuclei to provide detailed information
about the structure of a molecule.
Procedure:
Dissolve the hydromorphone sample in a deuterated solvent.
Place the sample in an NMR spectrometer.
Record the NMR spectrum.
Analyze the spectrum to identify and quantify hydromorphone.
Advantages: Provides detailed structural information, highly specific.
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6. Ultra-Performance Liquid Chromatography (UPLC)
Principle: Similar to HPLC but with smaller particle sizes in the column for higher
resolution and faster analysis.
Procedure:
Dissolve the hydromorphone sample in a suitable solvent.
Inject the sample into the UPLC system.
Use a suitable column and mobile phase to separate hydromorphone from
other components.
Detect and quantify hydromorphone using a suitable detector (e.g., UV or
MS).
Advantages: Higher resolution, faster analysis, and lower solvent consumption
compared to HPLC.
7. Capillary Electrophoresis (CE)
Principle: Separates ions based on their electrophoretic mobility with an electric
field applied to a capillary tube.
Procedure:
Prepare the hydromorphone sample and inject it into the capillary tube.
Apply an electric field to separate the ions.
Detect the separated components using a suitable detector (e.g., UV or
MS).
Advantages: High efficiency, small sample and reagent volumes, and fast analysis.
Confirmation and Quantification
Calibration: Use standards of known concentrations of hydromorphone to
calibrate the instrument.
Validation: Validate the method to ensure accuracy, precision, specificity,
and sensitivity.
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HYDROXYPETHEDINE
(Meperidine or Demerol)
Chemical Name: 4-phenyl-4-carbethoxy-1-methylpiperidine.
Molecular structure:
Physical Properties:
1. Appearance and colour:
Hydroxypethidine, commonly known as meperidine or Demerol, is
typically found in the form of a white to off-white crystalline powder.
However, its appearance can vary depending on the formulation and
specific preparation. It's important to note that the physical appearance
and color can be influenced by factors such as additives or fillers used in
pharmaceutical formulations.
2. Melting point: 186-189°C (367-372°F).
3. Solubility: Hydroxypethidine, also known as meperidine or Demerol, is typically
described with the following solubility characteristics:
Solubility: It is freely soluble in water and in alcohol (ethanol).
Insolubility: It is practically insoluble in non-polar solvents like ether and
chloroform.
4. Molecular framework: It consists of a piperidine ring (a six-membered ring
containing one nitrogen atom) with a phenyl group (C6H5) and a carbethoxy
(COOCH3) group attached.
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This structure is characteristic of opioids and is responsible for its
pharmacological effects and interactions with opioid receptors in the
body.
4. Molecular weight: 247.33 g/mol.
Chemical properties
1. Chemical formula: C15H21NO2.
2. Chemical classification: classified chemically as a synthetic opioid analgesic. It
belongs to the subclass of piperidine opioids, characterized by its molecular
structure that includes a piperidine ring.
3. Functional Group:
Piperidine Ring: This is a saturated heterocyclic ring containing five
carbon atoms and one nitrogen atom. The piperidine ring is central to the
structure of meperidine and is responsible for its opioid activity.
Phenyl Group (C6H5): Attached to the piperidine ring, the phenyl group
consists of a benzene ring (six carbon atoms arranged in a hexagonal ring)
with a hydrogen atom removed.
Carbethoxy Group (COOCH3): This functional group is an ester group
consisting of a carbonyl group (C=O) bonded to an oxygen atom, which in
turn is bonded to an ethoxy group (-OCH3).
4. pH : 5.5 to 7.
Methods of Analysis
Physical Methods:
Melting Point Determination:
Principle: Measuring the temperature at which hydroxypethidine changes
from solid to liquid state can confirm its identity and purity.
Procedure: A small amount of hydroxypethidine is placed in a melting
point apparatus, and the temperature at which it melts is recorded.
Microscopy:
Principle: Microscopic examination helps in the identification of
hydroxypethidine crystals or particles.
Procedure: A microscope is used to observe the morphology and
characteristics of crystals or particles of hydroxypethidine.
Density Measurement:
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Principle: Determining the density of hydroxypethidine can provide
information about its purity and concentration.
Procedure: Density is measured using a specific gravity bottle or
pycnometer, comparing the mass of a known volume of hydroxypethidine
solution with that of water.
Chemical Methods:
Titration Methods:
Acid-Base Titration:
Principle: Hydroxypethidine can be titrated with a standard acid or base
to determine its concentration.
Procedure: An acid-base titration is performed using a pH indicator to
detect the endpoint of the reaction.
Complexometric Titration:
Principle: Hydroxypethidine can form complexes with certain metal ions,
allowing for determination via complexometric titration.
Procedure: EDTA (ethylenediaminetetraacetic acid) titration is commonly
used where the endpoint is detected by a color change using a metal ion
indicator.
Chromatographic Methods:
High-Performance Liquid Chromatography (HPLC):
Principle: Separates and quantifies components based on their interaction
with a stationary phase and mobile phase.
Procedure: Hydroxypethidine is dissolved in a suitable solvent and
injected into an HPLC system. Detection is usually done using UV-Vis
spectroscopy.
Gas Chromatography (GC):
Principle: Separates components based on their volatility and interaction
with the stationary phase.
Procedure: Hydroxypethidine is vaporized and injected into a GC system
where it travels through a column, and detection is based on a detector
such as FID (flame ionization detector).
Spectroscopic Methods:
UV-Visible Spectroscopy:
Principle: Measures the absorption of light in the UV-Vis region to identify
and quantify hydroxypethidine.
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Procedure: A solution of hydroxypethidine is prepared and scanned in the
UV-Vis spectrophotometer to determine absorbance at specific
wavelengths.
Infrared Spectroscopy (IR):
Principle: Analyzes the vibrations of chemical bonds in hydroxypethidine
to identify functional groups.
Procedure: A solid sample of hydroxypethidine is mixed with KBr and
pressed into a pellet, then analyzed using IR spectroscopy.
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ISOMETHADONE:
(Isoamidone)
Chemical Name: (±)-6-(Dimethylamino)-5-methyl-4,4-diphenyl-3-hexanone
Molecular structure:
Physical Properties:
Appearance and colour: Solid and light brown in colour
Melting point: 176-177°.
Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly),
Methanol (Slightly)
Molecular weight: 309.45 g/mol
Chemical Properties:
Chemical formula: C21H27NO
Chemical classification: Isomethadone is a diarylmethane. Isomethadone
is a DEA Schedule II controlled substance. Substances in the DEA Schedule
II have a high potential for abuse which may lead to severe psychological
or physical dependence. It is a Opiates substance.
Functional group: Functional Group: Ketone (C=O) and tertiary amine
(N(CH3)2)
pH: Not applicable (solid substance)
How It is Made and Obtained: Isomethadone is synthesized chemically through a
multi-step process. Here is a simplified version of the process:
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