Pranesh Rajamuthiah - Capstone: Final DrafHeroin vs Fentanyl

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Fentanyl

Heroin vs

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VSEPR Theory and Molecular Geometry

Chemistry

Heroin vs Fentanyl

• Fentanyl --> Designed to rigid and flexible in the correct areas
• An amide group
• A phenyl ring
• A piperidine ring
• Heroin --> Has rigid areas but is not flexible in the necessary areas
• Ester groups
• Phenyl ring
• Morphinan backbone

Bonding – The Power of Hydrogen Bonds

Chemistry

Heroin vs Fentanyl

Fentanyl

• Contains electronegative atoms (nitrogen & oxygen)

Heroin

• Ester groups cannot form that many hydrogen bonds

Why does this matter?

Strength and number of bonds determine how long the drug stays bound to the receptor

Heroin Has some nonpolar regions, but rigidity doesn't allow effective bonds

Therefore, fentanyl's nonpolar areas ensures stronger and comprehensive binding with receptors

Fentanyl Has multiple nonpolar rings as part of its structure

Polarity and Nonpolarity

Chemistry

Heroin vs Fentanyl

Why does this matter?

Subject Name

Topic

• Fentanyl is 50 times more potent than heroin
• Its potency makes it very dangerous in unregulated use
• Its stronger binding and longer-lasting effects make it MUCH MORE addictive

Why does this matter?

Here's Why!

• Opoid receptors are NOT static
• They're always shifting in response to other molecules
• This translates into potency
• If fentanyl has a better match with the opioid receptor's structure, it will be MUCH MORE potent

Fentanyl

• Attracts electrons
• Readily accepts hydrogen atoms from receptor
• Forms HIGH number of hydrogen bonds, which holds fentanyl and opioid receptor together

Heroin

• Since not that many hydrogen bonds
• Less stable
• Less effective
• Does not bind with opioid receptor as well

Fentanyl

• Nonpolar rings
• Phenyl
• Piperidine
• Can interact with receptor's hydrophobic areas effectively

Heroin

• Can't bind to hydrophobic areas of opioid receptors
• Can't fully exploit these areas
• Less effective binding