| Revision as of 10:39, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{drugbox}} taken from revid 477318541 of page 6-Monoacetylmorphine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'StdInChI', 'StdInChIKey', 'CAS_number'). |
Latest revision as of 16:28, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,129 edits removed Category:Phenols; added Category:Hydroxyarenes using HotCat |
| Line 1: |
Line 1: |
|
|
{{Short description|Metabolite of Heroin}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
|
{{Redirect|6-AM|other uses|6AM (disambiguation){{!}}6AM}} |
|
|
{{cs1 config|name-list-style=vanc|display-authors=6}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 447557566 |
|
| verifiedrevid = 477345991 |
|
| IUPAC_name = 3-hydroxy-6-acetyl-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan |
|
| IUPAC_name = 3-Hydroxy-6-acetyl-(5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan |
|
| image = 6-MAM.svg |
|
| image = 6-monoacetylmorphine2DCSD.svg |
| ⚫ |
| width = 180 |
|
|
|
| alt = Structural formula |
|
⚫ |
| width = 190 |
|
|
| image2 = 6-Monoacetylmorphine molecule ball.png |
|
|
| alt2 = Ball-and-stick model |
|
|
| width2 = 215 |
|
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
| Line 14: |
Line 21: |
|
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
|
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
|
| legal_UK = Class A |
|
| legal_UK = Class A |
|
| legal_US = Schedule I |
|
|
| legal_status = |
|
| legal_status = |
|
| routes_of_administration = Intravenous |
|
| routes_of_administration = Intravenous |
| Line 22: |
Line 28: |
|
| protein_bound = |
|
| protein_bound = |
|
| metabolism = |
|
| metabolism = |
|
| elimination_half-life = |
|
| elimination_half-life = < 5 mins |
|
| excretion = |
|
| excretion = |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number_Ref = {{cascite|changed|??}} |
|
| CAS_number = <!-- blanked - oldvalue: 2784-73-8 --> |
|
| CAS_number = 2784-73-8 |
|
| ATC_prefix = none |
|
| ATC_prefix = none |
|
| ATC_suffix = |
|
| ATC_suffix = |
|
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL = 592009 |
|
| ChEMBL = 592009 |
|
| PubChem = 5462507 |
|
| PubChem = 5462507 |
| Line 36: |
Line 43: |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 4575434 |
|
| ChemSpiderID = 4575434 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = M5E47P1ZCH |
|
|
|
|
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=19 | H=21 | N=1 | O=4 |
|
| C=19 | H=21 | N=1 | O=4 |
|
⚫ |
| smiles = CC(=O)O1/C=C\23Cc4ccc(O)c5O12(CCN3C)c45 |
|
| molecular_weight = 327.374 g/mol |
|
|
⚫ |
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
| ⚫ |
| smiles = CC(=O)c3cc(O)c1O425CCN(C)(Cc3c12)5/C=C\4O |
|
|
| InChI = 1/C19H21NO4/c1-9(21)10-8-15(23)17-16-11(10)7-13-12-3-4-14(22)18(24-17)19(12,16)5-6-20(13)2/h3-4,8,12-14,18,22-23H,5-7H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 |
|
| StdInChI = 1S/C19H21NO4/c1-9(21)10-8-15(23)17-16-11(10)7-13-12-3-4-14(22)18(24-17)19(12,16)5-6-20(13)2/h3-4,8,12-14,18,22-23H,5-7H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 |
|
⚫ |
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| InChIKey = DUAISAINBBQDAF-LEPYJNQMBC |
|
| StdInChIKey = DUAISAINBBQDAF-LEPYJNQMSA-N |
| ⚫ |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChI = 1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1 |
|
| ⚫ |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChIKey = JJGYGPZNTOPXGV-SSTWWWIQSA-N |
|
|
| synonyms = 6-acetylmorphine |
|
| synonyms = 6-acetylmorphine |
|
}} |
|
}} |
|
|
|
|
|
'''6-Monoacetylmorphine''' ('''6-MAM''', '''6-acetylmorphine''', or '''6-AM''') is an ] and also one of three active ]s of ] (diacetylmorphine), the others being ] and the much less active ] (3-MAM). |
|
|
|
|
|
==Pharmacology== |
|
|
6-MAM occurs as a metabolite of heroin. Once it has passed ], 6-MAM is then metabolized into morphine or excreted in ].{{Citation needed|date=March 2023}} |
|
|
|
|
|
Heroin is rapidly metabolized by ] enzymes in the brain and has an extremely short half-life. It has also relatively weak affinity to ] because the 3-hydroxy group, essential for effective binding to the receptor, is masked by the acetyl group. Therefore, heroin acts as a ], serving as a lipophilic transporter for the systemic delivery of morphine, which actively binds with μ-opioid receptors.<ref>{{cite journal | vauthors = Inturrisi CE, Schultz M, Shin S, Umans JG, Angel L, Simon EJ | title = Evidence from opiate binding studies that heroin acts through its metabolites | journal = Life Sciences | volume = 33 | pages = 773–6 | year = 1983 | issue = Suppl 1 | pmid = 6319928 | doi = 10.1016/0024-3205(83)90616-1 }}</ref><ref>{{cite web|url=https://www.researchitaly.it/redirect/|title=Pagina di transizione|website=www.researchitaly.it}}</ref> |
|
|
|
|
|
]]] |
|
|
|
|
|
6-MAM already has a free 3-hydroxy group and shares the high ] of heroin, so it penetrates the brain just as quickly and does not need to be deacetylated at the 6-position in order to be bioactivated; this makes 6-MAM somewhat more potent than heroin.<ref>{{cite journal | vauthors = Tasker RA, Vander Velden PL, Nakatsu K | s2cid = 23566872 | title = Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 8 | issue = 4–6 | pages = 747–50 | year = 1984 | pmid = 6543399 | doi = 10.1016/0278-5846(84)90051-4 }}</ref> |
|
|
|
|
|
==Availability== |
|
|
6-MAM is rarely encountered in an isolated form due to the difficulty in selectively acetylating morphine at the 6-position without also acetylating the 3-position. However, it is found in significant amounts in ] along with heroin itself.<ref>{{cite journal | vauthors = Kapur BM, Aleksa K | title = What the lab can and cannot do: clinical interpretation of drug testing results | journal = Critical Reviews in Clinical Laboratory Sciences | volume = 57 | issue = 8 | pages = 548–585 | date = December 2020 | pmid = 32609540 | doi = 10.1080/10408363.2020.1774493 | doi-access = free }}</ref> |
|
|
|
|
|
==Synthesis== |
|
|
|
|
|
The production of black tar heroin results in significant amounts of 6-MAM in the final product.{{Citation needed|date=March 2023}} 6-MAM is approximately 30 percent more active than diacetylmorphine itself,{{fact|date=September 2016}} This is why despite lower heroin content, black tar heroin may be more potent than some other forms of heroin. 6-MAM can be synthesized from morphine using glacial ] with an ] as a catalyst. The acetic acid must be of a high purity (97–99 per cent) for the acid to properly acetylate the morphine at the 6th position effectively creating 6-MAM. Acetic acid is used rather than ], as acetic acid is not strong enough to acetylate the phenolic 3-hydroxy group but is able to acetylate the 6-hydroxy group, thus selectively producing 6-MAM rather than heroin. Acetic acid is a convenient way to produce 6-MAM, as acetic acid also is not a watched chemical as it is the main component of vinegar. |
|
|
|
|
|
==Chemistry== |
|
|
|
|
|
===Detection in bodily fluids=== |
|
|
Since 6-MAM is a metabolite unique to heroin, its presence in the urine confirms heroin use. This is significant because a urine ] drug screen typically tests for morphine, which is a metabolite of a number of legal and illegal opiates/opioids such as ], morphine sulfate, and heroin. Trace amounts of 6-MAM are excreted approximately 6–8 hours following heroin use.<ref>{{cite web|url=https://www.redwoodtoxicology.com/resources/drug_info/opiates|title=Opiates | Drug Info | Resources | Redwood Toxicology Laboratory|website=www.redwoodtoxicology.com}}</ref> |
|
|
|
|
|
6-MAM is naturally found in trace amounts in rat and cow brains. <ref>{{cite journal | vauthors = Weitz CJ, Lowney LI, Faull KF, Feistner G, Goldstein A | title = 6-Acetylmorphine: a natural product present in mammalian brain | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 85 | issue = 14 | pages = 5335–8 | date = July 1988 | pmid = 3393541 | pmc = 281745 | doi = 10.1073/pnas.85.14.5335 | bibcode = 1988PNAS...85.5335W | doi-access = free }}</ref> |
|
|
|
|
|
== See also == |
|
|
*], morphine-3-glucuronide an inactive metabolite of morphine much as 3-MAM is the less active metabolite of heroin (notably here as morphine is an active secondary metabolite of heroin itself with 6-Monoacetylmorphine being the intermediate stage) |
|
|
*], morphine-6-glucuronide the active variant in close relation to 6-MAM, being relative as twin metabolites of this articles very metabolite itself, morphine, twinned to a metabolite (3-MAM) of a parent compound (heroin) of this article's chemical |
|
|
] making ]-group in 3-position.]]{{clear left}} |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{Opioidergics}} |
|
|
|
|
|
{{DEFAULTSORT:Monoacetylmorphine, 6-}} |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |