https://www.wikidoc.org/index.php?title=Monoacetylmorphine&feed=atom&action=historyMonoacetylmorphine - Revision history2024-03-29T13:13:19ZRevision history for this page on the wikiMediaWiki 1.40.0https://www.wikidoc.org/index.php?title=Monoacetylmorphine&diff=719331&oldid=prevWikiBot: Robot: Automated text replacement (-{{WikiDoc Cardiology Network Infobox}} +, -<references /> +{{reflist|2}}, -{{reflist}} +{{reflist|2}})2012-09-04T19:39:28Z<p>Robot: Automated text replacement (-{{WikiDoc Cardiology Network Infobox}} +, -<references /> +{{reflist|2}}, -{{reflist}} +{{reflist|2}})</p>
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<p><b>New page</b></p><div>{{drugbox |<br />
| IUPAC_name = 3-hydroxy-6-acetyl-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan<br />
| image = 6-MAM.svg<br />
| width = 180<br />
| CAS_number = 2784-73-8<br />
| synonyms = Monoacetylmorphine, 6-acetylmorphine<br />
| ATC_prefix = <br />
| ATC_suffix = <br />
| PubChem = 5462507 <br />
| DrugBank = <br />
| C = 19 | H = 21 | N = 1 | O = 4<br />
| molecular_weight = 327.374 g/mol<br />
| bioavailability = <br />
| protein_bound = <br />
| metabolism = <br />
| elimination_half-life = <br />
| excretion = <br />
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --><br />
| pregnancy_US = <!-- A / B / C / D / X --><br />
| pregnancy_category= <br />
| legal_AU = S9<br />
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --><br />
| legal_UK = Class A<br />
| legal_US = Schedule I<br />
| legal_status = <br />
| routes_of_administration = Intravenous<br />
}}<br />
<br />
'''6-monoacetylmorphine''' (6-MAM) is one of 2 active [[metabolite]]s of [[heroin]] (diacetylmorphine), the other being the much less active 3-monoacetylmorphine (3-MAM).<br />
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Along with morphine, 6-MAM is rapidly created from heroin in the body, and is excreted in the urine. Since 6-MAM is a unique metabolite to heroin, its presence in the urine confirms that heroin was the [[opioid]] used. This is significant because on a urine immunoassay drug screen, the test typically tests for [[morphine]], which is a metabolite of a number of legal and illegal opiates/opioids such as [[codeine]], morphine sulphate, and heroin. 6-MAM remains in the urine for no more than 24 hours so a urine specimen must be collected soon after the last heroin use, but the presence of 6-MAM guarantees that heroin was in fact used as recently as within the last day. 6-MAM is naturally found in the brain,<ref> Weitz CJ, Lowney LI, Faull KF, Feistner G, Goldstein A. 6-Acetylmorphine: a natural product present in mammalian brain. Proceedings of the National Academy of Science U S A. 1988 Jul;85(14):5335-8. </ref> but in such small quantities that detection of this compound in urine virtually guarantees that heroin has recently been consumed.<br />
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Heroin is rapidly metabolized by esterase enzymes in the brain and has an extremely short half life . It has also very weak affinity to μ-opioid receptors because the 3-hydroxy group which is essential for binding to the receptor is masked by the acetyl group. So heroin is just a pro-drug , it is 6-MAM and other minor metabolites that actively bind with [[Mu opioid receptor|μ-opioid receptor]]s. <br />
<ref> Inturrisi CE, Schultz M, Shin S, Umans JG, Angel L, Simon EJ. Evidence from opiate binding studies that heroin acts through its metabolites. Life Sciences. 1983;33 Suppl 1:773-6. </ref><br />
<ref>http://www.ricercaitaliana.it/prin/dettaglio_completo_prin_en-2004052391.htm </ref><br />
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6-monoacetylmorphine already has a free 3-hydroxy group and shares the high lipophilicity of heroin, so it penetrates the brain just as quickly and does not need to be deacetylated at the 3-position in order to be bioactivated; this makes 6-monoacetylmorphine somewhat more potent than heroin,<ref> Tasker RA, Vander Velden PL, Nakatsu K. Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine. Progress in Neuropsychopharmacology and Biological Psychiatry. 1984;8(4-6):747-50. </ref> but it is rarely encountered as an illicit drug due to the difficulty in selectively acetylating morphine at the 6-position without also acetylating the 3-position. This can however be accomplished by using acetic acid with an appropriate catalyst to carry out the acetylation, rather than acetic anhydride, as acetic acid is not a strong enough acetylating agent to acetylate the phenolic 3-hydroxy group but is able to acetylate the 6-hydroxy group, thus selectively producing 6-MAM rather than heroin.<br />
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== References ==<br />
<references /><br />
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{{opioids}}<br />
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[[Category:Heroin]]<br />
[[Category:Metabolism]]<br />
[[Category:Biomolecules]]<br />
[[Category:Opioids]]<br />
[[Category:Drugs]]<br />
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