Amino Alcohols. III. The Potentiation of the Pressor Action of Epinephrine by Arylpropanolamines
Munch,James;Hartung,Walter
J. American. Pharmaceutical Assoc.
1929, Vol.40(3), pp.356-361
DOI: 10.1002/jps.3080190411


Abstract
The bioassay of ephedrine has been complicated by the findings (1, 5 and 6) that successive intravenous injections of the same quantity to dogs or cats give progressively smaller rises in blood pressure. To determine the pressor activity of ephedrine and its related homologues, Chen used the method first developed by Elliot (3) for the assay of epinephrine. Decerebate cats are injected intravenously with varying doses of a standard solution of ephinephrine, after which a single injection of ephedrine or related drug is given intravenously. The increase in blood pressure produced by this single injection is compared with the rises in the epinephrine series and the relative potency determined.





Amino Alcohols. XV. p-Aminopropadrine
Hartung,Walter;Foster,Carroll
J. American. Pharmaceutical Assoc.
1945, Vol.35(1),  pp.15-18
DOI: 10.1002/jps.3030350105


Abstract
Introduced into clinical practice as "Ephetonal" without adequate pharmacological background (1) p-aminoephedrine (2) is reported to possess activity similar, in many respects, to its p-hydroxy isoester. It is well tolerated and differs from ephedrine in that it is appreciably less toxic (3), does not cause tachyphylaxis and apparently causes a rise in the blood sugar level (4).




Amino alcohols. XVIII. Reduction studies on arylglyoxylohydroxamyl chlorides and amides
Larocca,Joseph; Walter H. Hartung,Walter;Levin,Nathan
J. American. Pharmaceutical Assoc.
1950, Vol.40(3),  pp.140-142
DOI: 10.1002/jps.3030400307


Abstract
A method for the preparation of arylgly-oxylohydroxamamides from aliphatic and aromatic amines is described. The reaction has been applied to two aromatic amines, eight aliphatic amines, and to ammonia. Reduction studies of the compounds prepared are reported.

Amino alcohols. XVII. Arylethanolamines
Simonoff,Robert;Hartung,Walter
J. American Pharmaceutical Assoc.
1946, Vol.35(10), pp.306-309
DOI: 10.1002/jps.3030351006


Abstract
Aracyl chlorides, Ar-CO-CH2Cl, were allowed to react with benzylamine or dibenzylamine to form aracylamines. These were then subjected to hydrogenolytic debenzylation, yielding primary aracylamines, ArCOCH2NH2; continued catalytic reduction, without previous isolation of the amino ketone, formed the corresponding arylethanolamines.

Synthesis of 2-Arylethylamines by the Curtius Rearrangement
Matthias Schulze
Synthetic Communications
2010, Volume 40, Issue 10,  pages 1461 - 1476
DOI: 10.1080/00397910903097302


Abstract
2-Arylethylamine derivatives were synthesized using the Curtius reaction and with three different methods of preparing the acyl azide functional group. Carbamates derived from isocyanate were convenient protecting groups for alkylation of amines. Starting from benzaldehyde, amphetamine was prepared in three steps through an oxazolidin-2-one intermediate in 62% overall yield.

Keywords: Curtius rearrangement; isocyanate; oxazolidin-2-one; potassium tert-butoxide

Modern methods for the radical deoxygenation of alcohols
Wolfgang Hartwig
Tetrahedron
1983,  Volume 39, Issue 16, Pages 2609-2645
doi:10.1016/S0040-4020(01)91972-6 [/color]

The Catalytic Oxidation of Benzoin to Benzil
Marvin Weiss, Mildred Appel
J. Am. Chem. Soc.
1948, 70 (11), pp 3666–3667
DOI: 10.1021/ja01191a036

SYNTHESIS OF EPHEDRINE AND STRUCTURALLY SIMILAR COMPOUNDS. III. A NEW SYNTHESIS OF ORTHO-DIKETONES
Harold W. Coles, Richard H. F. Manske, Treat B. Johnson
J. Am. Chem. Soc.
1929, 51 (7), pp 2269–2272
DOI: 10.1021/ja01382a046



AMINO ALCOHOLS. I. PHENYLPROPANOLAMINE AND PARA-TOLYLPROPANOLAMINE
Walter H. Hartung, J. C. Munch
J. Am. Chem. Soc.
1929, 51 (7), pp 2262–2266
DOI: 10.1021/ja01382a044



SYNTHESIS OF EPHEDRINE AND STRUCTURALLY SIMILAR COMPOUNDS. II. THE SYNTHESIS OF SOME EPHEDRINE HOMOLOGS AND THE RESOLUTION OF EPHEDRINE
Richard H. F. Manske, Treat B. Johnson
J. Am. Chem. Soc.
1929, 51 (6), pp 1906–1909
DOI: 10.1021/ja01381a042




SYNTHESIS OF EPHEDRINE AND STRUCTURALLY SIMILAR COMPOUNDS. I. A NEW SYNTHESIS OF EPHEDRINE
Richard H. F. Manske, Treat B. Johnson
J. Am. Chem. Soc.
1929, 51 (2), pp 580–582
DOI: 10.1021/ja01377a032

The Decomposition of a-Nitrocarboxylic Acids: With Some Remarks on the Decomposition of B-Ketocarboxylic Acids

Pederson,Kai

J. Phys. Chem.
Vol.38(5) 1934 pp.559–571
DOI: 10.1021/j150356a001
http://pubs.acs.org/doi/abs/10.1021/j150356a001

Abstract

The object of this paper is to contribute to our understanding of the tendency of a-nitrocarboxylic acids to split off carbon dioxide.

> CNO[size=-2]2[/size].COOH --> CHNO[size=-2]2[/size] + CO[size=-2]2[/size]

The simplest acid of this type, nitroacetic acid, was studied kinetically by Heuberger (2,3) and, independently, by the author of this paper (7). In the latter work, the rate of decomposition was determined on solutions of hydrochloric acid of various concentrations and in buffer solutions, mainly acetate buffers (pH = 4 to 5). The rate increases with decreasing hydrogen-ion concentration and reaches a maximum value in the acetate buffers. Here it is independent of the hydrogen-ion concentration. In sufficiently alkaline solution nitroacetic acid is stable.

Preparation of Diborane from Lithium Hydride and Boron Trihalide Ether Complexes

Elliot,J;Boldebuck,E;Roedel,G

J. Am. Chem. Soc.
Vol.74(20) 1952 pp.5047–5052
DOI: 10.1021/ja01140a017
http://pubs.acs.org/doi/abs/10.1021/ja01140a017

Abstract

The preparation of diborane from lithium hydride and boron trihalide etherates under different conditions is described and secondary reactions are discussed. The reaction between lithium hydride and boron trifluoride in ethyl ether has been shown to proceed by two different courses. If ether-soluble, active hydrogen-containing promoters are present, or if pressure is used to force the reaction between lithium hydride and diborane, the hydride is converted completely to lithium borohydride and lithium fluoride before diborane is evolved. In the absence of soluble promoters, diborane escapes continually from the solution, lithium borofluoride is formed and lithium borohydride does not accumulate. If less than a specified ratio of borohydride to hydride exists in the ether solution, the borohydride is consumed in the continuing reaction, and diborane is evolved. In tetrahydrofuran, a promoter is not required for the conversion of lithium hydride to lithium borohydride. Since the solubility of diborane is relatively high in tetrahydrofuran, conditions favor the production of borohydride by reaction of diborane with lithium hydride, as in the pressure reaction with ether as solvent.
 
Reaction between the Ether Complex of Boron Trifluoride and Lithium Hydride Communication. 1. Preparation of Pure Diborane

Mikheeva,V;Fedneva,E

Russian Chem. Bull.
Vol.5(8 ) 1956 pp.925-934
DOI: 10.1007/BF01166405
http://www.springerlink.com/content/x8245352g00v5048/

Summary
  
1. The reaction of lithium hydride with boron trifluoride etherate has a complex mechanism, which probably includes various parallel and successive reactions leading to the formation, as the ultimate boron-containing products, of diborane, lithium borohydride, and lithium fluoborate. The yield of diborane is dependent on reaction temperature, relative amounts of reactants, degree of agitation of the reaction mixture, and order of addition of reactants.
2. An almost quantitative yield with respect to both reactants is attained by carrying out the reaction at somewhat raised temperature (25–30°) in the initial stage, at a BF3 : LiH ratio of 1 : 2,4–2.8, and with gradual addition under constant stirring of lithium trifluoride etherate to lithium hydride.
3. The reaction studied is the simplest and most economical method for the preparation of highly pure diborane under laboratory conditions, and it opens up wide possibilities for the further study of the chemistry of boron hydrides and their derivatives.

Deuterium-Exchange Reaction on Trimethylamine-Borane with Sulfonate Cation Exchanger in the Deuterio Form

Muraviev,D;Rogachev,I;Bromberg,L;Warshawsky,A

J. Phys. Chem.
Vol.98(2) 1994 pp.718–724
DOI: 10.1021/j100053a055
http://pubs.acs.org/doi/abs/10.1021/j100053a055

Abstract

The kinetics of H-D exchange on trimethylamino-borane in bi- and triphase systems involving sulfonate cation exchangers in the D⁺ form show that the rate of isotope exchange is lower in triphase systems in comparison to the liquid-liquid extraction system; nevertheless the yield of deuterated product in polymeric deuterating systems is essentially much higher than that obtained in applying liquid deuterating agents. The cation-exchange resin when applied in a triphase system demonstrates ambivalent behaviour, acting as a catalyst toward deuterio-exchange reaction and as a suppressor towards the hydrolysis of TMAB. The hydrolysis of TMAB results in the formation of trimethylamine which accelerates the hydrolysis and inhibits the H-D exchange by saturation of the SO₃- resin sites. The immobilization of the aqueous phase (D₂O) in swollen ion exchanger creates unique conditions for isotope exchange, completely suppressing hydrolytic side reactions, and pure deuterated product can be acheived in quantitive yield.

Lithium Aluminum Hydride, Aluminum Hydride and Lithium Gallium Hydride, and Some of their Applications in Organic and Inorganic Chemistry

Finholt,A;Bond,A;Schlesinger,H

J. Am. Chem. Soc.
Vol.69(5) 1947 pp.1199–1203
DOI: 10.1021/ja01197a061
http://pubs.acs.org/doi/abs/10.1021/ja01197a061

Abstract

When lithium hydride is treated with an ether solution of aluminium chloride under the conditions described in the experimental part of this paper, the new ether soluble compound, lithium aluminium hydride, LiAlH₄ is formed according to the equation:

4LiH + AlCl₃ ----> LiAlH4 + 3LiCl

Addition of further quantities of aluminium chloride yields an ethereal solution of aluminium hydride:

3LiAlH₄ + AlCl₃ ----> 4AlH₃ + 3LiCl.

Syntheses of the Alkali Metal Borodeuterides

Atkinson,J;MacDonald,D;Stuart,R;Tremaine,P

Can. J. Chem
Vol.45(21) 1967 pp.2583-2588
http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=45&issue=21&startPage=2583

Abstract

A synthesis of sodium borodeuteride on a molar scale has been developed. Trimethylamine-borane was exchanged (6) with deuteriosulfuric acid in deuterium oxide to obtain trimethylaminborane-d₃ of a high isotopic purity. Reaction of trimethylaminborane-d₃ with sodium methoxide in diglyme at 120-150'C yielded sodium borodeuteride, which, after purification, was obtained in a 40-50% overall yield. The conditions for obtaining material of a high isotopic and chemical purity were found to be rather stringent but, once worked out, were easily reproducible.

Bufo alvarius: a potent hallucinogen of animal origin.  
Weil AT, Davis W.
Journal of Ethnopharmacology
1994, Volume 41, Issues 1-2,  Pages 1-8
doi:10.1016/0378-8741(94)90051-5



Abstract:
Anthropologists have long speculated that ancient peoples of Mesoamerica used a toad, Bufo marinus, as a ritual intoxicant. This hypothesis rests on many iconographic and mythological representations of toads and on a number of speculative ethnographic reports. The authors reject B. marinus as a candidate for such use because of the toxicity of its venom. A more likely candidate is the Sonoran desert toad, Bufo alvarius, which secretes large amounts of the potent known previous termhallucinogen,next term  5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT). The authors demonstrate that the venom of B. alvarius, although known to be toxic when consumed orally, may be safely smoked and is powerfully psychoactive by that route of administration. These experiments are the first documentation of an hallucinogenic agent from the animal kingdom, and they provide clear evidence of a psychoactive toad that could have been employed by Precolumbian peoples of the New World.

Keywords: Bufo; Hallucinogens; Tryptamine; Toad; Maya

@no1uno

Organometallic Photochemistry. I. The Photolysis of Ethyllithium

Glaze,William;Brewer,Terry

J. Am. Chem. Soc.
Vol.91(16) 1969 pp.4490–4493
DOI: 10.1021/ja01044a029
http://pubs.acs.org/doi/abs/10.1021/ja01044a029

Abstract

The photolysis of ehtyllithium with mercury resonance radiation apparently proceeds by two competing photolytic mechanisms: A lithium hydride elimination reaction which yields ethylene, and a homolytic process which yields lithium metal, ethane and ethylene. The absence of butane and deuterated ethane (when the photolysis is carried out in C6D4 or C6D12) indicates that the homolytic process occurs via an intraaggregate disproportionation mechanism. Photolysis in the solid state yields ethane, ethylene and butane as well as polymeric material. Solution photolysis in the presence of a mercury pool yields only ethane (and no LiH).

Poppy seed tea and opiate abuse in New Zealand

Klare Braye, Thomas Harwood, Rachel Inder, Richard Beasley, Geoffrey Robinson

Drug and Alcohol Review
Vol.26(2) 2007 pp.215-219
DOI: 10.1080/09595230601146637

Abstract

The opium poppy Papaver somniferum contains an array of opiates. There is a variety of methods of preparation that can be used by people with opiate dependence, with patterns of use determined by numerous factors including cost, safety, potency and legal status. The objective of this study was to determine the frequency and nature of poppy seed tea (PST) use by opiate-dependent patients in the form of a written questionnaire. The study took place at the Community Alcohol and Drug Clinic, Wellington, New Zealand, and comprised 24 opiate-dependent patients attending the clinic. A total of 11 of 24 (46%) patients reported having used PST. In five patients currently using PST it represented the major source of opiates, and two had managed to withdraw from use of other opiates with regular PST use. Patients reported a median onset of action of 15 minures and an effect lasting a median of 24 hours. The major limitation of PST use was the foul taste. PST is used commonly by opiate-dependent patients attending an alcohol and drug clinic in New Zealand. The use of PST as the major source of opiates could be considered favourably within ‘harm reduction’ philosophies, because of its low cost, legal availability and oral route of administration. Conversely, there is the potential for PST to act as a ‘gateway drug’ by inducing opioid dependence and introducing people to the culture of drug abuse.


The Preparation of Substituted Diphenylethylamines and Diphenylehtanolamines

McPhee,Warren;Erickson,Ernst

J. Am. Chem. Soc.
Vol.68(4) 1946 pp.624–627
DOI: 10.1021/ja01208a028


Abstract

In 1943, Dodds, Lawson and Williams published a note on the morphine-like properties of phenylethylamine and five related compounds. In a later publication the study was extended to include nine compounds not previously tested, several of which had hydroxyl or methoxyl groups in the aromatic rings. The most active substances of the English workers were the hydrochlorides of ?,?-diphenyl-?-hydroxyethylamine, ?,?-diphenylethylamine and dimethyldesylamine. These three were tested clinically in a small number of patients, the first substance giving results that it might be useful as a general analgesic.

Specialized Analgesic Effects of ?-Hydroxy-?,?-Diphenylethylamine

Dodds,E;Lawson,W;Williams,P

Nature
Vol.154 1944 pp.514-514
DOI: 10.1038/154514a0


Abstract

CLINICAL trials by other workers not yet reported have confirmed our original observation1 ?-Hydroxy-?,?-Diphenylethylamine will relieve pain due to pressure on nerve in patients with inoperable tumours. This was the only type of pain included in our trials, and it is now clear that the compound has no universal analgesic action and cannot be used generally as a substitute for morphine. Tests using the method of Sivadjian, which measures the tolerance of rats to electric shocks, have now been carried out with morphine and the diphenylethylamine compounds the morphine-like properties of which we have described. The results, which will be reported in detail elsewhere, were entirely negative for the diphenylethylamine compounds; but analgesic activity was demonstrated in the hydrochlorides of morphine and pethidine, showing that the negative results were not due to the method used. The cause of the specific action of ?-Hydroxy-?,?-Diphenylethylamine on nerve pressure pain awaits further pharmacological investigation.

Oxidation of Primary Alcohols to Carboxylic Acids at the Nickel Hydroxide Electrode
Kaulen, J.; Schäfer, H. J.
Synthesis
1979: 513-516
DOI: 10.1055/s-1979-28735

Katalytische oxydation von primären und sekundären hydroxylverbindungen mit sauerstoff am platinkontakt in flüssiger phase: Über katalytische oxydationen—XIV

K. Heyns and L. Blazejewicz
Tetrahedron
Volume 9, Issues 1-2, 1960, Pages 67-75
doi:10.1016/0040-4020(60)80054-3

Abstract:

Unter milden Bedingungen lassen sich in wässriger Lösung oder in organischen Lösungsmitteln mittels Sauerstoff am Platinkontakt primäre Alkohole je nach den Bedingungen zu Aldehyden oder Carbonsäuren, sekundäre Alkohole zu Ketonen oxydieren. Die Oxydation verschiedenster Alkohole wurde systematisch untersucht. Das Verfahren eignet sich besonders zur präparativen Darstellung langkettiger Aldehyde.