| Revision as of 23:39, 7 November 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit |
Latest revision as of 16:01, 11 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 459540629 |
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| Verifiedfields = changed |
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| verifiedrevid = 458445259 |
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| IUPAC_name = 3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan |
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| IUPAC_name = 3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan |
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| image = 3-MAM.svg |
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| image = 3-MAM.svg |
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| image_class = skin-invert-image |
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| width = 180 |
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| alt = Structural formula |
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| width = 200 |
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| image2 = 3-Monoacetylmorphine molecule ball.png |
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| alt2 = Ball-and-stick model |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = S9 |
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| legal_AU = S9 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = Class A |
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| legal_UK = Class A |
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| legal_US = Schedule I |
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| legal_US = Schedule I |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 5140-28-3 |
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| CAS_number = 5140-28-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9N7243EY5T |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem = 5462504 |
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| ChemSpiderID = 4575431 |
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| ChemSpiderID = 4575431 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=19 | H=21 | N=1 | O=4 |
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| C=19 | H=21 | N=1 | O=4 |
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| molecular_weight = 327.1471 g/mol |
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| smiles = CC(=O)OC1=C2C3=C(C453(CCN4C)(O2)(C=C5)O)C=C1 |
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| smiles = CC(=O)OC1=C2C3=C(C453(CCN4C)(O2)(C=C5)O)C=C1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3-6,12-14,18,22H,7-9H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 |
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| StdInChI = 1S/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3-6,12-14,18,22H,7-9H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 |
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| InChIKey = GMLREHXYJDLZOU-LEPYJNQMBG |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3-6,12-14,18,22H,7-9H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1 |
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| StdInChIKey = GMLREHXYJDLZOU-LEPYJNQMSA-N |
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| StdInChIKey = GMLREHXYJDLZOU-LEPYJNQMSA-N |
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| synonyms = 3-Acetylmorphine, O(3)-monoacetylmorphine |
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| synonyms = 3-Acetylmorphine, O(3)-monoacetylmorphine |
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'''3-Monoacetylmorphine''' (3-MAM) or '''3-Acetylmorphine''' is less active ] of ] (diacetylmorphine), the other two being ] and more active 6-] (6-MAM). |
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'''3-Monoacetylmorphine''' ('''3-MAM''') or '''3-acetylmorphine''' is a less active ] of ] (diacetylmorphine), the other two being ] and more active ] (6-MAM). |
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Because of the acetyl-group in 3-position, 3-MOM has relatively weak affinity to ]. |
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Because of the acetyl-group in 3-position, 3-MAM has relatively weak affinity to ]. |
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As ''3-O-Acetylmorphine-6-O-sulfate'' (C<sub>19</sub>H<sub>23</sub>NO<sub>7</sub>S), where 6-OH is changed to 6-O-SO<sub>3</sub>, it can act as potent, centrally acting morphine derivative and has important analgesic properties. <ref></ref> <ref></ref> <ref></ref> |
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] |
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As ''3-O-acetylmorphine-6-O-sulfate'' (C<sub>19</sub>H<sub>23</sub>NO<sub>7</sub>S), where 6-OH is changed to 6-O-SO<sub>3</sub>, it can act as a potent, centrally acting morphine derivative and has important analgesic properties.<ref>{{cite journal | vauthors = Houdi AA, Kottayil S, Crooks PA, Butterfield DA | title = 3-O-acetylmorphine-6-O-sulfate: a potent, centrally acting morphine derivative | journal = Pharmacology, Biochemistry, and Behavior | volume = 53 | issue = 3 | pages = 665–671 | date = March 1996 | pmid = 8866970 | doi = 10.1016/0091-3057(95)02067-5 | s2cid = 14870642 }}</ref><ref>{{cite journal | vauthors = Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA | title = Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners | journal = Bioorganic & Medicinal Chemistry Letters | volume = 16 | issue = 16 | pages = 4291–4295 | date = August 2006 | pmid = 16777416 | doi = 10.1016/j.bmcl.2006.05.060 }}</ref><ref>{{cite journal | vauthors = Brock CP, Kottayil S, Butterfield DA, Crooks PA | journal = Acta Crystallographica Section C | date = January 1996 | volume = 52 | issue = 1 | pages = 122–5 | url = http://scripts.iucr.org/cgi-bin/paper?cr1191 | title = A Dihydromorphine-6-''O''-sulfate | doi = 10.1107/S0108270195010250 }}</ref> |
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] making ]-group in 6-position.]] |
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] |
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] making ]-group in 6-position.]] |
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==References== |
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<references /> |
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== References == |
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{{reflist|30em}} |
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{{Opioidergics}} |
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{{DEFAULTSORT:Monoacetylmorphine, 3-}} |
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