Dr. Nichols originally conceived of a privately funded Institute as the most effective mechanism for bringing research on psychedelic agents into the modern era of neuroscience. He currently holds the position of Professor of Medicinal Chemistry, and a joint appointment as Professor of Pharmacology, in the School of Pharmacy and Pharmacal Sciences at Purdue University. The focus of his graduate training, beginning in 1969, and of much of his research subsequent to receiving his doctorate in 1973 has been the investigation of the relationship between molecular structure and the action of psychedelic agents and other substances which modify behavioral states. His research has been continuously funded by government agencies for more than two decades. He consults for the pharmaceutical industry and has served on numerous committees and government research review groups. Widely published in the scientific literature and internationally recognized for his research on centrally active drugs, he has studied all of the major classes of psychedelic agents, including LSD and other lysergic acid derivatives, psilocybin and the tryptamines, and phenethylamines related to mescaline. He will continue this research at the Institute, would set the overall tone for preclinical and animal studies, and will focus on mechanisms of drug action and drug-receptor interactions. His high standards and more than two decades of research experience will ensure that rigorous methods and quality science are pursued at the Institute.
Publications - David E. Nichols
Selected Publications Related to Hallucinogens 1971-1998
F. Antun, J.R. Smythies, F. Benington, R.D. Morin, C.F. Barfknecht and D.E. Nichols, "Native Fluorescence and Hallucinogenic Potency of Some Amphetamines", Experientia 27, 62-63 (1971).
C.F. Barfknecht and D.E. Nichols, "Potential Psychotomimetics, Bromomethoxy- amphetamines", J. Med. Chem. 14, 370-372 (1971).
C.F. Barfknecht and D.E. Nichols, "Effects of S-(+) and R-(-)-3,4-Dimethoxyphenyl- isopropylamines in the Rat", J. Med. Chem. 15, 109 (1972).
H.C. Cheng, J.P. Long, C.F. Barfknecht and D.E. Nichols, "Cardiovascular Effects of 2,5- Dimethoxy-4-methylamphetamine (DOM,STP)", J. Pharmacol. Exp. Therap. 186, 345-354 (1972).
D.E. Nichols, C.F. Barfknecht, D.B. Rusterholz, F. Benington and R.D. Morin, "Asymmetric Synthesis of Enantiomers of Psychotomimetic Amphetamines", J. Med. Chem. 16, 480-483 (1973).
C.F. Barfknecht, D.E. Nichols, D.B. Rusterholz, J.P. Long, J.A. Engelbrecht, J.M. Beaton, R.J. Bradley and D.C. Dyer, "Potential Psychotomimetics: 2-Amino-1,2,3,4-tetrahydro- naphthalene Analogs", J. Med. Chem. 16, 804-808 (1973).
D.C. Dyer, D.E. Nichols, D.B. Rusterholz and C.F. Barfknecht, "Comparative Effects of Stereoisomers of Psychotomimetic Phenylisopropylamines", Life Sci. 13, 885-896 (1973).
H.C. Cheng, J.P. Long, D.E. Nichols and C.F. Barfknecht, "Effects of Psychotomimetics on Vascular Strips: Studies of Methoxylated Amphetamines and Optical Isomers of 2,5- Dimethoxy-4-methylamphetamine (DOM) and 2,5-Dimethoxy-4-bromoamphetamine (DOB)", J. Pharmacol. Exp. Ther. 188, 114-123 (1974).
D.E. Nichols, C.F. Barfknecht, J.P. Long, R.T. Standridge, H.G. Howell, R.A. Partyka and D.C. Dyer, "Potential Psychotomimetics 2: Rigid Analogs of 2,5-Dimethoxy-4- methylphenylisopropylamine (DOM,STP)", J. Med. Chem. 17, 161-166 (1974).
H.C.Cheng, J.P. Long, D.E. Nichols, C.F. Barfknecht and D.B. Rusterholz, "Effects of Rigid Amphetamine Analogs on Vascular Strips: Studies of 2-Aminotetrahydronaphthalene and 2-Aminoindane Derivatives", Arch. Int. Pharmacodyn. Therap. 208, 264-273 (1974).
C.F. Barfknecht, D.E. Nichols and W.J. Dunn III, "Correlation of Psychotomimetic Activity of Phenethylamines and Amphetamines with 1- Octanol/Water Partition Coefficients", J. Med. Chem. 18, 208-210 (1975).
H.C. Cheng, J.P. Long, D.E. Nichols and C.F. Barfknecht, "Effects of Para- Methoxyamphetamine (PMA) on the Cardiovascular System of the Dog", Arch. Int. Pharmcodyn. Therap. 212, 83-88 (1974).
D.E. Nichols, M. Ilhan and J.P. Long, "Comparison of Cardiovascular, Hyperthermic and Toxic Effects of Para-Methoxyamphetamine (PMA) and 3,4-Methylenedioxyamphetamine (MDA)", Arch. Int. Pharmacodyn. Therap. 214, 133-140 (1975).
D.E. Nichols, "Structural Correlation between Apomorphine and LSD: Involvement of Dopamine as Well as Serotonin in the Actions of Hallucinogens", J. Theor. Biol. 59, 167-177 (1976).
D.E. Nichols and A.T. Shulgin, "Sulfur Analogs of Psychotomimetic Amines", J. Pharm. Sci. 65, 1554-1556 (1976).
D.E. Nichols and D.C. Dyer, "Lipophilicity and Serotonin Agonist Activity in a Series of 4- Substituted Mescaline Analogs", J. Med. Chem. 20, 299- 301 (1977).
D.E. Nichols, W.R. Pfister, G.K.W. Yim and R.J. Cosgrove, "A New View of the Structural Relationship between LSD and Mescaline", Brain Res. Bull. 2, 169-171 (1977).
D.E. Nichols, A.T. Shulgin and D.C. Dyer, "Directional Lipophilic Character in a Series of Psychotomimetic Phenethylamine Derivatives", Life Sciences 21, 569-575 (1977).
D.E. Nichols, W.R. Pfister and G.K.W. Yim, "LSD and Phenethylamine Hallucinogens: New Structural Analogy and Implications for Receptor Geometry", Life Sciences 22, 2165-2170 (1978).
H.J.R. Weintraub and D.E. Nichols, "Conformational Energy Calculations of Some Amphetamine Analogs Using a New Solvation Model", Int. J. Quantum Chem. QBS 5, 321- 343 (1978).
D.E. Nichols, R. Woodard, B. Hathaway, M.T. Lowy and G.K.W. Yim, "Resolution and Absolute Configuration of Trans-2-(2,5-dimethoxy-4-methylphenyl)-cyclopropylamine, an Hallucinogen Analogue", J. Med. Chem. 22, 458-460 (1979).
. D.B. Rusterholz, J.P. Long and D.E. Nichols, "Effect of *-Methyltryptamine on Spontaneous Activity in Mice", Pharmacol. Biochem. and Behav. 10, 223- 227 (1979).
D.E. Nichols and L.J. Kostuba, "Steric Effects of Substituents on Phenethylamine Hallucinogens. 3,4-(Methylenedioxy)amphetamine Analogues Alkylated on the Dioxole Ring", J. Med. Chem. 22, 1264-1267 (1979).
G.K.W. Yim, T.E. Prah, W.R. Pfister and D.E. Nichols, "An Economical Screen for Phenethylamine Type Hallucinogens: Mouse Ear Scratching", Commun. in Psychopharmacol. 3, 173-178 (1979).
H.J.R. Weintraub, D.E. Nichols, A. Makriyannis and S.W. Fesik, "Conformational Energy Differences between Side Chain-Alkylated Analogues of the Hallucinogen, DOM", J. Med. Chem. 23, 339-341 (1980).
G.P. Migliaccio, T.-L.N. Shieh, S.R. Byrn, B.A. Hathaway and D.E. Nichols, "Comparison of Solution Conformational Preferences for the Hallucinogens Bufotenin and Psilocin using 360 MHz Proton NMR Spectroscopy", J. Med. Chem. 24, 206-209 (1981).
D.E. Nichols, "Structure-Activity Relationships of Phenethylamine Hallucinogens", J. Pharm. Sci. 70, 839-849 (1981).
P.J. Kothari, B.A. Hathaway, D.E. Nichols and G.K.W. Yim, "Synthesis and Serotonin-like Activity of 2-Amino-5,8-dimethoxy-6-methyl-1,2-dihydronaphthalene", J. Med. Chem. 24, 882-884 (1981).
B.A. Hathaway, D.E. Nichols, M.B. Nichols and G.K.W. Yim, "A New Potent Conformationally-Restricted Analogue of Amphetamine: 2-Amino-1,2- Dihydro- naphthalene", J. Med. Chem. 25, 535-538 (1982).
D.E. Nichols, D.H. Lloyd, A.J. Hoffman, M.B. Nichols and G.K.W. Yim, "Effects of Certain Hallucinogenic Amphetamine Analogues on the Release of 3H-Serotonin from Rat Whole Brain Synaptosomes", J. Med. Chem. 25, 530-535 (1982).
J.N. Jacob and D.E. Nichols, "Isomeric Cyclopropyl Ring-methylated Homologues of Trans- 2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an Hallucinogen Analogue", J. Med. Chem. 25, 526-530 (1982).
D.E. Nichols and H.J.R. Weintraub, "Effects of Steric Interactions on Models of Charge- transfer Complexes", Int. J. Quantum Chem. QBS9, 205-211 (1982).
E.C.C. Si, D.E. Nichols, M.P. Holsapple and G.K.W. Yim, "In vitro and In vivo Evaluation of Cis-methyl-phencyclidine (Cis-MPCP) as a Potential Antagonist of Phencyclidine (PCP)", Life Sciences 33, 909-916 (1983).
D.H. Lloyd and D.E. Nichols, "A Simple Procedure for the Preparation of Indoles", Tetrahedron Letters 24, 4561-4562 (1983).
D.E. Nichols, P.J. Kothari, D.E. Nichols and J.E. Zabik, "Substituent Branching in Phenethylamine Type Hallucinogens: A Comparison of 1-[2,5-Dimethoxy-4-(2-butyl)phenyl] and 1-[2,5-Dimethoxy-4-(2-methylpropyl)]-2-aminopropane", J. Med. Chem. 27, 788-792 (1984).
D.E. Nichols, K.P. Jadhav, R.A. Oberlender, J.E. Zabik, J.F. Bossart, A. Hamada and D.D. Miller, "Synthesis and Evaluation of Substituted 2-Phenylcyclobutylamines as Analogues of Hallucinogenic Phenethylamines: Lack of Significant LSD-Like Activity", J. Med. Chem. 27, 1108-1111 (1984).
D.E. Nichols, D. Schooler, M.C. Yeung, R.A. Oberlender and J.E. Zabik, "Unreliability of the Rat Stomach Fundus as a Predictor of Hallucinogenic Activity in Substituted Phenethylamines", Life Sciences 35, 1343-1348 (1984).
A.J. Hoffman and D.E. Nichols, "Synthesis and LSD-Like Discriminative Stimulus Properties in a Series of N(6)-Alkyl Norlysergic Acid N,N-Diethylamide Derivatives," J. Med. Chem., 28, 1252-1255 (1985).
D.E. Nichols, A.J. Hoffman, R.A. Oberlender, and R.M. Riggs, "Synthesis and Evaluation of 2,3-Dihydrobenzofuran Analogues of the Hallucinogen 1- (2,5-Dimethoxy-4-methylphenyl)- 2-aminopropane, DOM: Drug Discrimination Studies in Rats," J. Med. Chem., 29, 302-304 (1986).
D.H. Lloyd and D.E. Nichols, "Nickel Boride/Hydrazine Hydrate: Convenient Reagents for the Reduction of Aromatic and Aliphatic Nitro Compounds," J. Org. Chem., 51, 4294-4295, (1986).
A.J. Hoffman, D.M. Maxwell and D.E. Nichols, "A Simple Organ Bath for Electrical Stimulation and Superfusion of Rat Brain Slices," J. Pharmacol. Meth., 16, 185-199, (1986).
D.E. Nichols, A.J. Hoffman, R.A. Oberlender, P. Jacob, III, and A.T. Shulgin, "Derivatives of 1-(1,3-benzodioxo-5-yl)-2-butanamine, Representatives of a novel therapeutic class." J. Med. Chem., 29, 2009- 2015, (1986).
M.P. Johnson, A.J. Hoffman and D.E. Nichols, "Effects of the Enantiomers of MDA, MDMA and Related Analogues on [3H]-Serotonin and [3H]-Dopamine Release from Superfused Rat Brain Slices," Eur. J. Pharmacol., 132, 269- 276, (1986).
D.E. Nichols, "The Discovery of Novel Psychoactive Drugs: Has it Ended?" J. Psychoact. Drugs, 19, 33-37, (1987).
G.A. Ricaurte, K.F. Finnegan, D.E. Nichols, L.E. DeLanney, I. Irwin and J.W. Langston, "3,4-Methylenedioxyethylamphetamine ("MDE"), a Novel Analogue of MDMA, Produces Long-lasting Depletion of Serotonin in the Rat Brain," Eur. J. Pharmacol., 137, 265-268 (1987).
T.D. Steele, D.E. Nichols, and G.K.W. Yim, "Stereochemical Effects of 3,4- Methylenedioxymethamphetamine (MDMA) and Related Amphetamine Derivatives on Inhibition of Uptake of [3H]-Monoamines into Synaptosomes from Different Regions of Rat Brain," Biochem. Pharmacol., 36, 2297-2303 (1987).
M.P. Johnson, A.J. Hoffman, D.E. Nichols and C.A. Mathis, "Binding to the Serotonin 5-HT2 Receptor by the Enantiomers of [125I]-DOI," Neuropharmacol., 26, 1803-1806 (1987). D.E. Nichols and D.E. Nichols, "Drug Discrimination Studies with MDMA and Amphetamine," Psychopharmacol., 95, 71-76 (1988).
D.E. Nichols, D.H. Lloyd, M.P. Johnson, and A.J. Hoffman, "Synthesis and Serotonin Receptor Affinities of a Series of *-Methyltrptamines: Evidence for the Tryptamine Binding Conformation at Serotonin 5-HT1B Receptors," J. Med. Chem., 31, 1406-1412 (1988).
C.A. Mathis, A.J. Hoffman, D.E. Nichols, and A.T. Shulgin, "Synthesis of High-Specific Activity 125I- and 123I-Labelled Enantiomers of 2,5-Dimethoxy-4-iodophenylisopropylamine (DOI)", J. Label. Compounds Radiopharm., XXV, 1255-1265 (1988).
D.J. McKenna, A.J. Nazarali, A.J. Hoffman, D.E. Nichols, C.A. Mathis, and J.M. Saavedra, "Common Receptors for Hallucinogens in Rat Brain: A Comparative Autoradiographic Study Using [125I]-LSD and [125I]-DOI, a New Psychotomimetic Radioligand," Brain Research, 476, 45-56 (1989).
W. Dimpfel, M. Sp¸ler, and D.E. Nichols, "Hallucinogenic and Stimulatory Amphetamine Derivatives: Fingerprinting DOM, DOI, DOB, MDMA, and MBDB by Spectral Analysis of Brain Field Potentials in the Freely Moving Rat (Tele-Stereo-EEG)," Psychopharmacology, 98, 297-303 (1989).
M.P. Johnson and D.E. Nichols, "Neurotoxic Effects of the Alpha-Ethyl Homologue of MDMA Following Subacute Administration," Pharmacol. Biochem. Behav., 33, 105-108 (1989).
T.D. Steele, D.E. Nichols, and G.K.W. Yim, "MDMA Transiently Alters Biogenic Amines and Metabolites in Mouse Brain and Heart," Pharmacol. Biochem. Behav., 34, 223-227 (1989).
D.E. Nichols, R. Oberlender, K. Burris, A.J. Hoffman, and M.P. Johnson, "Studies of Dioxole Ring Substituted 3,4-Methylenedioxyamphetamine (MDA) Analogues," Pharmacol. Biochem. Behav., 34, 571-576 (1989). M.P. Johnson, C.A. Mathis, A.T. Shulgin, A.J. Hoffman, and D.E. Nichols, "[125I]-2-(2,5- dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for the 5-HT2 receptor in rat frontal cortex," Pharmacol. Biochem. Behav., 35, 211-217 (1990).
D.E. Nichols, W.K. Brewster, M.P. Johnson, R. Oberlender, and R.M. Riggs, "Non- Neurotoxic Tetralin and Indan Analogues of 3,4-Methylenedioxyamphetamine (MDA)," J. Med. Chem., 33, 703-710 (1990).
M.P. Johnson and D.E. Nichols, "Comparative Serotonin Neurotoxicity of the Stereoisomers of Fenfluramine and Norfenfluramine," Pharmacol. Biochem. Behav., 36, 105-109 (1990).
M.P. Johnson, X. Huang, R. D.E. Nichols, J.F. Nash, and D.E. Nichols, "Behavioral, Biochemical and Neurotoxicological Actions of the *-Ethyl Homologue of p- Chloroamphetamine (PCA)," Eur. J. Pharmacol., 191, 1-10 (1990).
D.E. Nichols, M.P. Johnson, and R. Oberlender, "5-Iodo-2-Aminoindan, A Non-Neurotoxic Analogue of Para-Iodoamphetamine," Pharmacol. Biochem. Behavior, 38, 135-139 (1990).
D.E. Nichols and D.E. Nichols, "(+)-N-Methyl-1-(1,3-Benzodioxol-5-yl)-2-Butanamine as a Discriminative Stimulus in Studies of 3,4-Methylenedioxymethamphetamine-Like Behavioral Activity," J. Pharmacol. Exp. Ther., 255, 1098-1106 (1990). D.E. Nichols, S.E. Snyder, R. Oberlender, M. Johnson, and X. Huang, "2,3- Dihydrobenzofuran Analogues of Hallucinogenic Phenethylamines," J. Med. Chem., 34, 276-281 (1991).
T.D. Steele, W.K. Brewster, M.P. Johnson, D.E. Nichols, and G.K.W. Yim, "Assessment of the Role of *-Methylepinine in the Neurotoxicity of MDMA," Pharmacol. Biochem. Behav., 38, 345-351 (1991).
D.E. Nichols and D.E. Nichols, "Structural Variation and (+)-Amphetamine-Like Discriminative Stimulus Properties," Pharmacol. Biochem. Behav., 38, 581-586 (1991).
M.P. Johnson, S.P. Frescas, R. Oberlender, and D.E. Nichols, "Synthesis and Pharmacological Examination of 1-(3-Methoxy-4-Methylphenyl)-2-Aminopropane and 5- Methoxy-6-Methyl-2-Aminoindan: Similarities to 3,4-methylenedioxymethamphetamine (MDMA)," J. Med. Chem., 34, 1662-1668 (1991).
C.W. Callaway, M.P. Johnson, L.H. Gold, D.E. Nichols, and M.A. Geyer, "Amphetamine Derivatives Induce Locomotor Hyperactivity by Acting as Indirect Serotonin Agonists," Psychopharmacol., 104, 293-301 (1991).
M.P. Johnson, P.F. Conarty, and D.E. Nichols, "[3H]-Monoamine Releasing and Uptake Inhibition Properties of 3,4-Methylenedioxymethamphetamine and p-Chloroamphetamine Analogues," Eur. J. Pharmacol., 200, 9-16 (1991).
M.P. Johnson and D.E. Nichols, "Combined administration of a non-neurotoxic 3,4- methylenedioxymethamphetamine analogue with amphetamine produces serotonin neurotoxicity in rats," Neuropharmacology, 30, 819-822 (1991).
X. Huang, M.P. Johnson, and D.E. Nichols, "Reduction in brain serotonin markers by *- Ethyltryptamine (Monase)," Eur. J. Pharmacol., 200, 187-190 (1991).
J.F. Nash and D.E. Nichols, "Microdialysis Studies on 3,4-Methylenedioxyamphetamine and Structurally Related Analogues," Eur. J. Pharmacol., 200, 53-58 (1991).
M.P. Johnson, X. Huang, and D.E. Nichols, "Serotonin Neurotoxicity in Rats After Combined Treatment With a Dopaminergic Agent Followed by a Non-Neurotoxic 3,4- Methylenedioxymethamphetamine (MDMA) Analogue," Pharmacol. Biochem. Behav., 40, 915-922 (1991).
D.E. Nichols, R.C. Pfaff, M.P. Johnson, X. Huang, and D.E. Nichols, "Stereoselective LSD- like activity in d-lysergic acid amides of R- and S- 2-aminobutane," J. Med. Chem., 35, 203- 211 (1992).
Z. Tomaszewski, M.P. Johnson, and D.E. Nichols, "Benzofuran bioisosteres of hallucinogenic tryptamines," J. Med. Chem., 35, 2061-2064 (1992).
X. Huang, D. Marona-Lewicka, and D.E. Nichols, "Para-methylthioamphetamine is a potent new nonneurotoxic serotonin-releasing agent," Eur. J. Pharmacol., 229, 31-38 (1992).
C.W. Callaway, L.L. Wing, D.E. Nichols, and M.A. Geyer, "Suppression of behavioral activity by norfenfluramine and related drugs is not mediated by serotonin release," Psychopharmacology, 111, 169-178 (1993).
X. Huang and D.E. Nichols, "5-HT2 Receptor-Mediated Potentiation of Dopamine Synthesis and Central Serotonergic Deficits," Eur. J. Pharmacol., 238, 291-296 (1993).
A.P. Monte, D. Marona-Lewicka, N.V. Cozzi, and D.E. Nichols, "Synthesis and Pharmacological Examination of Benzofuran, Indan, and Tetralin Analogues of 3,4- (Methylenedioxy)amphetamine (MDA)," J. Med. Chem., 36, 3700-3706 (1993).
X. Huang, D. Marona-Lewicka, R.C. Pfaff, and D.E. Nichols, "Drug Discrimination and Receptor Binding Studies of N-isopropyl Lysergamide Derivatives," Pharmacol. Biochem. Behav., 47, 667-673 (1994).
D. Marona-Lewicka and D.E. Nichols, "Behavioral properties of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan (MMAI)," Eur. J. Pharmacol., 259, 1-13 (1994).
J.E. Sprague, X. Huang, A. Kanthasamy, and D.E. Nichols, "Attenuation of 3,4- methylenedioxymethamphetamine (MDMA) induced neurotoxicity with the serotonin precursors tryptophan and 5-hydroxytryptophan," Life Sciences, 55, 1193-1198 (1994).
J.F. Nash, B.L. Roth, J.D. Brodkin, D.E. Nichols, and G.A. Gudelsky, "Effect of the R(-) and S(+) Isomers of MDA and MDMA on Phosphotidyl Inositol Turnover in Cultured Cells Expressing 5-HT2A or 5-HT2C Receptors," Neuroscience Letters, 177, 111-115 (1994).
S. Frescas, D.E. Nichols, D. Marona-Lewicka, X. Huang, J.F. Nash, B.L. Roth, and G.A. Gudelsky, "1-(2,5-Dimethoxy-4-trifluoromethylphenyl)-2-aminopropane: A Potent Serotonin 5-HT2A/2C Agonist," J. Med. Chem., 9, 4346-4351 (1994).
A.P. Monte, D. Marona-Lewicka, E. Sanders-Bush, and D.E. Nichols, "Stereoselective LSD- like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes," J. Med. Chem., 38, 958-966 (1995).
J.E. Sprague and D.E. Nichols, "Inhibition of MAO-B protects against MDMA-induced neurotoxicity in the striatum," Psychopharmacol., 118, 357-359 (1995).
S. Vangveravong and D.E. Nichols, "Stereoselective synthesis of trans-2-(indol-3-yl)-cyclo-propyl-amines: rigid tryptamine analogues," J. Org. Chem., 60, 3409-3413 (1995).
J.E. Sprague and D.E. Nichols, "The monoamine oxidase-B inhibitor L-deprenyl protects against 3,4-methylenedioxymethamphetamine-induced lipid peroxidation and long-term serotonergic deficits," J. Pharmacol. Exp. Ther., 273, 667-673 (1995).
R. Oberlender, P.V. Ramachandran, M.P. Johnson, X. Huang, and D.E. Nichols, "Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines," J. Med. Chem., 38, 3593-3601 (1995).
D. Marona-Lewicka and D.E. Nichols, "Complex stimulus properties of LSD: a drug discrimination study with alpha2-adrenoceptor agonists and antagonists," Psychopharmacology, 120, 384-391 (1995).
A.P. Monte, D. Marona-Lewicka, N.V. Cozzi, D.L. Nelson, and D.E. Nichols, "Conformationally restricted tetrahydro-1-benzoxepin analogs of hallucinogenic phenethylamines," Medicinal Chemistry Research., 5, 651-663 (1995).
D. Marona-Lewicka, G.-S. Rhee, J.E. Sprague, and D.E. Nichols, "Reinforcing effects of certain serotonin-releasing amphetamine derivatives," Pharmacol. Biochem. Behav., 53, 99-105 (1995).
D. Marona-Lewicka, G.-S. Rhee, J.E. Sprague, and D.E. Nichols, "Psychostimulant-like effects of para-fluoroamphetamine," Eur. J. Pharmacol., 287, 105-113 (1995).
A.V. Stachulski, D.E. Nichols, F. Scheinmann, "Stereochemical and NMR Reassignment of 6-norlysergic acid diethylamide and 6-nor-6-allyllysergic acid diethylamide," J. Chem. Res. (S), 30-31 (1996).
A.P. Monte, D. Marona-Lewicka, M. Parker, B. Wainscott, D.L. Nelson, and D.E. Nichols, "Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-Substituted (2,5-dimethoxy-phenyl)alkylamine derivatives with rigidified methoxy groups," J. Med. Chem., 39, 2953-2961 (1996).
N.V. Cozzi and D.E. Nichols, "5-HT2A receptor antagonists inhibit postassium-stimulated g-aminobutyric acid release in rat frontal cortex," Eur. J. Pharmacol, 309, 25-31 (1996).
J.E. Sprague, M.P. Johnson, C.J. Schmidt, and D.E. Nichols, "Studies on the Mechanism of Para-chloroamphetamine neurotoxicity," Biochem. Pharmacol, 52, 1271-1277 (1996).
S.R. Waldman, A.P. Monte, A. Bracey, and D.E. Nichols, "One-pot Claisen rearrangement/O-methylation/alkene isomerization in the synthesis of ortho-methoxylated phenylisopropylamines," Tett. Letters, 37, 7889-7892 (1996).
Q. Li, I. Murakami, S. Stall, A.D. Levy, M.S. Brownfield, D.E. Nichols, and L.D. Van de Kar, "The neuroendocrine pharmacology of three serotonin releasers: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (MBDB), 5-methoxy-6-methyl-2-aminoindan (MMAI) and p-methylthioamphetamine (MTA)," J. Pharmacol. Exp. Ther., 279, 1261-1267 (1996).
M. Reyes-Parada, C. Scorza, V. Romero, R. Silveira, J.H. Medina, D. Andrus, D.E. Nichols, and B.K. Cassels, "(±)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane (ALEPH-2), a novel putative anxiolytic agent lacking affinity for benzodiazepine sites and serotonin-1A receptors," Naunyn-Schmiedebergâs Archives of Pharmacology, 34, 579-585, (1996).
A.P. Monte, S.R. Waldman, D. Marona-Lewicka, D.B. Wainscott, D.L. Nelson, E. Sanders-Bush, and D.E. Nichols, "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline Derivatives," J. Med. Chem., 40, 2997-3008 (1997).
D. Marona-Lewicka and D.E. Nichols, "5-HT2A/2C Receptor agonists potentiate the discriminative cue of (+)-amphetamine in the rat," Neuropharmacology, 36, 1471-1475 (1997).
D. Marona-Lewicka and D.E. Nichols, "The effect of selective serotonin releasing agents in the chonic mild stress model of depression in rats," Stress, 2, 91-100 (1997).
M.A. Parker, D. Marona-Lewicka, D. Kurrasch, A.T. Shulgin, and D.E. Nichols, "Synthesis and Pharmacological Evaluation of Ring-Methylated Derivatives of 3,4-Methylenedioxyamphetamine (MDA)," J. Med. Chem., 41, 1001-1005 (1998).
D. Marona-Lewicka and D.E. Nichols, "5-HT2A/2C Receptor agonists potentiate the discriminative cue of (+)-amphetamine in the rat," Neuropharmacology, 36, 1471-1475 (1997).
J.E. Sprague, S.L. Everman, and D.E. Nichols, "An integrated hypothesis for the serotonergic axonal loss induced by 3,4-methylenedioxymethamphetamine,"Neurotoxicol., 19, 427-442 (1998).
A.P. Monte, D. Marona-Lewicka, M.M. Lewis, R.B. Mailman, D.B. Wainscott, D.L. Nelson, and D.E. Nichols, "Substituted naphthofurans as hallucinogenic phenethylamine-ergoline hybrid molecules with unexpected muscarinic antagonist activity," J. Med. Chem., 41, 2134-2145 (1998).
D. Marona-Lewicka and D.E. Nichols, "Drug discrimination studies of the interoceptive cues produced by selective serotonin reuptake inhibitors andselective serotonin releasing agents, " Psychopharmacology, 138, 67-75 (1998).
Vangveravong, A. Kanthasamy, D.B. Wainscott, D.L. Nelson, and D.E. Nichols, "Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)-cyclopropylamine derivatives," J. Med. Chem., 41, 4995-5001 (1998).
M.A. Parker, D. Marona-Lewicka, D.B. Wainscott, D.L. Nelson, and D.E.Nichols, "A novel heterocyclic aminoalkane with extremely potent agonist activity at the 5-HT2A receptor," J. Med. Chem., 41, 5148-5149 (1998).
In Press:
Book Chapters and Monographs
D.E. Nichols, "Medicinal Chemistry and Structure-Activity Relationships," Chapter 2 in Amphetamine and Its Analogs: Neuropsychopharmacology, Toxicology and Abuse, A.K. Cho and D.S. Segal, Eds., Academic Press, New York, 1994, pp 3-41.
D.E. Nichols, R. Oberlender and D.J. McKenna, "Stereochemical Aspects of Hallucinogenesis," in Biochemistry and Physiology of Substance Abuse, Vol. III, R.R. Watson, Ed., CRC Press, Boca Raton, 1991, pp.1-39.
D.E. Nichols and R. Oberlender, "Structure-Activity Relationships of MDMA and Related Compounds: A New Class of Psychoactive Agents?", in ECSTASY: The Clinical, Pharmacological and Neurotoxicological Effects of the Drug MDMA, S.J. Peroutka, Ed., Kluwer Academic Publishers, Boston, 1990.
D.E. Nichols, "Hallucinogens", in CRC Handbook of CNS Agents and Local Anesthetics, M. Verdame, Ed., CRC Press, 1986, pp.303-325.
D.E. Nichols and R.A. Glennon, "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens", in Hallucinogens: Neurochemical, Behavioral and Clinical Perspectives, B.L. Jacobs, Ed., Raven Press, 1984, pp.95-142.
D.E. Nichols and R. Oberlender, "Behavioral Techniques in Neuroreceptor Research", in Neuroreceptors in Health and Disease, edited by J. Marwaha and W.J. Anderson, Karger AG, Basel, 1984, pp. 108-119.
D.E. Nichols, "Role of Serotonergic Neurons and 5-HT Receptors in the Action of Hallucinogens," in Handbook of Experimental Pharmacology. Serotoninergic Neurons and 5-HT Receptors in the CNS, H.G. Baumgarten and M. G?thert, Eds., Springer-Verlag GmbH & Co., Heidelberg, Germany, pp 563-585, 1997.
Published Symposium Proceedings
D.E. Nichols, W.R. Pfister, H.J.R. Weintraub and G.K.W. Yim, "The Use of Rigid Analogues to Probe Hallucinogen Receptors", NIDA Research Monograph Series, 22, 70-83 (1978).
G. Anderson, G. Braun, U. Braun, D.E. Nichols and A.T. Shulgin, "Absolute Configuration and Psychotomimetic Activity", NIDA Research Monograph Series, 22, 8-15 (1978).
U. Braun, G. Braun, P. Jacob, D.E. Nichols and A.T. Shulgin, "Mescaline Analogs: Substitutions at the 4-Position", NIDA Research Monograph Series, 22, 27-32 (1978).
A.T. Shulgin and D.E. Nichols, "Characterization of Three New Psychotomimetics", in The Psychopharmacology of Hallucinogens, ed. R.C. Stillman and R.E. Willette, Pergamon Press, 1978, pp. 74-83.
D.E. Nichols, "Use of Chemical Approaches to Probe the Serotonin Receptor Topography", VIIIth International Symposium on Medicinal Chemistry, Volume 2, Swedish Pharmaceutical Press, Stockholm, pp 103-115, 1985.
D.E. Nichols, "Studies of the Relationship Between Molecular Structure and Hallucinogenic Activity", Pharmacology, Biochemistry and Behavior, 24, 335- 340, 1986.
D.E. Nichols, "Differences Between the Mechanism of Action of MDMA, MBDB, and the Classical Hallucinogens: Identification of a New Therapeutic Class: Entactogens." J. Psychoactive Drugs, 18, 305-313 (1986).
D.E. Nichols, "Substituted Amphetamine Controlled Substance Analogs," in Cocaine, Marijuana, Designer Drugs: Chemistry, Pharmacology, and Behavior, CRC Press, Boca Raton, FL, 1989, pp.175-185. Proceedings of the Eleventh Annual Clinical Pharmacy Symposium, Florida A? University, College of Pharmacy and Pharmaceutical Sciences, March 1986.
D.E. Nichols and R. Oberlender, "Structure-Activity Relationships of MDMA-like Substances," NIDA Research Monograph Series, 94, 1-29, 1989.
D.E. Nichols and R. Oberlender, "Structure-Activity Relationships of MDMA and Related Compounds: A New Class of Psychoactive Drugs?," Ann. N.Y. Acad. Sci., Vol. 600, The Neuropharmacology of Serotonin, pp.613-625, 1990.
D.E. Nichols, D. Marona-Lewicka, X. Huang, and M.P. Johnson, "Novel Serotonergic Agents," Drug Design and Discovery, 9, 299-312, 1993.
R.C. Pfaff, X. Huang, D. Marona-Lewicka, R. Oberlender, and D.E. Nichols, "Lysergamides Revisited," NIDA Research Monograph Series, 146, 52-73, (1994).
