DE116806C - - Google Patents
Info
- Publication number
- DE116806C DE116806C DENDAT116806D DE116806DA DE116806C DE 116806 C DE116806 C DE 116806C DE NDAT116806 D DENDAT116806 D DE NDAT116806D DE 116806D A DE116806D A DE 116806DA DE 116806 C DE116806 C DE 116806C
- Authority
- DE
- Germany
- Prior art keywords
- acetic acid
- morphoxy
- morphine
- water
- substance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- BQJCRHHNABKAKU-KBQPJGBKSA-N Morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 5
- 229960005181 morphine Drugs 0.000 claims description 4
- 229930014694 morphine Natural products 0.000 claims description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 2
- 229940106681 chloroacetic acid Drugs 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000001476 alcoholic Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- NDQKGYXNMLOECO-UHFFFAOYSA-N acetic acid;potassium Chemical compound [K].CC(O)=O NDQKGYXNMLOECO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229930013930 alkaloids Natural products 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000003533 narcotic Effects 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
Die bisher unbekannte Morphoxylessigsäure, .welche die ZusammensetzungThe previously unknown morphoxy acetic acid, which has the composition
C17 Hls NO3 CH2COOHC 17 H ls NO 3 CH 2 COOH
besitzt, wirkt ähnlich wie das Morphin narkotisch, ist aber wesentlich, etwa um das 50fache, ungiftiger; sie erscheint daher geeignet zur medicinischen Verwendung. .possesses, has a narcotic effect similar to morphine, but is essentially, about 50 times less toxic; it therefore appears suitable for medical use. .
Die Morphoxylesstgsa'ure stellt eine in Nadeln schön krystaHisirch.de Substanz von neutraler Reaction dar; sie ist im Wasser leicht löslich. Der Körper bildet. sowohl mit Alkalien und Metalloxyden, als mit Sauren meist schön krystallisirende Salze und vermag auch vermöge seiner Carboxylgruppe vielfältige Umsetzungen einzugehen.The Morphoxylesstgsa'ure makes one in needles beautiful krystaHisirch.de substance of neutral reaction; it is easily soluble in water. The body forms. mostly beautiful with both alkalis and metal oxides, as well as with acids crystallizing salts and, by virtue of its carboxyl group, is capable of various reactions enter into.
Bei der Darstellung verführt man beispielsweise folgendermafsen: In the case of the representation, one seduces, for example, as follows:
30 g. wasserfreies Morphin werden in absolut alkoholischer Kalilauge von 5,9 g Kaligehalt gelöst und mit 14 g neutralem monochloressigsaurcm Kali unter Zusatz von 600 ecm absolutem Alkohol 3 Stunden lang auf dem Wasserbade erhitzt. Wahrend der Reaction scheidet sich Chlorkalium aus. Nach dieser Zeit-versetzt man die erhaltene Lösung noch 'warm/ mit alkoholischer Salzsäure, bis alles. Kali als Chlorkalium ausgefällt ist, und fügt nach dem Abfiltriren zum erkalteten Filtrat so lange absoluten Aether, bis eben eine Trübung entsteht. Im Laufe einiger Stunden scheidet sich die Morphoxylessigsäure in schönen weifsen Nädelchen ab. . . ■30 g. Anhydrous morphine is found in absolutely alcoholic potassium hydroxide solution with a potassium content of 5.9 g dissolved and with 14 g of neutral monochloroacetic acid Potash with the addition of 600 ecm of absolute alcohol for 3 hours on the Heated water bath. During the reaction, potassium chloride is separated out. After this Time is added to the solution obtained 'warm / with alcoholic hydrochloric acid until everything. Potash is precipitated as potassium chloride and adds after filtering off to the cooled filtrate, use absolute ether until it is cloudy arises. In the course of a few hours the morphoxy acetic acid separates into beautiful white Needle off. . . ■
Sie kann unter Umstanden, z. B. bei längerem Stehenlassen ihrer alkoholischen Lösung in der Hitze, mit einer gröfscren oder kleineren Menge eines Condensationsproductcs, vermuthlich ihres Laktons, vermengt sein. Letzteres j entsteht aus der Morphoxylessigsäure auch direct, ζ. B. durch Kochen derselben mit Alkohol. You can under certain circumstances, z. B. for longer Let your alcoholic solution stand in the heat, with a larger or smaller one Amount of a condensation product, presumably its lactone, may be mixed up. The latter j also arises from morphoxy acetic acid direct, ζ. B. by boiling the same with alcohol.
, Beim Erhitzen im Schmelzpunktröhrchen zersetzt sich die Substanz unter Schäumen bei :etwa 1920. Sie ist, wiegesagt, sehr leicht löslich in Wasser, unlöslich in Aether. Beim '■ Umkrystallisiren aus verdünntem Alkohol nimmt sie Krystallwasser auf. Versetzt man ihre alkoholische Lösung mit einem Molecül Kaliumhydroxyd, so erstarrt alsbald die ganze Masse zu einem Brei von dünnen Nüdelchen, welche aus morphoxylessigsaurem Kali bestehen. Beim Verdunsten der salzsauren Lösung hinterbleiben schön ausgebildete seidenglänzende Nadeln. Bei längerem Stehen des neuen Körpers mit rauchender Salzsäure bildet sich kein Morphin zurück.When heated in the melting point tube, the substance decomposes with foaming at: approx. 192 0 . As I said, it is very easily soluble in water and insoluble in ether. When '■ recrystallization from dilute alcohol it takes to crystallization. If you add a molecule of potassium hydroxide to its alcoholic solution, the whole mass soon solidifies into a paste of thin noodles, which consist of morphoxyl acetic acid potassium. When the hydrochloric acid solution evaporates, beautifully formed, silky-gloss needles are left behind. If the new body stands for a long time with fuming hydrochloric acid, no morphine is formed back.
Die Elementaranalyse der Substanz wird durch ihre Schwerverbrennlichkeit erschwert, weshalb die angeführten Zahlen nur unbefriedigend stimmen:The elemental analysis of the substance is made difficult by its flame-retardant properties, which is why the figures given are unsatisfactory:
gefunden: ber. für C17 Hn N0-„: Kohlenstoff... 65,11 pCt., 66,47 pCt.,found: calc. for C 17 H n N0- ": carbon ... 65.11 pCt., 66.47 pCt.,
Wasserstoff.. . 5,28 „ 6,12 „ .Hydrogen ... 5.28 "6.12".
Die Morphoxylessigsäure fällt aus alkoholischer Lösung mit Aether aus. Hierdurch und durch ihre Löslichkeit in Wasser unterscheidet sie sich leicht von allen bisher bekannt gewordenen Morphinderivaten, unter anderenThe morphoxy acetic acid precipitates from alcoholic solution with ether. Through this and due to its solubility in water, it differs slightly from all previously known Morphine derivatives, among others
auch von den in den Patenten 38729 und 91S13 beschriebenen, da letztere sämmtlich als freie Alkaloide in Wasser verhiiltnifsma'fsig schwer löslich sind, Der Grund hierfür liegt in der Fähigkeit der neuen Substanz, intramoleculare Salze zu bilden.also of those in patents 38729 and 91S13, since the latter are all called Free alkaloids are relatively sparingly soluble in water, the reason for this being in the ability of the new substance to form intramolecular salts.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE116806C true DE116806C (en) |
Family
ID=386125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT116806D Active DE116806C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE116806C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709868A (en) * | 1971-03-08 | 1973-01-09 | Hoffmann La Roche | Opium alkaloid antigens and antibodies specific therefor |
-
0
- DE DENDAT116806D patent/DE116806C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709868A (en) * | 1971-03-08 | 1973-01-09 | Hoffmann La Roche | Opium alkaloid antigens and antibodies specific therefor |
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