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)