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Galanthamine

  • D. S. Paskov
Chapter
Part of the Handbook of Experimental Pharmacology book series (HEP, volume 79)

Abstract

The alkaloid galanthamine is a valuable product from the group of natural anticholinesterase substances. It was the first isolated by Proskurnina and Yakovleva (1952) from Galanthus woronowi Los., family amaryllidaceae. Uyeo and Kobayashi (1953) isolated the same alkaloid from Lycoris radiata Herb., and called it lycoremine. Later, galanthamine was found in more than 50 species of the family Amaryllidaceae (Boit 1961). Yunusov and Abduazimov (1957) isolated galanthamine from various Ungernia species, Ungernia victoris Vved. proved to be the richest. In Bulgaria, galanthamine, isolated from Galanthus nivalis L. var. gracilis Čelak, family Amaryllidaceae, was studied and put into practice under the name Nivalin (Paskov 1957; Ivanova-Bubeva 1957). Later, a high galanthamine content was found in the plant Leucojum aestivum L., also family Amaryllidaceae, growing within the territory of Bulgaria (Ivanova-Bubeva and Ivanov 1961; Stefanov et al. 1974). At present, galanthaminum is manufactured industrially in the USSR from Ungernia vicions and in Bulgaria from Leucojum aestivum.

Keywords

Nictitate Membrane Human Peripheral Lymphocyte Polychromatic Erythrocyte Potassium Bichromate Progressive Muscular Dystrophy 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Baraka A, Cozanitis D (1973) Galanthamine versus neostigmine for reversal of non-depolarizing neuromuscular block in man. Anesth Anaig Curr Res 52:832–836Google Scholar
  2. Baraka A, Harik S (1977) Reversal of central anticholinergic syndrome by galanthamine. JAMA 238:2293–2294PubMedGoogle Scholar
  3. Barton DHR, Kirby GW (1960) Synthesis of galanthamine. Proc Chem Soc 392–393Google Scholar
  4. Barton DHR, Kirby GW, Taylor JB, Thomas GM (1962) Multiple labelling experiments in biosynthesis of Amaryllidaceae alkaloids. Proc Chem Soc 179Google Scholar
  5. Bergamini V, Baggiore P (1960) La nivalinterapia in alcune malatile neurologiche. Minerva Med 51:3553–3558Google Scholar
  6. Boissier JR, Lesbros J (1962) La galanthamine puissant cholinergique naturel. II — Activité anticholinesterasique de la gelanthamine et quelques derivés. Ann Pharm Fr 20:150–155Google Scholar
  7. Boissier JR, Combes G, Pagny J (1960) La galanthamine puissant cholinergique naturel. I — Sources. Structure chimique. Characterization. Extraction. Toxicité. Actions sur les fibres lisses. Ann Pharm Fr 18:888–900Google Scholar
  8. Boit HG (1961) Ergebnisse der Alkaloid-Chemie bis 1960. Akademie, Berlin, pp 410–475Google Scholar
  9. Boromei A, Daidone R (1962) On the use of nivalin in postoperative urinary retention in neurosurgery. Minerva Chir 17, 19:947–956Google Scholar
  10. Bretagne M, Valletta J (1965) Essais clinique en anesthesiologie d’un nouvel anticholineste-rasique la galanthamine. Anesth Analg Reanimat 22:285–292Google Scholar
  11. Cecchini M (1966) Il trattamento con galanthamina bromidrato dei postumi motori con-secutivi a vasculopathie cerebrale. Minerva Med 57:3385–3386PubMedGoogle Scholar
  12. Cheymol J, Boissier JR, Bourillet F, Fichelle-Pagny J, Roch-Arveiller M (1964) Activité neuromusculaire de la galanthamine, anticholinesterasique naturel. Ann Pharm Fr 22:1:41–48PubMedGoogle Scholar
  13. Chrusciel M, Varagic V (1966) The effect of galanthamine on the blood pressure of the rats. Br J Pharmacol 26:295–301Google Scholar
  14. Cozanitis DA (1971) Experiences with galanthamine hydrobromide as curare antagonist. Anaesthesist 20:226–229PubMedGoogle Scholar
  15. Cozanitis DA (1974) Galanthamine hydrobromide versus neostigmine; a plasma Cortisol study in man. Anaesthesia 29:163–168PubMedGoogle Scholar
  16. Cozanitis DA (1977 a) The potency ratio of galanthamine and neostigmine on the reversal of the tubocurarine block in the isolated rat diaphragm. Acta Anaesthesiol Belg 28:53–60PubMedGoogle Scholar
  17. Cozanitis DA (1977 b) Galanthamine hydrobromide, a longer acting anticholinesterase drug in the treatment of the central effects of scopolamine (Hyoscine). Anaesthesist 26:649–650PubMedGoogle Scholar
  18. Cozanitis DA, Rosenberg P (1974) Preliminary experiments with galanthamine hydrobro-mide on depressed respiration. Anaesthesist 23:302–305PubMedGoogle Scholar
  19. Cozanitis DA, Toivakka E (1971) A comparative study of nivaline and atropine/Neostigmine on conscious volunteers. Anaesthesist 20:416–421PubMedGoogle Scholar
  20. Cozanitis DA, Toivakka E (1974) Treatment of respiratory depression with the anticholinesterase drug galanthamine hydrobromide. Anaesthesia 29:581–584PubMedGoogle Scholar
  21. Cozanitis DA, Halttunen P, Edgren J (1972) A cinematographic study demonstrating the effect of galanthamine hydrobromide on conscious asthmatic volunteers. Anaesthesist 21:63–66PubMedGoogle Scholar
  22. Cozanitis DA, Nuutila K, Karhunen P, Baraka A (1973 a) Changes in cardiac rhythm with galanthamine hydrobromide. Anaesthesist 22:457–459PubMedGoogle Scholar
  23. Cozanitis DA, Toivakka E, Dessypris A (1973 b) Electroencephalographic and blood chemistry responses to galanthamine hydrobromide in epileptic volunteers. Anaesthesist 22:31–33PubMedGoogle Scholar
  24. Cozanitis DA, Freidmann T, Fürst S (1983) Study of the analgesic effects of galanthamine, a Cholinesterase inhibitor. Arch Intern Pharmacodyn Thér 266:229–238Google Scholar
  25. Daskalov D, Atanassov A (1980) Nivalin application in rehabitation treatment of cerebral diseases with aphasic syndrome (in English and Russian). Med Biol Inform 3:10–12Google Scholar
  26. Deredjan A, Krasteva E (1960) Our abservations on decurarization effect of nivalin (in Bulgarian). Khirurgia (Sofiia) 13:272–275Google Scholar
  27. De Renzi E (1961) Il nivalin in Therapia Neurologica. Minerva Med 58:253–257Google Scholar
  28. Döpke W (1976) Ergebnisse der Alkaloid-Chemie 1960–1968, vol 1. Akademie-Verlag, Berlin, pp 713–722Google Scholar
  29. Edelstein EA (1957) On the application of new agents in the progressive muscular dystrophia (in Russian). Zh Nevropatol Psikhiatr 57:856–859Google Scholar
  30. Eidinova MB, Pravdina-Vinarskaya EN (1957) Characteristic and treatment of residual motor disorders in children (in Russian). Zh Nevropatol Psikhiatr 57:814–819Google Scholar
  31. Ferrara L, Vidili F, Aletti L (1961) Risultati clinici e considerationi sul un anticholineste-rasico (Nivalina) nell trattamento dell’ileo postoperatoria. Minerva Anesthesiol 27, 2:74–78Google Scholar
  32. Georgiev IV, Jordanov B (1961) Effetto ipotensive della nivaline. Cultura Medica 23:305–312Google Scholar
  33. Georgiev IV, Pernov K, Dashin V, Jordanov B (1960) Our experiences in the treatment of myopathies and lesions of the peripheral nerves with the new Bulgarian preparation nivalin (in Bulgarian). Savr Med II,4:16–26Google Scholar
  34. Heddle JA, Hite M, Kirkhart B, Mavournin K, MacGregor J, Newell G, Salamone M (1983) The induction of micronuclei as a measure of genotoxicity. A report of US Environmental Protection Agency GeneTox Program. Mutation Res 123:61–118PubMedGoogle Scholar
  35. Iliyuchenok RJ (1965) Neurohumoral mechanism of reticular formation of brain stem (in Russian). Nauka, MoscowGoogle Scholar
  36. Iliyuchenok RJ, Pastukhov JF (1968) Effect of some cholinolytic substances and galanthamine upon the activity of single neurons of hippocampus (in Russian). Farmakol Toksikol 31:137–141Google Scholar
  37. Irwin RL, Smith HJ III (1960 a) Cholinesterase inhibition by galanthamine and lycor-amine. Biochem Pharmacol 3:147–148PubMedGoogle Scholar
  38. Irwin RL, Smith HJ III (1960 b) The activity of galanthamine and related compounds on muscle. Arch Int Pharmacodyn Ther 122:314–330Google Scholar
  39. Ivanova-Bubeva L (1957) Phytochemical examination of Galanthus nivalis var gracilis (in Bulgarian). Farmacia 7, 2:23–26Google Scholar
  40. Ivanova-Bubeva L, Ivanov V (1961) On the alkaloid content of Leucojum aestivum L (in Bulgarian). Trudove Nauchno-Issledov Institut Farmacia 3:89–91Google Scholar
  41. Khmelevsky JM, Gadalov VP (1977) Comparative characteristics of chinothyline, galanthamine and prozerine as antagonists of the myorelaxants (in Russian). Anesteziol Re-animatol 4:32–37Google Scholar
  42. Khmelevsky JM, Gadalov VP (1980) Influence of the antagonists of the myorelaxants on the cardiac activity (in Russian). Anesteziol Reanimatol 1:14–17Google Scholar
  43. Kilimov N (1961 a) Case of anaphylactic shock after use of Nivalin (in Bulgarian). Savr Med 11:11–112Google Scholar
  44. Kilimov N (1961 b) La cura dei postume paralitici da emorragia cerebrale mediante Niva-lina. Cultura Medica 23:313–319Google Scholar
  45. Kilimov N (1961c) Sul trattamento delle nevritti faciali con Nivalina. Cultura Medica 23:323–330Google Scholar
  46. Kilimov N (1961d) Trattamento della nevralgia del nervo trigemino. Cultura Medica 23:331–341Google Scholar
  47. Koizumi J, Kobayashi S, Uyeo S (1964) Galanthamine Chemistry. V.Formation of hy-droxyapogalanthamine from Galanthamine and the synthesis of its trimethyl ether. Chem Pharm Bull 12:696–705PubMedGoogle Scholar
  48. Kostowski W, Gumulka W (1968) Ganglion and central action of galanthamine. Int J Neuropharmacol 7:7–14PubMedGoogle Scholar
  49. Kovanev VA, Khmelevsky JM, Ganina SS (1967) Galanthamine (nivalin) as antidote of non-depolarizing myorelaxants (in Russian). Exp Khirurg Anesthez 4:65–69Google Scholar
  50. Krastev B, Pampulov Z (1963) Application of nivalin in the surgical practice (in Bulgarian). Khirurgiia (Sofiia) 16:257–265Google Scholar
  51. Kraus VA (1974) Interrelations between ventral and dorsal hippocampus in improvement and deterioration of shortterm memory. Zh Vissh Nervn Deyateln 24:33–41Google Scholar
  52. Kulov N (1967) Study upon the effect of nivalin stimulation in bladder atonias (in Bulgarian). Nauchni Trudove VMI Varna 6, 1:23–26Google Scholar
  53. Lanskaya SS (1950) Comparative assessment of the physiological action of the anticho-linesterasic substances on the nervous system (in Russian). Bull Biol Med 29:415–417Google Scholar
  54. Liebmann H, Matthies H (1961) Die Wirkung der Amaryllidaceen-Alkaloide Galanth-amin, Narwedin, Haemanthamin und Tazettin auf die neuromuskuläre Übertragung. Acta Biol Med Germ 7:411–419PubMedGoogle Scholar
  55. Lombardo G, Arena G (1962) L’impiego del bromodrato de galanthamine (nivalina) nei postumi paralitica da póliomielite, da nevrassit e nella distrophia musculare. Minerva Med 14:724–728Google Scholar
  56. Maron DM, Ames BN (1983) Revised methods for the Salmonella mutagenicity test. Mutation Res 113:173–215PubMedGoogle Scholar
  57. Mashkovsky MD (1955) Influence of the galanthamine upon the sensibility of the skeletal musculature to the acetylcholine (in Russian). Farmakol Toksikol 18, 4:21–27Google Scholar
  58. Mashkovsky MD, Al’tshuler RA (1962) Pharmacological properties of galanthamine iod-methylate (in Russian). Farmakol Toksikol 25:168–175Google Scholar
  59. Mashkovsky MD, Iliyuchenok RJ (1961) A propos of the problem of galanthamine effect upon the central nervous system (in Russian). Zh Nevropatol Psikhiatr 61, 2:166–175Google Scholar
  60. Mashkovsky MD, Kruglikova-L’vova RP (1951) On the pharmacology of the new alkaloid galanthamine (in Russian). Farmakol Toksikol 14, 6:26–30Google Scholar
  61. Mayrhover O (1966) Clinical experience with diallylnortoxiferine and curare antidote galanthamine. South Med J 52:1364–1368Google Scholar
  62. Mayrhover O (1967) Erfahrungen mit Galanthamine (Nivalin) als Antagonist der Relaxan-tien vom Curaretyp. Bull Schweiz Akad Med Wiss 23, 1–2:48–52Google Scholar
  63. Mikhno W, Kramarenko VF (1970) Distribution of galanthamine in organs of poisoned animals (in Ukrain). Farm Zh 25, 1:68–71PubMedGoogle Scholar
  64. Minami S, Uyeo S (1964) Galanthamine chemistry. VI. The synthesis of deoxymethyllycor-amine. Chem Pharm Bull 12:1012–1020PubMedGoogle Scholar
  65. Mitev L, Atanassov D (1965) Volumetric studies in decurarization with nivalin. In: First National Conference on Anesthesiology and Reanimation, Sofia, pp 49–51Google Scholar
  66. Mitzov V, Rudakov A (1978) Effect of home anticurare substances upon spinal cord reflexes (in Bulgarian). Farmacia 28, 2:42–46Google Scholar
  67. Nastev G, Koynov R, Ovcharova P, Petrov A, Rashev R, Abadjiev M (1960) Nivalin treatment of patients with diseases of the nervous system. Cultura Med 15:87–97Google Scholar
  68. Naumenko EV, Iliyuchenok RJ, Nesterenko LN (1965) A propos of the mechanism of nivalin effect upon the hypophyseal-adrenal system (in Russian). Farmakol Toksikol 28:659–662PubMedGoogle Scholar
  69. Nesterenko LN (1965) Influence of the galanthamine on the activity of the acetylcholinesterase in different regions of the brain (in Russian). Farmakol Toksikol 28:413–414PubMedGoogle Scholar
  70. Nikolkov V (1980) Nivalin — its application in the treatment of infantile cerebral paralysis (in English and Russian). Med Biol Inform 3:3–6Google Scholar
  71. Paskov DS (1957) Nivalin effect on striated musculature (in Bulgarian). Izvest Otdel Biol Mediz Nauki 1:29–34Google Scholar
  72. Paskov DS (1958) Pharmacological study on alkaloid nivalin from the plant Galanthus nivalis var. gracilis Celax (in Russian). In: Anitchkov SV (ed) Ganglionics and blockers of neuromuscular synapses. Inst Eksp Med AMN, LeningradGoogle Scholar
  73. Paskov DS (1959) Nivalin pharmacology and clinical application. Medizina i Fizkultura, SofiaGoogle Scholar
  74. Paskov DS (1960) Una nuova sostanza nella terapia delle paralisi poliomielitiche la niva-lina. Cultura Medica 16:1–6Google Scholar
  75. Paskov DS, Traykov D (1975) Nivalin treatment of psychic sexual impotence. Med Biol Inform 3:5–8Google Scholar
  76. Paskov DS, Stoyanov KA, Saev SK, Tenev KA, Mincheva ML (1962 a) Clinical experience with nivalin as anticholinesterase drug on anaesthesiological practice. Proceedings of First European Congress of Anaesthesiology, 3–9 September, WienGoogle Scholar
  77. Paskov DS, Stoyanov KA, Saev SK, Tenev KA, Mincheva ML, Kristov HD (1962 b) Clinical experience with nivalin as an anticholinesterase drug in anaesthesiological practice. Cultura Medica 30:222–224Google Scholar
  78. Paskov DS, Stoyanov K, Saev S, Deredjan A, Krasteva E, Tenev K, Mincheva M (1962c) Azione anticurarizante della Nivalina. Minerva Anestesiol 28, 6:213–219PubMedGoogle Scholar
  79. Paskov DS, Dobrev H, Nikiforov N (1964) Antagonistic action of Nivalin and morphine upon the respiratory center. In: Aviado DM, Palacek F (eds) Drugs and respiration. Proc 2nd int pharmacol meeting, 20–23 August 1963. Pergamon, New YorkGoogle Scholar
  80. Pernov K, Samardjiev A, Nikolkov V (1961) Treatment of muscular dystrophies with high Nivalin doses. I comm (in Bulgarian). Trudove Nautchen Inst Nevrol Psikhiatr 7:1–11Google Scholar
  81. Pernov K, Samardjiev A, Nikolkov W (1963) Über die zerebralen Kinderlähmungen mit Nivalin. Psychiatr Neurol Med Psychol Beih 11:425–428Google Scholar
  82. Porcelli G (1963) Contributo clinico sull uso della nivalina neglii esivi di poliomielite anteriore acuta. Minerva Pediatr 15:1034–1036PubMedGoogle Scholar
  83. Proskurnina NF, Yakovleva AP (1952) On the alkaloids of Galanthus woronovi. II. Isolation of a new alkaloid (in Russian). Zh Obshch Khim 22:1899–1902Google Scholar
  84. Proskurnina NF, Yakovleva AP (1955) On the alkaloids of Galanthus Woronovi. III. On the structure of galanthamine (in Russian). Zh Obshch Khim 25:1035–1039Google Scholar
  85. Prozorovsky VB, Khromova ON, Dubovitzkaya SI (1970) Comparative characteristics and analysis of the anticurare action of the cholinpotentiating agents (in Russian). Exp Khir Anesth 6:78–81Google Scholar
  86. Revelli U, Grasso E (1962) Le traitment de la poliomyelite a la nivalin. Minerva Med 53, 24:881–882PubMedGoogle Scholar
  87. Revelli U, Grasso E (1968) Therapeutic action of nivalin. Further contribution (in English). Med Biol Inform 1:17–20Google Scholar
  88. Roshchina LF (1969) Galanthamine effect on the disorders of conditioned reflexes and behaviour of rats induced by central cholinolytics (in Russian). Farmakol Toksikol 32, 2:143–146PubMedGoogle Scholar
  89. Rudakov A, Mitzov V (1977) Effect of pymadin, nivalin and their combination on polysynaptic lingual-mandibular reflex (in Bulgarian). Farmacia 27, 2:34–37Google Scholar
  90. Saev S (1968) Application of nivalin in anesthesiology. Med Biol Inform 1:4–16Google Scholar
  91. Saev S, Tenev KA (1963) Decurarization in the operations of patients with cardiovascular diseases by Nivalin (in Russian). Exp Khir Anesth 2:76–77Google Scholar
  92. Salvini L, Frosali L, Pacet AM (1962) Valutazione clinica delll’ antagonismo verso la d-tu-bocurarina di un nuovo anticholinesterasico (Nivalina). Minerva Anestesiol 28:201 – 204Google Scholar
  93. Schmid W (1980) The micronucleus test: an in vivo bone marrow method. In: Hsu TC (ed) Cytogenetic Assays of Environmental Mutagens. Osmum, Allanheld, pp 221–229Google Scholar
  94. Schmidt J, Matthias H (1961) Zur Pharmakologie der Amaryllidaceen-Alkalode Galanth-amin, Narwedin, Haemanthamin und Tazettin. Acta Biol Med Germ 7:402–410PubMedGoogle Scholar
  95. Sedloev S, Georgiev IV, Milev M (1964) On the effect of nivalin upon intestinal peristalsis. Acta Inst Sup Med (Sofia) 43,1:69–73Google Scholar
  96. Shenk NA, Eidinova MB, Mitbreit IM (1956) Therapeutic and diagnostic value of the galanthamine in the cases of patients with different stages of poliomyelitis (in Russian). Farmakol Toksikol 19, 4:36–41PubMedGoogle Scholar
  97. Spector W (1956) Handbook of toxicology, vol 1. Saunder, Philadelphia, pp 210–211Google Scholar
  98. Stefanov ZH, Slavchev P, Mitkov IV (1974) Qualitative and quantitative studies on alkaloid composition of wild-growing and introduced populations ofLeucojum aestivum L. Farmacia Sofia 24/6:16–19Google Scholar
  99. Stojanov E (1964 a) Spirographs evidence of anticurare effect of nivalin. Acta Med Inst Sup (Sofia) 43, 4:39–6Google Scholar
  100. Stojanov E (1964 b) Galanthamine hydrobromide (Nivalin) ein neues Antidot der nichtde-polarisierenden Muskelrelaxantien. Anaesthesist 13, 7:217–220PubMedGoogle Scholar
  101. Stojanov E (1965) Clinical experience with the new curare antidote galanthamine (Nivalin). In: International anaesthesiology clinics (European trends in anesthesiology 3) 4:675–685Google Scholar
  102. Stojanov E (1971) Clinical use of nivalin in decurarization (A six year experience). Anesthesia Reanimacija 3, 1:17–23Google Scholar
  103. Stojanov E, Vulchanova S (1963) The clinical application of Nivalin as an antidote of curare. Acta Med Inst Super (Sofia) 42, 4:1–4Google Scholar
  104. Tchakarov IV (1980) Nivalin — comparative studies of enuresis treatment in children via electrophoresis and interference current (in English and Russian). Med Biol Inform 3:6–10Google Scholar
  105. Uyeo S, Kobayashi (1953) Pharm Bull 1:139–142 (Ca, 1959, 13960)PubMedGoogle Scholar
  106. Vasilenko ET, Tonkopy VD (1974) Characteristic of the galanthamine as reversal inhibitor of the Cholinesterase (in Russian). Biokhimiia 39:701–703PubMedGoogle Scholar
  107. Wislicki L (1967) Ni valine (Galanthamine hydrobromide) an additional decurarizing agent. Some introductory observations. Br J Anaesth 39:963–968PubMedGoogle Scholar
  108. Yamboliev IA (1984) Experimental studies on some pharmacokinetic and pharmacobio-chemical behaviours of nivalin. Dissertation, Medical Academy, Pharmaceutical Faculty, SofiaGoogle Scholar
  109. Yunusov SY, Abduazimov KhA (1957) Study of the alkaloids of four species of Ungernia (in Russian). Zh Obshch Khim 27:3357–3361Google Scholar

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  • D. S. Paskov

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