AT77940B - Process for the production of homatropin methyl nitrate. - Google Patents
Process for the production of homatropin methyl nitrate.Info
- Publication number
- AT77940B AT77940B AT77940DA AT77940B AT 77940 B AT77940 B AT 77940B AT 77940D A AT77940D A AT 77940DA AT 77940 B AT77940 B AT 77940B
- Authority
- AT
- Austria
- Prior art keywords
- homatropin
- methyl nitrate
- production
- methyl
- nitrate
- Prior art date
Links
- ZTVIKZXZYLEVOL-MCOXGKPRSA-N Homatropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-MCOXGKPRSA-N 0.000 title claims description 10
- 229960000857 homatropine Drugs 0.000 title claims description 10
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 4
- 229930003347 Atropine Natural products 0.000 description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
- 229960000396 atropine Drugs 0.000 description 3
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- WTRRIQCGCGCMQA-CBZIJGRNSA-N 3-Hydroxyestra-1,3,5(10),6-tetraen-17-one Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 WTRRIQCGCGCMQA-CBZIJGRNSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Erzeugung von Homatropinmethylnitrat.
Die Erfindung betrifft die Darstellung von Homatropinmethylnitrat, einer bisher unbekannten Verbindung, welche aus Homatropin bzw. Homatropinmethyljodid nach Methoden erhalten werden kann, die bei der Darstellung von Methylnitraten der tertiären Basen üblich sind. Die neue, bei 1600 schmelzende Verbindung hat überraschenderweise geringere Giftigkeit, als Atropin, Homatropin und Atropinmethylnitrat, während ihre therapeutische Wirkung jene des Homatropins weit übertrifft und der Wirkung des Atropins nahekommt.
Da die letale Dosis (bei 65 kg Körpergewicht) gegenüber 01 bis 0'15 g des Atropins volle 4'9 9 beträgt, bildet die neue Verbindung eine wertvolle Anreicherung der Reihe jener Arzneien, welche trotz starker therapeutischer Wirkung gefahrlos dem Patienten ausgefolgt werden können.
Die Darstellung der neuen Verbindung kann aus Homatropinmethyljodid mit Silbernitrat oder aus der Base mit Methylnitrat erfolgen. Am zweckmässigsten wird die Base in absolutem Alkohol gelöst und mit 1'1 Mol. Methylnitrat unter Druck auf 1000 erhitzt.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the production of homatropin methyl nitrate.
The invention relates to the preparation of homatropin methyl nitrate, a previously unknown compound which can be obtained from homatropin or homatropin methyl iodide by methods which are customary in the preparation of methyl nitrates of the tertiary bases. The new compound, which melts at 1600, is surprisingly less toxic than atropine, homatropine and atropine methyl nitrate, while its therapeutic effect far exceeds that of homatropine and comes close to that of atropine.
Since the lethal dose (at 65 kg body weight) compared to 01 to 0.15 g of atropine is a full 4'9 9, the new compound forms a valuable addition to the range of drugs that can be safely administered to the patient despite their strong therapeutic effect.
The new compound can be prepared from homatropin methyl iodide with silver nitrate or from the base with methyl nitrate. Most conveniently, the base is dissolved in absolute alcohol and heated to 1000 with 1'1 mol. Of methyl nitrate under pressure.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT77940T | 1916-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT77940B true AT77940B (en) | 1919-08-25 |
Family
ID=3599520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT77940D AT77940B (en) | 1916-04-07 | 1916-04-07 | Process for the production of homatropin methyl nitrate. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT77940B (en) |
-
1916
- 1916-04-07 AT AT77940D patent/AT77940B/en active
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