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2 Isoquinoline Alkaloids

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Natural Poisons and Venoms
This chapter is in the book Natural Poisons and Venoms
2 Isoquinoline Alkaloids2.1 Chemistry and BiogenesisThe isoquinoline alkaloids are one of the largest groups of natural substances. Morethan 2,500 representatives are known. They have either an isoquinoline or a 1,2,3,4-tetrahydroisoquinoline ring system as base structural feature. Further rings or ringsystems can be fused. Alkaloids, in which ring A (fused pyridine ring) is extended,e.g., alkaloids of the protopine or rhoeadine type, are also assigned to them (over-views [265, 313, 318, 320,25, 42, 43, 129]).The following types of isoquinoline alkaloids are found in pharmacologically andtoxicologically significant plants:–benzylisoquinoline or tetrahydrobenzylisoquinoline type, e.g., papaverine, armepa-vine, coclaurine, higenamine and reticuline (Fig. 2.1, overviews [372,117:IV:p.29,VII:p. 423, X: p. 402; XX: p. 401]),–spirobenzylisoquinoline type, e.g., fumaricine, fumariline, fumaritine and parfu-mine (Fig. 2.1, overviews [274, 279,117: XIII: p. 165]),–proaporphine type, e.g., amuronine (Fig. 2.1) and amuroline,–bisbenzylisoquinoline type, e.g., aromoline, berbamine, calfatimine, chondrocur-arine, chondrocurine, curine, isotetrandine, Nb-norchondrocurine, obamegine,oxyacanthine and (+)-tubocurarine (Fig. 2.1, overviews [120,117: IV: p. 199; VII:p. 439; IX: p. 133; XIII: p. 303, XVI: p. 249, XXX: p. 1]),–phthalidisoquinoline and secophthalidisoquinoline type, e.g., adlumidiceine, ao-bamidine, (+)-bicuculline, capnoidine, corlumine,α-hydrastine, narceine, nosca-pine (also known as narcotine) and 5ʹ-desmethylnarcotine (Fig. 2.1, overviews [48,117: IV: p. 167, VII: p. 433, IX: p. 117, XXIV: p. 253]),–cularine and secocularine type, e.g., breoganine, cularine, noyaine and secocular-idine (Fig. 2.2, overviews [117: IV: p. 249; X: p. 463, XXIX: p. 287]),–aporphine type, e.g., aporheidine, aporheine, boldine, (+)-bulbocapnine, corydine,corytuberine, dicentrine, domesticine, glaucine, isoboldine, isocorydine, (+)-iso-thebaine, magnoflorine,N-methylasimilobine, predicentrine, orientidine and ste-phanine (Fig. 2.2, overviews [55, 124, 306,117: IV: p. 119, IX: p. 1]), the aporphinetype also includes apomorphine, an artifact resulting from exposure of morphineto strong acids,–isopavine type, e.g., amurensine andamurensinine (Fig. 2.2, overview [117:XXXI: p. 317]),–promorphinane type, e.g., salutaridine,–morphinane type, e.g., amurine, codeine, morphine, nudaurine, oripavine andthebaine (Fig. 2.2, overviews [4, 57,117: II: p. 1 and p. 161; VI: p. 219, XIII: p. 1]);heroin (diacetylmorphine, diamorphine), a semisynthetic derivative of morphine,https://doi.org/10.1515/9783111136219-002
© 2024 Walter de Gruyter GmbH, Berlin/Boston

2 Isoquinoline Alkaloids2.1 Chemistry and BiogenesisThe isoquinoline alkaloids are one of the largest groups of natural substances. Morethan 2,500 representatives are known. They have either an isoquinoline or a 1,2,3,4-tetrahydroisoquinoline ring system as base structural feature. Further rings or ringsystems can be fused. Alkaloids, in which ring A (fused pyridine ring) is extended,e.g., alkaloids of the protopine or rhoeadine type, are also assigned to them (over-views [265, 313, 318, 320,25, 42, 43, 129]).The following types of isoquinoline alkaloids are found in pharmacologically andtoxicologically significant plants:–benzylisoquinoline or tetrahydrobenzylisoquinoline type, e.g., papaverine, armepa-vine, coclaurine, higenamine and reticuline (Fig. 2.1, overviews [372,117:IV:p.29,VII:p. 423, X: p. 402; XX: p. 401]),–spirobenzylisoquinoline type, e.g., fumaricine, fumariline, fumaritine and parfu-mine (Fig. 2.1, overviews [274, 279,117: XIII: p. 165]),–proaporphine type, e.g., amuronine (Fig. 2.1) and amuroline,–bisbenzylisoquinoline type, e.g., aromoline, berbamine, calfatimine, chondrocur-arine, chondrocurine, curine, isotetrandine, Nb-norchondrocurine, obamegine,oxyacanthine and (+)-tubocurarine (Fig. 2.1, overviews [120,117: IV: p. 199; VII:p. 439; IX: p. 133; XIII: p. 303, XVI: p. 249, XXX: p. 1]),–phthalidisoquinoline and secophthalidisoquinoline type, e.g., adlumidiceine, ao-bamidine, (+)-bicuculline, capnoidine, corlumine,α-hydrastine, narceine, nosca-pine (also known as narcotine) and 5ʹ-desmethylnarcotine (Fig. 2.1, overviews [48,117: IV: p. 167, VII: p. 433, IX: p. 117, XXIV: p. 253]),–cularine and secocularine type, e.g., breoganine, cularine, noyaine and secocular-idine (Fig. 2.2, overviews [117: IV: p. 249; X: p. 463, XXIX: p. 287]),–aporphine type, e.g., aporheidine, aporheine, boldine, (+)-bulbocapnine, corydine,corytuberine, dicentrine, domesticine, glaucine, isoboldine, isocorydine, (+)-iso-thebaine, magnoflorine,N-methylasimilobine, predicentrine, orientidine and ste-phanine (Fig. 2.2, overviews [55, 124, 306,117: IV: p. 119, IX: p. 1]), the aporphinetype also includes apomorphine, an artifact resulting from exposure of morphineto strong acids,–isopavine type, e.g., amurensine andamurensinine (Fig. 2.2, overview [117:XXXI: p. 317]),–promorphinane type, e.g., salutaridine,–morphinane type, e.g., amurine, codeine, morphine, nudaurine, oripavine andthebaine (Fig. 2.2, overviews [4, 57,117: II: p. 1 and p. 161; VI: p. 219, XIII: p. 1]);heroin (diacetylmorphine, diamorphine), a semisynthetic derivative of morphine,https://doi.org/10.1515/9783111136219-002
© 2024 Walter de Gruyter GmbH, Berlin/Boston

Chapters in this book

  1. Frontmatter I
  2. Preface V
  3. A Short Glance on Volume 3 VII
  4. Contents IX
  5. Abbreviations and Icons XVII
  6. 1 Alkaloids 1
  7. 2 Isoquinoline Alkaloids 11
  8. 3 Erythrinane and Homoerythrinane Alkaloids 67
  9. 4 Tropolone Alkaloids 74
  10. 5 Amaryllidaceae Alkaloids 85
  11. 6 Indole Alkaloids 98
  12. 7 Quinoline Alkaloids 140
  13. 8 Quinazoline Alkaloids 151
  14. 9 Imidazole Alkaloids 155
  15. 10 Pyrrolizidine Alkaloids 158
  16. 11 Tropane Alkaloids 187
  17. 12 Pyridine Alkaloids and Related Compounds 219
  18. 13 Quinolizidine Alkaloids 262
  19. 14 Purine Alkaloids 285
  20. 15 Pyrimidine Derivatives 319
  21. 16 Terpene Alkaloids 326
  22. 17 Steroid Alkaloids 352
  23. 18 Peptides and Proteins 387
  24. 19 Lectins 389
  25. Cross Chapter Literature and Further Reading 413
  26. Poison Information Centers 421
  27. Index 423
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https://doi.org/10.1515/9783111136219-002

Chapters in this book

  1. Frontmatter I
  2. Preface V
  3. A Short Glance on Volume 3 VII
  4. Contents IX
  5. Abbreviations and Icons XVII
  6. 1 Alkaloids 1
  7. 2 Isoquinoline Alkaloids 11
  8. 3 Erythrinane and Homoerythrinane Alkaloids 67
  9. 4 Tropolone Alkaloids 74
  10. 5 Amaryllidaceae Alkaloids 85
  11. 6 Indole Alkaloids 98
  12. 7 Quinoline Alkaloids 140
  13. 8 Quinazoline Alkaloids 151
  14. 9 Imidazole Alkaloids 155
  15. 10 Pyrrolizidine Alkaloids 158
  16. 11 Tropane Alkaloids 187
  17. 12 Pyridine Alkaloids and Related Compounds 219
  18. 13 Quinolizidine Alkaloids 262
  19. 14 Purine Alkaloids 285
  20. 15 Pyrimidine Derivatives 319
  21. 16 Terpene Alkaloids 326
  22. 17 Steroid Alkaloids 352
  23. 18 Peptides and Proteins 387
  24. 19 Lectins 389
  25. Cross Chapter Literature and Further Reading 413
  26. Poison Information Centers 421
  27. Index 423
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