Chemistry of opioids

327 Pages·2011·4.791 MB·English

by  Noritaka Chida (auth.), Hiroshi Nagase (eds.)

299
Topics in Current Chemistry
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M. Venturi P. Vogel C.-H. Wong H. Wong H. Yamamoto
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Chemistry of Opioids
Volume Editor: Hiroshi Nagase
With Contributions by
S.N. Calderon (cid:1) N. Chida (cid:1) H. Fujii (cid:1) S. Hirono (cid:1) S.M. Husbands (cid:1)
J.W. Lewis (cid:1) K.M. Lovell (cid:1) A. Lozama (cid:1) H. Nagase (cid:1)
K.M. Prevatt-Smith (cid:1) T.E. Prisinzano (cid:1) H. Schmidhammer (cid:1)
M. Spetea (cid:1) N. Yamaotsu
Editor
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KitasatoUniversity
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ISSN0340-1022 e-ISSN1436-5049
ISBN978-3-642-18106-1 e-ISBN978-3-642-18107-8
DOI10.1007/978-3-642-18107-8
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Preface
AspartoftheTopicsinCurrentChemistryseries,thisvolume,entitled“Chemistry
ofOpioids,”presentstheprogressmadeinopioidresearchoverthepast5yearsin
thesynthesisandpharmacologyofopioids.
In1803,morphinewasfirstisolatedbyaGermanpharmacologist,Sertu¨rner,and
itsstructurewaslaterdetermined.Sincethen,manyresearchgroupshavetriedtosyn-
thesizeanidealanalgesicwithoutaddictiveproperties.Inthecourseofthosestudies,
anumberofopioidsweresynthesized.Morphinehasaunique4,5-epoxymorphinan
skeleton,whichcomprisesfivesequentialasymmetriccentersandaphenolichydroxy
group, a 4,5-epoxy ring, and a basic nitrogen. Due to this complex structure, early
researchgroupscouldnotsynthesizemorphine.Therefore,theytriedtodesigndrugs
with simpler structures that could be manufactured as an industrial product. These
trials produced many drugs, including pentazocine (benzomophan), butorphanol,
levorphanol(morphinan),pethidine(phenylpiperidine),fentanyl(anilinopiperidine),
etc. However, these compounds could not provide analgesics without addiction.
In 1975, when endogenous opioids were isolated, many researchers expected to be
able to produce a drug without addictive properties, and many peptide derivatives
were synthesized. Unfortunately, these opioid peptide mimetics also had addictive
properties,despitethefactthattheywerederivedfromendogenoussubstances.
Nevertheless,opioidresearchersdidnotgiveuptheirdreams.Thefirstcluewas
thattherewerethreetypesofopioidreceptors(m,d,k).Thisexplainedthediverse
pharmacological effects of the many synthetic drugs. Many of the syntheses and
pharmacologies of drugs produced before the early 1980s have been described
in detail in two excellent books published in 1986, entitled Opioid Analgesics;
Chemistry and Receptor and Opiates. After that, research focused on the k and d
opioid receptor types. In the 1990s, extensive research was conducted in mul-
tiple efforts to synthesize k selective agonists. However, there is no current book
regardingtheprogressinthewholeopioidfieldofd-andk-typeselectiveligands.
In particular, in the 1990s, a vast number of U-50,488H (discovered by Upjohn
Company) derivatives were synthesized to produce a nonaddictive drug. Unfortu-
nately,thesederivativesshowedaversiveeffects(psychotomimetics),anddevelop-
mentwassuspendedintheearlystages,bothasananalgesicandasanantipruritic
ix