2-chloroethyl Amine Hydrochloride Research Articles

A New Synthesis of P‐Substituted 2,3‐Dihydro‐1,3‐dimethyl‐1,3,2δ3‐benzodiazaphosphorin‐4(1H)‐ones and Alkylaminodifluorophosphanes with Chlorodifluorophosphane. — Synthesis and Structure of {cis‐Bis[bis(2‐chloroethyl)aminodifluorophosphane]dichloro}platinum(II)

Abstract2,3‐Dihydro‐1,3‐dimethyl‐2‐oxo‐1,3,2δ4‐benzodiazaphosphorin‐4(1H)‐one 1 reacted with diethylaminotrimethylsilane to give solely the 2‐trimethylsiloxy‐δ3‐diazaphosphorinone 2. The reaction of 2 with the 2‐chloro‐δ3‐diazaphosphorinone 3 yielded the P—O—P‐bridged compound 4 in an equilibrium reaction with elimination of trimethylchlorosilane. The synthesis of the P‐difluorophosphite‐substituted δ3‐benzodiaza‐phosphorinone 6 was effected by the reaction of chlorodifluorophosphane (5) with 1 in the presence of triethylamine in a 1:1 molar ratio, or in the reaction of 5 with 2 or 4. The reaction of 5 with 6 led, with elimination of μ‐oxo‐bis(difluoro‐phosphane), to the P(III)Cl species 3, 5 reacted with N,N'‐dimethylanthranilamide in the presence of triethylamine in a 2:1:2 molar ratio to give the N,N'‐bis(difluorophosphane) derivative 9, as evidenced by low temperature (‐30°C) 19F‐and 31P‐NMR data. At room temperature the 2‐fluoro‐δ3‐diazaphosphorinone 10 was formed from 9 with intramolecular elimination of phosphorus trifluoride. 2‐Chloroethyl‐ or bis(2‐chloroethyl)aminodifluorophosphane 11 and 12 were obtained in the reaction of 5 with 2‐chloroethyl‐ or bis(2‐chloroethyl)amine hydrochloride in the presence of triethylamine in a 1:1:2 molar ratio. 12 reacted with (COD)PtCl2 (COD = 1,5‐cyclooctadiene) in a 2:1 molar ratio to give the {cis‐bis[bis(2‐chloroethyl)aminodifluorophosphane]dichloro}platinum(II) complex 13. The characterization of 2, 4, 6, and 11–13 is based on their NMR and mass spectra. The structures of 10 and 13 were established by single‐crystal X‐ray analysis. 10 crystallizes with two independent molecules. Both six‐membered heterocycles display an envelope conformation with the phosphorus atoms 36.9 and 50.4 pm, respectively, out of the plane. The phosphorus atoms have pyramidal coordination geometry. The cis‐configuration at platinum(II) in the complex 13 was confirmed; two ligands (12) are coordinated to PtII via phosphorus. The platinum atom has a distorted square‐planar coordination geometry.

Darstellung von 5,6-Benzo-1,3-dialkyl-2-P-substituierten 1,3,2-Diazaphosphorinan-4-onen; Einkristall-Röntgenstrukturanalysen von 2-fluorsubstituierten 1,3,2λ 4-Benzodiazaphosphorinanon-Derivaten

The reactions of the 5,6-benzo-2-chloro-1,3-dimethyl- or 1-methyl-3-(2-chloroethyl)-1,3,2λ 3-diazaphosphorinan-4-ones 1 and 2 with the triethylamine · 3HF adduct in a molar ratio 3:1 in the presence of excess triethylamine furnished the 2-fluorosubstituted 1,3,2λ 3-diazaphosphorinanones 3 and 4 in good yield. In the reactions of 1 and 2 with trimethylsilylmethyl ether or methanol in the presence of free triethylamine, the 2-methoxy-substituted-1,3,2λ 3-benzodiazaphosphorinan-4-ones 5 and 6 were formed. Oxidation of 3 and 4 to the 2-fluoro-2-oxo-1,3,2λ 4-benzodiazaphosphorinanones 7 and 8 was effected either by aqueous hydrogen peroxide or by the hydrogen peroxide-urea 1:1 adduct. Furthermore, substitution of the 2-chloro-2-oxo-1,3,2λ 4-benzodiazaphosphorinanones 9 and 10 with the triethylamine·3HF adduct in a molar ratio of 3:1 in the presence of excess triethylamine furnished the corresponding derivatives 7 and 8, involving λ 4-phosphorus. The phosphoryl chloride derivatives 9 and 10 were obtained in the reaction of the 2-P-methoxy derivatives 5 and 6 with sulfuryl chloride. Compounds 9 and 10 were allowed to react with the amine derivatives, 2-chloroethylamine hydrochloride and bis(2-chloroethyl)amine hydrochloride, in the presence of triethylamine in a molar ratio of 1:2, forming the λ 4-phosphorus derivatives 11-13. Characterization of 3-13 was based on their NMR spectra and mass spectra. X-Ray structure determinations of 7 and 8 are described. In both structures the phosphorus atom has a distorted tetrahedral coordination geometry. The six-membered heterocycle of 7 displays an envelope conformation with the phosphorus atom out of plane, whereas the heterocycle of 8 displays a distorted envelope conformation with the phosphorus atom and one nitrogen atom out of plane.

Zur Chemie der 1,3,5-Triaza-2-phosphorinan-4,6-dione. Teil VIII. Weitere 1,3,5-Triaza-2 λ3-und 1,3,5-Triaza-2 λ4-phosphorinan-4,6-dione mit (2-Chlorethyl)amino-und Bis(2-chlorethyl)amino-Substituenten / Chemistry of the 1,3,5-Triaza-2-phosphorinan-4,6-diones. Part VIII. Further 1,3,5-Triaza-2λ3- and 1,3,5-Triaza-2λ4-phosphorinane-4,6-diones with (2-Chloroethyl)amino- and Bis(2-chloroethyl)amino Substituents

In the reaction of 2-chloro-1,5-dimethyl-3-phenyl-1,3,5-triaza-2λ3-phosphorinane-4,6- dione (1) and 2-chloro-1,3,5-triphenyl-1,3,5-triaza-2λ3-phosphorinane-4,6-dione (2) with (2-chloroethyl)amine hydrochloride or bis(2-chloroethyl)amine hydrochloride in the presence of triethylamine the corresponding (2-chloroethyl)amino- and bis(2-chloroethyl)amino-substituted 2λ3-phosphorinane-4,6-diones (3-6) are formed. Oxidation with the hydrogen peroxide- urea-1: 1-adduct gives the corresponding 2-oxo-2λ4-phosphorinane-4,6-diones (7-10), in the same manner as described in the literature for the 1,3,5-trimethyl-1,3,5-triaza-2λ4-phosphorinane- 4,6-diones [6]. Hydrolysis of 1 leads to 2-hydro-1,5-dimethyl-3-phenyl-1,3,5-triaza- 2λ4-phosphorinane-4,6-dione (11). Compounds 3 -11 have been characterized via their 1H, 13C and 31P NMR spectra, mass spectra, and, with the exception of 9, through elemental analyses.

Synthesis of 17O (and 18O) labelled isophosphoramide mustard

AbstractThe ifosfamide metabolite isophosphoramide mustard (IPM) was synthesized with isotopic enrichment at oxygen. Labelled benzaldehyde was made by exchange with isotopically enriched water (13.4 atom % 170, 25.5 atom % 180) and this was then reduced with sodium borohydride to give labelled benzyl alcohol (72% yield). Triethylamine and labelled benzyl alcohol were added to POCl3/CHCl3 at −23°C. Subsequent addition of 2‐chloroethylamine hydrochloride (2 equiv) and then triethylamine (4.4 equiv) (−15°C) provided 170/180 enriched N,N′‐bs‐(2‐chloroethyl)phosphorodiamidic acid phenylmethyl ester [61%, BzOP(O)(NHCH2CH2Cl)2]. Catalytic (10% Pd/C) hydrogenation of this ester at atmospheric pressure gave IPM (22%). GC/MS was used to determine mole percent enrichments of 9.3% 170 and 17.9% 180 for IPM (single labelling within one molecule).

Zur Chemie der 1,3,5-Triaza-2-phosphorinan-4,6-dione. Teil VII+. Über die Synthese von 2-Methoxy- und 2-Trimethylsiloxy-1,3,5-trimethyI- 1.3.5-triaza-2λ3-phosphorinan-4,6-dion sowie 2-Chlor-1,3,5-trimethyl- 1.3.5-triaza-2-oxo-2λ4-phosphorinan-4,6-dion / Chemistry of the 1,3,5-Triaza-2-phosphorinane-4,6-diones. Part VII. Synthesis of 2-Methoxy- and 2-Trimethylsiloxy-1,3,5-trimethyl-1.3.5-triaza-2λ3-phosphorinane-4,6-dione and 2-Chloro-1,3,5-trimethyl- 1.3.5-triaza-2-oxo-2λ4-phosphorinane-4,6-dione

The reactions of 1,3,5-trimethylbiuret with methyldichlorophosphite, and of 2-chloro- 1.3.5-trimethyl-1,3,5-triaza-2λ3-phosphorinane-4,6-dione 1 with methanol or methoxytrimethylsilane furnished the methoxy-substituted triazaphosphorinane-dione 3. In the reaction of 2-hydro-1,3,5-trimethyl-1,3,5-triaza-2-oxo-2λ4-phosphorinane-4,6-dione 2 with diethylaminotrimethylsilane the corresponding trimethylsiloxy-substituted triazaphosphorinane- dione 4 was formed. The reactions of 3 and 4 with sulphuryl chloride gave 2-chloro-1,3,5-trimethyl-1,3,5-triaza-2-oxo-2λ4-phosphorinane-4,6-dione 5, whose synthesis via another route was described previously [7]. In the reaction of 1 with 4 the λ3P-O-λ3P-bridged compound 6 and trimethylchlorosilane were formed. Condensation reactions of the P(:O)C1 compound 5 with 2-chloroethylamine hydrochloride and bis(2-chloroethyl)amine hydrochloride in the presence of triethylamine furnished the amide derivatives 7 and 8. Compounds 3-5, 7 and 8 were characterized via their 1H, 13C, 31P NMR and mass spectra, compound 6 was characterized from its 1H and 31P NMR spectra only.

DARSTELLUNG UND CHARAKTERISIERUNG VON 2-CHLORETHYLSUBSTITUIERTEN BENZODIAZAPHOSPHORINANONEN

Abstract The reaction of N-methylisatoic anhydride 1 with isopropylamine furnished the N-isopropyl-N'-methyl-substituted anthranilic acid amide 2. Its reaction with phosphorus trichloride led to the P-chlorobenzodiazaphosphorinanone 3. 3 and two further P-chlorobenzodiazaphosphorinanones, 5 and 7, were allowed to react with the amine derivatives, bis(2-chloroethyl)amine hydrochloride, 2-chloroethylamine hydrochloride, and dimethylaminotrimethylsilane, forming the corresponding P(III)-amino derivatives, 4, 6 and 8. Reaction of 8 with elemental sulfur yielded the thiobenzodiazaphosphorinanone 9. Careful hydrolysis of the P-chlorobenzodiazaphosphorinanones 3 and 7 gave rise to compounds 10 and 11, involving the P(:O)H grouping. The oxidation of 6, 12 and 13 to the 2-oxo-benzodiazaphosphorinanones 14–16 was effected in two ways: Aqueous hydrogen peroxide as well as the hydrogen peroxide-urea 1:1 adduct as the oxidizing agent furnished the corresponding λ4P(V) derivatives 14–16 in good yield. A discussion of t...

Partially protected D-glucopyranosyl isothiocyanates. Synthesis and transformations into thiourea and heterocyclic derivatives.

The syntheses of 2,3,4-tri-O-acetyl(benzoyl)-β-D-glucopyranosyl isothiocyanates ( 3, 4) from the corresponding acylated N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine are described. Reactions of 3 and 4 with phenacylamine hydrochloride yielded N-phenacyl-N′-(2,3,4-tri-O-acyl-β-D-glucopyranosyl)thioureas ( 6, 7) whereas treatments of the same compounds with aminoacetone hydrochloride gave the N-nucleoside analogues 5-methyl-1-(2′,3′,4′-tri-O-acyl-β-D-glucopyranosyl)-4-imidazoline-2-thiones ( 8, 9). The partially protected N-(2-thiazoline-2-yl)-β-D-glucopyranosylamine ( 10) and the thioureylenedisaccharide II were prepared from 4 and 2-chloroethylamine hydrochloride under different reaction conditions.

PET studies of potential chemotherapeutic agents—X. Synthesis of “no-carrier-added” ( 11C)-HECNU: The hydroxyethyl analog of the chemotherapeutic agent BCNU

Carbon-11-labeled HECNU [1-(2-chloroethyl)-1-nitroso-3-(2-hydroxyethyl) urea] a potential chemotherapeutic agent, has been prepared by the nitrosation of the corresponding carbon-11-labeled urea, HECU, [1-(2-chloroethyl)-3-(2-hydroxyethyl) urea]. The isomeric byproduct of nitrosation, 1-(2-chloroethyl)-3-nitroso-3-(2-hydroxyethyl) urea can be efficiently removed by preparative scale HPLC on a Partisil column. ( 11C)-HECU was prepared by reacting ethanolamine with ( 11C)-2-chloroethyl-isocyanate which was itself prepared by reacting ( 11C)-phosgene with 2-chloroethylamine hydrochloride suspended in dioxane at 60–65°C. This synthesis yielded ( 11C)-HECNU with an average radiochemical purity of 98% in an average radiochemical yield of 18% relative to the radioactivity measured at the end of the 11C-phosgene introduction.

ChemInform Abstract: Synthesis of Sugar N‐(2‐Thiazolin‐2‐yl)thioureas.

AbstractThe reaction of 2‐deoxy‐2‐isothiocyanato sugars such as (I) with 2‐chloroethylamine hydrochloride (II) in pyridine yields thiazolinylthioureas such as (III).

ChemInform Abstract: Synthesis of N,N′-Bis(aryl)-N-(2-thiazolin-2-yl)thioureas.

The aryl isothiocyanates (I) undergo ring closure reaction with 2-chloroethylamine hydrochloride (II) in pyridine to form the N,N'-bis(aryl)-N-(2-thiazolin-2-yl)thioureas (III).

Synthesis of sugar N-(2-thiazolin-2-yl)thioureas

1,3,4,6-Tetra- O-acetyl-2-deoxy-2-isothiocyanato-α- or -β- d-glucopyranose ( 4 or 5) was condensed with 2-chloroethylamine hydrochloride in pyridine to afford N,N′-bis(1,3,4,6-tetra- O-acetyl-2-deoxy-α- or -β- d-glucopyranos-2-yl)- N-(2-thiazolin-2-yl)thiourea ( 2 or 3). When the reactions were carried out in ether, 1,3,4,6-tetra- O-acetyl-2-deoxy-2-(2-thiazolin-2-yl)amino-α- and -β- d-glucopyranose ( 6 and 7) were isolated and converted into the mixed N-(2-thiazolin-2-yl)-urea and -thioureas ( 9–12) by reaction with iso(thio)cyanates. Bromine-promoted cyclisation of 1,3,4,6-tetra- O-acetyl-2-( N′-allylthioureido)-2-deoxy-α- d-glucopyranose ( 13) gave a mixture of the diastereomers 1,3,4,6-tetra- O-acetyl-2-[5( R and S)-5-bromomethyl-2-thiazolin-2-yl]amino-2-deoxy-α- d-glucopyranose hydrobromides ( 14 and 15), which was transformed into the analogous N-(2-thiazolin-2-yl)thioureas ( 16–18).

Reaction of Glycosylisothiocyanates with 2-Chloroethylamine. Synthesis and Structure of N-Nucleoside Analogues

Abstract Per-O-acetyl-β--glycopyranosylisothiocyanates (3 and 4) were condensed with 2-chloroethylamine hydrochloride to afford N,N'-bis(per-O-acetyl–β--glycopyranosyl)-N-(2-thiazolin-2-yl)thioureas (5 and 6) through the glycosylaminoheterocycles (7 and 8) as intermediates. Compounds 7 and 8 were converted into N-(2-thiazolin-2-yl)urea or thioureas (9–11) by reaction with iso(thio)cyanates. Compounds 5, 6 and 9–11 show a strong chelated structure due to an intramolecular hydrogen bond, which anchors the E,Z conformation in solution.

ChemInform Abstract: A Reconfirmation of the Reaction of Glucosyl Isothiocyanate with 2‐Chloroethylamine.

AbstractThe glucosyl isothiocyanate (I) is coupled with the chloroethylamine hydrochloride (II) to give the aminothiazoline (III) or the thiourea (IV).

ChemInform Abstract: A Simplified Procedure for Preparing the Cholinergic Neurotoxin 1‐Ethyl‐1‐(2‐hydroxyethyl)aziridinium Ion (AF64A).

AbstractThe 1‐ethyl‐1‐(2‐hydroxyethyl)aziridinium cation (II), a potent neurotoxin, is prepared from the chloroethylamine hydrochloride (I) in a mg‐scale by treatment with stoichiometric amounts of sodium hydroxide in aqueous solution.

Synthesis of 3′-CTNU radiolabelled with 14C in the alkylating moiety and 3H in the carbamoylating moiety

[6-3H]3′-[3-(2-Chloroethyl)-3-nitrosoureido]-3′-deoxythymidine ([3H]3′-CTNU) radiolabelled with 3H in the carbamoylating moiety has been synthesized in high yield by conversion of tritiated 3′-amino-3′-deoxythymidine([3H]3′-ATdR) to [6-3H]3′-[3-(2-chloroethylureido)]-3′-deoxythymidine ([3H]3′-UTdR), followed by nitrosation with N2O3 gas. The title compound radiolabelled with 14C in the alkylating moiety was prepared by conversion of [2-14C]ethanolamine hydrochloride to [1-14C]chloroethylamine hydrochloride, followed by reaction with phosgene to yield [1-14C] chloroethyl isocyanate. This was converted to 3′-3-([1-14C] 2-chloroethylureido)-3′-deoxythymidine([14C]3′-UTdR), and nitrosated to afford 3′-[3-([1-14C] 2-chloroethyl) -3-nitrosoureido]-3′-deoxythymidine ([14C]3′-CTNU). HPLC methodology was developed for the purification of intermediate and final products.

Binary ethylenimine as an inactivant for foot-and-mouth disease virus and its application for vaccine production

Foot-and-mouth disease virus was inactivated with binary ethylenimine formed apart from or directly in the virus suspension by the cyclization of 2-bromoethylamine hydrobromide or 2-chloroethylamine hydrochloride under alkaline conditions. The inactivation rates with binary ethylenimine prepared apart from the virus suspension in dilute sodium hydroxide with either 2-bromoethylamine hydrobromide or 2-chlorethylamine hydrochloride were higher than with pure ethylenimine. When binary ethylenime was prepared directly in the virus suspension only 2-bromoethylamine hydrobromide gave acceptable inactivation rates. The reduced inactivation rates for binary ethylenimine directly prepared in the virus suspension are due to the different cyclization rates of 2-bromoethylamine hydrobromide and 2-chloroethylamine hydrochloride and to the interference of bicarbonate in the cyclization reaction. The complement fixing antigen of foot-and-mouth disease virus was not affected by binary ethylenimine inactivation. Vaccines prepared with foot-and-mouth disease virus inactivated by binary ethylenimine were comparable in their immunogenicity to vaccines prepared with ethylenimine or N-acetylethylenimine used as inactivants. Application of binary ethylenimine in the preparation of foot-and-mouth disease vaccines considerably reduces the potential danger associated with handling pure ethylenimine and other aziridines.

Limb malformation production in chicken embryos treated with nitrogen mustard at 48 hours of incubation.

Nitrogen mustard (methyl bis chloroethylamine hydrochloride), a radiomimetic and cytotoxic agent, has proved to be also a powerful teratogenic agent. When administered to vertebrate embryos at a particular stage of development and at doses which allow survival of the embryo, nitrogen mustard produces a very similar type of malformation in different animal species. Limb malformations were obtained in amphibians, mammals and birds (1,2).

Antineoplastic agents. XIX. N-Bis(2-haloethyl)glycine amides

A number of routes to N-bis(2-fluoroethyl)glycine (IIIa) were explored. Of these, condensation between N-bis(2-fluoroethyl)amine and bromoacetic acid in tetrahydrofuran proved to be the most satisfactory. Reaction between a carbonic anhydride derivative of, for example, glycine IIIa and the appropriate aromatic amine provided the glycine amides summarized by structures IVb-IVi. Treatment of N-bis(2-chloroethyl)glycine hydrochloride with oxalyl chloride at steam-bath temperature yielded N-bis(2-chloroethyl)amine hydrochloride as the major product.

N, N-bis (2-chloroethyl) amides and N, N-bis(2-chloroethyl) hydrazides of carboxylic acids of the furan series

Reaction of N, N-bis(2-chloroethyl)amine hydrochloride with chloroanhydrides of carboxylic acids of the furan series, in chloroform in the presence of pyridine gives N, N-bis(2-chloroethyl)amides of furan carboxylic acid, furylacrylic acid, 5-nitrofuran carboxylic acid, and 5-nitrofurylacrylic acid.

Intra-arterial nitrogen mustard in the treatment of pelvic cancer.

Article1 April 1958INTRA-ARTERIAL NITROGEN MUSTARD IN THE TREATMENT OF PELVIC CANCERIRWIN H. KRAKOFF, M.D., ROBERT D. SULLIVAN, M.D.IRWIN H. KRAKOFF, M.D.Search for more papers by this author, ROBERT D. SULLIVAN, M.D.Search for more papers by this authorAuthor, Article, and Disclosure Informationhttps://doi.org/10.7326/0003-4819-48-4-839 SectionsAboutPDF ToolsAdd to favoritesDownload CitationsTrack CitationsPermissions ShareFacebookTwitterLinkedInRedditEmail ExcerptIn advanced and nonresectable neoplastic disease certain chemical agents have been found to have some effect in slowing the growth or in producing temporary regression of the tumor tissue. Nearly all of the agents which are capable of producing such effects, when administered systemically, also have toxic effects on the bone marrow, liver or other organs. Host toxicity is the limiting factor in dosage, and prevents the use of sufficient amounts of drug to produce drastic effects on the tumor.Klopp et al.1-4reported that in patients with inoperable cancer in whom the principal manifestations of the disease were largely...Bibliography1. KloppBatemanBerryAlfordWinship CTJCNCT: Fractionated regional cancer chemotherapy, Cancer Research 10: 229, 1950. Google Scholar2. KloppAlfordBatemanBerryWinship CTTCJCGNT: Fractionated intra-arterial cancer chemotherapy with methyl bis amine hydrochloride: a preliminary report, Ann. Surg. 132: 811, 1950. CrossrefMedlineGoogle Scholar3. BatemanKloppCromer JCCTJK: Hematologic effects of regional nitrogen mustard therapy, Blood 6: 26, 1951. CrossrefMedlineGoogle Scholar4. CromerBatemanBerryKennellyKloppPlatt JKJCGNJMCTLI: Use of intra-arterial nitrogen mustard therapy in the treatment of cervical and vaginal cancer, Am. J. Obst. and Gynec. 63: 538, 1952. CrossrefMedlineGoogle Scholar5. BiermanShimkinByronMiller HRMBRLER: The effects of intra-arterial administration of nitrogen mustard. V. Congrès internationale du Cancer, 1950, Hermann, Paris, p. 186. Google Scholar6. BiermanByronKelly HRRLKH: Therapy of inoperable visceral and regional metastases by intra-arterial catheterization in man, Cancer Research 11: 236, 1951. Google Scholar7. BonnerThurmanHomburger CDAF: A critical study of regional intra-arterial nitrogen mustard therapy in cancer, Ann. Surg. 136: 912, 1952. CrossrefMedlineGoogle Scholar8. GradyKrantzBrown EGSPF: Treatment of cancer by intermittent injection of nitrogen mustard via cannulated arteries, Ann. Surg. 137: 366, 1953. CrossrefMedlineGoogle Scholar9. BoimanHolzaepfelBarnes REJHAC: Intra-arterial nitrogen mustard in advanced pelvic malignancies, Am. J. Obst. and Gynec. 72: 1319, 1956. CrossrefMedlineGoogle Scholar10. SullivanJonesSchnabelShorey RDRTGJM: The treatment of human cancer with intra-arterial nitrogen mustard (methyl bis (2-chloroethyl) amine hydrochloride) utilizing a simplified catheter technique, Cancer 6: 121, 1953. CrossrefMedlineGoogle Scholar This content is PDF only. To continue reading please click on the PDF icon. Author, Article, and Disclosure InformationAffiliations: New York, N. Y.*Received for publication August 26, 1957.From the Division of Clinical Chemotherapy, Sloan-Kettering Institute for Cancer Research, the Chemotherapy Service of Memorial and James Ewing Hospitals, and the Department of Medicine, Cornell University Medical College.†These studies were supported by research grants C1889 and CY3215 from the National Cancer Institute of the National Institutes of Health, Public Health Service; institutional grants from the American Cancer Society, the Damon Runyon Memorial Fund for Cancer Research, the Lasker Foundation and the Black-Stevenson Foundation.‡Present address: Manhattan Veterans Administration Hospital, New York, N. Y.Requests for reprints should be addressed to Irwin H. Krakoff, M.D., Memorial Center for Cancer and Allied Diseases, 444 East Sixty-eighth Street, New York 21, N. Y. 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