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Ростовский Государственный Медицинский Университет

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 Starting Materials: Phenylacetonitrile and dimethylamine.

Reaction Steps:

 Alkylation: Phenylacetonitrile is alkylated with dimethylaminoethyl

chloride.

 Hydrogenation: The resulting product undergoes hydrogenation to form

the corresponding amine.

 Acylation: The amine is then acylated with benzoyl chloride to produce

isomethadone.

Route of Administration

 Oral: The most common route, usually in tablet or liquid form.

Pharmacological Action

Mechanism of Action: Isomethadone acts primarily on the mu-opioid receptors in

the central nervous system (CNS) to produce analgesia, euphoria, and sedation. It

also has activity at the NMDA receptor, which can contribute to its effects.

Effects:

 Analgesia: Pain relief.

 Sedation: Drowsiness and relaxation.

 Euphoria: Feelings of well-being and pleasure.

 Respiratory Depression: Slowed breathing.

 Dependency: Potential for addiction and abuse.

Analysis Methods:

Physical Analysis:

Appearance and Melting Point Determination:

 The appearance can be confirmed by visual inspection, ensuring it

matches the description of a white crystalline powder.

 Melting point determination involves heating a small sample of the

substance and recording the temperature at which it transitions from

solid to liquid. The expected range for isomethadone is 98-100°C.

Solubility Testing:

 Water Solubility: A small amount of isomethadone is added to water, and

the mixture is stirred to observe how much dissolves.

 Alcohol Solubility: Similar procedure as with water, but using ethanol or

another alcohol.

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Chemical Analysis:

Identification:

 Mass Spectrometry (MS): Measures the mass-to-charge ratio of ions to

identify the molecular structure.

 Nuclear Magnetic Resonance (NMR) Spectroscopy: Provides detailed

information about the molecular structure based on the magnetic

properties of atomic nuclei.

 Infrared (IR) Spectroscopy: Identifies specific functional groups by

measuring the absorption of infrared light at different wavelengths.

Purity Testing:

 High-Performance Liquid Chromatography (HPLC): Separates components

of a mixture to determine the purity and identify impurities.

 Gas Chromatography (GC): Similar to HPLC but used for volatile

substances.

Functional Group Analysis:

 IR Spectroscopy: Can identify the presence of the ketone (C=O) stretch

typically around 1700 cm-1 and the amine (N(CH3)2) stretches.

 Other opioids, it carries risks of side effects and dependency, requiring

careful medical supervision during use.

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KETOBEMIDONE

Chemical Name: 1-methyl-4-(3-hydroxyphenyl)-4-propionylpiperidine. Also

known as Cliradon, Ketogan, Ketodur, Cymidon, Ketorax

Molecular Structure:

Physical Properties:

 Appearance: Ketobemidone typically appears as a crystalline solid.

 Colour: It is usually white or off-white.

 Odour: Ketobemidone is odorless.

 Taste: Information on the taste of ketobemidone is generally not provided

due to its pharmaceutical use.

 Melting Point: Approximately 150-155°C.

 Boiling Point: The boiling point is not well-documented, as ketobemidone

is usually used in solid form.

 Solubility: Ketobemidone is soluble in water and ethanol.

 Molar Mass: 269.33 g/mol.

Chemical Properties:

 Chemical Formula: C16H21NO2

 Chemical Classification: Opioid analgesic

 Functional Group: Ketone and amide

 pH: Ketobemidone solutions can have a pH range of 4.5 to 6.5.

How It is Made and Obtained From: Ketobemidone is synthesized chemically in

pharmaceutical laboratories. The synthesis involves multiple steps, starting from

simpler organic compounds and incorporating functional groups to form the final

opioid structure. The specific synthesis pathway can vary but typically involves

forming the morphinan skeleton and adding the ketone and amide groups through

various organic reactions.

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Route of Administration: Ketobemidone can be administered in several forms,

including:

 Oral tablets

 Injectable solutions

 Suppositories

Pharmacological Action: Ketobemidone is an opioid analgesic that acts on the

central nervous system to relieve pain. It binds to opioid receptors (mu, delta, and

kappa) in the brain and spinal cord, which leads to the inhibition of pain signals. It

has a rapid onset of action and is used for the management of moderate to severe

pain.

Analysis:

Physical Analysis:

 Crystallography: X-ray diffraction can be used to determine the crystal

structure of ketobemidone.

 Melting Point Determination: Melting point apparatus is used to confirm

the purity of the compound.

 Spectroscopy: Infrared (IR) spectroscopy can be employed to identify

functional groups present in ketobemidone.

Chemical Analysis:

 Mass Spectrometry (MS): MS can be used to determine the molecular

weight and structure of ketobemidone.

 Nuclear Magnetic Resonance (NMR) Spectroscopy: NMR can provide

detailed information about the molecular structure and functional groups.

 High-Performance Liquid Chromatography (HPLC): HPLC is used for the

quantitative analysis and purity determination of ketobemidone in

pharmaceutical formulations.

 pH Measurement: The pH of ketobemidone solutions can be measured

using a pH meter to ensure it falls within the acceptable range for

pharmaceutical use.

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LEVOMETHORPHAN

Chemical Name:

(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo [7.5.3.01,10.02,7] heptadeca-

2(7),3,5-triene; (4bR,8aR,9R)-3-Ethyl-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-

(epiminoethano)phenanthrene

Molecular structure

Physical Properties

 Appearance: Crystalline solid

 Colour: White

 Odour: Odorless

 Taste: Bitter

 Melting Point: Approximately 123-125°C

 Boiling Point: 250-255°C at 760 mmHg

 Molar Mass: 271.38 g/mol

Solubility:

 Water: Sparingly soluble

 Alcohol: Soluble

Chemical Properties

 Chemical Formula: C18H25NO

 Chemical Classification: Opioid analgesic

 Functional Group: Tertiary amine, methoxy group

 pH: Not applicable as it is a solid

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How It is Made and Obtained From: Levomethorphan is synthesized from

racemic methorphan by separating the dextrorotatory (dextromethorphan) and

levorotatory (levomethorphan) enantiomers. It is typically obtained through

chemical synthesis involving the reduction of levomethorphan intermediate

compounds.

Route of Administration: Oral

Pharmacological Action: Levomethorphan is an opioid analgesic, meaning it

works by binding to opioid receptors in the brain and spinal cord to reduce the

perception of pain. It is the levorotatory enantiomer of methorphan and is more

potent than its dextro counterpart in terms of analgesic properties. It has strong

central nervous system effects, including sedation and euphoria, and can lead to

dependence and tolerance.

Analysis:

Physical Analysis:

 Appearance: Crystalline form can be identified visually.

 Colour: Pure samples should appear white.

 Melting Point and Boiling Point: Can be determined using standard

laboratory equipment like a melting point apparatus and boiling point

distillation.

 Solubility: Solubility tests can be conducted by dissolving in water and

alcohol and observing the extent of dissolution.

 Molar Mass: Determined through mass spectrometry or calculated from

the chemical formula.

Chemical Analysis:

 Chemical Formula: Confirmed through elemental analysis (e.g., CHN

analysis).

 Chemical Structure: Verified using spectroscopic techniques like NMR

(Nuclear Magnetic Resonance) and IR (Infrared Spectroscopy).

 Functional Groups: Identified and confirmed using IR spectroscopy.

 Purity and Concentration: Determined through techniques like HPLC

(High-Performance Liquid Chromatography) or GC-MS (Gas

Chromatography-Mass Spectrometry).

 pH: Not applicable for solid compounds but relevant for aqueous solutions

of its salts or derivatives.

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LEVOMARAMIDE

Levomaramide is a synthetic opioid analgesic that was first developed as a

potential alternative to other opioid drugs. Below is detailed information about

Levomaramide:

Scientific Name: Levomaramide

IUPAC Name: (2R,6R)-2-Dimethylamino-4,4-diphenylheptan-6-ol

Physical Properties:

 Appearance: Typically appears as a crystalline solid.

 Colour: White to off-white.

 Odour: Odorless.

 Taste: Bitter.

 Melting Point: Approximately 185-186 °C.

 Boiling Point: Not well-documented due to its decomposition before

boiling.

 Solubility: Soluble in water and alcohol; highly soluble in methanol and

ethanol.

 Molar Mass: 362.51 g/mol.

Chemical Properties:

 Chemical Formula: C24H30N2O

 Chemical Classification: Synthetic opioid analgesic.

 Functional Group: Amines and alcohols.

 pH: The pH in a solution can vary, but typically around neutral to slightly

basic.

How It is Made and Obtained From: Levomaramide is synthesized through a

series of chemical reactions involving the precursor compounds. It involves

stereoselective synthesis to obtain the levo-isomer, which is the active form. The

synthesis typically includes steps like alkylation, reduction, and resolution of

racemic mixtures to isolate the levo-isomer.

Route of Administration:

 Oral (tablet or liquid form)

 Intravenous (injected directly into the bloodstream)

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 Intramuscular (injected into muscle tissue)

Pharmacological Action: Levomaramide acts primarily on the central nervous

system as an opioid agonist, specifically targeting the mu-opioid receptors. It

produces analgesia, sedation, and euphoria, similar to other opioids. It works by

mimicking the action of endogenous peptides like endorphins, binding to opioid

receptors, and inhibiting the transmission of pain signals.

Analysis:

Physical Analysis:

 Visual Inspection: Levamisole hydrochloride typically appears as a white

crystalline powder. Visual inspection can provide a basic indication of

purity and physical characteristics.

 Spot Tests: These are chemical tests designed to identify the presence of

specific substances. For levamisole, a common spot test involves reaction

with specific reagents that produce characteristic color changes or

precipitates.

 Colorimetric Analysis: This involves using instruments that measure the

absorbance or reflectance of light by a substance at different wavelengths,

often resulting in a quantitative measurement of levamisole concentration.

Chemical Analysis:

 Qualitative Analysis: Tests to determine the presence of functional groups,

such as amines and alcohols.

 Quantitative Analysis: Titration methods to determine the concentration

of active ingredients.

 pH Measurement: Using a pH meter to determine the pH of Levomaramide

solutions.

 Mass Spectrometry: For molecular weight determination and structure

confirmation.

 Solubility Tests: To determine the solubility in various solvents like water,

ethanol, methanol, etc.

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LEVOPHENOCYLMORPHAN

Levophenacylmorphan is an opioid analgesic that is not widely known or

used. Here's a detailed profile based on the available information:

Scientific Name: Levophenacylmorphan (common name)

IUPAC Name: 17-Phenylmorphinan-3-ol

Molecular Structure:

3D Structure:

Physical Properties:

 Appearance: Not widely documented; typically solid in pure form.

 Colour: Not specifically documented; likely white or off-white.

 Odour: Characteristic of opioids; often described as having a slight

medicinal or chemical smell.

 Taste: Bitter.

 Melting Point: Not well-documented.

 Boiling Point: Not well-documented.

 Molar Mass: Approximately 297.43 g/mol.

Solubility:

 Water: Limited information; opioids generally have low solubility in

water.

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 Alcohol: Likely more soluble in ethanol or other alcohols.

Chemical Properties:

 Chemical Formula: C17H19NO

 Chemical Classification: Opioid analgesic

 Functional Group: Alcohol (OH), aromatic hydrocarbon (phenyl group)

 pH: Typically neutral in its pure form; pH depends on the form (salt or

base) and the solution.

How It is Made? And Obtained From?

Levophenacylmorphan is synthesized chemically from morphinan

derivatives. The process involves the modification of the morphinan structure to

introduce a phenyl group and an alcohol functional group at specific positions. The

synthesis typically requires multiple steps, including:

 Derivatization of morphinan.

 Functional group transformations (e.g., introducing the hydroxyl group).

 Purification processes, such as recrystallization or chromatography.

Route of Administration:

 Oral: Tablets or capsules.

 Parenteral: Injection (intravenous, intramuscular).

 Others: Rectal suppositories, transdermal patches.

Pharmacological Action: Levophenacylmorphan acts as an agonist at the mu-

opioid receptors in the central nervous system. It produces analgesia (pain relief)

by mimicking endogenous opioids (endorphins) and binding to the opioid

receptors, which modulate the perception of pain and induce euphoria, sedation,

and other opioid effects. The drug can also depress the respiratory system, which

is a common risk with opioid use.

Analysis:

Physical Analysis:

 Appearance and Melting Point Determination: Visual inspection and use of

a melting point apparatus to verify purity.

 Solubility Testing: Dissolution in various solvents to understand its

solubility profile.

Chemical Analysis:

Chemical Structure Verification:

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