IC11 Flashcards
What is an alkaloid
Nitrogen-containing compound
Classification of cocaine
Tropane Alkaloid
Fg in cocaine
Two esters, tertiary amine
Where is cocaine extracted from
coca leaf
Apart from cocaine, coca also contains ______ and ____, with_____ as a minor constituent
cinnamoylcocaine; tropacocaine; methylecgonine
Strong bases have higher/lower pKa value?
Higher
What modifications in benzocaine retain the local anesthetic property and improve water solubility?
Replacement of tropine with amine to give procaine
Amide incr/ decr polarity?
Incr
Ester or amide group is more susceptible to hydrolysis?
Ester
Aminoester local anaesthetic formation: SN1 or SN2?
SN2 (1-step)
Aminoamide local anaesthetic formation: SN1 or SN2?
SN1 (2-step)
Generally, LA with ____and ____ exhibit faster onset and lower toxicity.
higher lipid solubility; lower pKa values
Most LA have pKa values of ____
7.5 – 9
Lidocaine is an amino___
amide
Lower conc of LA used may indicate lower/higher potency
Higher
_____is used clinically for treatment of heroin addiction
Methadone
Morphine is metabolized in the body to _____
morphine 3- O-glucuronide
Advantages of morphine 3- O-glucuronide over morphine
- more effective and longer lasting analgesic
- fewer side-effects
Codeine is the ____ of morphine which is a widely used analgesic and it has about ___ the potency of morphine.
3-O-methyl ether; 1/10
Long-term use of codeine can cause ___
constipation
How does codeine exert anti-tussive effect
depresses the cough centre & raise the threshold for sensory cough impulses.
3 examples of drugs that belong to morphinan class
Morphine, codeine and thebaine
How is Pholcodine derived from morphine
alkylation of morphine with N-(chloroethyl)morpholine
Dihydrocodeine is a____ form of codeine
reduced
Diamorphine or heroin is the____ of morphine
diacetate
PPty of heroin
- highly addictive analgesic
- hypnotic
- increased lipophilic character -> better transport & absorption
Advantages/ disadvantages of pentazocine
- good analgesic
- non- addictive
- can induce withdrawal symptoms
Pethidine is more/ less potent than morphine
Less
Advantages/ disadvantages of pethidine
- prompt, short-acting analgesia
- less constipating than morphine
- can be addictive
Structure of pethidine
Only the aromatic ring and the piperidine systems are retained.
Why is fentanyl more active than morphine?
Fentanyl has higher lipophilicity and excellent transport properties.
Fentanyl has ___ structure
4-anilino (contains N)
Fentanyl and derivatives are ___acting and used during ___
rapid; operative procedures
Nalbuphine, produced _____ from____
semi-synthetically; thebaine
Ppty of nalbuphine
mixed agonist– antagonist properties
____ is used to treat opiate poisoning, including that in children born to heroin addicts.
Naloxone
MOA for naloxone
potent antagonist at all opioid receptors; no agonist activity
MOA for Naltrexone
antagonist at opioid receptors
