DE556734C - Process for the preparation of a double salt of d-pseudococaine - Google Patents

Process for the preparation of a double salt of d-pseudococaine

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Publication number
DE556734C
DE556734C DEM114876D DEM0114876D DE556734C DE 556734 C DE556734 C DE 556734C DE M114876 D DEM114876 D DE M114876D DE M0114876 D DEM0114876 D DE M0114876D DE 556734 C DE556734 C DE 556734C
Authority
DE
Germany
Prior art keywords
pseudococaine
double salt
preparation
salt
ephedrine
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.)
Expired
Application number
DEM114876D
Other languages
German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck KGaA
Original Assignee
E Merck AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by E Merck AG filed Critical E Merck AG
Priority to DEM114876D priority Critical patent/DE556734C/en
Application granted granted Critical
Publication of DE556734C publication Critical patent/DE556734C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung eines Doppelsalzes des d-Pseudococains d-Pseudococain findet als Bitartrat unter der Bezeichnung Psicain als stark wirkendes, nicht zur Gewöhnung führendes Lokalanästheticum medizinische Verwendung. Dieses saure, weinsaure Salz erfüllt zwar die Anforderungen, die hinsichtlich Luftbeständigkeit des krystallisierten Stoffes und leichter Löslichkeit in Wasser an ein derartiges Präparat gestellt werden müssen. Da aber die Wirksamkeit lokalanästhetisch wirksamer Stoffe von der Wasserstoffionenkonzentration wesentlich beeinflußt wird, so würde ein neutrales Salzdes d-Pseudococains in der therapeutischen Anwendung noch vorteilhafter sich erweisen als das obenerwähnte Bitartrat Psicain. Ein solches neutrales Salz fehlte bisher. Das Hydrochlorid und Nitrat kristallisieren zwar gut, lösen sich aber zu wenig in Wasser. Das neutrale Tartrat des Pseudococains und das Natriumdoppelsalz (1 Mol. d-Pseudococain + 1 At. Na + i Mol. Weinsäure) kristallisieren schlecht und zerfließen leicht.Process for the preparation of a double salt of d-pseudococaine d-pseudococaine found as bitartrate under the name psicain as a strong, not used Habituation leading local anesthetic medical use. This sour, tartaric Although salt meets the requirements regarding air resistance of the crystallized Substance and easy solubility in water can be placed on such a preparation have to. But since the effectiveness of locally anesthetically effective substances depends on the hydrogen ion concentration is significantly affected, a neutral salt of d-pseudococaine in the therapeutic application prove to be even more advantageous than the above Bitartrate psicain. Such a neutral salt has so far been missing. The hydrochloride and Nitrates crystallize well, but do not dissolve enough in water. The neutral one Tartrate of pseudococaine and the sodium double salt (1 mol. D-pseudococaine + 1 at. Na + 1 mol. Tartaric acid) crystallize poorly and dissolve easily.

Es wurde nun gefunden, daß d-Pseudococain mit 1-Ephedrin ein Weinsäuredoppelsalz zu bilden vermag, welches ausgezeichnet kristallisiert, an der Luft nicht zerfließt und doch leicht in Wasser löslich ist. Eine besondere Bedeutung besitzt das neue Doppelsalz dadurch, daß auch das 1-Ephedrin eine anästhesierende Wirkung besitzt und daß seine bekannte gefäßverengernde Wirkung eine erwünschte Ergänzung der pharmakologischen Eigenschaften des d-Pseudococains bedeutet.It has now been found that d-pseudococaine and 1-ephedrine form a tartaric acid double salt capable of forming which crystallizes excellently and does not dissolve in air and yet is easily soluble in water. The new one has a special meaning Double salt in that 1-ephedrine also has an anesthetic effect and that its well-known vasoconstricting effect is a desirable addition to the pharmacological one Means properties of d-pseudococaine.

Es ist zwar bekannt, daß Paranephrin mit Psicain kombiniert therapeutische Verwendung gefunden hat (vgl. Chem. Zentralblatt, 1926, I, Seite 7a0), doch ist die Wirkung des Paranephrins von zu kurzer Dauer, und ferner darf Paranephrin wegen seiner hohen Giftigkeit nicht mit d-Pseudococain in molekularem Verhältnis, wie es im Doppelsalz vorliegt, verwendet werden.Although it is known that paranephrine combined with psicain is therapeutic Has found use (see. Chem. Zentralblatt, 1926, I, page 7a0), but is the effect of paranephrine is of too short a duration, and furthermore paranephrine may because of its high toxicity not with d-pseudococaine in a molecular ratio like that it is present in the double salt, can be used.

Ephedrin dagegen übt eine sehr lang dauernde Wirkung auf die Gefäße aus und ist so wenig giftig, daß es in molekularer Menge zusammen mit d-Pseudococain therapeutisch angewendet werden darf. Beispiel 465 Teile d-Pseudococain-d-bitartrat (Psicain) werden in 5oo Teilen heißen Wassers gelöst. 165 Teile 1-Ephedrinbase werden in 15o Teilen Methanol gelöst. Beide Flüssigkeiten werden gemischt und dann der Kristallisation überlassen. Das Doppelsalz kristallisiert in großen scharf umgrenzten Kristallplatten aus. Durch Einengen der Lauge erhält man weitere Mengen des gleichen Salzes.Ephedrine, on the other hand, has a very long-lasting effect on the blood vessels and is so little toxic that it is present in molecular quantities together with d-pseudococaine may be used therapeutically. Example 465 parts of d-pseudococaine-d-bitartrate (Psicain) are dissolved in 500 parts of hot water. 165 parts of 1-ephedrine base become dissolved in 150 parts of methanol. Both liquids are mixed and then the Leave to crystallization. The double salt crystallizes in large, sharply demarcated areas Crystal plates. By concentrating the lye, more amounts of the same can be obtained Salt.

Die Analyse ergibt die Formel: 1 Mol. d-Pseudococain, i Mol. 1-Ephedrin, 1 Mol. d-Weinsäure, i Mol. H20.The analysis gives the formula: 1 mol. D-pseudococaine, 1 mol. 1-ephedrine, 1 mole of d-tartaric acid, 1 mole of H20.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Doppelsalzes des d-Pseudococains, dadurch gekennzeichnet, daß d-Pseudococain mit molekularen Mengen 1-Ephedrin und d-Weinsäure zur Umsetzung gebracht wird.PATENT CLAIM: Process for the production of a double salt of d-pseudococaine, characterized in that d-pseudococaine with molecular amounts of 1-ephedrine and d-tartaric acid is made to react.
DEM114876D 1931-04-11 1931-04-11 Process for the preparation of a double salt of d-pseudococaine Expired DE556734C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEM114876D DE556734C (en) 1931-04-11 1931-04-11 Process for the preparation of a double salt of d-pseudococaine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEM114876D DE556734C (en) 1931-04-11 1931-04-11 Process for the preparation of a double salt of d-pseudococaine

Publications (1)

Publication Number Publication Date
DE556734C true DE556734C (en) 1932-08-13

Family

ID=7328149

Family Applications (1)

Application Number Title Priority Date Filing Date
DEM114876D Expired DE556734C (en) 1931-04-11 1931-04-11 Process for the preparation of a double salt of d-pseudococaine

Country Status (1)

Country Link
DE (1) DE556734C (en)

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