,
, Wilson and Gisvold’s
Textbook of
ORGANIC MEDICINAL
AND PHARMACEUTICAL
CHEMISTRY
T W E L F T H E D I T I O N
Edited by
John M. Beale, Jr., PhD
Associate Professor of Medicinal Chemistry
Division of Basic and Pharmaceutical Sciences
St. Louis College of Pharmacy
Saint Louis, Missouri
John H. Block, PhD, RPh
Professor Emeritus, Medicinal Chemistry
Department of Pharmaceutical Sciences
College of Pharmacy
Oregon State University
Corvallis, Oregon
, Editor: David B. Troy
Product Manager: Meredith L. Brittain
Vendor Manager: Kevin Johnson
Designer: Holly McLaughlin
Compositor: Absolute Service, Inc./Maryland Composition
12th Edition
Copyright © 2011 by Lippincott Williams & Wilkins, a Wolters Kluwer business.
First Edition, 1949 Fifth Edition, 1966 Ninth Edition, 1991
Second Edition, 1954 Sixth Edition, 1971 Tenth Edition, 1998
Third Edition, 1956 Seventh Edition, 1977 Eleventh Edition, 2004
Fourth Edition, 1962 Eighth Edition, 1982
351 West Camden Street 530 Walnut Street
Baltimore, MD 21201 Philadelphia, PA 19106
Printed in The People’s Republic of China
All rights reserved. This book is protected by copyright. No part of this book may be reproduced or transmitted
in any form or by any means, including as photocopies or scanned-in or other electronic copies, or utilized by any
information storage and retrieval system without written permission from the copyright owner, except for brief
quotations embodied in critical articles and reviews. Materials appearing in this book prepared by individuals as
part of their official duties as U.S. government employees are not covered by the above-mentioned copyright. To
request permission, please contact Lippincott Williams & Wilkins at 530 Walnut Street, Philadelphia, PA 19106,
via email at , or via Web site at http://www.lww.com (products and services).
9 8 7 6 5 4 3 2 1
Library of Congress Cataloging-in-Publication Data
Wilson and Gisvold’s textbook of organic medicinal and pharmaceutical chemistry. — 12th ed. / edited by John
M. Beale, Jr., John H. Block.
p. ; cm.
Includes bibliographical references and index.
ISBN 978-0-7817-7929-6
1. Pharmaceutical chemistry. 2. Chemistry, Organic. I. Wilson, Charles Owens, 1911- II. Beale, John Marlowe.
III. Block, John H. IV. Title: Textbook of organic medicinal and pharmaceutical chemistry.
[DNLM: 1. Chemistry, Pharmaceutical. 2. Chemistry, Organic. QV 744 W754 2011]
RS403.T43 2011
615'.19—dc22
2009043714
DISCLAIMER
Care has been taken to confirm the accuracy of the information present and to describe generally accepted prac-
tices. However, the authors, editors, and publisher are not responsible for errors or omissions or for any con-
sequences from application of the information in this book and make no warranty, expressed or implied, with
respect to the currency, completeness, or accuracy of the contents of the publication. Application of this informa-
tion in a particular situation remains the professional responsibility of the practitioner; the clinical treatments
described and recommended may not be considered absolute and universal recommendations.
The authors, editors, and publisher have exerted every effort to ensure that drug selection and dosage set forth
in this text are in accordance with the current recommendations and practice at the time of publication. However,
in view of ongoing research, changes in government regulations, and the constant flow of information relating to
drug therapy and drug reactions, the reader is urged to check the package insert for each drug for any change in
indications and dosage and for added warnings and precautions. This is particularly important when the recom-
mended agent is a new or infrequently employed drug.
Some drugs and medical devices presented in this publication have Food and Drug Administration (FDA)
clearance for limited use in restricted research settings. It is the responsibility of the healthcare provider to ascer-
tain the FDA status of each drug or device planned for use in their clinical practice.
To purchase additional copies of this book, call our customer service department at (800) 638-3030 or fax orders
to (301) 223-2320. International customers should call (301) 223-2300.
Visit Lippincott Williams & Wilkins on the Internet: http://www.lww.com. Lippincott Williams & Wilkins cus-
tomer service representatives are available from 8:30 am to 6:00 pm, EST.
, Wilson and Gisvold’s
Textbook of
ORGANIC MEDICINAL
AND PHARMACEUTICAL
CHEMISTRY
T W E L F T H E D I T I O N
Edited by
John M. Beale, Jr., PhD
Associate Professor of Medicinal Chemistry
Division of Basic and Pharmaceutical Sciences
St. Louis College of Pharmacy
Saint Louis, Missouri
John H. Block, PhD, RPh
Professor Emeritus, Medicinal Chemistry
Department of Pharmaceutical Sciences
College of Pharmacy
Oregon State University
Corvallis, Oregon
, Editor: David B. Troy
Product Manager: Meredith L. Brittain
Vendor Manager: Kevin Johnson
Designer: Holly McLaughlin
Compositor: Absolute Service, Inc./Maryland Composition
12th Edition
Copyright © 2011 by Lippincott Williams & Wilkins, a Wolters Kluwer business.
First Edition, 1949 Fifth Edition, 1966 Ninth Edition, 1991
Second Edition, 1954 Sixth Edition, 1971 Tenth Edition, 1998
Third Edition, 1956 Seventh Edition, 1977 Eleventh Edition, 2004
Fourth Edition, 1962 Eighth Edition, 1982
351 West Camden Street 530 Walnut Street
Baltimore, MD 21201 Philadelphia, PA 19106
Printed in The People’s Republic of China
All rights reserved. This book is protected by copyright. No part of this book may be reproduced or transmitted
in any form or by any means, including as photocopies or scanned-in or other electronic copies, or utilized by any
information storage and retrieval system without written permission from the copyright owner, except for brief
quotations embodied in critical articles and reviews. Materials appearing in this book prepared by individuals as
part of their official duties as U.S. government employees are not covered by the above-mentioned copyright. To
request permission, please contact Lippincott Williams & Wilkins at 530 Walnut Street, Philadelphia, PA 19106,
via email at , or via Web site at http://www.lww.com (products and services).
9 8 7 6 5 4 3 2 1
Library of Congress Cataloging-in-Publication Data
Wilson and Gisvold’s textbook of organic medicinal and pharmaceutical chemistry. — 12th ed. / edited by John
M. Beale, Jr., John H. Block.
p. ; cm.
Includes bibliographical references and index.
ISBN 978-0-7817-7929-6
1. Pharmaceutical chemistry. 2. Chemistry, Organic. I. Wilson, Charles Owens, 1911- II. Beale, John Marlowe.
III. Block, John H. IV. Title: Textbook of organic medicinal and pharmaceutical chemistry.
[DNLM: 1. Chemistry, Pharmaceutical. 2. Chemistry, Organic. QV 744 W754 2011]
RS403.T43 2011
615'.19—dc22
2009043714
DISCLAIMER
Care has been taken to confirm the accuracy of the information present and to describe generally accepted prac-
tices. However, the authors, editors, and publisher are not responsible for errors or omissions or for any con-
sequences from application of the information in this book and make no warranty, expressed or implied, with
respect to the currency, completeness, or accuracy of the contents of the publication. Application of this informa-
tion in a particular situation remains the professional responsibility of the practitioner; the clinical treatments
described and recommended may not be considered absolute and universal recommendations.
The authors, editors, and publisher have exerted every effort to ensure that drug selection and dosage set forth
in this text are in accordance with the current recommendations and practice at the time of publication. However,
in view of ongoing research, changes in government regulations, and the constant flow of information relating to
drug therapy and drug reactions, the reader is urged to check the package insert for each drug for any change in
indications and dosage and for added warnings and precautions. This is particularly important when the recom-
mended agent is a new or infrequently employed drug.
Some drugs and medical devices presented in this publication have Food and Drug Administration (FDA)
clearance for limited use in restricted research settings. It is the responsibility of the healthcare provider to ascer-
tain the FDA status of each drug or device planned for use in their clinical practice.
To purchase additional copies of this book, call our customer service department at (800) 638-3030 or fax orders
to (301) 223-2320. International customers should call (301) 223-2300.
Visit Lippincott Williams & Wilkins on the Internet: http://www.lww.com. Lippincott Williams & Wilkins cus-
tomer service representatives are available from 8:30 am to 6:00 pm, EST.
