CH373382A - Process for the production of the previously unknown 4-hydroxy-N, N-dimethyltryptamine-O-sulfate - Google Patents
Process for the production of the previously unknown 4-hydroxy-N, N-dimethyltryptamine-O-sulfateInfo
- Publication number
- CH373382A CH373382A CH7673159A CH7673159A CH373382A CH 373382 A CH373382 A CH 373382A CH 7673159 A CH7673159 A CH 7673159A CH 7673159 A CH7673159 A CH 7673159A CH 373382 A CH373382 A CH 373382A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroxy
- dimethyltryptamine
- sulfate
- production
- previously unknown
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- SPCIYGNTAMCTRO-UHFFFAOYSA-N psilocin Chemical compound C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 SPCIYGNTAMCTRO-UHFFFAOYSA-N 0.000 claims description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung des bisher unbekannten 4-Hydroxy-N,N-dimethyltryptamin- O-sulfates Es wurde gefunden, dass man zum bisher unbe kannten 4-Hydroxy-N,N-dimethyltryptamin-O-sulfat der Formel 1,
EMI0001.0004
gelangen kann, indem man 4-Hydroxy-N,N-dimethyl- tryptamin der Formel 1I,
EMI0001.0008
in Form eines Alkalisalzes, in einem inerten organi schen Lösungsmittel mit Chlorsulfonsäure umsetzt.
<I>Beispiel</I> 4-Hydroxy-N,N-dimethyltryptamin-O-sulfat Zu einer Natriumäthylatlösung (hergestellt aus 58 mg Natriummetall und 30 cm?, abs. Äthanol) gibt man unter Stickstoffatmosphäre 510 mg 4-Hydroxy- N,N-dimethyltryptamin. Nach 15 Minuten verdampft man zur Trockne und trocknet den Rückstand noch 1 Stunde im Hochvakuum bei 70 .
Danach versetzt man mit 20 cm3 abs. 1,2-Dimethoxy-äthan und gibt 305 mg Chlorsulfonsäure hinzu. Nach 1 Stunde wird zur Trockne eingedampft und der Rückstand an der 50fachen Menge Cellulose-Pulver mit wassergesät tigtem n-Butanol chromatographiert. Beim Ein dampfen der Fraktionen kristallisiert 4-Hydroxy- N,N-dimethyltryptamin-O-sulfat. Aus Methanol kri stallisiert es in Nadeln vom Smp. 251-252 .
Kellersche Farbreaktion: königsblau.
Van Urksche Farbreaktion: dunkelblauviolett.
Process for the preparation of the previously unknown 4-hydroxy-N, N-dimethyltryptamine-O-sulfate It has been found that the previously unknown 4-hydroxy-N, N-dimethyltryptamine-O-sulfate of the formula 1,
EMI0001.0004
can be achieved by 4-hydroxy-N, N-dimethyl tryptamine of the formula 1I,
EMI0001.0008
in the form of an alkali salt in an inert organic solvent with chlorosulfonic acid.
<I> Example </I> 4-Hydroxy-N, N-dimethyltryptamine-O-sulfate 510 mg of 4-hydroxy-N are added to a sodium ethylate solution (prepared from 58 mg of sodium metal and 30 cm? , N-dimethyltryptamine. After 15 minutes, it is evaporated to dryness and the residue is dried in a high vacuum at 70 for a further hour.
Then 20 cm3 of abs are added. 1,2-dimethoxyethane and 305 mg of chlorosulfonic acid are added. After 1 hour, the mixture is evaporated to dryness and the residue is chromatographed on 50 times the amount of cellulose powder with water-saturated n-butanol. When the fractions evaporate, 4-hydroxy-N, N-dimethyltryptamine-O-sulfate crystallizes. It crystallizes from methanol in needles with a melting point of 251-252.
Keller's color reaction: royal blue.
Van Urk's color reaction: dark blue-violet.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7673159A CH373382A (en) | 1959-04-07 | 1959-04-07 | Process for the production of the previously unknown 4-hydroxy-N, N-dimethyltryptamine-O-sulfate |
| GB10168/60A GB941707A (en) | 1959-04-07 | 1960-03-22 | Improvements in or relating to 4-hydroxy tryptamine esters |
| BE589424A BE589424A (en) | 1959-04-07 | 1960-04-05 | New esters of the indole series and their preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7673159A CH373382A (en) | 1959-04-07 | 1959-04-07 | Process for the production of the previously unknown 4-hydroxy-N, N-dimethyltryptamine-O-sulfate |
| CH371116T | 1959-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH373382A true CH373382A (en) | 1963-11-30 |
Family
ID=25737355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7673159A CH373382A (en) | 1959-04-07 | 1959-04-07 | Process for the production of the previously unknown 4-hydroxy-N, N-dimethyltryptamine-O-sulfate |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH373382A (en) |
-
1959
- 1959-04-07 CH CH7673159A patent/CH373382A/en unknown
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