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chemistry Flashcards

1
Q

opium alkaloids

A

aka opiates
centrally acting analgesics
strong narcotic effect

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2
Q

indication of opioids

A
  • moderate to severe pain
  • cough
  • diarrhoea
  • opioid dependence
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3
Q

common adr of opioids

A

respiratory depression
nausea and vomiting
drowsiness

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4
Q

delta (opioid receptor) and its agonist function

A

analgesia
antidepressant
physical dependece

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5
Q

kappa and its agonist function

A

spinal analgesia
sedation
miosis
inhibition of ADH release

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6
Q

mu and its agonist function

A

u1- supraspinal analgesia
physical dependence

u2-respiratory depression
miosis and reduced GI motility

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7
Q

nociceptin receptor and agonist function

A

anxiety
depression
appetite
toelrance to mu agonist

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8
Q

body snatural antiiniceceptives

A

endorphins (EnDOgenous moRPHINES)

enkephalin
-smaller peptides

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9
Q

morphine structure

A 
5 rings (A-E)
T shape
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10
Q

functional modificaiton of the R groups on morphine to yield codeine, ethylmorphine and 3-acetylmorphine leadsw to what in terms of analgesic activity

A

decreased analgesic activity

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11
Q

how does codeine act as prodrug for morphine

A

codeien is converted to morphine in the liver

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12
Q

functional modification of the 5-OH led to what in terms of activity

A

4-5 fold increase

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13
Q

testing of analgesics

A

performed in vivo

many factors must be considered as to why activity increase

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14
Q

ultimate resistance of opioid analgeics to CNS

A

BBB

6-acetylmorphine and heroin highly lipophilic therefore can penetrate the lipophilic bilayer and enter CNS

more polar morphine cannot readily penetrate the BBB

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15
Q

how do we get dihydromiorphine

A

preapred by hydrogenation of morphine

double bond at c7-c8

activity is not comprimised therefore double bond not essential for activity

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16
Q

N methyl groups in morphine functional modification

A

n-oxide or n methyl quayernary salts are ianctive in vivo as they are charged molecules therefore cannot cross BBB

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17
Q

N methyl groups in morphine functional modification and interaction with the receptor

A

since molecules are permanent cationsn nitrogen must be charged wihen inteacting with the receptor

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18
Q

normorphine in terms of polarity and activity

A

increased polarity therefore decreased activity

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19
Q

normorphine and removal of notrigen atoms

A

leads to total abolition of activity

nitrogen atoms is essential for activity and interacts with the receptor in ionised form

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20
Q

aroamtic ring in morphine

A

essentials

removal leads to loss of activity

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21
Q

ether bridge in morphine

A

not required for analgesic activity

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22
Q

mehtly group in morphine

A

not essential for analgesic activity

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23
Q

sterochemistry of morphine

A

contains everal chiral centers

enantiomer is completely inactive

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24
Q

enantiomer of morphine and why its completely inactive

A

morphine forms 3 receptor interactions with the binding regions

enenatiomer has no alagesic activity as it only has 1 receptor interaction

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25
Q

eprimerixation of morphine and its effects

A

leads to drastic change in molecular shape

result in poor conformation for receptor bindsing

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26
Q

pharmacophore of morphine

A

3D positioning of the key function groups with respect to each other

orginal structure-skeletal pharmaocophore-pharmacophoric triangles

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27
Q

metabolic pathway of codine

A

morphine via o-demethylatuion

norcodeine (N-demethylation)

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28
Q

morphine metabolic pathway

A

N demethylaton-normorphine

ugt2b7- morphine -6-glucoronide (mroe active)

ugt2b7, paps-morphine 3 glucorodine or sulfate (inactive)

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29
Q

which metaboltie of morphine is more reactiube than itself

A

morphine 6 glucoronide

30
Q

phase 1 reaction of morphine

A

many mu receptor agonists have an N methyl group which is readily dealkylated by CYP3A4

31
Q

nor metabolite from dealkylation

A

nor-lacking a methyl group

32
Q

why nor metabolites have limited clincial relevance

A

dicreas ein distribution enhancing lipophilicity

loss of agonist promoting hydrophobic interaction witht he receptor

33
Q

patients deficient in cyp2D6

A

unable to 0-dealkylate codeine and therfore show little or no response to codeine based analgesic

34
Q

common metabolic reactions phase 2

A

phenols conjugate with either glucoroic acid

35
Q

what impacts oral bioavailability of many phenolic opioids

A

phase 2 conjugation in the GI tract

36
Q

morphine 6 glucoronide and morphine. potency

A

estimated to be 50:1

37
Q

in whom can m6G accumulate in

A

although readily excreted it can accumulate in patients with renal failure or poor renal function

38
Q

varying substittuents to develop morphine monologues

A

a series of phenolic alkylation products led to a group of poor or inactive compounds

39
Q

extending molecular structure in developemt of morphine analogues

A

drug extension is a strategy in which the molecule is extended by addition of potential extra binding groups

easiest position to add substituent uto is the nitrogen atoms
-N demethylation required

40
Q

in N alkylmorphines. activity of the structure if the R2 is ch2ch2Ph (phenethyl)

A

14x activity of morphine

41
Q

in N alkylmorphines activity of the structure if the R2 is pentanyl, hexanyl

A

agonists

42
Q

in N alkymorphines activity of the strucutre if the R2 is Bu

A

zero activity

43
Q

in N alkylmorphines activity of the strucure if the R2 is me, Et, Pr

A

agonism decreases

antyagonism increases

44
Q

allyl and cyclopropylmethyl

A

when these groups were attached yield astounduing resutls

poses no analgesic activity therefore used to tx of opiates overdose

45
Q

agonists and the equilibrium between active conformation and inactive conformation

A

switches the equilibrium in favour for the active confromation which increases signal transduction

46
Q

antagonsits and the equlibrium between active and inactive conformation

A

switches the equilibrium in favour of the inactive conformation which leads to a decreased signal transduction

47
Q

amount of rings in morphine

A

5

48
Q

loss of ring E

A

complete loss of activity

49
Q

loss of ring d

A

removal of cyclic ether

formation of morphinans

50
Q

n-methylmorphinans

A

20% analgeisc activity

51
Q

levorphanol

A

5x more potent that morphine

52
Q

removal of rings c and d

A

benzomorphans

retain analgesic activity

53
Q

removal of b c and rings

A

4-phenylpiperidines

54
Q

fentanyl

A

successful piperidicine deivatibe

100x more potent that morphione

55
Q

what does fentanalyl strucutre lack

A

phenolic-oh

extrememly lipophilic

56
Q

removal of b c d e ring

A

methadone

57
Q

methadone in terms of severity of side effects

A

dispalays less servere emesis, constipation, sedation, euphoria

58
Q

r isomer of methadones activity

A

responsible for the analgesic activity

59
Q

s isomer of methadones activity

A

anatagonises the nmda receptor

60
Q

where is methadone beneficial in

A

neuropathic and opioid resistant pain

61
Q

why does methadone have a prolonged duration of action

A

generation of serveral active n-dealkylated and c3 redyuced metabolites

some metabolites also have long t0.5

62
Q

administration of methandone

A

oral

injection

63
Q

methandone and its risk of fatal cardiac arrhythmias

A

prlonged qt interval

64
Q

tramadol

A

analgesic with multiple moa

weak mu agonist

65
Q

pateitns allergic to cordine should not recieve tramadol why

A

risk for anaphylatic shock

66
Q

tramadol and enantiomer differences

A

1r, 2r enantiomer 30x more potent than 1s,2s enantiomer

67
Q

tramadol and its metabolsm which is similar to codeine

A

o-demethylate via cyp2d6 to a mroe potent opioiid rceptor agonist

68
Q

diels alder reaction

A

cycloaddition reaction between diene and dienophile to form a six membrered ring containing a double bond

69
Q

formation of oripavines

A

using methyl vinyl ketones as the dienophile intriduces reactive ketone group into molecule

70
Q

etorphine

A

1000x mroe ptoent than morphine

used as tranquilizers for large animals

71
Q

bupernorphine

A

drug extension led to this

good analgeisc activity

pain (6 decks)

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