O<sup>3</sup>,O<sup>4</sup>,N-Triacetyl-(-)-epinephrine

Welsh, Llewellyn H

doi:10.1021/ja01139a525

Cited by 13 publications

(6 citation statements)

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“…2,4,5-triacetoxy-1 -$-N-acetylaminoethylbenzene, (IX)] [cf. preparation of 03, 04,N-triacetyladrenaline by Welsh (1952)l.…”

Section: Imentioning

confidence: 99%

The oxidation of 6-hydroxydopamine

Powell¹,

Heacock²

1973

Journal of Pharmacy and Pharmacology

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The oxidation of 6‐hydroxydopamine (I) with molecular oxygen or potassium ferricyanide in aqueous solution has been shown to lead mainly to the formation of the uncyclized quinone 2‐(β‐aminoethyl)‐5‐hydroxy‐p‐benzoquinone (VII). However this quinone cyclized slowly, presumably to norepinochrome (i.e. indoline‐5,6‐quinone, XII), since 5,6‐dihydroxyindole (II), known to be readily formed by rearrangement of norepinochrome (XII), can be isolated from these solutions. 5,6‐Dihydroxyindolines (cf. XIII) can also be isolated (as their acetyl derivatives) from the products obtained by the addition of reducing agents to solutions containing 6‐hydroxydopamine oxidation products. No evidence was found to suggest that the possible alternative cyclization of the quinone VII to the p‐quinonoid aminochrome 6‐hydroxyindoline‐4,7‐quinone (III) occurred to any significant extent.

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“…2,4,5-triacetoxy-1 -$-N-acetylaminoethylbenzene, (IX)] [cf. preparation of 03, 04,N-triacetyladrenaline by Welsh (1952)l.…”

Section: Imentioning

confidence: 99%

The oxidation of 6-hydroxydopamine

Powell¹,

Heacock²

1973

Journal of Pharmacy and Pharmacology

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“…Since the free aminoalcohols 12a,b and ent-12a,b, the triacetylated [33] derivatives 18b,c and ent-18b,c, and the triphenylsulfonyl substituted [34] compounds 18a and ent-18a could not be separated by HPLC on substituted cellulose as stationary phase, and 1 H NMR spectra using enantiomerically pure shift reagents or mandelic acid [35] as chiral probes did not give any information on the enantiomeric excess, we decided to apply our own method established earlier [19]. Since the free aminoalcohols 12a,b and ent-12a,b, the triacetylated [33] derivatives 18b,c and ent-18b,c, and the triphenylsulfonyl substituted [34] compounds 18a and ent-18a could not be separated by HPLC on substituted cellulose as stationary phase, and 1 H NMR spectra using enantiomerically pure shift reagents or mandelic acid [35] as chiral probes did not give any information on the enantiomeric excess, we decided to apply our own method established earlier [19].…”

Section: Resultsmentioning

confidence: 99%

Aminoalcohols V [1]: A Methodfor the Synthesis of EnantiomericallyPure Ring-Chlorinated Epinephrinesand Norepinephrines

Knollmüller

Gärtner

Pernerstorfer

et al. 1999

Monatshefte fuer Chemie

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The synthesis of enantiomerically pure 5-and 6-chloroepinephrine hydrochloride, resp., as well as 6-chloronorepinephrine hydrochloride is described starting from ring chlorinated O-benzylated dihydroxybenzaldehyde cyanohydrins, which are O-protected using an enantiomerically pure acetal-type protecting group (MBE). After lithium aluminum hydride reduction, followed ± if necessary ± by N-protection and methylation, removal of the chiral auxiliar and deprotection by hydrogenation furnished the target compounds with enantiomeric purities above 96% ee in high chemical yield, if well de®ned reaction conditions during the hydrogenation process were closely observed.

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“…Die [8,24,37,38,39,52], ebenso /iberstiegen die MN nicht den Referenzwert [8,59]. Keinen bedeutsamen Anstieg der Katecholamine stellten Cardon und Guggenheim [8] [9,23,60,65]. -Die HVS-Ausscheidung unterliegt offenbar keinerlei Nahrungsmitteleinflfissen [20,59].…”

Section: Diskussionunclassified

Der Einfluß von Nahrungsmitteln und Rauchen auf die klinisch-chemische Diagnostik von Phäochromozytom, Neuroblastom und Karzinoid-Syndrom

et al. 1981

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The interference of various foodstuffs on methods to determine epinephrine (E), norepinephrine (NE), vanillylmandelic acid (VMA), metanephrines (MN), homovanillic acid (HVA), and 6-hydroxyindole acetic acid (5-HIA) in the 24 h urine for diagnosis of pheochromocytoma and carcinoid syndrome, respectively, was investigated. The foodstuffs included were: tea, coffee, almonds, pineapples, cheese, walnuts, vanilla pudding, bananas, tomatoes, and chocolate. Further, the interference of cigarette smoking on the determination of E, NE, VMA, and MN was also investigated. Walnuts caused a rather high elevation of 5-HIA in the urine. After eating bananas elevated excretion of E, NE, VMA, MN, and 5-HIA was observed. Small increases of the MN values were noticed after coffee and pineapples. Smoking of 20-30 cigarettes/day had no influence on the variables measured. If the methods described are used, thus, only bananas and walnuts have to be restricted some days before and during urine sampling, but not coffee and pineapples if consumed in the usual small quantities. There is no reason to insist on diet restriction except for bananas and walnuts.

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O³,O⁴,N-Triacetyl-(-)-epinephrine

Cited by 13 publications

References 0 publications

The oxidation of 6-hydroxydopamine

The oxidation of 6-hydroxydopamine

Aminoalcohols V [1]: A Methodfor the Synthesis of EnantiomericallyPure Ring-Chlorinated Epinephrinesand Norepinephrines

Der Einfluß von Nahrungsmitteln und Rauchen auf die klinisch-chemische Diagnostik von Phäochromozytom, Neuroblastom und Karzinoid-Syndrom

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O3,O4,N-Triacetyl-(-)-epinephrine

Cited by 13 publications

References 0 publications

The oxidation of 6-hydroxydopamine

The oxidation of 6-hydroxydopamine

Aminoalcohols V [1]: A Methodfor the Synthesis of EnantiomericallyPure Ring-Chlorinated Epinephrinesand Norepinephrines

Der Einfluß von Nahrungsmitteln und Rauchen auf die klinisch-chemische Diagnostik von Phäochromozytom, Neuroblastom und Karzinoid-Syndrom

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O³,O⁴,N-Triacetyl-(-)-epinephrine