DE903215C - Process for the extraction of the opium alkaloids - Google Patents
Process for the extraction of the opium alkaloidsInfo
- Publication number
- DE903215C DE903215C DE1948P0002735 DEP0002735D DE903215C DE 903215 C DE903215 C DE 903215C DE 1948P0002735 DE1948P0002735 DE 1948P0002735 DE P0002735 D DEP0002735 D DE P0002735D DE 903215 C DE903215 C DE 903215C
- Authority
- DE
- Germany
- Prior art keywords
- morphine
- extraction
- alkaloids
- drug
- opium
- 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
Links
- 229930013930 alkaloid Natural products 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- 239000008896 Opium Substances 0.000 title claims description 6
- 229960001027 opium Drugs 0.000 title claims description 6
- 238000000605 extraction Methods 0.000 title claims description 5
- 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 22
- 229960005181 morphine Drugs 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 3
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 239000004571 lime Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000003640 drug residue Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- RAMQAMYGQDRQKW-UHFFFAOYSA-N benzene;butan-1-ol Chemical compound CCCCO.C1=CC=CC=C1 RAMQAMYGQDRQKW-UHFFFAOYSA-N 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229930003945 thebaine Natural products 0.000 description 1
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 description 1
- 238000005303 weighing Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G5/00—Alkaloids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Extraction Or Liquid Replacement (AREA)
Description
Verfahren zur Gewinnung der Opiumalkaloide Es wurde gefunden, daB man die Alkaloide des Opiums auf einfache Weise aus der Droge dadurch gewinnen kann, daB man die Droge mit flüssiger schwefliger Säure extrahiert. Während die Nebenalkaloide Codein, Narcotin, Papaverin und Thebain in flüssiger schwefliger Säure leicht löslich sind und quantitativ in die Extraktionslösung gehen, bleibt das in flüssiger schwefliger Säure unlösliche Morphin in den Trestern zurück und kann daraus ebenfalls quantitativ in an sich bekannter Weise durch Exträktion mit Wasser, gegebenenfalls nach vorherigem Vermischen mit Kalk, gewonnen werden.Process for obtaining the opium alkaloids It has been found that the alkaloids of opium can be obtained from the drug in a simple manner by that the drug is extracted with liquid sulphurous acid. While the minor alkaloids Codeine, narcotine, papaverine and thebaine are easily soluble in liquid sulphurous acid and go quantitatively into the extraction solution, that remains in liquid sulphurous Acid insoluble morphine returns to the pomace and can also be used quantitatively in a manner known per se, by extraction with water, if necessary after prior Mixing with lime, are obtained.
Dieses neue Verfahren gestattet Morphin von den Nebenalkaloiden auf höchst einfache Weise zu trennen, wobei Morphin schon bei der ersten Fällung in hoher Reinheit anfällt. Die wichtigen Nebenalkaloide des Opiums werden aus der Droge in genuiner Form und frei von Morphin und Ballaststoffen gewonnen. Das Verfahren liefert eine gegenüber den bekannten Verfahren erhöhte Ausbeute an Morphin.This new process allows morphine to be removed from the minor alkaloids very simple way to separate, with morphine already in the first precipitation high purity. The important secondary alkaloids of opium are derived from the drug Obtained in genuine form and free from morphine and dietary fiber. The procedure provides an increased yield of morphine compared to the known processes.
Beispiel 2o 'kg Opium mit einem Morphingehalt von 2,55okg= 12,750/0 (Analyse nach Harrison) werden mit einer geeigneten Vorrichtung in dünne Scheiben geschnitten und auf Horden bei 6o° im Vakuum 3 Tage getrocknet. Der Wasserverlust beträgt 3,0701g= 15,4%. Das getrocknete Gut wird zu einem groben Pulver gemahlen und zur Erleichterung der Vermischung mit dem Lösungsmittel über Nacht im Eisschrank gekühlt. Die erschöpfende Extraktion mit flüssiger schwefliger Säure geschieht durch mehrmaliges Ausziehen im offenen Gefäß oder durch Ausziehen im geschlossenen Soxleth-Apparat (2 atü). Die vereinigten Extrakte werden zuletzt erforderlichenfalls im Vakuum von der schwefligen Säure befreit und stellen ein hellbraunes trocknes Pulver im Gewicht von 6,oo3'kg dar. ,Der extrahierte Opiumrückstand beträgt nach der Befreiung von der schwefligen Säure i r,883 kg. Zur Gewinnung des Morphins wird derselbe mit 2'kg Ätzkalk vermischt und darauf mit Wasser extrahiert. Aus den klaren wäßrigen Auszügen wird der Kalk durch Ansäuern mit Oxalsäure entfernt und darauf durch Versetzen mit Ammoniak Morphin im Gewicht von 2,3q.0 kg ausgefällt. F. 25q.°. Durch Ausrühren der Mutterlauge mit Butanol-Benzol werden weitere 414 9 Morphin vom F. 25o° erhalten..-Gesamtausbeute an Morphin. 2754 kg.Example 20 kg of opium with a morphine content of 2.55 kg = 12.750 / 0 (analysis according to Harrison) are cut into thin slices with a suitable device and dried on trays at 60 ° in a vacuum for 3 days. The water loss is 3.0701g = 15.4%. The dried material is ground to a coarse powder and cooled in the refrigerator overnight to make it easier to mix it with the solvent. The exhaustive extraction with liquid sulphurous acid is done by pulling out several times in an open vessel or by pulling out in a closed Soxleth apparatus (2 atmospheres). The combined extracts are finally freed from the sulphurous acid in a vacuum, if necessary, and represent a light brown, dry powder weighing 6,000 pounds. To obtain the morphine, it is mixed with 2kg quicklime and then extracted with water. The lime is removed from the clear aqueous extracts by acidification with oxalic acid and then morphine with a weight of 2.3q.0 kg is precipitated by adding ammonia. F. 25q. °. Stirring out the mother liquor with butanol-benzene gives a further 414 9 morphine with a temperature of 25o °. Total yield of morphine. 2754 kg.
Der die Nebenalkaloide enthaltende Extrakt kann durch Behandeln mit verdünnter Schwefelsäure vom Harz befreit werden. Aus der sauren Lösung werden die Alkaloide nach dem AYkalisieren mit Benzol ausgeschüttelt und nach bekannten Methoden getrennt.The extract containing the minor alkaloids can be treated with dilute sulfuric acid can be freed from the resin. The acidic solution becomes the Alkaloids shaken out after alkaliizing with benzene and using known methods separated.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1015463T | 1948-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE903215C true DE903215C (en) | 1955-11-17 |
Family
ID=9573026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1948P0002735 Expired DE903215C (en) | 1948-09-01 | 1948-10-02 | Process for the extraction of the opium alkaloids |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE903215C (en) |
| FR (1) | FR1015463A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2712018A (en) * | 1955-06-28 | Method of recovering opium alkaloids |
-
1948
- 1948-09-01 FR FR1015463D patent/FR1015463A/en not_active Expired
- 1948-10-02 DE DE1948P0002735 patent/DE903215C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1015463A (en) | 1952-10-13 |
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