Help me determine which molecule is more lipophillic?

Hello! Can anyone explain how to arrange the following molecules in order of lipophillicity?

Codeine
Morphine
Benzylmorphine

Thank you for any help :smile:

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Reply 2

username913907

10

Original post by Bonjour

Hello! Can anyone explain how to arrange the following molecules in order of lipophillicity?

Codeine
Morphine
Benzylmorphine

Thank you for any help :smile:

Well start out by looking up their structures...... I just think that should have been obvious.
Then look at what the actual difference is between them all (a clue it's just different groups at one position)

Reply 3

moldoveanun

Very interesting and useful tips I think.I read step by step this informations and help me so much.Thank you for this great informations

Reply 4

thegodofgod

19

Original post by moldoveanun

Very interesting and useful tips I think.I read step by step this informations and help me so much.Thank you for this great informations

Yes, codeine is also known as methylmorphine - the only difference between codeine and morphine is that codeine has a methoxy group on the benzene group instead of a hydroxyl group. Benzylmorphine (as you can probably tell from the name) has a benzyloxy group instead of the hydroxyl group on the benzene ring in morphine.

So, you look at the different R groups: OH in morphine, OCH₃ in codeine, and OCH₂C₆H₅, and you should be able to work out the order of lipophilicity of the drugs.

Reply 5

Bonjour

OP

8

Original post by thegodofgod

Yes, codeine is also known as methylmorphine - the only difference between codeine and morphine is that codeine has a methoxy group on the benzene group instead of a hydroxyl group. Benzylmorphine (as you can probably tell from the name) has a benzyloxy group instead of the hydroxyl group on the benzene ring in morphine.

So, you look at the different R groups: OH in morphine, OCH₃ in codeine, and OCH₂C₆H₅, and you should be able to work out the order of lipophilicity of the drugs.

Thank you! So can I just check I am right - the order of lipophilicity (starting with most lipophillic) would be benzylmorphine, codeine, then morphine? As more hydrocarbon chains on a molecule will make it more lipophillic?

Reply 6

thegodofgod

19

Original post by Bonjour

Thank you! So can I just check I am right - the order of lipophilicity (starting with most lipophillic) would be benzylmorphine, codeine, then morphine? As more hydrocarbon chains on a molecule will make it more lipophillic?

Exactly

Help me determine which molecule is more lipophillic?

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