Heroin: Difference between revisions

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'''Diacetylmorphine''' (also known as '''heroin''' and colloquially as '''H''', '''dope''', '''smack''', '''junk''', '''brown''', '''boy''', and others) is a semi-synthetic [[psychoactive class::opioid]] substance of the [[chemical class::morphinan]] class. It is a derivative of [[morphine]], a natural product of the opium poppy (''Papaver somniferum'').{{citation needed}} Heroin is known for its highly addictive properties and it makes up a large portion of the illicit traffic in narcotics.

'''Diacetylmorphine''' or morphine diacetate (also known as '''heroin''' and colloquially as '''H''', '''dope''', '''smack''', '''junk''', '''brown''', '''boy''', and others) is a semi-synthetic [[psychoactive class::opioid]] substance of the [[chemical class::morphinan]] class. It is a derivative of [[morphine]], a natural product of the opium poppy (''Papaver somniferum'').{{citation needed}} Heroin is known for its highly addictive properties and it makes up a large portion of the illicit traffic in narcotics.

Heroin was first synthesized from morphine by a British chemist in 1874 and was introduced as a commercial product by the Bayer Company of Germany in 1898.<ref>Wright, C.R.A. (1874). "On the Action of Organic Acids and their Anhydrides on the Natural Alkaloids". Journal of the Chemical Society. 27: 1031–1043. doi:10.1039/js8742701031|https://web.archive.org/web/20040606103721/http://adhpage.dilaudid.net/heroin.html</ref> Although the name heroin is a trade name, it has since been widely adopted for all intents and purposes and may describe a recreational depressant that may or may not contain pure diacetylmorphine.

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==Chemistry==

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, or morphine diacetate or diacetylmorphine (diamorphine hydrochloride), is an opiate and an ester of morphine. 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.

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 {{SubstanceBox/Heroin}}
-'''Diacetylmorphine''' (also known as '''heroin''' and colloquially as  '''H''', '''dope''', '''smack''', '''junk''', '''brown''', '''boy''', and others) is a semi-synthetic [[psychoactive class::opioid]] substance of the [[chemical class::morphinan]] class. It is a derivative of [[morphine]], a natural product of the opium poppy (''Papaver somniferum'').{{citation needed}} Heroin is known for its highly addictive properties and it makes up a large portion of the illicit traffic in narcotics.
+'''Diacetylmorphine''' or morphine diacetate (also known as '''heroin''' and colloquially as  '''H''', '''dope''', '''smack''', '''junk''', '''brown''', '''boy''', and others) is a semi-synthetic [[psychoactive class::opioid]] substance of the [[chemical class::morphinan]] class. It is a derivative of [[morphine]], a natural product of the opium poppy (''Papaver somniferum'').{{citation needed}} Heroin is known for its highly addictive properties and it makes up a large portion of the illicit traffic in narcotics.
 Heroin was first synthesized from morphine by a British chemist in 1874 and was introduced as a commercial product by the Bayer Company of Germany in 1898.<ref>Wright, C.R.A. (1874). "On the Action of Organic Acids and their Anhydrides on the Natural Alkaloids". Journal of the Chemical Society. 27: 1031–1043. doi:10.1039/js8742701031|https://web.archive.org/web/20040606103721/http://adhpage.dilaudid.net/heroin.html</ref> Although the name heroin is a trade name, it has since been widely adopted for all intents and purposes and may describe a recreational depressant that may or may not contain pure diacetylmorphine.
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 ==Chemistry==
-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 R<sub>9</sub> and R<sub>13</sub>, with the nitrogen member looking at R<sub>17</sub> of the combined structure. This structure is called morphinan.
+Heroin, or morphine diacetate or diacetylmorphine (diamorphine hydrochloride), is an opiate and an ester of morphine. 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 R<sub>9</sub> and R<sub>13</sub>, with the nitrogen member looking at R<sub>17</sub> of the combined structure. This structure is called morphinan.
 Heroin, along with other morphinans, contains an ether bridge between two of its rings, connecting R<sub>4</sub> and R<sub>5</sub> through an oxygen group. Heroin contains two acetate (CH3COO−) groups bonded to R<sub>3</sub> and R<sub>6</sub> of its structure, and a methyl group located on the nitrogen atom at R<sub>17</sub>. On the same ring containing the 6-acetyl group, heroin contains a double bond.