Diacetylmorphine
Definition
The IUPAC name for heroin; the 3,6-diacetyl ester of morphine, produced by acetylation with acetic anhydride. More lipophilic than morphine, crosses the blood-brain barrier rapidly.
- Common name
- Heroin
- Chemical class
- 3,6-diacetyl ester of morphine
- Synthesis reagent
- Acetic anhydride
- Key property
- Higher lipophilicity than morphine
Common questions
Why does acetylation of morphine matter pharmacologically?+
Adding two acetyl groups increases lipophilicity, letting the molecule cross the blood-brain barrier much faster than morphine itself. Once inside the brain, diacetylmorphine is rapidly deacetylated back to 6-monoacetylmorphine and then morphine, which is why the onset of effect is quicker and more intense than morphine administered directly.
How do toxicologists confirm heroin use rather than morphine use alone?+
The presence of 6-monoacetylmorphine (6-MAM) in blood or urine is the key marker, because it is a unique intermediate metabolite of diacetylmorphine that is not produced from ingesting morphine or codeine directly, though it is short-lived and may not be detectable if sampling is delayed.
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