Skip to main content

Identification of Acetylcholine and Related Esters of Biological Origin

  • Chapter
Cholinesterases and Anticholinesterase Agents

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 15))

Abstract

Although acetylcholine (ACh) has been shown beyond reasonable doubt to be the transmitter substance at certain cholinergic nerve endings, there are several facts which warn us against attributing a too exclusive role to this compound. First, by analogy with other transmitters (e.g., the catecholamines) the transmitter role is likely to be subserved by a group of related substances rather than by a single compound. Second, ACh occurs in non-nervous tissue and is so widely distributed in nature as to suggest a non-nervous function for it. Third, several other carboxylic esters of choline possessing related or contrasting pharmacological properties are known to occur in nature. Though so far their presence in nervous tissue has not been unequivocally demonstrated, this tissue can undoubtedly synthesize homologues of ACh in vitro (Gardiner and Whittaker 1954, Frontali 1958, Berry and Whittaker 1959) and is well equipped, by its possession of two forms of cholinesterase (ChE), to destroy them rapidly. The possibility that ACh may not be the only transmitter substance at cholinergic nerve endings or that its function may be interfered with under pathological conditions by the appearance of similar compounds must be borne in mind when considering the mode of action of anti-cholinesterase (anti-ChE) agents and justifies the inclusion of a chapter on the identification of ACh and related esters in a monograph on this subject.

D’autre part, la présence d’acétylcholine parmi les composants actifs de l’ergot de seigle, qui vient d’être signalée par Ewins, permet de supposer que, dans l’organisme animal, qui renferme, côte à côte, la choline et les acides gras supérieurs, et même certains dérivés contenant à la fois ces deux sortes de substances (lécithines), on pourra rencontrer un jour les homologues de l’acétylcholine, soit comme des constituants normaux des humeurs, soit comme les produits de certains états pathologiques.

(Fourneau and Page, 1914)

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature

  • Abderhalden, E., H. Paffrath U. H. Sickel: Beitrag zur Frage der Inkret-(Hormon-) Wirkung des Cholins auf die motorischen Funktionen des Verdauungskanales. II. Mitt. Pflügers Arch. ges. Physiol. 207, 241–253 (1925).

    Article  CAS  Google Scholar 

  • Ackermann, D., u. H. Mauer: Über einen empfindlichen Nachweis des Acetylcholins mit Hilfe von Dipikrylamin. Hoppe-Seylers Z. physiol. Chem. 279, 114–116 (1943).

    CAS  Google Scholar 

  • Ahmed, A., and N. R. W. Taylor: The assay of acetylcholine on the superfused frog rectus muscle. J. Pharm. (Lond.) 9, 536–540 (1957).

    Article  CAS  Google Scholar 

  • Alm, A., and K.-B. Augustinsson: The presence of acetylcholine in milk. Acta physiol. scand. 39, 203–208 (1957).

    Article  PubMed  CAS  Google Scholar 

  • Aprison, M. H., and P. Nathan: Determination of acetylcholine in small samples of fresh brain tissue. Arch. Biochem. Biophys. 66, 388–395 (1957).

    Article  PubMed  CAS  Google Scholar 

  • Aucustnnsson, K.-B.: Hippurylcholine. Acta chem. scand. 9, 793–796 (1955).

    Article  Google Scholar 

  • Aucustnnsson, K.-B. R. Fänge, A. Johnels and E. Östlund: Histological, physiological and biochemical studies on the heart of two cyclostomes, hagfish (Myxine) and lamprey (Lampetra). J. Physiol. (Lond.) 131, 257–276 (1955).

    Google Scholar 

  • Aucustnnsson, K.-B. and M. Grahn: The separation of choline esters by paper chromatography. Acta chem. scand. 7, 906–912 (1953).

    Article  Google Scholar 

  • Aucustnnsson, K.-B. and M. Grahn: The occurrence of choline esters in the honey-bee. Acta physiol. scand. 32, 174–190 (1954).

    Article  Google Scholar 

  • Bano, L. vow, u. M. Hirschbrunn: Über das Sinapin. Justus Liebigs Ann Chem. 84, 10–32 (1852). BAC@, Z. M. L’acétylcholine et l’adrénaline chez les invertébrés. Biol. Rev. 22, 73–91 (1947).

    Google Scholar 

  • Bano, L. vow, u. M. Hirschbrunn: Un test marin pour l’acétylcholine. Arch. int. Physiol. 49, 20–24 (1939).

    Google Scholar 

  • Bano, L. vow, u. M. Hirschbrunn: et F. P. MAZZARecherches sur la physiologie et la pharmacologie du système nerveux autonome. XVIII. Isolement de chloroaurate d’acétylcholine à partir d’un extrait de cellules nerveuses d’Octopus vulgaris. Arch. int. Physiol. 42, 43–46 (1935).

    Google Scholar 

  • Baeyer, A.: Über das Neurin. Justus Liebigs Ann. Chem. 142, 322–326 (1867).

    Article  Google Scholar 

  • Banister, R. J., V. P. Whrttaker and S. Wijesundera: The chromatographic identification of propionylcholine in ox spleen. J. Physiol. (Lond.) 115, 55 P (1951).

    Google Scholar 

  • Banister, R. J., V. P. Whrttaker and S. Wijesundera: The occurrence of homologues of acetylcholine in ox spleen. J. Physiol. (Lond.) 121, 55–71 (1953).

    CAS  Google Scholar 

  • Barlow, R. B.: Introduction to Chemical Pharmacology. London Methuen 1955.

    Google Scholar 

  • Beilstein, F. K.: Handbuch der Organischen Chemie. Berlin: Springer 1918–1957.

    Google Scholar 

  • Bell, F. K., and J. C. Carr: The preparation and properties of the perchlorates of some choline esters. J. Amer. pharm. Ass. 36, 272–273 (1947).

    Google Scholar 

  • Bentley, G. A. and F. H. Shaw: The separation and assay of acetylcholine in tissue extracts. J. Pharmacol. exp. Ther. 106, 193–199 (1952).

    PubMed  CAS  Google Scholar 

  • Berry, J. F., and V. P. Whittaker: The acyl-group specificity of choline acetylase. Biochem. J. 73, 447–458 (1959).

    PubMed  CAS  Google Scholar 

  • Bnoola, K. D., J. D. Calle and M. Schachter: The identification of acetylcholine, 5-hydroxytryptamine and other substances in hornet venom (Vespa crabo). J. Physiol. (Lond.) 151, 35–36 P (1960).

    Google Scholar 

  • Bischoff, C., W. Grab u. J. Kapfhammer: Acetylcholin im Warmblüter. 4. Mitteilung. Hoppe-Seylers Z. physiol. Chem. 207, 57–77 (1932).

    Google Scholar 

  • Bisset, G. W. J. F. D. Frazer, M. Rotscuild and M. Sciachter: A pharmacologically active choline ester and other substances in the Garden Tiger Moth, Arctia raja (L). Proc. roy. Soc. 152 B, 255–262 (1960).

    Google Scholar 

  • Boriittaii, H., u. H. Cappenberg: Beiträge zur Kenntnis der wirksamen Bestandteile des Hirtentäschelkrautes (Herba Capsellae bursae pastoris). Arch. Pharm. (Berl.) 259, 33–52 (1921).

    Article  Google Scholar 

  • Boyet, D., et F. Bovet-Nitti: Structure et Activité Pharmacodynamique des Médicaments du Système Nerveux Végétatif; Adrénaline, Acétylcholine, Histamine, et leurs Antagonistes. BâleKarger 1948.

    Google Scholar 

  • Brante, G.: Iodine as a means of development in paper chromatography. Nature (Lond.) 163, 651–652 (1949).

    Article  CAS  Google Scholar 

  • Bregoff, H. M., E. Roberts and C. C. Delwiche: Paper chromatography of quaternary mmonium bases and related compounds. J. biol. Chem. 205, 565–574 (1953).

    Google Scholar 

  • Brtttain, R. T., B. G. Chesher, H. O. J. Collier and J. J. Grimshaw: Assay of suxa-methonium and laudexium on the frog rectus abdominis. B.it. J. Pharmacol. 14, 158–163 1959 ).

    Google Scholar 

  • Bülbring, E., E. M. ’,Curie and U. Pardoe: The presence of acetylcholine in Trypanosoma rhodesiense and its absence from Plasmodium gallinaceum. Brit. J. Pharmacol. 4, 290–294 (1949).

    Google Scholar 

  • Bülbring, E., E. M. ’,Curie and U. Pardoe: J. H. BURN and H. J. SHELLEY Acetylcholine and ciliary movement in the gill plates of Mytilus edulis. Proc. roy. Soc. 141 B, 445–466 (1953).

    Google Scholar 

  • Burn, H. J., D. J. Finney and L. G. Goodwin: Biological Standardization. 2nd ed. London.xford University Press 1950.

    Google Scholar 

  • Chang, C. H., and J. H. Gaddum: Choline esters in tissue extracts. J. Physiol. (Lond.) 79, 255–285 (1933).

    CAS  Google Scholar 

  • Chefurka, W., and B. N. Smallman: The occurrence of acetylcholine in the housefly, Musca domestica L. Canad. J. Biochem. 34, 731–742 (1956).

    Article  PubMed  CAS  Google Scholar 

  • Corsten, M.: Bestimmung kleinster Acetylcholinmengen am Lungenpräparat des Frosches. Pflügers Arch. ges. Physiol. 244, 281–291 (1940).

    CAS  Google Scholar 

  • Crossland, J.: The use of liquid air in the extraction of acetylcholine. J. Physiol. (Lond.) 142, 165–172 (1951).

    Google Scholar 

  • Curtis, D R, J W Phillis and J. C. Watkins: Cholinergic and non-cholinergic transmission in the mammalian spinal cord. J. Physiol. (Lond.) 158, 296–323 (1961).

    CAS  Google Scholar 

  • Dale, H. H., and H. W. Dudley: The presence of histamine and acetylcholine in the spleen of the ox and the horse. J. Physiol. (Lond.) 68, 97–123 (1929).

    CAS  Google Scholar 

  • Dale, H. H., and H. W. Dudley and W. FELDBERG: The chemical transmitter of vagus effects to the stomach. J. Physiol. (Lond.) 81, 320–334 (1934).

    CAS  Google Scholar 

  • David, W. A. L.: The systemic insecticidal action of paraoxon on the eggs of Pieris brassicae (L). J. insect. Physiol. 3, 14–27 (1959).

    Article  CAS  Google Scholar 

  • Davis, J. E.: Acetylcholine estimation in body fluids by the acetone-sensitized frog rectus muscle test. Amer. J. Physiol. 162, 616–618 (1950).

    PubMed  CAS  Google Scholar 

  • Dubois, R.: Recherches sur la pourpre et sur quelques autres pigments animaux. Arch. Zool. exp. gén. (5) 2, 471–590 (1909).

    Google Scholar 

  • Dudley, H. W.: Co-ordination compounds of the chloroplatinates of choline and its esters. J. them. Soc. 763–769 (1931).

    Google Scholar 

  • Dudley, H. W.: The alleged occurrence of acetylcholine in ox blood. J. Physiol. (Lond.) 79, 249–254 (1933).

    CAS  Google Scholar 

  • Elliott, K. A. C., and E. Florey: Factor I — inhibitory factor from brain. J. Neurochem. 1, 181–191 (1956).

    Google Scholar 

  • Emmelin, N., and R. Fänge: Comparison between biological effects of neurine and a salivary gland extract of Neptunea antiqua. Acta zool. (Stockh.) 39, 47–52 (1958).

    Article  CAS  Google Scholar 

  • Emmelin, N., and R. Fänge and W. Feldberg: The mechanism of the sting of the common nettle (Urtica urens). J. Physiol. (Lond.) 106, 440 455 (1947).

    Google Scholar 

  • Erspamer, V., U. O. Benati: Isolierung des Murexins aus Hypobranchialdrusenextrakten von Murex trunculus und seine Identifizierung als ß-[Imidazolyl-4(5)]-acryl-cholin. Biochem. Z. 324, 66–73 (1953).

    PubMed  CAS  Google Scholar 

  • Erspamer, V., U. O. Benati e F. Dordoni: Chemical and pharmacological researches on extracts of the hypobranchial gland of Murex trunculus, M. brandaris and Tritonalia erinacea. III Presence in the extracts of a new derivative of choline or of a choline homologue murexine (in Italian). Arch. in Pharmacodyn. 74, 263–285 (1947).

    Google Scholar 

  • Erspamer, V., U. O. Benati e F. Dordoni and A. Glässer: The pharmacological actions of murexine (urocanylcholine). Brit. J. Pharmacol. 12, 176–184 (1957).

    PubMed  CAS  Google Scholar 

  • Erspamer, V., U. O. Benati e F. Dordoni The pharmacological actions of some murexine-like substances. Brit. J. Pharmacol. 13, 378–384 (1958).

    CAS  Google Scholar 

  • Ewrxs, A. J.: Acetylcholine, a new active principle of ergot. Biochem. J. 8, 44 49 (1914).

    Google Scholar 

  • Fänge, R.: Paper chromatography and biological effects of extracts of the salivary gland of Neptunea antiqua (Gastropoda). Acta zool. (Stockh.) 39, 39–46 (1958).

    Article  Google Scholar 

  • Fänge, R.: and A. Matisson Studies on the physiology of the radula-muscle of Buccinum undatum. Acta zool. (Stockh.) 39, 53–64 (1958).

    Article  Google Scholar 

  • Feigl, F.: Qualitative Analysis by Spot Tests, Inorganic and Organic Applications. 3rd English ed. New YorkElsevier 1947.

    Google Scholar 

  • Feigl, F.: V. Anger U. O. Frehden Über die Verwendung von Tüpfelreaktionen zum Nachweis von organischen Verbindungen (II). Mikrochemie 15, 12–24 (1934).

    Google Scholar 

  • Feldberg, W., and J. H. Gaddum: The chemical transmitter at synapses in a sympathetic ganglion. J. Physiol. (Lond.) 81, 305–319 (1934).

    CAS  Google Scholar 

  • Feldberg, W., and C. Hebb: The effect of magnesium ions and of creatine phosphate on the synthesis of acetylcholine. J. Physiol. (Lond.) 106, 8–17 (1947).

    CAS  Google Scholar 

  • Fiedler, U., G. Hildebrand u. R. Neu: Weitere Inhaltsstoffe des Weißdorns der Nachweis von Cholin und Acetylcholin. Arzneimittel-Forsch. 3, 436–437 (1953).

    CAS  Google Scholar 

  • Fleisher, J. H., J. P. Corrigan and J. W. Howard: Reciprocal potentiating action of depolarizing drugs on the isolated frog rectus abdominis muscle. Brit. J. Pharmacol. 15, 23–28 (1960).

    PubMed  CAS  Google Scholar 

  • Florey, E.: An inhibitory and an excitatory factor of mammalian central nervous system, and their action on a single sensory neurone. Arch. int. Physiol. 62, 33–53 (1954).

    CAS  Google Scholar 

  • Florey, E.: The action of Factor I on certain invertebrate organs. Canad. J. Biochem. Physiol. 34, 669–681 (1956).

    Article  PubMed  CAS  Google Scholar 

  • Florey, E. and H. Mclennan: The effects of Factor I and of gamma-aminobutyric acid on smooth muscle preparations. J. Physiol. (Lond.) 145, 66–76 (1959).

    CAS  Google Scholar 

  • Foldes, F. F., E. G. Erdös, N. Baart and S. P. Shandor: Interrelationship of murexine, dihydromurexine and human cholinesterases. Proc. Soc. exp. Biol. (N. Y.) 94, 500–503 (1957).

    Article  CAS  Google Scholar 

  • Fourneau, E., et H. J. Page: Sur les éthers de la choline. Bull. Soc. chim. Fr. (4) 15, 544–553 (1914).

    CAS  Google Scholar 

  • Fowler, K. S., and S. E. Lewis: The extraction of acetylcholine from frozen insect tissue. J. Physiol. (Lond.) 142, 165–172 (1958).

    CAS  Google Scholar 

  • Freudenberg, K., u. H. Biller: Über Oxytocin. Naturwissenschaften 24, 523 (1936).

    Article  CAS  Google Scholar 

  • Frontali, N.: Acetylcholine synthesis in the housefly head. J. insect. Physiol. 1, 319–326 (1958).

    Article  CAS  Google Scholar 

  • Gadamer, I.: Über das Sinapin. Ber. dtsch. them. Ges. 30, 2328–2330 (1897).

    Article  Google Scholar 

  • Gaddum, J. H., and Z. P. Picarelli: Two kinds of tryptamine receptor. Brit. J. Pharmacol. 12, 323–328 (1957).

    PubMed  CAS  Google Scholar 

  • Gaddum, J. H., and Z. P. Picarelli and R. P. Stephenson: A microbath. Brit. J. Parmacol. 13, 493–497 (1958).

    CAS  Google Scholar 

  • Gardiner, J. E., and V. P. Whittaker: The identification of propionylcholine as a constituent of ox spleen. Biochem. J. 58, 24–29 (1954).

    Google Scholar 

  • Goffart, M.: Acétylcholine tissulaire du tube digestif chez le chien. Influence de l’énervation. Arch. int. Physiol. 49, 153–178 (1939).

    Google Scholar 

  • Goldschmidt, S., u. H. Burkert: Die Hydrolyse des cholinergischen Honigwirkstoffes und anderer Cholinester mittels Cholinesterasen und deren Hemmung im Honig. Hoppe-Seylers Z. physiol. Chem. 301, 78–89 (1955).

    CAS  Google Scholar 

  • Gray, E. G., and V. P. Whittaker: The isolation of nerve-endings from brain an electron microscopic study of cell fragments derived by homogenization and centrifugation. J. Anat. (Lond.) 96, 79–88 (1962).

    CAS  Google Scholar 

  • Grelis, M. E., and I. A. A. Tabachnick: The enzymatic hydrolysis of imidazoleacryloylcholine (murexine) and imidazolepropionylcholine (dihydromurexine) by various cholinesterases. Brit. J. Pharmacol. 12, 320–322 (1957).

    PubMed  CAS  Google Scholar 

  • Gruner, G., u. H. Kewitz: Das Vorkommen von Imidazyl-Essigsäure-Cholinester im Gehirn von Warmblütern. Naturwissenschaften 42, 628–629 (1955).

    Article  CAS  Google Scholar 

  • Guggenheim, M.: Die biogenen Amine und ihre Bedeutung für die Physiologie und Pathologie des pflanzlichen und tierischen Stoffwechsels. 4te Aufl., Basel Karger 1951.

    Google Scholar 

  • Harrison, K.: Isolation of acetylcholine from bacteria. Meth. med. Res. 3, 93–94 (1950).

    Google Scholar 

  • Hebb, C. O., and V. P. Whittaker: Intracellular distributions of acetylcholine and choline acetylase. J. Physiol. (Lond.) 142, 187–196 (1958).

    CAS  Google Scholar 

  • Heilbronn, E.: Hydrolysis of carboxylic acid esters of thiocholine and its analogues. 1. Acid hydrolysis. Acta them. stand. 12, 1481–1491 (1958).

    Article  CAS  Google Scholar 

  • Henschler, D.: Zur Identifizierung von Cholinestern in biologischem Material, insbesondere von Acetylcholin in Bienenfuttersäften. Hoppe-Seylers Z. physiol. Chem. 305, 34–41 (1956 a).

    Google Scholar 

  • Henschler, D.: Zur Frage des Vorkommens von Butyrylcholin im Rindergehirn. Hoppe-Seylers Z. physiol. Chem. 305, 97–104 (1956b).

    CAS  Google Scholar 

  • Henschler, D.: Die Cholinester der Rindermilz. Hoppe-Seylers Z. physiol. Chem. 309, 276–285 (1957).

    Google Scholar 

  • Hestrin, S.: The reaction of acetylcholine and other carboxylic acid derivatives with hy-droxylamine, and its analytical application. J. biol. Chem. 180, 249–261 (1949).

    PubMed  CAS  Google Scholar 

  • Hobbiger, F.: Antagonism by y-aminobutyric acid to the actions of 5-hydroxytryptamine and nicotine on isolated organs. J. Physiol. (Loud.) 144, 349–360 (1958).

    CAS  Google Scholar 

  • Holmstedt, B., L. Larsson and A. Sundwall: Synthesis and pharmacology of nicotinyl-choline and three bisquaternary related derivatives. Biochem. Pharmacol. 3, 155–162 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Holmstedt, B., L. Larsson and A. Sundwall and F. Sjöqvist: Pharmalogical properties of y-aminoburyrylcholine a supposed inhibitory neurotransmitter. Biochem. Pharmacol. 3, 297–304 (1960).

    Article  PubMed  CAS  Google Scholar 

  • F. Sjöqvist and V. P. Whrrtaker: Pharmacological properties of ßß-dimethylacryloylcholine and some other ß-substituted acryloylcholines. Brit. J. Pharmacol. 13, 308–314 (1958).

    Google Scholar 

  • Holtz, P., u. H. J. Schumann: Butyrylcholin in Gehirnextrakten. Naturwissenschaften 41, 306 (1954).

    Article  CAS  Google Scholar 

  • Honor, A. J., and H. Mclennan: The effects of y-aminobutyric acid and other compounds on structures of the mammalian nervous system which are inhibited by factor I. J. Physiol. (Lond.) 150, 306–318 (1960).

    Google Scholar 

  • Horenstein, H., u. H. Pählicke: Über eine neue Umlagerungsreaktion und ihre Anwendung zur Darstellung von Estern der Aminoalkohole. Ber. dtsch. chem. Ges. 71, 1644–1657 (1938).

    Google Scholar 

  • Hughes, B.: The isolated heart of Mya arenaria as a sensitive preparation for the assay of acetylcholine. Brit. J. Pharmacol. 10, 36–38 (1955).

    PubMed  CAS  Google Scholar 

  • Hunt, R, and R. De M. Taveau: The Effects of a Number of Derivatives of Choline and Analogous Compounds on the Blood Pressure. Bull. U.S. Publ. Hlth. Serv. (Hyg. Lab.), No. 73. Washington Government Printing Office 1911.

    Google Scholar 

  • Kahane, E., et J. Levy: Biochimie de la Choline et de ses Derives. III. Colamine, Triméthylamine, Bétaïne, Carnitine, Muscarine, Bétaïnaldéhyde, Sinapine. Actualités scientifiques et industrielles, nr. 753. Paris Hermann 1938.

    Google Scholar 

  • Kapfjammer, J., u. C. Bischoff: Acetylcholin und Cholin aus tierischen Organen. I. Mitteilung. Darstellung aus Rinderblut. Hoppe-Seylers Z. physiol. Chem. 191, 179–182 (1930).

    Google Scholar 

  • Kennedy, E. P.: The biological synthesis of phospholipids. Canad. J. Biochem. 34, 334–347 (1956).

    Article  Google Scholar 

  • Kewrrz, H.: Nachweis von 4-Amino-n-butyrylcholin im Warmblütergehirn. Naunyn-Schmiede. berg’s Arch. exp. Path. Pharmak. 237, 308–318 (1959).

    Google Scholar 

  • Keyl, M. J.: The distribution and some physiological properties of naturally occurring choline esters. Ph.D. Dissertation, University of Cincinnati, 1957.

    Google Scholar 

  • Keyl, M. J. I. A. Michaelson and V. P. Whittaker: Physiologically active choline esters in certain marine gastropods and other invertebrates. J. Physiol. (Lond.) 139, 434–454 (1957).

    CAS  Google Scholar 

  • Keyl, M. J. and V. P. Whtttaker: Some pharmacological properties of murexine (urocanoylcholine). Brit. J. Pharmacol. 13, 103–106 (1958).

    PubMed  CAS  Google Scholar 

  • Kosterlitz, H. W., and J. A. Robinson: The inhibitory action of morphine on the contraction of the longitudinal muscle coat of the isolated guinea-pig ileum. Brit. J. Pharmacol. 13, 296–303 (1958).

    PubMed  CAS  Google Scholar 

  • Kung, H. P., and W.-Y. Huang: Chemical investigation of Draba nemorosa, L. The isolation of sinapine iodide. J. Amer. chem. Soc. 71, 1836–1837 (1949).

    Article  CAS  Google Scholar 

  • Kuriaki, K., T. Yakushiji, T. Nord, T. SnrMrzu and SH. Saji: Gamma-aminobutyrylcholine. Nature (Lond.) 181, 1336–1337 (1958).

    Article  CAS  Google Scholar 

  • Ladd, R. J., and G. D. Thorburn: New test animal for acetylcholine assay. Aust. J. exp. Biol. med. Sci. 33, 207–213 (1955).

    Article  PubMed  CAS  Google Scholar 

  • Levy, J., et B. Tchoiibar: Relations entre la vitesse d’hydrolyse de divers esters de la choline par les cholinestérases et la constitution chimique des substrats. C.R. Acad. Sci. (Paris) 231, 1262–1264 (1950).

    CAS  Google Scholar 

  • Lewis, S. E.: Acetylcholine in blowflies. Nature (Lond.) 172, 1004–1005 (1953).

    Article  CAS  Google Scholar 

  • Lin, R. C. Y.: Presence of acetylcholine in the Malayan jack-fruit, Artocarpus intel’ra. Brit. J. Pharmacol. 10, 247–253 (1955).

    PubMed  CAS  Google Scholar 

  • Lipmann, F., and L. C. Tuttle: Lipase-catalysed condensation of fatty acids with hydroxyl-amine. Biochim. biophys. Acta 4, 301–309 (1950).

    CAS  Google Scholar 

  • Macintosh, F. C., and W. M. L. Perry: Biological estimation of acetylcholine. Meth. med. Res. 3, 78–92 (1950).

    Google Scholar 

  • Malyoth, G., u. H. W. Stein: Beitrag zur Papierchromatographie der Cholinester und der Zucker. Biochem. Z. 322, 165–167 (1951).

    CAS  Google Scholar 

  • Marquardt, P., u. H. H. Hirsch: Acetylcholin im Säugetierblut. Hoppe-Seylers Z. physiol. Chem. 289, 131–153 (1952).

    Article  CAS  Google Scholar 

  • Marquardt, P., u. H. H. Hirsch H. Schumacher u. G. Vogg: Die chemische Konstitution des blutdrucksenkenden Faktors in der Kartoffel. Arzneimittel-Forsch. 2, 301–304 (1952).

    CAS  Google Scholar 

  • Marquardt, P., u. H. H. Hirsch, u. G. Vonu: Vorkommen, Eigenschaften und chemische Konstitution des cholinergischen Faktors im Honig, 1. Mitteilung. Arzneimittel-Forsch. 2, 152–155 (1952a).

    CAS  Google Scholar 

  • Marquardt, P., u. H. H. Hirsch Vorkommen, Eigenschaften und chemische Konstitution des cholinergischen Faktors im Honig, 2. Mitteilung. Arzneimittel-Forsch. 2, 205–211 (1952b).

    CAS  Google Scholar 

  • Marquardt, P., u. H. H. Hirsch Über einen empfindlichen Nachweis des Cholins und Acetylcholins mit Hilfe von Tetraphenyl-bor-natrium. Hoppe-Seylers Z. physiol. Chem. 291, 143–147 (1952c).

    CAS  Google Scholar 

  • Mclennan, H.: The identification of one active component from brain extracts containing Factor I. J. Physiol. (Lond.) 146, 358–368 (1959).

    CAS  Google Scholar 

  • Meeter, E.: The heart of Mya arenaria as a test object for acetylcholine. Acta physiol. pharm. néerl. 4, 233–242 (1955).

    CAS  Google Scholar 

  • Mehler, A. H., and H. Tabor: Deamination of histidine to form urocanic acid in liver. J. biol. Chem. 201, 775–784 (1953).

    PubMed  CAS  Google Scholar 

  • Michaelson, I. A.: The chromatographic separation of choline esters with special reference to urocanylcholine, a constituent of certain marine invertebrates. M.S. Dissertation, University of Cincinnati, 1955.

    Google Scholar 

  • Minz, B.: Pharmakologische Untersuchungen am Blutegelpräparat, zugleich eine Methode zum biologischen Nachweis von Azetylcholin bei Anwesenheit anderer pharmakologisch wirksamer körpereigener Stoffe. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 168, 292–304 (1932).

    CAS  Google Scholar 

  • Mttchell, R., and B. B. Clark: Determination of quaternary ammonium compounds including acetylcholine, tetraethylammonium and hexamethonium. Proc. Soc. exp. Biol. (N. Y.) 81, 105–109 (1952).

    Article  Google Scholar 

  • Morley, J., and M. Schachter: Identification of acetylcholine in the silk gland of the caterpillar of Arctia caja (L.). J. Physiol. (Lond.) 151, 1–2 P (1961).

    Google Scholar 

  • Murnaohan, M. F.: The morphini7ed-eserinized leech muscle for the assay of acetylcholine. Nature (Lond.) 182, 317 (1958).

    Article  Google Scholar 

  • Nothnagel, G.: Über Cholin und verwandte Verbindungen, mit besonderer Berücksichtigung des Muscarins. Arch. Pharm. (Berl.) 232, 261–306 (1894).

    Article  Google Scholar 

  • Ocry, A., et Z. M. Bacq: Ester instable de la choline sans cholinesterase dans la pomme de terre et un champignon. Arch. int. Physiol. 47, 92–101 (1938).

    Google Scholar 

  • Pasini, C., e S. Coda: Murexine and related imidazole derivatives. Note L On some routes of synthesis and on some properties of murexine. Isomurexine (in Italian). Gazz. chim. ital. 87, 1440–1449 (1957a).

    CAS  Google Scholar 

  • Pasini, C., e S. Coda: Murexine and related imidazole derivatives. Note II. Murexine and 4(5)-imidazolylcarboxycholine isomerization and demethylation (in Italian). Gazz. chim. ital. 87, 1450 to 1463 (1957b).

    Google Scholar 

  • Pasini, C., e S. Coda u. A. Vercellone: Ein nues Reagens für die quantitative Bestimmung des Pikrat-Ions das 4-Octoxy-phenyl-guanidiniumchlorid. Z. anal. Chem. 143, 172–176 (1954).

    CAS  Google Scholar 

  • Pasini, C., e S. Coda u. A. Vercellone: Alkoxyphenylguanidinium salts. Their preparation and employment as precipitants of picric acid (in Italian). Farmaco 10, 823–835 (1955 a).

    Google Scholar 

  • Pasini, C., e S. Coda u. A. Vercellone: On the cis-trans isomerism of ß-(4(5)-imidazole) acrylic acid (urocanic acid) and on murexine (in Italian). Gazz. chim. ital. 85, 349–363 (1955b).

    CAS  Google Scholar 

  • Pasini, C., e S. Coda u. A. Vercellone u. V. Erspamer: Synthese des Murexins (ß-[Imidazolyl-4(5)]-acrylcholin. Justus Liebigs Ann Chem. 578, 6–10 (1953).

    Article  Google Scholar 

  • Quilliam, J P: The mechanism of action of murexine on neuromuscular transmission in the frog. Brit. J. Pharmacol. 12, 388–392 (1957).

    PubMed  CAS  Google Scholar 

  • Raacke, I. D.: On the reaction of hydroxylamine with esters of amino acids. Biochim. biophys. Acta 27, 416 (1958).

    CAS  Google Scholar 

  • Rotschuh, K. E.: Das herzmuskeleigene Acetylcholin. I. Mitteilung. Freisetzung und Bestimmungsmethodik. Pflügers Arch. ges. Physiol 258, 406 414 (1954).

    Google Scholar 

  • Schneider, R., and A. R. Timms: Some aspects of the pharmacology of an homologous series of choline esters of fatty acids. Brit. J. Pharmacol. 12, 30–37 (1957).

    PubMed  CAS  Google Scholar 

  • Schwarze, P.: Über den Bitterstoff der Rapssamen. Naturwissenschaften 36, 88–89 (1949).

    Article  CAS  Google Scholar 

  • Shaw, F. H.: The estimation of choline and acetylcholine. Biochem. J. 32, 1002–1007 (1938).

    PubMed  CAS  Google Scholar 

  • Shepherd, D. M., and G. B. West: Effect of trichloracetic acid on adrenaline chromatograms. Nature (Lond.) 169, 797 (1952).

    Article  CAS  Google Scholar 

  • Sheppard, C. W., W. E. Coax and P. J. Mathias: The estimation of choline esters by ion exchange. Arch. Biochem. Biophys. 47, 475–477 (1953).

    Article  PubMed  CAS  Google Scholar 

  • Si1uonart, A.: On the action of certain derivatives of choline. J. Pharmacol. exp. Ther. 46, 157–193 (1932).

    Google Scholar 

  • Smith, C. C., and L. Levine: The use of the clam heart as a test object for acetylcholine. Biol. Bull. Woods Hole 75, 365 (1938).

    Google Scholar 

  • Sörum, H.: The crystal and molecular structure of acetylcholine bromide. Acta them. stand. 13, 345–359 (1959).

    Article  Google Scholar 

  • Späth, E.: Die Synthese des sinapins. Mh. Chem. 41, 271–285 (1920).

    Google Scholar 

  • Stedman, E., and E. Stedman: The mechanism of the biological synthesis of acetylcholine. I. The isolation of acetylcholine produced by brain tissue in vitro. Biochem. J. 31, 817 to 827 (1937).

    Google Scholar 

  • Stephenson, M., and E. Rowatt: The production of acetylcholine by a strain of Lactobacillus plantarum. J. gen. Microbiol. 1, 279–298 (1947).

    Article  PubMed  CAS  Google Scholar 

  • Stone, W. E.: Acetylcholine in the brain. 1. “Free”, “bound” and total acetylcholine. Arch. Biochem. 59, 181–192 (1955a).

    Article  PubMed  CAS  Google Scholar 

  • Stone, W. E.: Acetylcholine in the brain. II. Chemical measurement of choline esters. Arch. Biochem. 59, 193–198 (1955b).

    Article  PubMed  CAS  Google Scholar 

  • Straughan, D. W.: Assay of acetylcholine on the rat blood pressure. J. Pharm. (Lond.) 10, 783–784 (1958).

    Article  CAS  Google Scholar 

  • Strecker, A.: Über einige neue Bestandteile der Schweinegalle. Justus Liebigs Ann. Chem. 123, 353–360 (1862).

    Article  Google Scholar 

  • Szerb, J. C.: The estimation of acetylcholine, using leech muscle in a microbath. J. Physiol. (Lond.) 158, 8–9 P (1961).

    Google Scholar 

  • Tabachnick, I. I. A., and F. E. Roth: The potentiation of histamine by imidazoleacrylcholine (murexine) and imidazolepropionylcholine (dihydromurexine). J. Pharmacol. exp. Ther. 121, 191–198 (1957).

    PubMed  CAS  Google Scholar 

  • Takahashi, Hidehiko, A. Najashtia and C. Koshino: Effect of y-aminobutyrylcholine upon the electrical activity of the cerebral cortex. Nature (Lond.) 182, 1443–1444 (1958).

    Article  CAS  Google Scholar 

  • Takahashi, Hidehiko, A. Najashtia and C. Koshino and Hisashi Takahashi: Effects of y-aminobutyric acid (GABA), y-aminobutyrylcholine (GABA-Ch) and their related substances on the cortical activity. Jap. J. Physiol. 9, 257–265 (1959).

    Google Scholar 

  • Tammelin, L.-E.: Choline esters substrates and inhibitors of cholinesterases. Svensk kern. Tidskr. 70, 157–181 (1958).

    CAS  Google Scholar 

  • Thesleff, S.: The mode of neuromuscular block caused by acetylcholine, nicotine, deca- methonium and succinylcholine. Acta physiol. scand. 34, 218–231 (1955).

    Article  CAS  Google Scholar 

  • Vincent, D., et A. Jullien: Richesse de la glande it pourpre des Murex en esters de la choline. C. R. Soc. Biol. (Paris) 127, 1506–1509 (1938).

    CAS  Google Scholar 

  • Wait, R. B.: The action of acetylcholine on the isolated heart of Venus mercenaria. Biol. Bull., Woods Hole 85, 79–85 (1943).

    Article  Google Scholar 

  • Welsh, J. H., and R. Taub: The action of choline and related compounds on the heart of Venus mercenaria. Biol. Bull., Woods Hole 95, 346–353 (1948).

    Article  CAS  Google Scholar 

  • West, G. B., and J. F. Riley: Chromatography of tissue histamine. Nature (Lond.) 174, 882–883 (1954).

    Article  CAS  Google Scholar 

  • Whittaker, V. P.: Specificity, mode of action and distribution of cholinesterases. Physiol. Rev. 31, 312–343 (1951a).

    PubMed  CAS  Google Scholar 

  • Whittaker, V. P.: Hydrolysis of succinylcholine by cholinesterases simultaneous utilization of paper chromatography and the Warburg technique (in Italian). Experientia (Basel) 7 217–218 (1951 b).

    Google Scholar 

  • Whittaker, V. P.: Identification of the F component of ox spleen. Biochem. biophys. Acta 22, 590 (1956).

    CAS  Google Scholar 

  • Whittaker, V. P.: ß,ß-Dimethylacrylylcholine, a new naturally occurring, physiologically active ester of choline. Biochem. J. 66, 35 P (1957).

    Google Scholar 

  • Whittaker, V. P.: Acetylcholine in milk Nature (Lond.) 181, 856–857 (1958).

    Article  CAS  Google Scholar 

  • Whittaker, V. P.: Acrylylcholine a new naturally occurring pharmacologically active choline ester from Buccinum undatum. Biochem. Pharmacol. 1, 342–346 (1959a).

    Article  Google Scholar 

  • Whittaker, V. P.: The identity of natural and synthetic ß,ß-dimethylacrylylcholine. Biochem. J. 71 32–34 (1959 b).

    Google Scholar 

  • Whittaker, V. P.: The isolation and characterization of acetylcholine-containing particles from brain. Biochem. J. 72 694–706 (1959 c).

    Google Scholar 

  • Whittaker, V. P. and I. A. Michaelson: Studies on urocanylcholine. Biol. Bull., Woods Hole 107, 304 (1954).

    Google Scholar 

  • Whittaker, V. P. and S. Wijesundera: The separation of esters of choline by paper chromatography. Biochem. J. 49, xlv (1951).

    Google Scholar 

  • Whittaker, V. P. and S. Wijesundera: The separation of esters of choline by filter-paper chromatography. Biochem. J. 51, 348–351 (1952a).

    PubMed  CAS  Google Scholar 

  • Whittaker, V. P. and S. Wijesundera: The hydrolysis of succinyldicholine by cholinesterase. Biochem. J. 52, 475–479 (1952b).

    PubMed  CAS  Google Scholar 

  • Winterfeld, K.: Über die Inhaltsstoffe der Mistel. Pharm. Ind. 9, 37–41 (1942).

    CAS  Google Scholar 

  • Wood, D. L.: The identification of spleen propionylcholine by infrared microspectroscopy. Biochem. J. 58, 30–31 (1954).

    PubMed  CAS  Google Scholar 

  • Yosbihara, H.: Comparative studies in isolated molluscan hearts as biological assay material for various drugs. Nippon Yakurigaku Zasshi 53, 393–399 (1957), abstracted in Chem. Abstr. 52, 10406e (1958).

    Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1963 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Whittaker, V.P. (1963). Identification of Acetylcholine and Related Esters of Biological Origin. In: Koelle, G.B. (eds) Cholinesterases and Anticholinesterase Agents. Handbook of Experimental Pharmacology, vol 15. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-99875-1_1

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-99875-1_1

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-99877-5

  • Online ISBN: 978-3-642-99875-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics