CH158448A - Process for the preparation of the hydroiodic acid carbaminoycholine. - Google Patents
Process for the preparation of the hydroiodic acid carbaminoycholine.Info
- Publication number
- CH158448A CH158448A CH158448DA CH158448A CH 158448 A CH158448 A CH 158448A CH 158448D A CH158448D A CH 158448DA CH 158448 A CH158448 A CH 158448A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- hydroiodic acid
- carbaminoycholine
- carbaminoylcholine
- iodomethyl
- Prior art date
Links
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims description 5
- 229940071870 hydroiodic acid Drugs 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 carbamic acid ß-dimethylaminoethyl ester Chemical class 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical group CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- 210000001002 parasympathetic nervous system Anatomy 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung des jodwasserstoifsauren Carbaminoylcholins. Körper vom Cholintypus aus der Reihe der Carbaminsäure sind bisher weder be schrieben noch bekannt geworden. Im all gemeinen weisen Cholinkörper unangenehme physikalische Eigenschaften auf, welche ihrer therapeutischen Verwendung vielfach im Wege stehen.
Es wurde nun gefunden, dass man zu dem bisher noch nicht bekannten jodwasserstoff- sauren Carbaminoyloholin gelangt, wenn man Jodmethyl an das tertiäre Dimethyl-äthyl- amin, dessen Äthylgruppe in der ss-Stellung den Carbaminoyl-ogy-Rest trägt, anlagert.
Die Reaktion vollzieht sich nach der For mulierung
EMI0001.0016
Es ist dies eine schön kristallisierte, che misch wie physikalisch scharf definierte Ver- bindung, die sich vor allem durch Kochbe ständigkeit ihrer wässrigen Lösung und eine ungewöhnlich starke Wirkung auf das ge samte parasympathische Nervensystem aus zeichnet. Sie soll zu therapeutischen Zwecken Verwendung finden.
Beispiel: 132 gr Carbamirisäure-p-dimethylamino- äthylester werden mit 150 gr Methyljodid unter Zusatz von wenig Methanol 1/2 Stunde in schwachem Sieden erhalten. Nach dem Erkalten zieht man das Reaktionsprodukt mit Äther aus; saugt ab und kristallisiert aus Methanol um. Man erhält so in nahezu quantitativer Ausbeute das Carbaminoylcholin- jodid als schneeweisses am Licht sich schwach gelb färbendes Kristallpulver vom Schmelz punkt 2000. Die Substanz löst sich leicht und mit neutraler Reaktion in Wasser.
Process for the preparation of the hydroiodic acid carbaminoylcholine. Choline-type bodies from the carbamic acid series have so far neither been written nor known. In general, choline bodies have unpleasant physical properties which often stand in the way of their therapeutic use.
It has now been found that the hitherto unknown hydroiodic acid carbaminoyloholin is obtained if iodomethyl is added to the tertiary dimethylethylamine, the ethyl group of which has the carbaminoyl-ogy radical in the ss position.
The reaction takes place according to the formulation
EMI0001.0016
This is a nicely crystallized, chemically and physically sharply defined compound, which is characterized above all by the boiling resistance of its aqueous solution and an unusually strong effect on the entire parasympathetic nervous system. It should be used for therapeutic purposes.
Example: 132 g of p-dimethylaminoethyl carbamirate are obtained with 150 g of methyl iodide with the addition of a little methanol for 1/2 hour at low boiling. After cooling, the reaction product is extracted with ether; sucks off and recrystallizes from methanol. The carbaminoylcholine iodide is thus obtained in almost quantitative yield as a snow-white crystal powder that turns pale yellow in the light and has a melting point of 2000. The substance dissolves easily in water with a neutral reaction.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE553148T | 1930-05-08 | ||
| CH154952T | 1931-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH158448A true CH158448A (en) | 1932-11-15 |
Family
ID=27623572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH158448D CH158448A (en) | 1930-05-08 | 1931-04-25 | Process for the preparation of the hydroiodic acid carbaminoycholine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH158448A (en) |
-
1931
- 1931-04-25 CH CH158448D patent/CH158448A/en unknown
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