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{{Short description|Opioid analgesic drug}} |
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{{drugbox | verifiedrevid = 399909991 |
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{{Drugbox |
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| IUPAC_name = (5α,6α)-7,8-Didehydro- 4,5-epoxy- 17-methylmorphinan- 3,6-dipropionate |
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| verifiedrevid = 437356401 |
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| IUPAC_name = (5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan 3,6-dipropionate |
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| image = Dipropanoylmorphine.svg |
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| image = Dipropanoylmorphine.svg |
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| width = 200 |
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<!-- | width = 200 --> |
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<!--Clinical data-->| tradename = |
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| InChI = 1/C23H27NO5/c1-4-14(25)17-11-10-13-12-6-7-16(27)22-23(12,8-9-24(13)3)19(11)21(29-22)20(28)18(17)15(26)5-2/h6-7,12-13,16,22,27-28H,4-5,8-10H2,1-3H3/t12-,13+,16-,22-,23-/m0/s1 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| InChIKey = KDFWILUISXRMIK-LISRSHBKBL |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| smiles = CCC(=O)c3c1C4N(C)CC25(Oc(c12)c(O)c3C(=O)CC)(O)\C=C/45 |
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| pregnancy_category = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| StdInChI = 1S/C23H27NO5/c1-4-14(25)17-11-10-13-12-6-7-16(27)22-23(12,8-9-24(13)3)19(11)21(29-22)20(28)18(17)15(26)5-2/h6-7,12-13,16,22,27-28H,4-5,8-10H2,1-3H3/t12-,13+,16-,22-,23-/m0/s1 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| legal_UK = |
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| StdInChIKey = KDFWILUISXRMIK-LISRSHBKSA-N |
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| CAS_number = 10589-79-4 |
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| legal_US = Schedule I |
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| legal_status = |
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| synonyms = Dipropanoylmorphine, Dipropionylmorphine |
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| routes_of_administration = <!--Pharmacokinetic data--> |
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| ATC_prefix = none |
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| ATC_suffix = |
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| bioavailability = |
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| PubChem = 165894 |
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| protein_bound = |
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| metabolism = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID= 20053814 |
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| DrugBank = |
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| C = 23 | H = 27 | N = 1 | O = 5 |
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| molecular_weight = 397.464 g/mol |
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| bioavailability = |
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| protein_bound = |
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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 = <!--Identifiers--> |
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| index2_label = hydrochloride |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| CAS_number = 10589-79-4 |
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| pregnancy_category= |
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| CAS_number2_Ref = {{cascite|correct|CAS}} |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| CAS_number2 = 62268-07-9 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = Class |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| legal_US = Schedule I |
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| UNII = RT28EEO2YA |
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| legal_status = |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = TTM24Y869Z |
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| routes_of_administration = |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 165894 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 145387 |
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<!--Chemical data-->| C = 23 |
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| H = 27 |
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| N = 1 |
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| O = 5 |
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| smiles = CCC(=O)c3c1C4N(C)CC25(Oc(c12)c(O)c3C(=O)CC)(O)\C=C/45 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C23H27NO5/c1-4-14(25)17-11-10-13-12-6-7-16(27)22-23(12,8-9-24(13)3)19(11)21(29-22)20(28)18(17)15(26)5-2/h6-7,12-13,16,22,27-28H,4-5,8-10H2,1-3H3/t12-,13+,16-,22-,23-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KDFWILUISXRMIK-LISRSHBKSA-N |
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| synonyms = Morphine dipropionate, Dipropanoylmorphine, 3,6-dipropanoylmorphine, Dipropionylmorphine |
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'''Dipropanoylmorphine''' ('''Dipropionylmorphine''' in U.S. English) is an ] derivative, the 3,6-dipropanoyl ] of ]. It was developed in 1974 as an ].<ref> May EL, Jacobson AE. "Chemistry and pharmacology of homologs of 6-acetyl-and 3,6-diacetylmorphine." ''Journal of Pharmaceutical Sciences''. 1977 Feb;'''66'''(2):285-6. PMID 402470</ref> It is rarely used in some countries for the relief of severe ] such as that caused by terminal ], as an alternative to ] (heroin) and morphine. |
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'''Dipropanoylmorphine''' ('''dipropionylmorphine''' in US English) is an ] derivative, the 3,6-dipropanoyl ] of ]. It was developed in 1972 as an ].<ref name = "May_1977">{{cite journal | vauthors = May EL, Jacobson AE | title = Chemistry and pharmacology of homologs of 6-acetyl-and 3,6-diacetylmorphine | journal = Journal of Pharmaceutical Sciences | volume = 66 | issue = 2 | pages = 285–6 | date = February 1977 | pmid = 402470 | doi = 10.1002/jps.2600660242 }}</ref> It is rarely used in some countries for the relief of severe ] such as that caused by terminal ], as an alternative to ] (heroin) and morphine. The drug was first synthesised circa or about 1875 in Great Britain along with many other esters of morphine, all of which were shelved at the time, some of which were later developed such as ] (1898), ] (1924), ] (1900 and/or 1924), and so on. The name of this drug is also given as 3,6-dipropanoylmorphine and its 6-mono-acetylated homologue is also a longer-acting heroin-like drug, as are 3,6-diformylmorphine and 6-formylmorphine.<ref name = "May_1977" /> |
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Dipropanoylmorphine, though rarely used, is considered to be a safer and less addictive alternative to ]. Studies and clinical trials comparing dipropanoylmorphine to morphine have produced results that indicate the incidence of side-effects are far more common with morphine. Respiratory depression, ], excessive sedation and somnolence (so-called 'nodding' by opiate abusers), constipation, ] (pinpoint pupils), nausea, ], behavioral disturbances, and severe physical and psychological dependence on morphine is more likely with the use of morphine versus dipropanoylmorphine. |
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Dipropanoylmorphine, though rarely used, is considered to be a safer and less addictive alternative to ]. Studies and clinical trials comparing dipropanoylmorphine to ] have produced results that indicate the incidence of side-effects are far more common with ]. ], ], excessive sedation and ] (so-called 'nodding' by recreational opioid users), constipation, ] (pinpoint pupils), ], ], behavioral disturbances, and severe physical and psychological dependence on ] is more likely with the use of morphine versus dipropanoylmorphine. |
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Dipropanoylmorphine is slightly slower acting than diamorphine and morphine, but longer lasting, and is slightly more potent by weight due to its higher lipophilicity.<ref> Owen JA, Nakatsu K. "Morphine diesters. II. Blood metabolism and analgesic activity in the rat." ''Canadian Journal of Physiology and Pharmacology''. 1984 Apr;'''62'''(4):452-6. PMID 6733592</ref> Side effects are generally relatively mild for an opioid with a similar profile to morphine/heroin and typical of other ]. The most common side effects associated with dipropanoylmorphine are ], ] and ]. |
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Dipropanoylmorphine is slightly slower acting than ] and ], but longer lasting, and is slightly more potent by weight due to its higher ].<ref>{{cite journal | vauthors = Owen JA, Nakatsu K | title = Morphine diesters. II. Blood metabolism and analgesic activity in the rat | journal = Canadian Journal of Physiology and Pharmacology | volume = 62 | issue = 4 | pages = 452–6 | date = April 1984 | pmid = 6733592 | doi = 10.1139/y84-072 }}</ref> Side effects are generally relatively mild for an opioid with a similar profile to morphine/heroin and typical of other ]. The most common side effects associated with dipropanoylmorphine are ], ] and ]. |
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Dipropanoylmorphine is prepared by reacting morphine with ], in an analogous manner to how heroin is produced by reacting morphine with ]. |
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Dipropanoylmorphine is prepared by reacting morphine with ], in an analogous manner to how heroin is produced by reacting morphine with ]. |
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While ] is a restricted chemical around the world due to its potential uses in making heroin from morphine for the illicit market, it is used in vast amounts by the chemical industry for the manufacture of drugs such as ]. Propanoic anhydride however is much less widely used. Although it is used in the manufacture of a range of pharmaceuticals, none of these are produced in nearly as large quantities, and sales of propanoic anhydride in quantities larger than one gram must be reported in many countries because of its potential use in making ] type synthetic opiates. |
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While ] is a restricted chemical around the world due to its potential uses in making heroin from morphine for the illicit market, it is used in vast amounts by the chemical industry for the manufacture of drugs such as ]. Propanoic anhydride however is much less widely used. Although it is used in the manufacture of a range of pharmaceuticals, none of these are produced in nearly as large quantities, and sales of propanoic anhydride in quantities larger than one gram must be reported in many countries because of its potential use in making ] type synthetic opiates. |
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== References == |
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== References == |
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{{reflist}} |
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{{Reflist|2}} |
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{{Opioidergics}} |
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{{analgesic-stub}} |
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