================================================================================ Phenalkylamine Article List ================================================================================ 1. "Psychotomimetic Phenylisopropylamines. 5." A Shulgin, JMC, 18(12) 1201 (1975) 2. "Synthesis of Some Analogues of [DOM]" R T Coutts, Can J Chem, 51, 1402, (1973) 3. "Sulfur Analogues of Psychotomimetic Amines" A Shulgin, J Pharm Sci 65(10), 1554 (1976) 4. "Monomethylthio Analogues of [TMA-2]" Peyton Jacob III, JMC, 20(10), 1235 (1977) 5. "Sulfur Analogues of Psychotomimetic Agents. 2." P. Jacob III, A Shulgin, JMC, 26, 746 (1983) 6. "Behavioral and Serotonin Receptor Properties of ... [analogues of 2, -DMA] Richard Glennon, JMC, 25, 1163 (1982) 7. "The Ethyl Homologues of [TMA-2]" A Shulgin, Nature, 11, 186 (1968) 8. "Demethyl Analogues of Psychoactive [phenalkylamines]" R Glennon, JMC, 23, 990 (1980) 9. "Amphetamine Analogues. II." Beng T. Ho, Nature, 13, 134 (1970) 10. "Substituent Branching in Phenethylamine-Type Hallucinogens" Robert A. Oberlander, JMC, 27(6), 788 (1984) 11. "2,3-Dihydrobenzofuran Analogues of Hallucinogenic Phenethylamines" David E. Nichols, JMC, 34, 276, (1991) [mescaline from tannin by myself] 12. "Composition of Myristicn Fraction from Oil of Nutmeg" A Shulgin, Nature, 197, 379 (1963) 13. "Convenient Synthesis of Myristicinaldehyde" eidem, Can J Chem, 46, 75 (1968) 14. "Synthesis of Arylalkyamines and Their Quaternary Ammonium Derivs." Yutaka Kasuya, Yakugaku Zasshi, 78, 509 (1958?); CA, 52, 17196f (19 8) 15. "Preparation of [MDMA] and [3,4-DMA]" Stanislaw Binieki, Acta Polon. Pharm., 17, 421 (1960) (Polish); CA, 16. "Synthesis and Pharmacology of 1-(3-Methoxy-4-methylphenyl)-2-aminopr pane" David Nichols, Michael P. Johnson, JMC, 34, 1662 (1991) 17. "Steric Effects of Substituents on Phenethylamine Hallucinogens" David Nichols, JMC, 22, 1264 (1979) 18. "The Six Trimethoxyphenylisopropylamines" A Shulgin, Nature 213?, 445 (1965?) 19. "Psychotropic Phenylisopropylamines Derived from Apiole and Dillapiol " A Shulgin, Nature, 215, 1494 (1967) 20. "Potential Psychotomimetics. Bromomethoxyamphetamines" C F Barfknecht, David Nichols, JMC, 14, 370 (1971) 21. "Potential Psychotomimetics.New Bromoalkoxyamphetamines" Silvia Sepulveda, B K Cassels, JMC, 15, 413 (1972) 22. "Two New Alkaloids in Cacti" [macromerine and gigantine] J E Hodgkins, Tet. Lett., 14, 1321 (1967) >>> --------------------- 23. "Derivatives of 1-(1,3-Benozdioxol-5-yl)-2-butanamine" David Nichols, JMC, 29, 2009, (1986) 24. "Substituted Phenylbutylamines" A Shulgin, Brit. Pat. 1,421,052 (1976) >>> --------------------- 25. "Resolution and Absolute Configuration of trans-[DiMeOPh-cyclopropyla ine]" David Nichols, JMC, 22, 458 (1979) 26. "Isomeric Cyclopropyl Ring-Methylated Homologues of trans-[DiMeOPh-cy ...]" David Nichols, JMC, 25, 526 (1982) 27. "Synthesis of Substituted 2-Phenylcyclobutylamines..." David Nichols, JMC, 27, 1108 (1984) >>> -------------------- 28. "5-Iodo-2-Aminoindan..." David Nichols, Pharmacol. Biochem. Behav., 38, 135 (1990) 29. "2-Aminoindan-2-carboxylic Acdis..." Roger M Pinder, JMC, 14, 892 (1971) 20. "Potential Psychotomimetics. 2-Amino-1,2,3,4-tetrehydronaphthalene An logs" C F Barfknecht, David Nichols, JMC, 16, 804 (1973) 21. "Nonneurotoxic Tetralin and Indan Analogues of [MDA]" David Nichols, JMC, 33, 703 (1990) 22. "Potential Psychomimetics. 2. Rigid Analogues of [DOM]" David Nichols, C F Barfknecht, JMC, 17, 161 (1974) 23. "Etude pharmacologique et biochimique d'amino-3 chromannes" Nicole Sarda et al, Eur. J Med Chem - Chim Ther 11(3), 257, (1976) Fr) 24. "Conformationally Constrained Analogues of Mescaline" Robert J Walters, J Pharm Sci, 63(9), 1379 (1974) 25. [Phenyl Adamantamines] J Dubois, Eur J Med Chem - Chim Ther, 11(3), 229 (1976) (Fr) 26. "alpha-Aryl or Aralkyl Furfurylamines" Robert L. Clarke US pat 3,194,818 (1965 to Sterling Drug); CA, 63, 1500h ================================================================================ Shulgin, A. T., S. Bunnell, and T. Sargent. 1961. The psychotomimetic properties of 3,4,5-trimethoxyamphetamine. Nature 189: 10011-1012. 12 .XP _____. 1963. Psychotomimetic agents related to mescaline. Experientia 19: 127. 19 .XP _____. 1963. Composition of the myristicin fraction from oil of nutmeg. Nature 197: 379. 20 .XP _____. 1963. Concerning the pharmacology of nutmeg. Mind 1: 299-302. 23 .XP _____. 1964. 3-methoxy-4,5-methylenedioxy amphetamine, a new psychotomimetic agent. Nature 201: 1120-1121. 29 .XP _____. 1964. Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines Experientia 20: 366. 30 .XP _____, and H. O. Kerlinger. 1964. Isolation of methoxyeugenol and trans- isoelemicin from oil of nutmeg. Naturwissenschaften 15: 360-361. 31 .XP _____. 1965. Synthesis of the trimethoxyphenylpropenes. Can. J. Chem. 43: 3437-3440. 43 .XP _____. 1966. Possible implication of myristicin as a psychotropic substance Nature 210: 380-384. 45 .XP _____. 1966. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem. 9: 445-446. 46 .XP _____, T. Sargent, and C. Naranjo. 1966. Role of 3,4-dimethoxyphenethylamin in schizophrenia. Nature 212: 1606-1607. 48 .XP _____, T. Sargent, and C. Naranjo. 1967. The chemistry and psychopharmacolo of nutmeg and of several related phenylisopropylamines. \fIIn\fR D. H. Efron [ed.]: Ethnopharmacologic search for psychoactive drugs. U. S. Dept. of H. E. W., Public Health Service Publication No. 1645. Pp. 202-214. Discussion: ibid. pp. 223-229. 49 .XP _____, and T. Sargent. 1967. Psychotropic phenylisopropylamines derived from apiole and dillapiole. Nature 215: 1494-1495. 50 .XP Sargent, T. W., D. M. Israelstam, A. T. Shulgin, S. A. Landaw, and N. N. Finley. 1967. A note concerning the fate of the 4-methoxyl group in 3,4-dimethoxyphenethylamine (DMPEA). Biochem. Biophys. Res. Commun. 29: 126-130. 52 .XP Naranjo, C., A. T. Shulgin, and T. Sargent. 1967. Evaluation of 3,4-methylenedioxyamphetamine (MDA) as an adjunct to psychotherapy. Med. Pharmacol. Exp. 17: 359-364. 53 .XP Shulgin, A. T. 1968. The ethyl homologs of 2,4,5-trimethoxyphenylisopropyl- amine. J. Med. Chem. 11: 186-187. 54 .XP _____, T. Sargent, and C. Naranjo. 1969. Structure activity relationships of one-ring psychotomimetics. Nature 221: 537-541. 57 .XP _____. 1969. Recent developments in cannabis chemistry. J. Psyched. Drugs 2: 15-29. 58 .XP _____. 1969. Psychotomimetic agents related to the catecholamines. J. Psyched. Drugs 2(2): 12-26. 59 .XP _____. 1970. Chemistry and structure-activity relationships of the psychotomimetics. \fIIn\fR: D. H. Efron [ed.]. Psychotomimetic Drugs. Raven Press, New York. Pp. 21-41. 60 .XP _____. 1970. The mode of action of psychotomimetic drugs; some qualitative properties of the psychotomimetics. Neur. Res. Prog. Bull. 8: 72-78. 61 .XP _____. 1970. 4-alkyl-dialkoxy-\fGa\fR-methyl-phenethylamines and their pharmacologically-acceptable salts. U. S. Patent 3,547,999, issued Dec. 15, 1970. 63 .XP _____, T. Sargent, and C. Naranjo. 1971. 4-bromo-2,5-dimethoxyphenyliso- propylamine, a new centrally active amphetamine analog. Pharmacology 5: 103-107. 64 .XP _____. 1971. Chemistry and sources. \fIIn\fR: S. S. Epstein [ed]. Drugs of abuse: their genetic and other chronic nonpsychiatric hazards. The MIT Press, Cambridge, Mass. Pp 3-26. 65 .XP _____. 1971. Preliminary studies of the synthesis of nitrogen analogs of \fGD\fR\u\s-21\s+2\d-THC. Acta Pharm. Suec. 8: 680-681. 66 .XP _____. 1972. Hallucinogens, CNS stimulants, and cannabis. \fIIn\fR: S. J. Mule/*' and H. Brill [eds.]: Chemical and biological aspects of drug dependence. CRC Press, Cleveland, Ohio. Pp. 163-175. 67 .XP _____. 1973. Stereospecific requirements for hallucinogenesis. J. Pharm. Pharmac. 25: 271-272. 68 .XP _____. 1973. Mescaline: the chemistry and pharmacology of its analogs. Lloydia 36: 46-58. 69 .XP _____. 1973. The narcotic pepper - the chemistry and pharmacology of \fIPiper methysticum\fR and related species. Bull. Narc. 25: 59-74. Le poivre stupe\*'fiant - chemie et pharmacologie du \fIPiper methysticum\fR et des espe\*'ces apparente\*'es. Bull. Stupe\*'fiants 25: 61-77. 70 .XP _____, T. Sargent, and C. Naranjo. 1973. Animal pharmacology and human psychopharmacology of 3-methoxy-4,5-methylenedioxyphenylisopropylamine (MMDA). Pharmacology 10: 12-18. 71 .XP _____. Drugs of abuse in the future. Drug abuse in America Vol. 1. pp. 209-236. U.S.G.P.O. 5266-00004. Reprinted: Clin. Tox. 8: 405-456. 72 .XP Kalbhen, D. A., T. Sargent, A. T. Shulgin, G. Braun, H. Stauffer, N. Kusubov, and M. L. Nohr. 1974. Human pharmacodynamics of the psychodysleptic 4-bromo-2,5-dimethoxyphenylisopropylamine labelled with \u82\dBr. IRCS (Int. Res. Comm. Sys.) 2: 1091. 73 .XP Sargent, T., D. A. Kalbhen, A. T. Shulgin, H. Stauffer, and N. Kusubov. 1975 A potential new brain-scanning agent: 4-\u77\dBr-2,5-dimethoxyphenyliso- propylamine (4-Br-DPIA). J. Nucl. Med. 16: 243-245. 74 .XP Shulgin, A. T., and M. F. Carter. 1975. Centrally active phenethylamines. Psychopharm. Commun. 1: 93-98. 75 .XP Sargent, T., D. A. Kalbhen, A. T. Shulgin, G. Braun, H. Stauffer, and N. Kusubov. 1975. \fIIn vivo\fR human pharmacodynamics of the psychodysleptic 4-Br-2,5-dimethoxyphenylisopropylamine labelled with \u82\dBr or \u77\dBr. Neuropharmacology 14: 165-174. 76 .XP _____. 1975. The chemical catalysis of altered states of consciousness. Altered states of consciousness, current views and research problems. The drug abuse council, Washington, D. C. Pp. 123-134. 77 .XP _____. 1975. Drug use and anti-drug legislation. The PharmChem Newsletter 4 (#8). 79 .XP _____, and D. C. Dyer. 1975. Psychotomimetic phenylisopropylamines. 5. 4-alkyl-2,5-dimethoxyphenylisopropylamines. J. Med. Chem. 18: 1201-1204. 80 .XP _____, and C. Helisten. 1975. Differentiation of PCP, TCP, and a contaminating precursor PCC, by thin layer chromatography. Microgram 8: 171-172. 81 .XP Helisten, C., and A. T. Shulgin. The detection of 1-piperidinodydlohexane- carbonitrile contamination in illicit preparations of 1-(1-phenylcyclohexyl) piperidine and 1-(1-(2-thienyl)cyclohexyl)piperidine. J. Chrom. 117: 232-235. 82 .XP Shulgin, A. T. 1976. Psychotomimetic agents. \fIIn\fR: M. Gordon [ed.] Psychopharmacological agents, Vol. 4. Academic Press, New York. Pp. 59-146. 83 .XP _____. 1976. Abuse of the term "amphetamines". Clin. Tox. 9: 351-352. 84 .XP _____. 1976. Profiles of psychedelic drugs. 1. DMT. J. Psychedelic Drugs 8: 167-168. 85 .XP _____. 1976. Profiles of psychedelic drugs. 2. TMA-2. J. Psychedelic Drugs 8: 169. 86 .XP _____, and D. E. MacLean. 1976. Illicit synthesis of phencyclidine (PCP) and several of its analogs. Clin. Tox. 9: 553-560. 87 .XP Nichols, D. E., and A. T. Shulgin. 1976. Sulfur analogs of psychotomimetic amines. J. Pharm. Sci. 65: 1554-1556. 89 .XP Sargent, T., A. T. Shulgin, and N. Kusubov. 1976. Quantitative measurement of demethylation of \u14\dC-methoxyl labeled DMPEA and TMA-2 in rats. Psychopharm. Commun. 2: 199-206. 90 .XP Standridge, R. T., H. G. Howell, J. A. Gylys, R. A. Partyka, and A. T. Shulgin. 1976. Phenylalkylamines with potential psychotherapeutic utility. 1. 2-amino-1-(2,5,-dimethoxy-4-methylphenyl)butane. J. Med. Chem. 19: 1400-1404. 91 .XP _____. 1976. Profiles of psychedelic drugs. 3. MMDA. J. Psychedelic Drugs 8: 331. 92 .XP _____. 1977. Profiles of psychedelic drugs. 4. Harmaline. J. Psychedelic Drugs 9: 79-80. 93 .XP _____. 1977. Profiles of psychedelic drugs. 5. STP. J. Psychedelic Drugs 9: 171-172. 94 .XP Nichols, D. E., A. T. Shulgin, and D. C. Dyer. 1977. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sciences 21: 569-576. 95 .XP Jacob, P. III, G. Anderson III, C. K. Meshul, A. T. Shulgin, and N. Castagnoli Jr. 1977. Mononethylthio analogues of 1-(2,4,5-trimethoxyphenyl) 2-aminopropane. J. Med. Chem. 20: 1235-1239. 96 .XP White, T. J., D. Goodman, A. T. Shulgin, N. Castagnoli Jr., R. Lee, and N. L. Petrakis. 1977. Mutagenic activity of some centrally active aromatic amines in \fISalmonella typhimurium\fR. Mutation Research 56: 199-202. 97 .XP Braun, U., A. T. Shulgin, G. Braun, and T. Sargent III. 1977. Synthesis and body distribution of several iodine-131 labeled centrally acting drugs. J. Med. Chem. 20: 1543-1546. 98 .XP Sargent, T. III, T. F. Budinger, G. Braun, A. T. Shulgin, and U. Braun. 1978. An iodated catecholamine congener for brain imaging and metabolic studies. J. Nucl. Med. 19: 71-76. 99 .XP Shulgin, A. T. 1978. Psychotomimetic drugs: structure-activity relationships. \fIIn\fR: L. L. Iversen, S. D. Iversen, and S. H. Snyder [eds.], Handbook of psychopharmacology, Vol. 11. Plenum Press, New York. Pp. 243-333. .XP Sargent, T. III, G. Braun, U. Braun, T. F. Budinger, and A. T. Shulgin. 1978. Brain and retina uptake of a radio-iodine labeled psychotomimetic in dog and monkey. Commun. Psychopharm. 2: 1-10. 101 .XP Braun, G., A. T. Shulgin, and T. Sargent III. 1978. Synthesis of \u123\dI-labelled 4-iodo-2,5-dimethoxyphenylisopropylamine. J. Labelled Comp. and Radiopharm. 14: 767-773. 102 .XP Murdock, J. E., J. R. Patty, and A. T. Shulgin. 1978. A novel illicit amphetamine laboratory. Microgram 11: 98-101. 103 .XP Anderson, G. M. III, G. Braun, U. Braun, D. E. Nichols, and A. T. Shulgin. 1978. Absolute configuration and psychotomimetic activity. \fIIn\fR: G. Barnett, M. Trsic, and R. Willette [eds.], QuaSAR Research Monograph 22. N.I.D.A. Washington, D.C. Pp. 8-15. 104 .XP Braun, U., G. Braun, P. Jacob III, D. E. Nichols, and A. T. Shulgin. Mescaline analogs: substitutions at the 4-position. \fIIn\fR: G. Barnett, M. Trsic, and R. Willette [eds.], QuaSAR Research Monograph 22. N.I.D.A. Washington, D.C. Pp. 27-37. 105 .XP Partyka, R. A., R. T. Standridge, H. G. Howell, and A. T. Shulgin. 1978. 2-amino-1-(2,5-dimethoxyphenyl)butanes. U.S. Patent 4,105,695, issued Aug. 8, 1978. 106 .XP Shulgin, A. T., and D. E. Nichols. 1978. Characterization of three new psychotomimetics. \fIIn\fR: R. C. Stillman and R. E. Willette [eds.], The psychopharmacology of hallucinogens. Pergamon Press, New York. Pp. 74-83. 107 .XP Glennon, R. A., L. B. Kier, and A. T. Shulgin. 1979. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci. 68: 906-907. 108 .XP Shulgin, A. T. 1979. Chemistry of phenethylamines related to mescaline. J. Psychedelic Drugs 11: 41-52. 109 .XP _____. 1979. Profiles of psychedelic drugs. 6. \fGa\fR,O-DMS. J. Psychedelic Drugs 11: 247. 110 .XP _____. 1979. Profiles of psychedelic drugs. 7. Mescaline. J. Psychedelic Drugs 11: 355. 111 .XP Standridge, R. T., H. G. Howell, H. A. Tilson, J. H. Chamberlain, H. M. Holava, J. A. Gylys, R. A. Partyka, and A. T. Shulgin. 1980. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem. 23: 154-162. 112 .XP Braun, U., A. T. Shulgin, and G. Braun. 1980. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci. 69: 192-195. 113 .XP Kantor, R. E., S. D. Dudlettes, and A. T. Shulgin. 1980. 5-methoxy- \fGa\fR-methyltryptamine (\fGa\fR,O-dimethylserotonine) a hallucinogenic homolog of serotonin. Biol. Psychiat. 15: 349-352. 114 .XP Shulgin, A. T. 1980. Profiles of psychedelic drugs. 8. psilocybin. J. Psychedelic Drugs 12: 79. 115 .XP Braun, U., A. T. Shulgin, and G. Braun. 1980. Pru\*:fung auf Aktivita\*:t und Analgesia von N-substituierten Analogen des Amphetamin- Derivates 3,4-Methylendioxyphenylisopropylamin. Arzneim. Forsch. 30: 825-830. 116 .XP Shulgin, A. T. 1980. Profiles of psychedelic drugs. 9. LSD. J. Psychedelic Drugs 12: 173-174. 117 .XP _____. 1981. Hallucinogens. \fIIn\fR: M. E. Wolff [ed.], Burger's medicinal chemistry. Wiley & Co. Pp. 1109-1137. .XP _____. 1981. Profiles of psychedelic drugs. 10. DOB. J. Psychoactive Drugs 13: 99. 119 .XP _____, and M. F. Carter. 1981. N,N-diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity. Commun. Psychopharmacol. 4: 363-369. 120 .XP Jacob, P., and A. T. Shulgin. 1981. Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline. J. Med. Chem. 24: 1348. 121 .XP Domelsmith, L. N., T. A. Eaton, K. N. Houk, G. M. Anderson, R. A. Glennon, A. T. Shulgin, N. Castagnoli, and P. A. Kollman. 1981. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem. 24: 1414. 122 .XP Shulgin, A. T. 1981. Chemistry of psychotomimetics. \fIIn\fR: F. Hoffmeister and G. Stille [eds.], Handbook of experimental pharmacology, Vol. 55/III. Springer-Verlag, Berlin Heidelberg. Pp. 3-29. .XP _____. 1981. Profiles of psychedelic drugs. 11. Bufotenine. J. Psychoactive Drugs 13: 389. 124 .XP _____, and P. Jacob. 1982. Potential misrepresentation of 3,4-methylene- dioxyamphetamine (MDA). A toxicological warning. J. Anal. Tox. 6: 71. 127 .XP _____, and P. Jacob. 1982. 1-(3,4-methylenedioxyphenyl)-3-aminobutane: a potential toxicological problem. J. Toxicol. - Clin. Toxicol. 19: 109. 12 .XP Jacob, P., and A. T. Shulgin. 1983. Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)- and (2,5- dimethoxy-4-ethylphenyl)-isopropylamine. J. Med. Chem. 26: 746. 130 .XP Shulgin, A. T. 1983. Twenty years on an ever-changing quest. \fIIn\fR: L. Grinspoon and J. B. Bakalar [eds.], Psychedelic Reflections. Human Sciences Press, New York. 131 .XP Sargent, T., A. T. Shulgin, and C. A. Mathis. 1982. New iodinated amphetamines by rapid synthesis for use as brain blood flow indicators. J. Lab. Cmpds. and Radiopharm. 19: 1307. 132 .XP Jacob, P., and A. T. Shulgin. 1984. Sulfur analogues of psychotomimetic agents. 3. The ethyl homologues of mescaline and their monothio analogues. J. Med. Chem. 27: 881-888. 133 .XP Sargent, T., A. T. Shulgin, and C. A. Mathis. 1984. Radiohalogen-labeled imaging agents. 3. Compounds for measurement of brain blood flow by emission tomography. J. Med. Chem. 27: 1071-1077. 135 .XP Repke, D. B., D. B. Grotjahn, and A. T. Shulgin. 1985. Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents. J. Med. Chem. 28: 892. 136 .XP Shulgin, A. T. 1985. What is MDMA? PharmChem Newsletter 14: 3 (May-June, #3). 137 .XP Lemaire, D., P. Jacob, and A. T. Shulgin. 1985. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol. 37: 575. 138 .XP Mathis, C. A., T. Sargent, and A. T. Shulgin. 1985. Iodine-122 labeled amphetamine derivatives with potential for PET brain blood-flow studies. J. Nucl. Med. 26: 1295. 139 .XP _____, _____, and _____. 1986. Synthesis of 122-I and 125-I-labeled- \fImeta\fR-dimethoxy-N,N-dimethyliodophenylisopropylamines. J. Labelled Comp. Radiopharm. 23: 115. 140 .XP Shulgin, A. T., L. A. Shulgin, and P. Jacob. 1986. A protocol for the evaluation of new psychoactive drugs. Methods and Findings in Experimental and Clinical Pharmacology 8: 313. 141 .XP Nichols, D. E., A. J. Hoffman, R. A. Oberlender, P. Jacob, and A. T. Shulgin. 1986. Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class. J. Med. Chem. 29: 2009. 143 .XP Mathis, C. A., A. T. Shulgin, Y. Yano, and T. Sargent. 1986. \u18\dF- labelled N,N-dimethylamphetamine analogues for brain imaging studies. Appl. Radiat. Isot. 37: 865. 144 .XP Shulgin, A. T. 1986. The background and chemistry of MDMA. J. Psychoactive Drugs 18: 291-304. 145 .XP Sargent, T. W., A. T. Shulgin, and C. A. Mathis. 1987. Rapid brain scanning pharmaceutical. U. S. Patent 4,647,446. 146 .XP McKenna, D. J., C. A. Mathis, A. T. Shulgin, T. Sargent, and J. M. Saavedra. 1987. Autoradiographic localization of binding sites for \u125\dI-DOI, a new psychotomimetic radioligand, in the rat brain. Eur. J. Pharmacol. 137: 289-290. 147 .XP Shulgin, A. T. 1987. The 'social-chemistry' of pharmacological discovery. Social Pharmacology 1: 279-290. 148 .XP _____. 1987. Reference information on MDMA. Analog 9: #4 (page 10). 149 .XP _____. 1988. DIPT: the distortion of music. Reality Hackers #6 (Winter 1988) p. 27. 152. .XP _____. 1988. THE CONTROLLED SUBSTANCES ACT: A resource manual of the current status of the federal drug laws. 383 pp., published in Lafayette, California 94549 April 1988. 154 .XP _____. In press. History of MDMA. \fIIn\fR: S. Peroutka [ed.], MDMA: "Ecstasy" and human neurotoxin? Kluwer Academic Publishers, Norwell, MA, 02061. ================================================================================ Indole and Tryptamine Reference List ================================================================================ Date: Sat, 3 Apr 93 16:47:20 MST From: aankrom@nyx.cs.du.edu (Anthony Ankrom) This is a list of some pertinant and perhaps some not so pertinant indole and tryptamine references. It could use some updating which I will do whenever I feel like it. This list has had some 3 or 4 years in the making. I provide this list with hopes that some people can make good use of it. a lot of the articles are very technical and many are in German. I have provided the Chmical Abstract references where I could. The Hofmann articles are notably exceptional. Enjoy St. Anthony The List: Tryptamines and Indoles "Biochemistry and Pharmcology of Tryptamines and B-Carbolines" Dennis McKenna, J Psych Drugs 16, 347 (1984) "Tryptamine and Related Compounds in Plants" Terrence Smith, Phytochem., 16, 171 (1977) <> Hofmann et al, HCA 42, 1557 (1959) <> F Troxler, F Seeman, A Hofmann, HCA 42, 2073 (1959); CA 54:18471f "SAR of Analogs of 5-MeO-N,N-DMT, Psilocin, etc..." PK Gessner, P D Godse, Life Sci, 7, 267 (1968) "Serotonin Receptor Binding Affinity of Tryptamine Analogues" Richard Glennon, JMC, 22, 428 (1979) "SAR in Potentially Hallucinogenic N,N-Dialkyltryptamines..." Toni B Kline, F Benington, JMC, 25, 908 (1982) (Tryptamine from Tryptophan) Barton et al, JCS 3992 (1965) "Studies in the Indole Series. I. Indolalklyamines" B Heath-Brown, PG Philpott, JCS 7165 (1965) <> R Stauffer, HCA 49, 1199 (1966) "Tryptamines" Robert Bucourt et al, US 2,920,080 (1960); CA 54:13018 "Indole Derivatives" HJ Enenkel et al, US 3,104,241 (1963) "Psychotomimetic N-Me,N-iPr-Tryptamines. Effects of Aryloxy Substitution" David Repke, A Shulgin, JMC, 28, 892 (1985) "Synthesis of Some Secondary Methylalkylamines" D Repke, Tet Lett 4183 (1979) "Process for the Preparation of Hydroxylated Indole Derivatives" A Hofmann, F Troxler, Swiss 375,712 (1964) "Psilocin Analogues III. Synthesis of 5-Methoxy- and 5-hydroxy-1,2,3,4- tetrahydro-9H-pyrido[3,4-b]indoles" D Repke, WJ Ferguson, J Het Chem 19, 845 (1982) "II. Synthesis of 3-[2-(Dialkylamino)ethyl]-, 3-[2-(N-Methyl-N-alkylamino) ethyl]-, and 3-[2-(Cycloalkylamino0ethyl]indol-4-ols" eidem, ibid, 18, 175 (1981) "I. Synthesis of 3-[2-(Dialkylamino)ethyl]- and 3-[2-(Cycloalkylamino)ethyl]- indol-4-ols" eidem, ibid, 14, 71 (1977) "Nitro Olefination of Indoles and Some Substituted Benzenes with 1-Dimethylamino-2-nitroethylene" G. Bu(e)chi, JOC 42, 1784 (1977) "3-(2-Dimethylaminoethyl)-4-mercaptoindole" A Hofmann, F Troxler, Swiss 421,960 (1967); CA 68:95680n "3-(2-Aminoethyl)-2-(alkylthio)indoles" Bourdais et al Ger Offen 2,033,668 (1971); CA74: 87824w "Synthesis and Characterization of 5H-1,3-Dioxolo[4,5-f]indoleethylamines" DB Grotjahn, J Het Chem 20, 1031 (1983) "SAR for Hallucinogenic Dialkyltryptamines" [Methylenedioxy and Methylthio] T Kline, F Benington, JMC, 25, 1381 (1982) "DIPT and 5-MeO-DIPT" A Shulgin, Comm in Psychopharm, 4, 363 (1980) [alpha-methyl tryptamine] "Effects in Normal Man of AMT and AET" Henry Murphree, Clin Pharm Ther, 2(6), 722 [alpha-Alkyl Tryptamines and Tryptophans] Heinzelman, et al, JOC 23, 1548 (1960) [patent for AET] Brit. 933,786 (1963) "Alkaloids of B. caapi and P. amazonica" Hochstein, JACS, 89, 5735 (1957) [DMT] Szara, Experientia, 12, 441 (1956) "Indoles from Macuna pruriens" SK Bhattacharya, Ind J Physiol, 25, 53 (1971) <> M Julia, et al, BSCF 2046 (1973) [5,6,7-TNDT and 4,5,6-TNDT in Rat] I Nir, Psychophramacologia, 39, 323 (1974) *[5,6,7-TNDT] E Hardeggar, H Corrodi, Pharm Acta Helv 39, 401 (1964) *[4,5,6-TNDT] Carlsson, Helv Chim Acta, 46, 1231 (1963) (Ger); CA "Acute and Chronic Effect of 5-MeO-DMT on a Primate Social Colony" WJ Heinze, Biol Psychiat, 15(6), 829 (1980) "Improved Synthesis of the Sulfur Analogue of Serotonin" E Campaine, A Dinner, JPS 58, 892 (1969) "Sulfur Analogues of B-Carbolines" W Herz, JACS 72, 4999 (1950) "B-Aminoalkylthianaphthene and B-Aminoalkylbenzofuran Derivatives" SK&F Brit 855,115 (1960); CA 55:12423c "Amides of B-(3-thianaphthenyl)ethylamines" JT Suh, US 3,528,994 (1970); CA 74:87817w "The Synthesis of O-Methylnordehydrobufotenine, a New Psychoactive Indole" FGH Lee, et al JMC 12, 321 (1969) ------------------------ "Chemistry of Aminochromes. II" RA Heacock, Can J Chem 36, 1550 (1958) "Chemistry of Aminochromes. I" ibid., 853 "Betaine Hydrazones of Aminochromes" Harry Sobotken, JACS, 73, 3077 (1951) "Adrenochrome as a Psychotomimetic Agent" RA Heacock, Chim Ther, (4), 302 (1971) ------------------------ <> HG Leemann, S Fabbri, HCA 42, 2698 (1959) "Synthesis of Amides of Lysergic Acid" WL Garbrecht, JOC 24, 368 (1958) "Psychoactive Properties of Mitragynine" Karl Jansen, J Psych Drugs 20(4), 455 (1988) "Totalsynthese des (+,-)-Chanoclavin" Hans Pleininger, Tet Lett 22-23, 1827 (1975) "Total Synthesis of (+,-)-Chanoclavine and (+,-)-Dihydrosetoclavine" Mitsuka Natsume, Heterocycles 16(3), 375 (1981) "10-MeO-6,7-dihydro-12H-indolo[2,3-a]pyridocholinium Halide..." CA 64:11212c "Neuropharmacological Studies on Ibogaine..." JA Snyder, Annal NY Acad Sci ??? -------------------------------------------------- "Indoles from 2-Methyl Nitrobenzenes..." Org Syn ??? "5-Hydroxyindoles" S Ordzhonikidze, Fr M 5,142 (1967); CA 72:66812j "Indoles from Phenylhydrazones" NN Suorov et al, Brit 1,174,034 (1969); CA 72:66814m "Indole from Formyl-toluidine" A Galat, HL Friedman, JACS 70, 1280 (1948) "Indole" FT Tyson, Org Syn III, 479 "Indole-3-aldehyde" PN James, HR Snyder, Org Syn col vol. ?? 539 "3-Indolylacetaldehyde and 3-Indolylacetone" JB Brown et al, JCS 3172 (1952) ================================================================================ SAR and Pharmacology of Pheylisopropylamine Derivatives ================================================================================ Date: Sat, 3 Apr 93 16:48:20 MST From: aankrom@nyx.cs.du.edu (Anthony Ankrom) Here are some references related to the Pharmacology and Structure Activity Relationships of Phenalkylamines. The list is sadly incomplete and needs revamped which I will do whenever I feel like it... :-) Enjoy St. Anthony SAR and Pharmacology of Pheylisopropylamine Derivatives "Chemistry of Phenethylamines Related to Mescaline" A Shulgin, J Psych Drugs 11, 41 (1979) "SAR of One-ring Psychotomimetics" eidem, Nature 221, 537 (1969) "SAR in Psychotimietic Phenalkamines" FAB Aldous, RM Pinder, JMC 17, 1100 (1974) "SAR Studies on Mescaline. II" JR Smythies, Psychopharmacologia 10, 379 (1967) "Relationship of the Structures of Mescaline and Analogs" Harold F Hardman, Toxicol Appl Pharmacol 25, 299 (1973) "LSD and Phenethylamine Hallucinogens: New Structural Analogy" D Nichols, Life Sci 22, 2165 (1978) "Behavioural Effects of Some Derivatives of Amphetamines & LSD" JR Smythies, Nature 226, 644 (1970) "Correlation between Activity and Electronic States of Hallucinogenic..." Sungzong Kang, ibid. 645 "Effects of [3,4-DMA] in the Rat" CF Barfknecht, JMC 15, 109 "Behavioural Effects of Some 4-Substituted Amphetamines" JM Beaton, JR Smythies, Nature 220 ? (1968) "Some New Behaviour-disrupting Amphetamines and Their Significance" JR Smythies, Nature 216, 128 (1967) "[DOM] in man" Leo Hollister, Psychopharmacologia 14, 62 (1969) "[DOM]...and [DOET], Effects in Normal Subjects" Solomon Snyder, Am J Psychiat 125(3), 357 (1968) "[DOM]: a New Hallucinogenic Drug" eidem, Science 158, 669 "Behavioural Effects of 2,5-DiMeO-4-alkyl Amphetamines" RD Morin, JR Smythies, Experientia 31, 93 (1975) "The Psychotomimetic Properties of TMA" A Shulgin, Nature ??? "[MMDA] a New Psychotomimeti Agent" A Shulgin, Nature 201, ? (1964) "Animal Pharmacology and Human Psychopharamcology of [MMDA]" A Shulgin, Pharmacology 10, 12 (1973) "[DOM] a New Centrally Active Amphetamine Analog" A Shulgin, ibid. 5, 103 (1971) "Pharmacological Studies on p-Bromo-methamphetamine" J Knoll, Acta Physiol Acad Sci Hung 37, 151 (1970) "PMA Deaths in Ontario" Cimbura, CMA J 110, 1203 (1974) "Preliminary Behavioural Investigation of PMMA" R Glennon, Pharmacol Biochem Behav 31, 9 (1988) ================================================================================ Claviceps Fungi References ================================================================================ From: pjordan@cs.ualberta.ca (Peter Jordan) Newsgroups: alt.drugs Subject: Claviceps paspali references are HERE! Date: 29 Aug 1994 23:57:22 GMT Message-ID: <33tsl2$k1r@scapa.cs.ualberta.ca> Interesting Chemical Abstracts References: CA: 71:P69351y : describes mutants of strain NRRL 3027 producing 2270mg/l of ergoline compounds of which 85% were amides of lysergic and isolysergic acids. (Swiss patent application) CA: 77:P156333n : describes a method used to get 9.75g pure lysergamides from a 10 litre fermentation originally containing an estimated 15g. CA: 94:13992r : reference Indian Drugs; 1980; 17(8) 228-31 Eng. CA: 90:118108c : reference Indian Drugs; 1979; 16(4) 88-93 Eng. Very interesting>:-|| CA: 102:219574y : Serbo-Croat areticle describing 2.2g/l prod. by C. paspali Stevens and Hall (1984). Nature reference: Nature: 187:238-239. I can't remember this one but I have written down "-production by C. paspali in submerged culture" . Lloydia references: lots; just go check the indexes for each volume. An absolute Gem from 1916: Life History and Poisonous Properties of Claviceps paspali; H. B. Brown (Mississippi Agricultural Experiment Station); Journal of Agricultural Research ,vol. 7(9), pgs 401-405. describes on brief glance through it --- germination of the yellowish-grey sclerotia found on Paspalum dilatatum Poir. observed in the region of the Mississippi Agricultural College. Also contains reference to Stevens and Halls' original article (1910). "So there you have it gentlemen, what more evidence do we need" Yow!!! If you find this usefull/helpfull/interesting, let me know and I'll post a whole lot more. My willingness to post this stuff is directly correlated to the magnitude of the responses I get. Thanks very much for the encouragement from those who responded to the earlier postings. (Two from Germany and Two from USA). P.S. If you find a good culture of this stuff, I would LOVE to have some. P.P.S. If you take your rights, you'll never have them. ME! Peter Jordan ============================================================================= From: pjordan@cs.ualberta.ca (Peter Jordan) Newsgroups: alt.drugs Subject: More Claviceps references! Date: 31 Aug 1994 20:16:23 GMT Message-ID: <342oen$o4n@scapa.cs.ualberta.ca> Hi again, Enjoy these goodies: * Biotechnological Exploitation of the Ergot Fungus (Claviceps Purpurea); Karl Esser and Andrea Duvell; Process Biochemistry, August 1984 pgs 142-149. Synopsis: "The alkaloids of the ergot fungus C. purpurea and related species already known as drugs in the middle ages are still finding many uses in medical therapy (he he). Since the supply of natural grown ergots is not sufficient, the biotechnological production of ergot alkaloids has gained in importance. This requires not only an undestanding of physiological and environmental conditions, but also concerted breeding in order to increase and stabilize the production level." * Biology of Claviceps; Willard A. Taber; Chapter 15 (sorry - i don't remember which book this came from, but it should be indexed under Taber in Biological Abstracts) pgs 449-486. "If one desires isolates of C. paspali (which are high producers of simple amides), one must go to paspalum grass. ... C. paspali differs from all other species in possesing a yellowish tan cauliflower- shaped sclerotium rather than the purplish banana-shaped sclerotium, and it has been suggested that this species be trasnsferred to the genus Mothesia. " *The Ergot Alkaloids; A. Stoll and A. Hofmann (THE); Chapter 21, The Alkaloids, Manske (ed. ?) vol. VIII, pgs 725-779+. Describes lots and lots and lots of chemical detail regarding everything from biogenesis to complete chemical synthesis as a means of confirming structure. Also has a section completely devoted to "Derivatives of Ergot Alkaloids" in which the following processes for synthesizing amides are discussed: => The azide process. => DMF-SO3 mixed anhydride method. => mixed Lysergic acid trifluoroacetic anhydride. => Lysergic acid chloride hydrochloride method. => N,N'- carbonyldiimidazole as condensing agent (Best IMHO). My fingers are tired, PLEASE do not rip any articles or pages from journals/books, as this is the most insidious kind of censorship (something a pig might do). Untill Later; Peter Jordan P.S. The P.P.S. of my previous posting should have read: "If you DON'T ........" ============================================================================= CA: 71:P69351y : describes mutants of strain NRRL 3027 producing 2270mg/l of ergoline compounds of which 85% were amides of lysergic and isolysergic acids. (Swiss patent application) CA: 77:P156333n : describes a method used to get 9.75g pure lysergamides from a 10 litre fermentation originally containing an estimated 15g. CA: 94:13992r : reference Indian Drugs; 1980; 17(8) 228-31 Eng. CA: 90:118108c : reference Indian Drugs; 1979; 16(4) 88-93 Eng. Very interesting>:-|| CA: 102:219574y : Serbo-Croat areticle describing 2.2g/l prod. by C. paspali Stevens and Hall (1984). Life History and Poisonous Properties of Claviceps paspali; H. B. Brown (Mississippi Agricultural Experiment Station); Journal of Agricultural Research ,vol. 7(9), pgs 401-405. describes on brief glance through it --- germination of the yellowish-grey sclerotia found on Paspalum dilatatum Poir. observed in the region of the Mississippi Agricultural College. Also contains reference to Stevens and Halls' original article (1910). * Biotechnological Exploitation of the Ergot Fungus (Claviceps Purpurea); Karl Esser and Andrea Duvell; Process Biochemistry, August 1984 pgs 142-149. Synopsis: "The alkaloids of the ergot fungus C. purpurea and related species already known as drugs in the middle ages are still finding many uses in medical therapy (he he). Since the supply of natural grown ergots is not sufficient, the biotechnological production of ergot alkaloids has gained in importance. This requires not only an undestanding of physiological and environmental conditions, but also concerted breeding in order to increase and stabilize the production level." * Biology of Claviceps; Willard A. Taber; Chapter 15 (sorry - i don't remember which book this came from, but it should be indexed under Taber in Biological Abstracts) pgs 449-486. "If one desires isolates of C. paspali (which are high producers of simple amides), one must go to paspalum grass. ... C. paspali differs from all other species in possesing a yellowish tan cauliflower- shaped sclerotium rather than the purplish banana-shaped sclerotium, and it has been suggested that this species be trasnsferred to the genus Mothesia. " *The Ergot Alkaloids; A. Stoll and A. Hofmann (THE); Chapter 21, The Alkaloids, Manske (ed. ?) vol. VIII, pgs 725-779+. Describes lots and lots and lots of chemical detail regarding everything from biogenesis to complete chemical synthesis as a means of confirming structure. Also has a section completely devoted to "Derivatives of Ergot Alkaloids" in which the following processes for synthesizing amides are discussed: => The azide process. => DMF-SO3 mixed anhydride method. => mixed Lysergic acid trifluoroacetic anhydride. => Lysergic acid chloride hydrochloride method. => N,N'- carbonyldiimidazole as condensing agent (Best IMHO). ============================================================================= Production of peptide ergot alkaloids in submerged culture by three isolates of Claviceps purpurea. Amici et al. 1969-464 Amici, A. M.; Minghetti, A.; Scotti, T.; Spalla, C.; Tognoli, L. (1969) Appl Microbiol 18(3):464-468 On an alkaloid from ergot. Anonymous (1935) Science 82(2114):16 A note on the variability of alkaloid content of domestic ergot. Atal, C. K.; Schwarting, A. E. (1957) J Am Pharmaceut Assoc Sci Ed 46:451 The new ergot alkaloid. Dale, H. H. (1935) Science 82(2118):99-101 Effect of autoclaving and conventional and microwave baking on the ergot alkaloid and chlorogenic acid contents of morning glory (Ipomoea tricolor Cav. cv.) heavenly blue seeds Friedman, M.; Dao, L. (1990) J Agr Food Chem 38(3):805-808 Ergot alkaloid and chlorogenic acid content in different varieties of morning glory Ipomoea-spp seeds. Friedman, M.; Dao, L.; Gumbmann, M. R. (1989) J Agr Food Chem 37:708-712 Recent advances in ergot pharmacology. Phillipson JD & Zenk MH (ed) Indole & biogenetically related alkaloids. Academic Press, London :285-291 Fluckiger, E. (1980) Studies on cultural requirements of Claviceps purpurea and inactivation of ergotamine. Michener, H. D.; Snell, N. (1950) Am J Bot 37(Jan):52-59 Title: Biosynthesis of Ergot Alkaloids by Immobilized Mycelium of Claviceps paspali Authors: Matošić, Srećko; Mehak, Milena; Ercegović, Lidija; Okwor, James Journal: Prehrambeno-tehnol. biotehnol. rev Number: 2 ISSN: 0352-9193 Volume:30, pgs83-88 (1992) Language: hrvatski Summary: The effect of the selected parameters on the biosynthesis ofergot alkaloids during semicontinuous cultivation of immobilizedmycelium of Claviceps paspali F-2057 was investigated. Comparingthe effect of various substrate mass in the me of biosynthesis ofergot alkaloids medium, it was established that the mediumcontaining 6% mannitol and 5% ammonium succinate yields moreergot alkaloids. For the biosynthesis of ergot alkaloids, 4.25g/L 6 days old mycelial inoculum appeared to be most favorable. Investigation of the effect of alginic acid concentration usedfor the immobilization, showed 4% alginic acid concentration tobe the mest favorable for alkaloid biosynthesis. Insemicontinuous process, the immobilized Claviceps paspalimycelium produced alkaloids over a period of 60 days (6 reincubations). Productivity of the process in each of thereincubations with immobilized cells is 75 to 120 % higher thanin corresponding free cell cultivations and the totalproductivity with immobilized cells is two times higher than thatof free cells. The results obtained here show that immobilization of mycelia forming microorganisms, might be effective inbiotechnological production of complex metabolites, such as ergotalkaloids. Title: Effect of antifoams on the biosinthesis of ergot alkaloids by high-productive strain of Claviceps paspali F-2057 Authors: Matošić, Srećko; Mehak, Milena; Šušković, Jagoda; Golob, Zoran Journal: Acta Bot. Croat. ISSN: 0365-0588; Volume:53, pgs.39-47 (1994) Language: engleski Summary: The effect of several surfactants i.e. commercial antifoams on biosynthesis of ergot alkaloids was studied. Addition of some surfactants of polyglycole structure and Tweens to submerged cultures of high-productive strain of C. paspali F-2057 caused a change in alkaloid synthesis intesity. Pluronik (polyetoxypolypropoxy polymer) added in the range of 0.25 to 0.75 % markedly stimulated the production of ergot alkaloids. The Pluronik-supplemented culture reached maximal alkaloid yields one or two days erlier than the control. Production of alkaloids increased twice. The maximal yield achieved was 5.35 g/L with the process productivity amounting to 17.2 mg/L h. Title: Physiological diferentiation of alkaloid producing strains of Claviceps purpurea Authors: Matošić, Srećko; Mehak, Milena; Šušković, Jagoda Journal: Acta Bot. Croat. ISSN: 0365-0588 53, pgs.21-30 (1994) Summary: Four different strains of Claviceps purpurea IC/39/20-B, G, R and W have been selected and isolated using common selection method. The relationship between intensity of pigmentation of the culture and the accumulation of ergot alkaloids have been noticed. Maximal alkaloid yields have been obtained with more pigmented strains R and W in the sucrose- asparagine medium (1.30 and 1.50 g/L respectively) and with less pigmented strains B and G in the sucrose-peptone medium (0.30 and 0.80 g/L). Title(Thesis): Biosynthesis of Ergot Alkaloids by means of Immobiliyed mycelium of Claviceps paspali Summary: Comparing the effect of various substrate concentration on the biosynthesis of ergot alkaloid, it was obtained that a mediumcontaining 6% manitol and 5% ammonium succinate yields more ergotalkaloid. For the biosynthesis of ergot alkaloid, 4.25 g/L dayold mycelial inoculum appeared most favorable. Investigating theeffect of alginic acid concentration used for immobilization,obtained results showed 4% alginic acid to be most favorable for alkaloid biosynthesis. In semicontinuous process the immobilized, Claviceps paspali mycelium produced alkaloids over a period of 60 days (6 reincubations). Dilution of basic medium, or reducing the substrate concentration reduces alkaloid yields almost in a proportional manner. However, basic media diluted in the ratio of1:10 gave in a relative ratio higher alkaloid yield. Productivityof the process in each of the reincubations with immobilizedcells is 35% and 50% higher then in corresponding free cell- cultivations in all tested substrate media, and total productivity with immobilized cells is three times higher than of free cells. Effect of surfactant-pluronik (0.25%) on ergotalkaloid biosynthesis in the medium diluted in the ratioo of 1:4was tested and obtained results showed that alkaloid yield increased by about 35%. The results obtained here show that immobilization technique, also of mycelia forming microorganisms, might be effecttive in biotechnological production of complex metabilites such as ergot alkaloids. =============================================================================