Abstract
Antidepressant activity in the human has been described for a large number of compounds and it is difficult to organize the available data in a systematic way. Here they are grouped not into strict chemical classes but according to major research topics. Although some of the tricyclic major tranquillizers described in Chap. 1 such as Thioridazine (Overall et al., 1964) and Flupenthixol (Young et al., 1976) also show clinically useful antidepressant activity, the chapter on thymoleptics (Chap. 16) starts with a discussion of imipramine, which was the first thymoleptic compound not to show additional neuroleptic activity.
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References
Abraham, R.J., Kricka, L.J., Ledwith, A.: The nuclear magnetic resonance spectra and conformations of cyclic compounds. J. Chem. Soc. [Perkin II], 1648 (1974)
Abraham, R.J., Lewtas, K., Thomas, W.A.: A nuclear magnetic resonance investigation of complex formation between imipramine and related psychotropic drugs with benzylalcohol and other aromatic solutes. J. Chem. Soc. [Perkin II], 1964 (1977)
Acébal, E., Subirá, S., Spatz, J., Falent, R., Merzberger, B., Gales, A., Moizeszowicz, J.: A double blind comparative trial of nomifensine and desimipramine in depression. Eur. J. Clin. Pharmacol. 10, 109 (1976)
Agedal: Bericht über das Symposium anläßlich der Einführung des Antidepressivums. Arzneim. Forsch. 19, 833 (1969)
Aichinger, G., Behner, O., Hoffmeister, F., Schütz, S.: Basische tricyclische Oximinoaether und ihre pharmacologische Eigenschaften. Arzneim. Forsch. 19, 838 (1969)
Åsberg, M., Crönholm, B., Sjöqvist, F., Tuck, D.: Relationship between plasma level and therapeutic effect of nortriptyline. Br. Med. J. 3, 331 (1971)
Asselin, A.A., Humber, L.G., Komlossy, J., Charest, M.P.: Cycloalkanindols. J. Med. Chem. 19, 792 (1976)
Bastian, J.M., Ebnöther, A., Jucker, E., Risse, E., Stoll, A.P.: 4H-Benzo[4,5]-cyclohepta[1,2-b]thiophene. Helv. Chim. Acta 49, 214 (1966)
Bastian, J.M., Ebnöther, A., Jucker, E., Risse, E., Stoll, A.P.: Beiträge zur Chemie des 4,5-Di-hydro-10H-benzo[5,6]cyclohepta[1,2-b]thiophens. Helv. Chim. Acta 54, 277 (1971)
Bastian, J.M., Weber, H.P.: Die molekulare und kristalline Struktur von 9,10-Dihydro-4-(3-di-methylamino-propylidene)-4H-benzo[4,5]cyclohepta[l,2-b]thiophen-hydrochlorid. Helv. Chim. Acta 54, 293 (1971)
Bauer, V.J., Duffy, B.J., Hoffman, D., Klioze, S.S., Kosley, R.W., McFadden, A.R., Martin, L.L., Org, H.H., Geyer, H.M.: Synthesis of Spiro[isobenzofuran-1(3H),4′-piperidines] as potential central nervous system agents. J. Med. Chem. 19, 1315 (1976)
Baumann, P.A., Maître, L.: Blockade of presynaptic α-receptors and of amine uptake in the rat brain by the antidepressant mianserine. Naunyn-Schmiedeberg’s Arch. Pharmacol. 300, 31 (1977)
Berendsen, H., de Graaf, J., Nickolson, V., Schönbaum, E.: Mianserin affects thermoregulation bimodally via 5-HT and NA. Abs. of paper 7 th Int. Congr. Pharmacol., Paris (1978).
Bevan, P., Bradshaw, C.M., Szabadi, E.: Effects of iprindol on responses of single cortical and caudate neurones to monoamines and acetylcholine. Br. J. Pharmacol. 55, 17 (1975)
Bickel, M.H., Brodie, B.B.: Structure and antidepressant activity of imipramine analogues. Int. J. Neuropharmacol. 3, 611 (1964)
Braithwaite, R.A., Goulding, R., Theano, G., Bailey, J., Coppen, A.: Plasma concentration amitriptyline and clinical response. Lancet I, 1297 (1972)
Brodie, B.B., Dick, P., Kielholz, P., Poeldinger, W., Theobold, W.: Preliminary pharmacological and clinical results with desmethylimipramine, a metabolite of imipramine. Psychopharmacologia 2, 467 (1961)
Brodie, R.B., Chasseaud, L.F., Crampton, E.L., Hawkins, D.R., Risdall, P.C.: High performance liquid chromatographic determination of dothiophen and northiaden in human plasma and serum. J. Int. Med. Res. 5, 388 (1977)
Brugmans, J., van Lommel, R., Baro, F.: Clinical aspects of tetramisol, an anthelmintic with antidepressant activity. Psychopharmacologia 26, 85S (1972)
Buczko, W., de Gaetano, G., Garattini, S.: Influence of some tricyclic antidepressive drugs on the uptake of 5-hydroxytryptamine by rat blood platelets. J. Pharm. Pharmacol. 26, 814 (1974)
v.d. Burg, W.J., Bonta, I.L., Delobelle, J., Ramon, C, Vergaftig, B.: A novel type of substituted piperazine with high antiserotonine potency. J. Med. Chem. 13, 35 (1970)
Butriptyline, International Symposium on J. Med. (Basel) 2, 250 (1971)
Buus-Lassen, J., Squires, R.F., Christiansen, J.A., Molander, L.: Neurochemical and pharmacological studies on a new 5HT-uptake inhibitor, FG 4363, with potential antidepressant properties. Psychopharmacologia 42, 21 (1975)
Carlsson, A.: Drugs which block the storage of 5-hydroxytryptamine and related amines. In: Handbook of Experimental Pharmacology, Vol. XIX. Berlin, Heidelberg, New York: Springer 1966, p. 529
Carlsson, A., Corrodi, H., Fuxe, K., Hökfelt, T.: Effect of antidepressant drugs on the depletion of intraneuronal brain 5-hydroxytryptamine stores caused by 4-methyl-α-ethyl-metatyramine. Eur. J. Pharmacol. 5, 357 (1969)
Carnmalm, B., Jacupovic, E., Johansson, L., de Paulis, T., Rämsby, S., Stjernström, N.E., Renyi, A.L., Ross, S.B., Ogren, S.O.: Antidepressive agents. J. Med. Chem. 17, 65 (1974)
Charampous, K.D., Johnson, P.C.: Studies of C14-Protriptyline in man: plasma levels and excretion. J. Pharmacol. 7, 93 (1967)
Christiansen, J., Gram, L.F.: Imipramine and its metabolites in human brain. J. Pharm. Pharmacol. 25, 604 (1973)
Christy, M.E., Boland, C.C., Williams, J.G., Engelhardt, E.L.: Antidepressants. J. Med. Chem. 13, 191 (1970)
Colpaert, F.C., Lenaerts, F.M., Niemegeers, C.J.E., Janssen, P.A.J.: A critical study on RO-4-1284 antagonism in mice. Arch. Int. Pharmacodyn. Ther. 215, 40 (1975)
Coppen, A., Gupta, R., Montgomery, S., Ghose, K., Baily, J., Burns, B., deRidder, J.J.: Mianserin hydrochloride, a novel antidepressant. Br. J. Psychiatr. 129, 342 (1976)
Coppen, A., Ghose, K., Swade, C., Wood, K.: Effect of mianserin hydrochloride on peripheral uptake mechanisms for noradrenaline and 5-hydroxytryptamine in man. Br. J. Clin. Pharmacol. 5, 13S (1978)
Coyne, W.E., Cusic, J.W.: Aminoalkyldibenzo[a,e]cyclopropa[c]cycloheptene derivatives, a series of potent antidepressants. J. Med. Chem. 17, 72 (1974)
Devriendt, E., Weemaes, J., Jansen, F.H.: Colorometric, ultra violet spectrometric and spectrofluorometric determination of doxepine and some of its metabolites in serum and urine. Arzneim. Forsch. 23, 863 (1973)
Dijkstra, S.J., Berdahl, J.M., Campbell, K.N., Coombs, C.M., Lankin, D.G.: Phenylindenes and phenylindanes with antireserpine activity. J. Med. Chem. 10, 418 (1967)
Dostert, P., Jalfre, M.: Tricyclic compounds with an alkylaminoalkylthio chain. Eur. J. Med. Chem. 9, 259 (1974)
Doxepine, a review. Drugs 1, 194 (1971)
Ehsanullah, R.S.B., Ghose, K., Kirby, M.J., Turner, P., Witts, D.: Clinical pharmacological studies of tandamine, a potential antidepressive drug. Psychopharmacology 52, 73 (1977)
Engelhardt, E.L., Zell, H.C., Saari, W.S., Christy, M.E., Colton, C.D., Stone, C.A., Stavorski, J.M., Wenger, H.C., Luddon, C.T.: Structure-activity relationships in the cyproheptadine series. J. Med. Chem. 8, 829 (1965)
Engelhardt, E.L., Christy, M.E., Colton, C.D., Friedman, M.B., Boland, C.C., Halpern, L.M., Vermeer, V.C., Stone, C.A.: Antidepressants. J. Med. Chem. 11, 325 (1968)
Eriksoo, R., Rohte, O.: Chemistry and pharmacology of a new potential antidepressant. Arzneim. Forsch. 20, 1561 (1970)
Fukushima, H., Nakamura, M., Yamamoto, H.: Pharmacology of 9-γ-Methylaminopropyl-9,10-methanoanthracene. HCl (ID-9206.HC1), a new potent antidepressant. Arch. Int. Pharmacodyn. Ther. 229, 163 (1977)
Fuller, R.W., Perry, K.W.: Increase of pineal noradrenaline concentrations in rats by desimipramine but not fluoxetine: implications concerning the specificity of these uptake inhibitors. J. Pharm. Pharmacol. 29, 710 (1977)
Fuller, R.W, Perry, K.W., Molloy, B.B.: Effect of 3-(p-trifluoromethylphenoxy)-N-methyl-3-phenylpropylamine on the depletion of brain serotonin by 4-chloramphetamine. J. Pharmacol. Exp. Ther. 193, 796 (1975)
Gannon, P., Itil, T., Keskiner, A., Hsu, B.: Clinical and quantitative encephalographical effects of MK 940. Arzneim. Forsch. 20, 971 (1970)
Gillette, J.R., Dingelt, J.V., Sulser, F., Kuntzman, R., Brodie, B.B.: Isolation from rat brain of a metabolic product, desmethylimipramine, that mediates the antidepressant activity of imipramine. Experientia 17, 417 (1961)
Goodlet, I., Mireylees, S.E., Sugrue, M.F.: The selective inhibition of 5-hydroxytryptamine reuptake by Org 6582. Br. J. Pharmacol. 56, 367 (1976)
Gordon, A.M.: The biochemistry of depression. J. Int. Med. Res. 5, Suppl. 4, 81 (1977)
Gram, L.F., Christiansen, J.: First-pass metabolism of imipramine in man. Clin. Pharmacol. Ther. 17, 555 (1975)
Greenwood, D.T., Malliou, K.B., Todel, A.H., Turner, R.W.: 2-Aryloxymethyl-2,3,5,6-tetra-hydr-l,4-oxazines, a new class of antidepressants. J. Med. Chem. 18, 573 (1975)
Heptner, W., Hornke, J., Cavagna, F., Fehlhaber, H.W., Rupp, W., Neubauer, H.P.: Metabolism of nomifensin in man and animal species. Arzneim. Forsch. 28, 58 (1978)
Hobbs, D.C: Distribution and metabolism of doxepin. Biochem. Pharmacol. 18, 1941 (1969)
Hoffmann, I., Ehrhart, G., Schmitt, K.: 8-Amino-4-phenyl-1,2,3,4-tetrahydroisochinoline, eine neue Gruppe antidepressiver Psychopharmaka. Arzneim. Forsch. 21, 1045 (1971)
Hollister, L.E.: Clinical use of psychotherapeutic drugs. Drugs 4, 361 (1972)
Horn, A.S., Trace, R.C.A.M.: Structure-activity relations for the inhibition of 5-hydroxytryptamine uptake by tricyclic antidepressants into synaptosomes from serotonergic neurones in rat brain homogenates. Br. J. Pharmacol. 51, 399 (1974)
Howe, R., Leigh, T., Rao, B.S., Todd, A.H.: Optical isomers of 2-(2-ethoxyphenoxymethyl)tetrahydro-l,4-oxazine (Viloxazine) and related compounds. J. Med. Chem. 19, 1074 (1976)
Hucker, H.B., Balletto, A.J., Demetriades, J., Arison, B.H., Zacchei, A.G.: Expoxide metabolites of protriptyline in rat urine. Drug Metab. Dispos. 3, 80 (1975)
Hunt, P., Kannengiesser, M.H., Raynaud, J.P.: Nomifensine, a new potent inhibitor of dopamine uptake into synaptosomes from rat brain corpus striatum. J. Pharm. Pharmacol. 26, 370 (1974)
Hunziker, F., Lauener, H., Schmutz, J.: Zur Chemie und Pharmakologie von in 10 Stellungen basisch substituierten 5-Dibenzo-[b,e][l,4]diazepin Derivaten. Arzneim. Forsch. 13, 324 (1963)
Itil, T.M., Polvan, N., Hsu, W.: Clinical and EEG effects of GB-94,a “tetracyclic” antidepressant. Curr. Ther. Res. 14, 395 (1972)
Itil, I.M.: Drug developments in Europe: discovery of “tetracyclic” psychotropic drugs. Psycho-pharmacol. Bull. 9, 41 (1973)
Jaskari, M.O., Ahlfors, U.G., Ginman, L., Lydeken, K., Tienari, P.: Three double-blind comparative trials of Mianserine (Org GB-94) and Amitriptyline in the treatment of depressive illness. Pharmakopsychiatr. Neuropsychopharmacol. 10, 101 (1977)
Jirkovsky, I., Humber, L.G., Voith, K., Charest, M.P.: Synthesis and primary pharmacological sceening of tandamine and related tetrahydrothiopyranoindoles with potential antidepressant properties. Arzneim. Forsch. 27, 1642 (1977)
Julou, L., Leau, O., Ducrot, R., Fournel, J., Bardone, M.C.: Propriétés pharmacodynamiques générales du (dimethylamino-3′methyl-2′propyl-1′)-5-iminodibenzyl et de ses isomères optiques, droit et gauche. Compt. Rend. Soc. Biol. 755, 307 (1961)
Kaiser, C., Tedeschi, D.H., Fowler, P.J., Pavloff, A.M., Lester, B.M., Zirkle, C.L.: Analogues of phenothiazines. J. Med. Chem. 14, 179 (1971)
Kielholz, P.: Depressive Zustände. Bern: Hans Huber Verlag 1972
Klerman, G.L., Cole, J.O.: Clinical pharmacology of imipramine and related antidepressant compounds. Pharmacol. Rev. 17, 101 (1965)
Kliose, S.S., Bauer, V.J., Geyer, H.M.: Synthesis of Spiro[isobenzofuran-1(3H),4′-piperidines] as potential central nervous system agents. J. Med. Chem. 20, 610 (1977)
Kobayashi, S.: Synthesis of pyrimidines and condensed pyrimidines. Bull. Chem. Soc. Japan 46, 2835 (1973)
Kopera, H.: Anticholinergic and blood pressure effects of mianserin, amitriptyline and placebo. Br. J. Clin. Pharmacol. 5, 29S (1978)
Kuhn, R.: Über die Behandlung depressiver Zustände mit einem Iminodibenzylderivat. Schweiz. Med. Wochenschr. 87, 1135 (1957)
Lambert, P.A., Guyotat, J.: Un nouvel antidépresseur sédatif. Presse Medicale 31, 1425 (1961)
Lambourn, J., Rees, J.A.: A general practioner study of dothiopin and amitriptyline. J. Int. Med. Res. 2, 210 (1974)
Lapin, J.P., Ksenofontova, T.A., Ya Kvitko, I., Porai-Koshits, B.A.: Central neurotropic activity of aminopropyl and aminopropionyl derivatives of iminodibenzyl and diphenylamine and its relation to their ionisation constants. Farmakol. Toksikol. (Moscow) 33, 8 (1970) in Chem. Abstracts 73, 12760t (1970)
Lehmann, E., Hopes, H.: Experimentelle Untersuchung der psychophysiologischen Wirkung eines neuen Antidepressivums (Lofepramin) im Vergleich zu Imipramin und Plazebo. Arzneim. Forsch. 27, 1100(1977)
Lemberger, L., Rowe, H., Carmichael, R., Oldham, S., Horng, J.S., Bijmaster, F.P., Wong, D.T.: Pharmacologic effects in man of a specific serotonin-reuptake inhibitor. Science 199, 436 (1978)
Ludiomil in general practise, a symposium. J. Int. Med. Res. 5, Suppl. 4, (1977)
Maître, L., Waldmeier, P.C., Greengrass, P.M., Jackel, J., Sedlacek, S., Delini-Stula, A.: Maprotiline-Its position as an antidepressant in the light of recent neuropharmacological and neurobiochemical findings. J. Int. Med. Res. 3, Suppl. 2, 2 (1975)
Malliou, K.D., Todd, A.H., Turner, R.W., Bainbridge, J.G., Greenwood, D.T., Madinaveitia, J., Sommerville, A.R., Whittle, B.A.: 2-(2-Ethoxyphenoxymethyl)-tetrahydro-l,4-oxazine hydrochloride, a potential psychotropic agent. Nature 238, 157 (1972)
Metysšováa, J., Metysš, J., Votava, Z.: Pharmakologische Eigenschaften der 6,11-Dihydrodibenz-(b,e)thiepin Derivate. Arzneim. Forsch. 75, 524 (1965)
Modestin, J.: Über die Abhängigkeit der klinischen Wirksamkeit des Dibenzepins (Noveril) von seiner Plasma-Konzentration. Pharmakopsychiatr. 6, 29 (1973)
Moncovic, I., Perran, Y.G., Martel, R., Simpson, W.J., Gylys, J.A.: Substituted tetrahydrofurfurylamines as potential antidepressants. J. Med. Chem. 16, 403 (1973)
Monro, A.M., Quinton, R.M., Wrighley, T.J.: Some analogues of imipramine. J. Med. Chem. 6, 255 (1963)
Montgomery, S., Cronholm, B., Åsberg, M., Montgomery, D.B.: Differential effects on suicidal ideation of mianserin, maprotiline and amitriptyline. Br. J. Clin. Pharmacol. 5, 77S (1978)
Moody, J.S., Whyte, S.F., Naylor, G.J.: A simple method for the determination of protriptyline in plasma. Clin. Chim. Acta 43, 355 (1973)
Murphy, J.E., Donald, J.F., Beaumont, G.: Opipramol and chlordiazoepoxide in the treatment of anxiety in general practise. Practitioner 205, 677 (1970)
Murphy, J.E.: Ludiomil symposium. J. Intern. Med. Res. 3, Suppl. 2 (1975)
Murphy, J.E., Donald, J.F., Molla, A.L.: Mianserin in the treatment of depression in general practise. Practitioner 217, 135 (1976)
Nagy, A., Treiber, L.: Quantitative determination of imipramine and desimipramine in human blood plasma by direct densitometry of thin layer chromatograms. J. Pharm. Pharmacol. 25, 599 (1973)
Nakra, B.R.S., Class, R.C., Rees, J.A.: Steady-state serum concentrations of Dothiepin and northiaden after two dosage regimes of dothiepin hydrochloride. J. Int. Med. Res. 5, 391 (1977)
Niemegeers, C.J.E.: On the pharmacology of tetramisole, an anthelmintic with antidepressant activity in man. Psychopharmacologia 26, Suppl. 84 (1972)
Otsuki, J., Ishiko, J., Sakai, M., Shimahara, K., Momiyama, T.: Pharmacological activities of doxepine hydrochloride in relation to its geometrical isomers. Chem. Abstracts 78, 131954 (1973)
Overall, J.E., Hollister, L.E., Meyer, F., Kimbell, I., Shelton, J.: Imipramine and Thioridazine in depressed and schizophrenic patients. J. Am. Med. Assoc. 189, 605 (1964)
Peet, M., Behagel, H.: Mianserin, a decade of scientific development. Br. J. Clin. Pharmacol. 5, 5S (1978)
Petersen, P.V., Lassen, N., Hansen, V., Huld, T., Hjortkjaer, J., Holmblad, J., Møller-Nielsen, I., Nijmark, M., Pedersen, V., Jørgensen, A., Hongs, W.: Pharmacological studies of a new series of bicyclic thymoleptics. Acta Pharmacol. Toxicol. 24, 121 (1966)
Pinder, R.M., Brogden, R.N., Speight, T.M., Avery, G.S.: Doxepin, a review. Drugs 13, 161 (1977 a)
Pinder, R.M., Brogden, R.N., Speight, T.M., Avery, G.S.: Maprotiline, a review. Drugs 13, 321 (1977b)
Pinder, R.M., Brogden, R.N., Speight, T.M., Avery, G.S.: Viloxazine, a review. Drugs 13, 401 (1977 c)
Post, M.L., Kennard, O., Horn, A.S.: Possible pharmacological and theoretical implications of X-ray structure of the tricyclic antidepressant imipramine. Nature 252, 493 (1974)
Raiteri, M., Angelini, F., Bertollini, A.: Comparative study of the effects of mianserin, a tetracyclic antidepressant, and of imipramine on uptake and release of neurotransmitters in synaptosomes. J. Pharm. Pharmacol. 28, 483 (1976)
Randrup, A., Braestrup, C.: Uptake inhibition of biogenic amines by newer antidepressant drugs. Psychopharmacology 53, 309 (1977)
Reboul, J.P., Cristau, B.: Analyse pharmacochimique des données fournies par la radiocristallographie des amines psychotropes polycycliques. I. Définition et calcul des paramètres conformationnels. Eur. J. Med. Chem. 12, 71 (1977 a)
Reboul, J.P., Cristau, B.: Analyse pharmacochimique des données fournies par la radiocristallographie des amines psychotropes polycycliques. II. Confrontation des valeurs paramétriques. Eur. J. Med. Chem. 12, 76 (1977 b)
Remy, D.C., Rittle, K.E., Hunt, C.A., Anderson, P.S., Engelhardt, A.L., Clineschmidt, B.V., Scriabine, A.: (+) and (-)-3methoxy cyproheptadine. J. Med. Chem. 20, 1681 (1977)
Ribbentrop, A., Schaumann, W.: Pharmakologische Untersuchungen mit Doxepin, einem Antidepressivum mit zentral anticholinerger und sedierender Wirkung. Arzneim. Forsch. 15, 863 (1965)
Rice, L.M., Hertz, E., Freed, M.E.: Antidepressive Agents. J. Med. Chem. 7, 313 (1964)
Rickeis, K., Chung, H.R., Csanolosi, I., Sablosky, L., Simon, J.H.: Iprindole and imipramine in non-psychotic depressed out-patients. Br. J. Psychiatr. 123, 329 (1973)
Rogers, S.C., Davies, F.J., Galbraith, A.W.: A study of depression in two general practises, including a double blind comparison of desimipramine and opipramol. Clin. Trials J. 6, 5 (1969)
Roszkowski, A.P., Schuler, M.E., Marx, M., Edwards, J.A.: A central nervous system depressant-antidepressant. Experientia 31, 960 (1975)
van Rij, C., Feil, D.: The molecular and crystal structure of (+)mianserin hydrobromide. Tetrahedron 29, 1891 (1973)
Saletu, B., Krieger, P., Grünberger, J., Schanda, H., Sletten, I.: Tandamine- a new norepinephrine reuptake inhibitor. Int. Pharmacopsychiatr. 12, 137 (1977)
Sanghoi, I., Gershon, S.: Effect of acute and chronic iprindole on serotonin turnover in mouse brain. Biochem. Pharmacol. 24, 2103 (1975)
Schindler, W., Häfliger, F.: Über Derivate des Iminodibenzyls. Helv. Chim. Acta 37, 472 (1954)
Siwers, B., Ringberger, V.A., Tuck, J.R., Sjöqvist, F.: Initial clinical trial based on biochemical methodology of zimelidine (a serotonin uptake inhibitor) in depressed patients. Clin. Pharmacol. Ther. 21, 194 (1977)
Sparatore, F., Sommovigo, P.G., Boida, V.: Research on nitrogen-containing seven-atom heterocycles of pharmacologic interest. Boll. Chim. Farm. 113, 219 (1974)
Speight, T.M., Avery, G.S.: Pizotifen: a review. Drugs 3, 159 (1972)
Stach, K., Pöldinger, W.: Strukturelle Betrachtungen der Psychopharmaka: Versuch einer Korrelation von chemischer Konstitution und klinischer Wirkung. Prog. Drug Res. 9, 129 (1966)
v.d. Stelt, C., Funcke, A.B.H., Tersteege, H.M., Nauta, W.Th.: The effect of alkyl substitution in drugs. Arzneim. Forsch. 16, 1342 (1966)
Swaisland, A.I., Franklin, R.A., Southgate, P.J., Coleman, A.J.: The pharmacokinetics of ciclazindol (Wy 23409) in human volunteers. Br. J. Clin. Pharmacol. 4, 61 (1977)
Theobald, W., Bück, O., Kunz, H.A., Morpurgo, C., Stenger, E.G., Wilhelmi, G.: Vergleichende Pharmakologische Untersuchungen mit Tofranil, Pertofran und Insidon. Arch. Int. Pharmacodyn. Ther. 148, 560 (1964)
Thomas, P.C., Jones, R.B.: The effects of clomipramide and desmethylclomipramine on the in vitro uptake of radiolabeled 5-HT and noradrenaline into rat brain cortical slices. J. Pharm. Pharmacol. 29, 562 (1977)
Todrick, A., Tait, A.C.: The inhibition of human platelet 5-hydroxytryptamine uptake by tricyclic antidepressive drugs. The relation between structure and potency. J. Pharm. Pharmacol. 21, 751 (1969)
Toscano, L., Grisanti, G., Fionello, G., Seghetti, E., Bianchetti, A., Bossoni, G., Riva, M.: Basic derivatives of 6,7-dihydroindolo[1,7-a,b][1]benzazepine and 6H-indolo[7,l-c,d][l,5]benzoxazepine as potential antidepressant agents. J. Med. Chem. 19, 208 (1976)
Tuomisto, J.: A new modification for studying 5-HT uptake by blood platelets: a re-evaluation of tricyclic antidepressants as uptake inhibitors. J. Pharm. Pharmacol. 26, 92 (1974)
Uzan, A., LeFur, G.: Effets de différents hétérocycles sur l’incorporation de 5-hydroxytryptamine et de noradrenaline par une préperation de cerveau de rat. Ann. Pharm. Fr. 33, 345 (1975)
Vencovský, E., Sšedivec, VI., Peterová, E., Baudis, P.: Vorläufige Mitteilung über die Behandlung der Manien mit IB-503 Sandoz. Arzneim. Forsch. 19, 491 (1969)
Villani, F.J., Mann, T.A.: The synthesis and pharmacological properties of dibenz[b,c][1,4]ox-azepin-11(5H)-ones. J. Med. Chem. 11, 894 (1968)
Villani, F.J., Daniels, P.J.L., Ellis, C.A., Mann, T.A., Wang, K.C., Wefer, E.A.: Derivatives of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene and related compounds. J. Med. Chem. 15, 750 (1972)
Vivalan: International Symposium. J. Int. Med. Res. 3, Suppl. 3 (1975)
Walter, C.J.S.: Clinical significance of plasma imipramin levels. Proc. R. Soc. Med. 64, 282 (1971)
Wilhelm, M., Schmidt, P.: Synthese und Eigenschaften von l-Aminoalkyldibenzo[b,c]bicy-clo[2,2,2]octadienen. Helv. Chim. Acta 52, 1385 (1969)
Wilhelm, M.: Die Chemie polyzyklischer Psychopharmaka. In: Depressive Zustände, P. Kielholz (ed.). Bern: Hans Huber Verlag 1972, p. 129
Winthrop, S.O., Davis, M.A., Herr, F., Stewart, J., Gaudry, R.: New Psychotropic Agents. J. Med. Pharm. Chem. 5, 1199 (1962a)
Winthrop, S.O., Davis, M.A., Herr, F., Stewart, J., Gaudry, R.: New psychotropic agents. J. Med. Pharm. Chem. 5, 1207 (1962b)
Wong, D.T., Bijmaster, F.P., Horng, J.S., Molloy, B.B.: A new selective inhibitor for uptake of serotonin into synaptosomes of rat brain-3-(p-trifluomethylphenoxy)-N-methyl-3-phenylpropylamine. J. Pharmacol. Exp. Ther. 193, 804 (1975)
Wright, S., Herrmann, L.: Doppelblindversuch zum Wirkungsvergleich von Lofepramin und Amitriptylin bei ambulant behandelten Patienten mit depressiven Zustandsbildern. Arzneim. Forsch. 26, 1167(1976)
Yale, H.L., Sowinski, F.: Novel polycyclic Heterocycles. J. Med. Chem. 7, 609 (1964)
Young, J.P.R., Hughes, W.C., Lader, M.H.: A controlled comparison of flupenthixol and amitriptyline in depressed out patients. Br. Med. J. 1, 1116 (1976)
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Zeelen, F.J. (1980). Chemistry (Structure and Activity). In: Hoffmeister, F., Stille, G. (eds) Psychotropic Agents. Handbook of Experimental Pharmacology, vol 55 / 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-67538-6_16
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