|Common names||Heroin, H, Smack, Junk, Brown|
|Substitutive name||Diacetylmorphine (Diamorphine)|
|Systematic name||(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate|
diacetylmorphine (also known as heroin, h, and colloquially as smack, junk, brown, and boy) is a semisynthetic opioid substance of the morphinan class that produces analgesic, relaxing, sedating and euphoric effects when administered.
heroin was originally synthesized by c.r. alder wright in 1874 from morphine, a natural product of the opium poppy (papaver somniferum). although the name heroin is a traditional trade name for a bayer product containing diacetylmorphine, the name has since been widely adopted for all intents and purposes and may describe a recreational depressant that may or may not contain pure diacetylmorphine.
in its pure form, heroin is active at doses of 5 mg and above; however, the substance is most commonly found in a preparation containing significant impurities. these impurities can result from including processing faults during synthesis, the addition of harmful or benign cutting agents, or the substitution of significantly more potent and dangerous analogous substances such as fentanyl adulterated into the end-product before distribution. this makes accurate dosing is particularly difficult.
history and culture
diacetylmorphine was first synthesized by alder wright in 1874 when attempting to combine morphine with various acids. the synthesis was achieved through boiling anhydrous morphine with morphine alkaloid with acetic anhydride.
heroin, or diacetylmorphine, is an opioid of the morphinan class. heroin and other molecules of this class contain a polycyclic core of three benzene rings fused in a zig-zag pattern called a phenanthrene. a fourth nitrogen containing ring is fused to the phenanthrene at r9 and r13, with the nitrogen member looking at r17 of the combined structure. this structure is called morphinan.
heroin, along with other morphinans, contains an ether bridge between two of its rings, connecting r4 and r5 through an oxygen group. heroin contains two acetate (ch3coo−) groups bonded to r3 and r6 of its structure, and a methyl group located on the nitrogen atom at r17. on the same ring containing the 6-acetyl group, heroin contains a double bond.
heroin’s chemical structure is closely related to morphine. heroin is the 3,6-diacetyl derivative of the diol morphine, meaning it contains acetate functional groups at the same locations hydroxy groups are found in morphine (3,6). heroin is analogous to the other morphinans including dihydrocodeine, codeine, ethylmorphine, hydrocodone, and oxycodone.
heroin itself is an inactive drug, but it is metabolized into morphine when inserted into the body. when taken orally, heroin undergoes extensive first-pass metabolism via deacetylation, making it a prodrug for the systemic delivery of morphine. when the drug is injected, however, it avoids this first-pass effect, very rapidly crossing the blood–brain barrier because of the presence of the acetyl groups which render it much more fat soluble, and thus more potent, than morphine itself.
once in the brain, it is deacetylated variously into the inactive 3-monoacetylmorphine and the active 6-monoacetylmorphine (6-mam). 6-mam is found in some commerically prepared batches of black tar heroin, often found on the west coast of the united states. it is then deacetylated into morphine, which binds to μ-opioid receptors. heroin itself exhibits relatively low affinity for the μ receptor, suggesting that much of the psychoactive effects of the substance come from the metabolites of heroin rather than the diacetylmorphine itself.
the recreational effects of this compound, including cognitive euphoria and physical euphoria, occur because opioids structurally mimic endogenous endorphins which are naturally produced within the body and are also active on the μ-opioid receptor set in the brain. the way in which synthetic opioids such as heroin structurally mimic these natural endorphins results in their euphoric, pain relief and anxiolytic effects. this is because natural endorphins are responsible for reducing pain, causing sleepiness, and feelings of pleasure. the endorphins can be released in response to pain, strenuous exercise, orgasm, or general excitement.