Heroin: Difference between revisions

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'''Diacetylmorphine''' (also known as '''heroin''' and colloquially as '''H''', '''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''' (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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Heroin itself is an inactive drug, but it is metabolized into [[morphine]] when inserted into the body.<ref>The therapeutic use of heroin: a review of the pharmacological literature | http://www.nrcresearchpress.com/doi/abs/10.1139/y86-001</ref> When taken orally, heroin undergoes extensive first-pass metabolism via deacetylation, making it a prodrug for the systemic delivery of morphine.<ref>The therapeutic use of heroin: a review of the pharmacological literature (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/2420426</ref> 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.<ref>Development of pharmaceutical heroin preparations for medical co-prescription to opioid-dependent patients (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0376871605001511</ref>

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.<ref>Evidence from opiate binding studies that heroin acts through its metabolites (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/6319928</ref>

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 commercially 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.<ref>Evidence from opiate binding studies that heroin acts through its metabolites (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/6319928</ref>

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 [[physical euphoria|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.

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 {{SubstanceBox/Heroin}}
-'''Diacetylmorphine''' (also known as '''heroin''' and colloquially as  '''H''', '''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''' (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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 Heroin itself is an inactive drug, but it is metabolized into [[morphine]] when inserted into the body.<ref>The therapeutic use of heroin: a review of the pharmacological literature | http://www.nrcresearchpress.com/doi/abs/10.1139/y86-001</ref> When taken orally, heroin undergoes extensive first-pass metabolism via deacetylation, making it a prodrug for the systemic delivery of morphine.<ref>The therapeutic use of heroin: a review of the pharmacological literature (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/2420426</ref> 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.<ref>Development of pharmaceutical heroin preparations for medical co-prescription to opioid-dependent patients (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0376871605001511</ref>
-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.<ref>Evidence from opiate binding studies that heroin acts through its metabolites (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/6319928</ref>
+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 commercially 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.<ref>Evidence from opiate binding studies that heroin acts through its metabolites (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/6319928</ref>
 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 [[physical euphoria|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.