Molecular geometry and adrenergic drug activity

P. N. Patil, Duane Miller, U. Trendelenburg

Research output: Contribution to journalReview article

166 Citations (Scopus)

Abstract

The literature on the relationship between stereochemical structure and its influence on the biochemical and pharmacologic activity of adrenergic drugs has been reviewed. For the proper appreciation of the steric structure activity relationship, stereochemical definitions and notations are provided. Throughout the review, the value of stereoisomers as a tool to study and dissociate various drug actions has been emphasized. At the adrenergic neuroeffector junction the enzymes which are involved in the biosynthesis and metabolic degradation of norepinephrine show marked stereoselectivity. As a matter of fact, stereoisomers of tyrosine were used in early studies to dissociate activity of tyrosinase from that of tyrosine hydroxylase. Only the latter enzyme exhibits a high degree of stereoselectivity (276). The enzymatic decarboxylation proceeds with the retention of configuration at the α carbon atom of (-) α methyldopa (38) and the β hydroxylation is stereospecific (152, 208, 389). These processes are very important in understanding the formation of (-) α methylnorepinephrine from (-) α methyldopa or formation of corresponding false neurotransmitters from (-) α methyl m tyramine and (+) amphetamine. Recently, the isolation of isoquinoline alkaloids has been demonstrated from urine of a patient treated with (-) dopa (334). A study of the epiphysis and retention of stereoisomeric isoquinoline alkaloids by the storage vesicles should be rewarding. rheumatoid references).

Original languageEnglish (US)
Pages (from-to)323-392
Number of pages70
JournalPharmacological Reviews
Volume26
Issue number4
StatePublished - 1974
Externally publishedYes

Fingerprint

Methyldopa
Stereoisomerism
Alkaloids
Adrenergic Agents
Neuroeffector Junction
Nordefrin
Dihydroxyphenylalanine
Epiphyses
Decarboxylation
Monophenol Monooxygenase
Tyrosine 3-Monooxygenase
Amphetamine
Enzymes
Structure-Activity Relationship
Hydroxylation
Neurotransmitter Agents
Tyrosine
Norepinephrine
Carbon
Urine

All Science Journal Classification (ASJC) codes

  • Pharmacology

Cite this

Patil, P. N., Miller, D., & Trendelenburg, U. (1974). Molecular geometry and adrenergic drug activity. Pharmacological Reviews, 26(4), 323-392.

Molecular geometry and adrenergic drug activity. / Patil, P. N.; Miller, Duane; Trendelenburg, U.

In: Pharmacological Reviews, Vol. 26, No. 4, 1974, p. 323-392.

Research output: Contribution to journalReview article

Patil, PN, Miller, D & Trendelenburg, U 1974, 'Molecular geometry and adrenergic drug activity', Pharmacological Reviews, vol. 26, no. 4, pp. 323-392.
Patil, P. N. ; Miller, Duane ; Trendelenburg, U. / Molecular geometry and adrenergic drug activity. In: Pharmacological Reviews. 1974 ; Vol. 26, No. 4. pp. 323-392.
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