Philip Morris
Application for Research Grant Factors Controlling the Biological Disposition of Pyridine Compounds of Tobacco Smoke
Fields
- Author
- Crooks, L.D.
- Mckennis, H., J.R.
- Area
- JOHN-WARE,JUDY/SHB FILE ROOM
- Type
- FORM, FORM
- BUDG, BUDGET/BUDGET REVIEW
- RESU, RESUME
- SREP, SCIENTIFIC RESEARCH PROPOSAL
- BUDG, BUDGET/BUDGET REVIEW
- Site
- R22
- Request
- Stmn/R1-037
- Named Organization
- Ama
- Ctr, Council for Tobacco Research
- Education + Research Foundation
- Medical College of Va
- Ctr, Council for Tobacco Research
- Named Person
- Bing
- Bowman, E.R.
- Cattell
- Craig, J.C.
- Jacobson
- Larson
- Mckennis, H., J.R.
- Bowman, E.R.
- Document File
- 1003546610/1003547082/Meeting Scientific Advisory Board 670923 670924 Book 1 of 1
- Litigation
- Stmn/Produced
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- Ctr, Council for Tobacco Research
- Master ID
- 1003546610/7082
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-2-
11. Depressor activity from nicotine metabolites.
Edward R. Bowman, H. B. Kennedy, Jr., Einosuke Wada, and
Herbert McKennis, Jr. -
Abstracts of Communications, XXI. International Congress of
Physiological Sciences., 41, Buenos Aires, August 9-15, 1959.
The isolation andistructure of a ketoamide formed in the
metabolism of nicotine.
Herbert McKennis, Jr., Edward R. Bowman, and Lennox B. Turnbull.
Journal of the American Chemical Society, 82, 3974 (1960).
13. Methylation-in the.metabolism of (-)-nicotine.
Lennox B. Turnbull, Edward R. Bowman, and Herbert'McKennis, Jr.
Federation Proceedings, 19, 268 (1960).
14. The excretion and metabolism of nicotine.
Herbert MeKennis, Jr.
Annals of the New York Academy of Sciences, 90, 36 (1960).
15. Norcotinine (desmethylcotinine) as a urinary metabolite of
nornicotine.
Einosuke Wada, Edward R. Bowman, Lennox B. Turnbull, and
Herbert McKennis, Jr.
Journal of Medicinal and:Pharmaceutical Chemistry, 4, 21 (1961).
16. Depressor effects arising from (-)-cotinine.
Joseph F. Borzelleca, Edward R. Bowman, and Herbert McKennis, Jr.
The Pharmacologist, 2, 72 (1960).
17. Oxidation of nicotine-C-14 and nicotine-methyl-C-14 in vivo.
Lennox B. Turnbull, Einosuke Wada, Edward R. Bowman, and
Herbert McKennis, Jr.
Federation Proceedings, 20, 172 (1961).
18. Metabolism,of nicotine in the human.
Edward!R. Bowman, Lennox B. Turnbull, and-Herbert McKennis, Jr.
Virginia Journal of Science, 9, 438 (1948).
19. Degradation of (-)-cotinine in the human.
Herbert McKennis, Jr., and Edward R. Bowman.
Abstracts of Communications, V. International Congress of
Biochemistry, Moscow, August 10-16, 1961, p. 393.
20. The mammalian degradation of (-)-nicotine to 3-pyridylacetic acid
and other compounds.
Herbert McKennis, Jr., Edward R. Bowman, and Lennox B. Turnbull.
Proceedings of the Society for Experimental Biology and Medicine,
107, 145 (1961).
21. Metabolism of (-)-cotinine in the rat.
Is Sorell L. Schwartz, Edward R. Bowman, and Herbert McKennis, Jr.
Virginia Journal of Science, 12, 196 (1961).

-3-
22. Demethylation in the metabolism of (-)-nicotine.
Herbert McKennis, Jr., Lennox B. Turnbull., Sorell L. Schwartz,
Einosuke Tamaki. and Edward R. Bowman.
The Journal of Biological Chemistry, 237, 541 (1962).
.23. Metabolism of (-)-cotinine to a keto acid.
. Sorell L. Schwartz, and Herbert McKennis, Jr.
-Federation Proceedings, 21, 183 (1962).
24. .Studies on the respiratory and cardiovascular effects of (-)-cotinine.
Joseph F. Borzelleca, Edward R. Bowman., and Herbert McKennis, Jr.
The Journal of Pharmacology and Experimental Therapeutics, 137,
313 (1962).
25. Studies on the metabolism of (-)-cotinine in the human.
Edward R. Bowman, and Herbert McKennis, Jr.
The Journal of Pharmacology and Experimental Therapeutics, 135,
306 (1962). _
26. Routes in the mammalian metabolism of (-)-nicotine to
3-pyridylacetic acid.
Sorell L. Schwartz, Edward R. Bowman, and,Herbert McKennis, Jr.
Abstracts of Papers, 16th Tobacco Chemists' Research Conference,
Richmond, Virginia, Sept. 26-28, 1962, p. 7.
27. Studies on the metabolic fate of 3-acetylpyridine.
Lennox B. Turnbull, Edward R'. Bowman, and Herbert McKennis, Jr.
Abstracts of Papers, 16th Tobacco Chemists' Research Conference,
Richmond, Virginia, Sept. 26-28, 1962, p. 6.
28. The corrected structure of a ketoamide arising from the metabolism
of (-)-nicotine.
Herbert McKennis, Jr., Lennox B. Turnbull, Edward R. Bowman, and
Sorell L. Schwartz.
Journal of the American Chemical Society, 84, 4598 (1962).
29. N-Methylation of nicotine and cotinine in vivo.'
Herbert McKennis, Jr.,Lennox B. Turnbull, and Edward R. Bowman.
The Journal of Biological Chemistry, 238, 719 (1963).
30. Studies on-the degradation of the pyrrolidine ring of (-)-nicotine
in vivo. Formation of Y-(3-pyri,dyl)-Y,-oxobutyric acid.
Sorell L. Schwartz, and Herbert Afcf:ennis, Jr.
The Journal of Biological Chemistry, 238, 1807 (1963).
31. The synthesis of hydroxycotinine and studies on its structure.
Herbert McKennis, Jr., Lennox B. Turnbull, Edward R. Bowman, and
Einosuke Tamaki.
Journal of Organic Chemistry, 28, 383 (1963).
32. (-)-Cotinine.
Edward R. Bowman, and Herbert McKennis, Jr.
Biochemical Preparations, 10, 36 (1963).

33. Conjugate formation in the metabolisni of 3-acetylpyridine..'
Lennox B. Turnbull, Edward R. Bowman, and Herbert McKennis, Jr.
Abstracts of Papers, 17th-Tobacco Chemists' Research Conference,
Montreal, Quebec, Canada, Sept. 22-25, 1963, p. 11.
A comparative study of the metabolic release of methyl groups
from a series of N-methylpyridinium compounds.
Herbert McKennis, Jr., Edward'R. Bowman, Antonio Horvath, and
John P. Bederka, Jr. ~
Nature, 202, 699 (1964).
i
35. Mammalian degradation of (-)-demethylcotinine.
Sorell L. Schwartz, and Herbert McKennis, Jr.
Nature, 202, 594 (1964).
36. Disposition and fate of (-)-cotinine-H3 in the mouse.
Edward R: Bowman, Eskil Hansson, Lennox B. Turnbull, Herbert
McKennis, Jr., and Carl G_ Schmiterlt5w.
The Journal of Pharmacology and!Experimental Therapeutics,
143, 301 (1964).
40. Alternate routes in the metabolic degradation of the pyrrolidine
ring of nicotine.
Herbert McKennis, Jr., Sorell L. Schwartz, and-Edward R. Bowman.
The Journal of Biological Chemistry,, 239, 3990 (1964).
Herbert MeF:ennis, Jr., Sorell L. Schwartz, Lennox B. Turnbull,
Einosuke Tamaki, and Edward R. Bowman.
The Journal of Biological Chemistry, 239, 3981 (1964).
37. Additional routes in the metabolism:of 3-acetylpyridine.
Herbert McKennis, Jr., Lennox B. Turnbull, and Edward R. Bowman.
The Journal of Biological Chemistry, 239, 121S (1964).
38. Effect of cotinine and other nicotine metabolites in-yitro
on duod'enum-and;ileum segments.
K. S. Kim, Joseph F. Borzelleca, Edward R. Bowman, and
Herbert McKennis, Jr.
Federation Proceedings, 23, 330. (1964).
39. The metabolic formation of y-(3-pyridyl)-y-hydroxybutyric acid and its
possible intermediary role in the mammalian metabolism of nicotine.
41. Metabolism of 3-acetylpyridine to an analog of mandelic acid.
Lennox B. Turnbull, C. N1. Lukhard,, and Herbert McKennis, Jr.
Toxicology and Applied Pharmacology, 6, 362 (1964).
42. Disposition and fate of nicotine in animals.
Herbert McKennis, Jr.
Tobacco Alkaloids and Related Compounds, U. S. Von Euler, editor,
Pergamon Press, Oxford, 1965, p. 53.

43. Urinary excretion of conjugate forms.of 1-(3-pyridyl)ethanol aftei
administration of 3-acetylpyridine.
Herbert McKennis, Jr., Lennox B. Turnbull, Edward R. Bowman., and
C. Norman Lukhard.
The Journal of Biological Chemistry, 241, 1878 (1966).
44. The structure of dibromoticonine, a bromination product of nicotine.
New York, N. Y., Sept. 12-16, 1966.
Abstracts of Papers, 152nd Meeting, American Chemical Society,
Herbert McKennis, Jr., Edward R. Bowman, L. D. Quin, and R. C. Denney:
45. Studies on the synthesis and metabolism*of 4-(3-pyridyl)-4-
methylaminobutyric acid-4-14C.
Paolo L. Morselli, Edward R. Bowman, Helen H. 0ng, and!
Herbert McKennis, Jr.
Virginia Journal of Science, 17, 345 (1966).
46. The fate and distribution of 1-(3-pyridyl)ethanol methiodide in
relation to the toxicity.of 1-(3-pyridyl)ethanol and 3-acetylpyridine.
John P. Bederka, Jr., Eskil Hansson, Edward R. Bowman, and
Herbert McKennis, Jr.
Biochemical Pharmacology, 16, 1 (1967).
47. Studies on the separation of acidic metabolites of nicotine by
gas chromatography.
Herbert McKennis, Jr., Edward R. Bowman, and Mohammad Saeed Dar.
Virginia Journal of Science, 18, 13 (1967).
48. Pharmacological action and intermediary role of 5-(3-
-pyridyl)tetrahydrofuranone-2.
Edward R. Bowman, Pavol lirdina and; Herbert McKennis, Jr.
Federation Proceedings, 26, 616 (1967).
49. Metabolism of (')-Cotinine-2-Z 4C in the rat.
Paolo L. Morselli, Helen H. Ong, Edward R. Bowman, and
Herbert McKennis, Jr.
Journal of Medicinal Chemistry, in press.
50. 1`1ethylamine metabolism in normal and, mao-inhibitor-treated
Paolo L. biorselli, Edward R. Bowman,, and Herbert McKennis,
The Pllarmacologist, in press.
rats.
Jr.

-6-
51. Onthe congeners of whiskey.
Herbert McKennis, Jr.,:-and;Harvey B. Haag.
Journal of the American Geriatrics Society, 7, 848 (1959).
52. ,Depressor effects arising from (-)-cotinine.
Joseph F. Borzelleca, Edwar.d R. Bowman, and Herbert McKennis, Jr.
The Pharmacologist, 2, 72 (1960).
53. The excretion and metabolism of nicotine.
Herbert McKennis, Jr.
Annals of the New York Academy of Sciences, 90, 36 (1960).
54. The isolation and structure of a ketoamide formed in the metabolism
of nicotine.
Herbert McKennis, Jr., Edward R. Bowman, and: Lennox B. Turnbull.
. Journal of the American Chemical Society, 82, 3974 (1960).
5S. Methylation in the metabolism of (-)-nicotine.
Lennox B. Turnbull, Edward R. Bowman, and Herbert McKennis, Jr.
Federation Proceedings, 19, 268' (1960).
56. L-y-Glutamylhydrazine and the metabolism of hydrazine.
Herbert McKennis, Jr., Allan S. Yard, Elizabeth J. Adair, and
J. H. Weatherby.
The Journal of Pharmacology and Experimental Therapeutics, 131,
152 (1961). `
57. Demethylation in the metabolism,of (-)-nicotine in vivo.
Herbert McKennis, Jr., Einosuke Wada, Edward R. Bowman, and
Lennox B. Turnbull.
Nature, 190, 910 (1961).
58. Norcotinine (Desmethylcotinine) as a urinary metabolite of
nornicotine.
Einosuke R'ada, Edward R. Bowman, Lennox B. Turnbull, and
Herbert McKennis, Jr.
Journal of Medicinal and Pharmaceutical Chemistry, 4, 21 (1961).
59. The isolation of 3-pyridylacetic acidi, a urinary metabolite
of (-)-cotinine.
Edward R. Bowman,, Lennox B. Turnbull, and Herbert McKennis, Jr.
Abstracts of Papers, 14th Tobacco Chemists'- Research Conference,
Oct. 13-14, 1960, Winston-Salem, North-Carolina.
60. Oxidation,of nicotine-C14 and nicotine-methyl-C14 in viyo.
Lennox B. Turnbull, Einosuke iiada-, Edward R. Bowman, and
Herbert McKennis, Jr. "
Federation Proceedings, 20, 172 (1961).
61. Inhibition by thyroxine of y-aminobutyrate-a-ketoglutarate
transaminasc.
Antonio Horva:th, Fernando Orrego, and Herbert McKennis, Jr.
Federation Proceedings, 20, S (1961).

62. Factors controlling the metabolism of Y-aminobutyric acid.
Antonio Horvath, Fernando Orrego, and Herbert McKennis, Jr.
The Journal of Pharmacologyy and Experimental Therapeutics, 134,
,222 (1961).
63. Mammalian degradation of (-)-nicotine to 3-pyridylacetic acid
and other compounds.
.
Herbert McKennis, Jr., Edward R. Bowman, and Lennox B: Turnbull.
Proceedings of the Society for Experimental Biology and Medicine,
107, 145 (1961).
64. Selective toxicity. (Book review).
Herbert McKennis, Jr.
Revista Medica de Chile, 88, 864 (1960).
65. Los oxoesteroides, el uso de-hidrazidos fen6licos para su-
detecci6n, caracterizaci6n y medici6n,. (Book review).
Herbert McKennis, Jr.
Revista Medica de Chile, 88, 626 (1960).
66. Metabolism of nicotine in the human.
Edward R. Bowman, Lennox B. Turnbull, and Herbert McKennis, Jr.
Virginia Journal of Science, 9, 438 (1958).
67. Metabolism of (-)-cotinine in the rat.
Sorell L. Schwartz, Edward:R. Bowman, andiHerbert McKennis, Jr.
Virginia Journal of Science, 12, 196 (1961).
68. Degradation of (-)!-cotinine in the human..
Herbert McKennis, Jr., and Edward,R. Bowman.
Abstracts of Communications, V. International Congress of
Biochemistry, Moscow, August 10-16, 1961, p. 393.
69. Aspects of the metabolism of isoniazid and acetylisoniazid in
the human and the dog.
Allan S. Yard, and Herbert McKennis, Jr.
Journal of Medicinal and Pharmaceutical Chemistry, 5, 196 (1962).
70. Demethylation in the metabolism of (-)-nicotine.
,
Herbert McKennis, Jr., Lennox B. Turnbull, Sorell L. Schwartz,
Einosuke Tamaki, and Edward R. Bowman..
The Journal of Biol~ogical Chemistry, 237, 541 (1962).
Inhibition of the catabolism of aspartic-4-C14 acid by thyroxine
in vivo.
Antonio Horvath, andHerbert McKennis, Jr.
Enzymologia
24
91 (1962)
N
0
,
,
.
Studies on-the metabolism of (-)-cotinine in the human. G.?
C11
.~
Edward R. Bowman, and Herbert McKennis, Jr. ~
The Journal of Pharmacology and Experimental Therapeutics, ~
135, 306 (1962).
~

73. Metabolism.of (-)-cotinine to a keto acid.
Sorell L. Schwartz, and Herbert McKennis, Jr.
Federation Proceedings, 21, 183 (1962).
74. The_excretion and metabolism of triethylene glycol.
Herbert McKennis, Jr., Robert A. Turner, Lennox B: Trunbull,
.and Edward R. Bowman.
W. W. Muelder, M. P. Neidhardt, and"Carl L. Hake. -
Richard Henderson, Herbert G. Nadaeu, and Samuel Spencer.
Toxicology and Applied Pharmacology, 4, 411 (1962)1.
75. Studies on the respiratory and cardiovascular effects of
(-)-cotinine.
Joseph F. Borzelleca, Edward R. Bowman, and Herbert McKennis, Jr.
The Journal of Pharmacology and-Experimental Therapeutics, 137,
313 (1962).
76. Routes in the mammalian metabolism of (-)-nicotine to
3-pyridylacetic acid.
Sorell L. Schwartz, Edward R. Bowman, and Herbert hlcKennis, Jr.
Abstracts of Papers, 16th. Tobacco Chemists' Research Conference,
Sept. 26-28, 1962, Richmond, Virginia, p. 7.
77. Studies on the metabolic fate of 3-acetylpyridine.
Lennox B. Turnbull, Edward R. Bowman, and Herbert McKennis, Jr.
Abstracts of Papers, 16th Tobacco Chemists' Research Conference,
Sept. 26-28, 1962, Richmond, Virginia, p. 6.
78. Acetylhydrazine as an intermediate inthe metabolism of
aroylhydrazines.
Lennox B. Turnbull, Allan S. Yard, and Herbert McKennis, Jr.
Journal of Medicinal and Pharmaceutical Chemistry, 5, 1327 (1962).
79. N-Methylation of nicotine and cotinine in vivo.
Herbert McKennis, Jr., Lennox B. Turnbull~, aE-d Edward R. Bowman.
The Journal of Biological Chemistry, 238, 719.(1963).
>
80. The synthesis of hydroxycotinine and:studies on its structure.
Herbert McKennis, Jr., Lennox B. Turnbull, Edward R. Bowman,
and Einosuke Tamaki.
Journal of Organic Chemistry, 28, 383 (1963).
81. The corrected structure of a ketoamide arising from the
metabolism of (-)-nicotine.
Herbert McKennis, Jr., Lennox B. Turnbull, Edward R. Bowman,
82.
and Sorell L. Schwartz.
Journal of the American Chemical Society, 84~,
4598 (1962).
(-)-Cotinine.
Edward R. Bowman, and Herbert McKennis, Jr.
Biochemical Preparations, 10., 36 (1963).
ti

83.. Studies on the degradation of the pyrrolidine ring of (-)-nicotine
in vivo. Formationm of.7-(3-pyridyl)-Y-oxobutyric acid.
Sorell L., Schwartz, and Hkerbert McKennis, Jr.
The Journal of Biological Chemistry, 238, 1807 (1963).
84. Conjugate formation in the metabolism of 3-acetylpyridine.
Lennox R. Turnbull, Edward R. Bowman, and Herbert McKennis, Jr.
Abstracts of Papers, 17th Tobacco Chemists', Research Conference,
Sept. 22-25, 1963, Montreal, Quebec, p. 11.
85. Metabolic release of methyl groups from a series of
N-methylpyridinium compounds.
Herbert McKennis, Jr., Edward R. Bowman, Antonio Horvath,
and John P. Bederka, Jr.
Nature, 202, 699 (1964).
86. Mammalian degradationbf (-)-demethylcotinine.
Sorell L. Schwartz, and Herbert McKennis,, Jr.
Nature, 202, 594 (1964).
87. Disposition and fate of (-)-cotinine-H3'in the mouse.
Edward R. Bowman, Eskil Hansson, Lennox B. Turnbull,
Herbert McKennis, Jr.; and Carl G. Schmiterlbw.
The Journal of Pharmacology and:Experimental Therapeutics,
143, 301 (1964).
88. Additional routes in the metabolism of 3-acetylpyridine.
Herbert McKennis, Jr., Lennox B. Turnbull, and Edtaard R. Bowman.
The Journal of Biological Chemistry, 239, 1215 (1964).
89. The metabolic formation of Y-(3-pyridyl)-y-hydroxybutyric acid
and its possible intermediary role in the mammalian metabolism
of nicotine.
Herbert McKennis, Jr., Sorell L. Schwartz, Lennox B. Turnbull,
Einosuke Tamaki, and Edward R. Bowman.
The Journal of Biological Chemistry, 239, 3981 (1964).
90. Alternate routes in the metabolic degradation of the pyrrolidine
ring of nicotine.
Herbert McKennis, Jr., Sorell L. Schwartz, and Edward R. Bowman.
The Journal of Biological Chemistry, 239, 3990 (1964).
91. Effect of cotinine and other nicotine nmetabolites in vitro on
duodenum and ileum segments.
K. S. Kim, Joseph F. Borzelleca, Edward R. Bowman, and
Herbert McKennis, Jr.
Federation Proceedings, 23, 330 (1964).
92. Metabolism of 3-acetylpyridine to an, analog of mandelic acid.
Lennox B. Turnbull, C. N_ Lukhard, and Herbert McKennis, Jr.
Toxicology and Applied°Pharmacology, 6, 362 (1964).
..~,.~._.;~::....,..d.~~...~.».-.: ~~w...

.-10-
+ 93.
Disposition and fate of nicotine irn animals.
Herbert McKennis, Jr. '
Tobacco Alkaloids and Related Compounds, U. S. Von Euler,
editor, Perganon Press, Oxford, 1965, p.'53.
94. Viewpoints of the study of drug toxicity. (Book review).
Herbert McKennis, Jr.
American Journal of Pharmaceutical Education, 28,469 (1964).
95. Urinary excretion of conjugate forms of 1-(3-pyridyl)ethanol
after administration of 3-acetylpyrid2ne.
Herbert McKennis, Jr., Lennox B. Turnbull, Edward R. Bowman,
and C. Norman Lukhard.
The Journal of Biological Chemistry, 241,.1878 (1966).
96. The structure of dibromoticonine, a bromination product of nicotine.
Herbert McKennis, Jr., Edward R. Bowman, L. D. Quin, and
R. C. Denney.

Papers Published
During the Period of This Report
i
1. Urinary excretion of conjugate forms of 1-(3-pyridyl)ethanol after
administration of 3-acetylpyridine.
Herbert McKennis, Jr., Lennox B. Turnbull, Edward R. Bowman,, and
C. Norman Lukhard.
The Journal of Biological Chemistry, 241, 1878 (1966).
2. The structure of dibromoticonine, a bromination.product of nicotine.
Herbert McKennis, Jr., Edward R. Bowman, L. D. Quin, and R. C. Denney.
Abstracts of Papers, 152nd Meeting, American Chemical Society,
New York, N. Y., Sept. 12-16, 1966.
3. Studies on the synthesis and metabolism of 4-(3-pyridy.l)-4-
methylam%nobutyric acid-4~I`'C.
Paolo L. Morselli, Edward R. Bowman, Helen H. Ong, and
Herbert McKennis, Jr.
, Virginia Journal of Science, 17, 345 (1966).
4. The fate and distribution, of I-(3-pyridyl)ethanol methiodide im
relation to the toxicity of 1-(3-pyridyl)ethanol and 3-acetylpyridine.
John P. Bederka, Jr., Eskil Hansson, Edward R. Bowman, and
Herbert McKennis, Jr.
Biochemical Pharmacology, 16, 1 (1967).
5. Studies on the separation of acidic metabolites of nicotine by
gas chromatography. `
Herbert bicKemtis, Jr., Edward R. Bowman, and Mohammad Saeed Dar.
Virginia Journal of Science., 18, 13 (1967).
6. Pharmacological action and intermediary role of 5-(3-
pyrid'y1)tetrahydrofuranone-2. -
Edward R. Bowman, Pavol lirdina and Herbert McKennis, Jr.
Federation Proceedings, 26, 616 (1967).
7. b1etabolism of (=)-cotinine-2-14C in the rat.
Paolo L. Morselli, Helen H. Ong, Edward R. Bowman, and
Herbert McKennis, Jr.
Journal of Medicinal Chemistry, in press.
8. Methylamine metabolism in normal and mao-inhibitor-treated rats. F.1
Paolo L. Morselli, Edi,rard~ R. Bowman, and Herbert McKennis, Jr. O
The Pharmacologist, in press. CO
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