A) Select the natural product from which each synthetic product is derived. hero

Question

A) Select the natural product from which each synthetic product is derived.

heroin: morphine codeine

oxycodone: morphine codeine

hydrocodone: morphine codeine

B) One of the three synthetic alkaloids is made via nucleophilic acyl substitution using one of the natural alkaloids as the nucleophile. Select the one made via this route.

heroin

oxycodone

hydrocodone

Draw an acid derivative that can be used in conjunction with the natural product to yield this synthetic alkaloid via nucleophilic acyl substitution.

C) Heroin and cocaine come as the hydrochloride salt (HCl) and can be neutralized to the free base.

"Hydrochloride" can be misleading if one thinks that the hydrogen is bonded to the chlorine. The chloride is the anion and the drug is protonated making it the counter cation. Select the atom the hydrogen is really bonded to in the salt.

O

N

C

D) Heroin can either be injected or inhaled. One method uses the salt and the other uses the free base. When the injection route is used, the heroin is first dissolved in water. Select the species used for the injection method.

salt

free base

E) The next time you see a drug name containing "hydrochloride," which functional group should you first consider to be present in the drug?

amine

acyl chloride

carboxylic acid

ester

ketone

aldehyde

anhydride

alcohol

Explanation / Answer

A) morphine; codeine; codeine

B) heroin; anhydride

C) N; salt; amine

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