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Date November 2016 Marks available 1 Reference code 16N.3.sl.TZ0.20
Level SL Paper 3 Time zone TZ0
Command term Outline Question number 20 Adapted from N/A

Question

Methadone, a synthetic opioid, binds to opioid receptors in the brain.

Compare and contrast the functional groups present in methadone and diamorphine (heroin), giving their names. Use section 37 of the data booklet.

[2]
a.

Methadone is sometimes used to help reduce withdrawal symptoms in the treatment of heroin addiction. Outline one withdrawal symptom that an addict may experience.

[1]
b.

Markscheme

Similarity:

both contain «at least one» benzene/aromatic ring
OR
both contain amino «group»  

Difference:

diamorphine has one benzene/aromatic ring AND methadone has two phenyl «groups»
OR
diamorphine has one vinylene/ethenylene/1,2-ethenediyl «group» AND methadone has no vinylene/ethenylene/1,2-ethenediyl «group» 
OR
diamorphine has one ether «group» AND methadone has no ether «group»
OR
diamorphine has «two» ethanoate/acetate «groups» AND methadone has no ethanoate/acetate «groups»

Accept “both contain carbonyl «groups»”.
Accept “amine” for “amino «group»”.
Accept “phenyl” for “benzene ring” in M1 and M2 although there are no phenyl groups in diamorphine, as the benzene ring in this compound is a part of a polycyclic structure.
Do not accept “arene” or “benzene” alone in M1 and M2.
Accept “alkenyl/alkene” for “vinylene/ethenylene/1,2-ethenediyl” and “ester” for “ethanoate/acetate”.
Accept “methadone has a ketone/carbonyl AND diamorphine does not/has an ester/ethanoate/acetate”.
Accept “diamorphine is a heterocycle/heterocyclic compound AND methadone is not a heterocycle/heterocyclic compound”.

a.

feeling depressed/anxious/irritable
OR
craving for opioids/heroin
OR
experience fever/cold sweats/nausea/vomiting/insomnia/muscle pain/cramps/diarrhea/increased rate of respiration/increased heartbeat/lacrimation

Accept listed symptoms (eg, depression, anxiety, fever etc.).
Some of the most common symptoms are listed here – there may be other valid ones. Accept “headaches”.

b.

Examiners report

[N/A]
a.
[N/A]
b.

Syllabus sections

Options » D: Medicinal chemistry » D.3 Opiates
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Options » D: Medicinal chemistry
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