CXCIV.—Synthetical experiments in the group of the isoquinoline alkaloids. Part IV. The synthesis of β-gnoscopine

Hope, Edward; Robinson, Robert

doi:10.1039/ct9140502085

Cited by 17 publications

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“…112 A similar procedure was conducted by Hope and Robinson in 1914, and both Roser's procedure and Hope and Robinson's procedures were repeated in 1933 by Addinall. 113,114 Papaverine. Isolation.…”

Section: Acs Chemical Neurosciencementioning

confidence: 99%

“…In 1888, Roser found that if noscapeine methychloride ( 30 ) was subjected to a Hoffmann elimination with silver chloride and then heating with base, narceine was the resulting product (Figure ). A similar procedure was conducted by Hope and Robinson in 1914, and both Roser’s procedure and Hope and Robinson’s procedures were repeated in 1933 by Addinall. , …”

Section: Introductionmentioning

confidence: 99%

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DARK Classics in Chemical Neuroscience: Opium, a Historical Perspective

Presley

Lindsley

2018

ACS Chem. Neurosci.

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Opium is the latex from the opium poppy Papaver somniferum L., which humankind has utilized since ancient Mesopotamia all the way to modern times. Opium used to be surrounded in divine mystery or magic-like abilities and was given to cure a wide variety of diseases until its analgesic, antitussive, and antidiarrheal properties were understood, the resulting alkaloids were isolated, and their structure and properties unmasked. Opium went from being sold in any store front in the form of pills or tinctures with no prescription necessary for purchase or smoked in an opium den down the street, to then bringing about consumer advocacy and the right to know what is in a medication. Legislation was created to limit the prescribing and selling of medications to doctors and pharmacists as well as outlawing opium dens and smoking opium. This review focuses primarily on the uses of opium throughout history, the isolation of the principle alkaloids, and their structure elucidation.

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Section: Acs Chemical Neurosciencementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

DARK Classics in Chemical Neuroscience: Opium, a Historical Perspective

Presley

Lindsley

2018

ACS Chem. Neurosci.

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“…Oritentalidine (178), isolated from Papaver species [155], [156], has a fused m-dioxin system on ring D. Coryenchirine (179) carries a methyl group at the C-8 position. Berberine (180) and palmatine (181) are the dehydro quaternary bases. The structure that was initially proposed for capaurimine [157], was revised to 177 on the basis of spectroscopic [158] and synthetic studies [159] confirmed by X-ray analysis [160].…”

Section: Protoberberine Alkaloidsmentioning

confidence: 99%

“…Berberine (180) (180) is moderately toxic to larger animals, causing cardiac damage, dyspnoea, lowered blood pressure, and paresis in rabbits. After oral administration to humans large amounts appear in the urine.…”

Section: Protoberberine Alkaloidsmentioning

confidence: 99%

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Alkaloids

Hoshino¹,

Murakata²,

Ishizaki³

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

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Über die Konstitution des Cotarnolins und die Spaltung des Narcotolins

Göber

Pfeifer

1966

Archiv der Pharmazie

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Archlv der 196a o b e r und P f e i f e r Pharmazie 0,44 g (0,001 Mol) I-Pikrat gibt man auf eine Anionenaushuschersie (Wofatit L 160 1 = 10 cm, 0 = 2,6 om) und eluiert die Base I bei 6 6 ' Siulentemp. emchapfend mit Methanol. Dee Eluat engt man bei 20" im Luftatrom auf wenige ml ein, gibt 500 ml Ather hmzu und fiillt in praktisah quant. Ausbeute daa I-Monohydrochlorid-monohydrat durch vorsichtigen Zusatz von n HCl (methanol.), feine gelbe Nadeln.2. 5(6)-Furfurylaminobenzimidazol (11) 0.86 g (0,006 Mol) 6(6)-Aminobenzimidazol-hemihydrochloridmonohydrat1~) (B) setzt men um wie fiir I besohrieben und erhiilt 1,24 g (56% d. Th.) 1 1 -P i k r a t , gelbe Nadeln, Schmp. 130-136".ClOHIIN6Oa (442,4) Ber.: C 48,87 H 3,19 Gef.: C 49,00 H 3,16 Aus 0,44 g (0,001 Mol) II-Pikrat erhiilt man nach der oben begchriebenen Methode in praktiach quant. Ausbeute 11-Dihydrochlorid, farblose Nadeln. 3. Benzylaminobenzimidazole (111-VIII) 0,006 Mol4(7)-Aminobenzimidazol-dihydrochlond (A)") bzw. 5(6)-Aminobenzimidazolhemihydroohlorid-monohydrat (B)'8) setzt man mit den in Tab. 1 aufgefiihrten entaprechenden Aldehyden (0,005 Mol) um, wie oben fiir die Furfurylaminoderivate beschrieben. Die Atherextraktion nach der N a t r i u m b o r a n a t -R o n eriibrigt sich, da bei Zugabe von Waaser zum methanol. Reektionsgemiach die gesuchten Substanzen auakristallisiemn. Die W i g u n g erfolgt durch Umkristalliaieren aus Athanol/Wmser mit Aktivkohle. Durch vergleichende Untersuchungen an Cotamoh, Hydrocotamolin und dem erstmals dargestellten Tarkonin sowie uber daa reaktive Verhalten von Cotarnolin und Cotarnin wird die Struktur des Cotarnolins ale Phenolbetain gesiohert. Es wird ein Reaktionsmeohaniemus der Narcotolinspaltung diskutiert. Neben der phenoliachen OH-Gruppe begiinstigt auch die Lactongruppierung die Spaltung. Am leichtesten wird ein vollstiindig O-demethyliertes Narmtin (= Narcotosoh) gespalten. Die offnung des Lactonrings in Phthalidisochinolinalkaloiden bewirkt eine hypsochrome Verschiebung der UV-Absorptionsmaxime. Nachdem schon Baumgarten und Christ') eine Verfarbung alkalisoher Narcotolinlosungen beobachteten, konnte gezeigt werden, daD dieses Papaveralkaloid (I a) *) Herrn Prof. Dr. W. Awe zum 65. Geburtatag gewidmet. l ) C. BaumgaPten und W. Chriet, Pharmazie 5.80 (1960). *) Im Verlaufe unserer Untersuchungen konnten wir feststellcn, da6 sich Cotssnolin mit Hg(II)-*) 5. Pfeiler und F . Veib, Arch. Pharmaz. 289, 24 (1956). 8 ) S. Pfeifer, Arch. Pharmaz. 290, 261 (1957). 9 M. Iflubek, Dissertation Marburg 1959. 6) J . Holubek und J . Volke, Collect. czechodov. chem. Commun. 24, 1436 (1969). 6 ) J . Knube, Arch. Pharmaz. 292,416 (1969). acetet/ADTA nicht aromatisieren UBt. Archiv der Pharrnazte __ G i i b e r und P f e i f e r ~--

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CXCIV.—Synthetical experiments in the group of the isoquinoline alkaloids. Part IV. The synthesis of β-gnoscopine

Cited by 17 publications

References 0 publications

DARK Classics in Chemical Neuroscience: Opium, a Historical Perspective

DARK Classics in Chemical Neuroscience: Opium, a Historical Perspective

Alkaloids

Über die Konstitution des Cotarnolins und die Spaltung des Narcotolins

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