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journal articles about benzomorphans
Mon May 02, 2005 11:51 pm |
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here are journal articles about benzomorphans from J. Med Chem
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Note thanks to scarmani for securing this collection of citations
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New Benzomorphan Analgetics
Maxwell Gordon, John J. Lafferty, David H. Tedeschi, Blaine M. Sutton, Nathan B. Eddy, Everett L. May;,
J. Med. Chem.; 1962; 5(3); 633-635.
PDF
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Acyl derivatives of 5-hydroxy-6,7-benzomorphans. Prodine congeners
Mikio Takeda, Everette L. May;,
J. Med. Chem.; 1970; 13(6); 1223-1224.
PDF
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Interesting Pharmacological Properties of the Optical Isomers of -5,9-Diethyl-2'-hydroxy-2-methyl-6,7-benzomorphan
Everette L. May, Nathan B. Eddy;,
J. Med. Chem.; 1966; 9(6); 851-852.
PDF
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Homologs of benzomorphan derivatives. 1
Mikio Takeda, Hiroshi Kugita;,
J. Med. Chem.; 1970; 13(4); 630-634.
PDF
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Absolute configuration of some benzomorphan analgetics and related compounds
Alan F. Casy, Anilkumar P. Parulkar;,
J. Med. Chem.; 1969; 12(1); 178-180.
PDF
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N-(2-Cyanoethyl) derivatives of meperidine, ketobemidone, and a potent 6,7-benzomorphan
Ibrahim M. Uwaydah, M. Kathleen Waddle, Michael E. Rogers;,
J. Med. Chem.; 1979; 22(7); 889-890.
PDF
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Synthesis and analgetic activity of the diastereomeric 8-hydroxy-6,7-benzomorphans
Jon J. Fauley, Jules B. LaPidus;,
J. Med. Chem.; 1973; 16(2); 181-182.
PDF
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Structures Related to Morphine. XXV. 5-Propyl- and 5,9-Dipropyl-6,7-benzomorphans and a Pharmacologic Summary
J. Harrison Ager, S. E. Fullerton, Everette L. May;,
J. Med. Chem.; 1963; 6(3); 322-325.
PDF
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Structures Related to Morphine. XXXII.1 - and -2,9-Dimethyl-5-propyl-6,7-benzomorphan from 3-Methyl-4-propylpyridine
Bhuwan C. Joshi, Everette L. May;,
J. Med. Chem.; 1965; 8(5); 696-697.
PDF
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Structures Related to Morphine. XXX.1 N-Hexyl- and 5-Butyl-, -Amyl-, and -Hexyl-6,7-benzomorphans
Bhuwan C. Joshi, Colin F. Chignell, Everette L. May;,
J. Med. Chem.; 1965; 8(5); 694-696.
PDF
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Structures Related to Morphine. XXII.1 A Benzomorphan Congener of Meperidine
Hiroshi Kugita, Seiichi Saito, Everette L. May;,
J. Med. Chem.; 1962; 5(2); 357-361.
PDF
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Benzomorphans. Optically Active and trans Isomers
B. F. Tullar, L. S. Harris, R. L. Perry, Anne K. Pierson, A. E. Soria, W. F. Wetterau, N. F. Albertson;,
J. Med. Chem.; 1967; 10(3); 383-386.
PDF
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3'-Methyl, 8-methyl, and 8-phenyl derivatives of 5,9-dimethyl-6,7-benzomorphans
Albert Ziering, Nicholas Malatestinic, Thomas Williams, Arnold Brossi;,
J. Med. Chem.; 1970; 13(1); 9-13.
PDF
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Structures Related to Morphine. XXXI.1 2'-Substituted Benzomorphans
Arthur E. Jacobson, Everette L. May;,
J. Med. Chem.; 1965; 8(5); 563-566.
PDF
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Synthesis and in Vitro and in Vivo Activity of (-)-(1R,5R,9R)- and (+)-(1S,5S,9S)-N-Alkenyl-, -N-Alkynyl-, and -N-Cyanoalkyl-5,9-dimethyl-2'-hydroxy-6,7-benzomorphan Homologues
May, E. L.; Jacobson, A. E.; Mattson, M. V.; Traynor, J. R.; Woods, J. H.; Harris, L. S.; Bowman, E. R.; Aceto, M. D.;,
J. Med. Chem.; (Article); 2000; 43(26); 5030-5036.
PDF
PDF (Supporting Info)
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Optical resolution of (+-)-2,5-dimethyl-2'-hydroxy-9.alpha.- and -9.beta.-propyl-6,7-benzomorphans and their pharmacological properties
Kenner C. Rice, Arthur E. Jacobson;,
J. Med. Chem.; 1976; 19(3); 430-432.
PDF
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Effect of 9-hydroxylation on benzomorphan antagonist activity
Noel F. Albertson;,
J. Med. Chem.; 1975; 18(6); 619-621.
PDF
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Synthesis of 6,7-benzomorphan and related nonquaternary carbon structures with marked analgetic activity
Ken Kanematsu, Mikio Takeda, Arthur E. Jacobson, Everette L. May;,
J. Med. Chem.; 1969; 12(3); 405-408.
PDF
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Benzomorphans. Structure of a position isomer
N. F. Albertson, W. F. Michne, B. F. Tullar;,
J. Med. Chem.; 1978; 21(5); 471-474.
PDF
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Synthesis and Opioid Receptor Affinity of Morphinan and Benzomorphan Derivatives: Mixed k Agonists and m Agonists/Antagonists as Potential Pharmacotherapeutics for Cocaine Dependence
Neumeyer, J. L.; Bidlack, J. M.; Zong, R.; Bakthavachalam, V.; Gao, P.; Cohen, D. J.; Negus, S. S.; Mello, N. K.;,
J. Med. Chem.; (Article); 2000; 43(1); 114-122.
PDF
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Synthesis and pharmacological activity of some N-alkyl-substituted 9.alpha.-ethyl-2'-hydroxy-5-methyl-6,7-benzomorphans
Ibrahim M. Uwaydah, Everette L. May, Louis S. Harris;,
J. Med. Chem.; 1977; 20(11); 1374-1377.
PDF
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Synthesis and analgetic activity of 3- and 4-methyl-6,7-benzomorphans
Robert T. Parfitt, Susan M. Walters;,
J. Med. Chem.; 1971; 14(7); 565-568.
PDF
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Synthesis and pharmacology of 2,9.alpha.-dimethyl-2'-hydroxy-6,7-benzomorphan
Hirozumi Inoue, Everette L. May;,
J. Med. Chem.; 1976; 19(2); 259-262.
PDF
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Structures Related to Morphine. XXVII.1 - and -5,9-Diethyl-2-methyl-6,7-benzomorphans
Arthur E. Jacobson, Everette L. May;,
J. Med. Chem.; 1964; 7(4); 409-412.
PDF
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Analgesics and narcotic antagonists in the benzomorphan and 8-oxamorphinan series. 5
Yvon Lambert, Jean Paul Daris, Ivo Monkovic, Anthony W. Pircio;,
J. Med. Chem.; 1978; 21(5); 423-427.
PDF
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Synthesis and analgesic activities of 2,5-dimethyl-2'-hydroxy-9.alpha.- and -.beta.-propyl-6,7-benzomorphans
Kenner C. Rice, Arthur E. Jacobson, Everette L. May;,
J. Med. Chem.; 1975; 18(8 ); 854-857.
PDF
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Constitution and Analgetic Activity of a New Product in the Benzomorphan Synthesis
Bhuwan C. Joshi, Everette L. May, H. M. Fales, J. W. Daly, A. E. Jacobson;,
J. Med. Chem.; 1965; 8(5); 559-563.
PDF
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Structures Related to Morphine. XXVIII.1 Alternative Syntheses of - and -2,9-Dimethyl-2'-hydroxy-5-propyl-6,7-benzomorphan
Colin F. Chignell, J. Harrison Ager, Everette L. May;,
J. Med. Chem.; 1965; 8(2); 235-238
PDF
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Pentazocine.1 Strong Analgesics and Analgesic Antagonists in the Benzomorphan Series
S. Archer, N. F. Albertson, L. S. Harris, Anne K. Pierson, J. G. Bird;,
J. Med. Chem.; 1964; 7(2); 123-127.
PDF
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Asymmetric Synthesis of 9-Alkyl-2-benzyl-6,7-benzomorphans: Characterization as Novel Receptor Ligands
Carroll, F. I.; Bai, X.; Dehghani, A.; Mascarella, S. W.; Williams, W.; Bowen, W. D.;,
J. Med. Chem.; (Article); 1999; 42(22); 4621-4629.
PDF
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5-Allyl-9-oxobenzomorphans. 3. Potent narcotic antagonists and analgesics-antagonists in the series of substituted 2',9.beta.-dihydroxy-6,7-benzomorphans
Michel Saucier, Jean Paul Daris, Yvon Lambert, Ivo Monkovic, Anthony W. Pircio;,
J. Med. Chem.; 1977; 20(5); 676-682.
PDF
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Stereoisomeric 5,9-dimethyl-2'-hydroxy-2-tetrahydrofurfuryl-6,7-benzomorphans, strong analgesics with nonmorphinelike action profiles
Herbert Merz, Klaus Stockhaus, Helmut Wick;,
J. Med. Chem.; 1975; 18(10); 996-1000.
PDF
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Synthesis and .sigma. Binding Properties of 2'-Substituted 5,9.alpha.-Dimethyl-6,7-benzomorphans
Richmond Danso-Danquah, Xu Bai, X. Zhang, S. Wayne Mascarella, Wanda Williams, Bethel Sine, Wayne D. Bowen, F. Ivy Carroll;,
J. Med. Chem.; 1995; 38(15); 2978-2985.
PDF
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Synthesis and analgetic activity of some benzomorphan analogs
Tadashi Kometani, Shunsaku Shiotani;,
J. Med. Chem.; 1978; 21(11); 1105-1110.
PDF
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Conformation of 2,9-dimethyl-3'-hydroxy-5-phenyl-6,7-benzomorphan and its relation to other analgetics and enkephalin
Frank H. Clarke, Hermann Jaggi, Richard A. Lovell;,
J. Med. Chem.; 1978; 21(7); 600-606.
PDF
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Synthesis and Structure-Activity Relationships of 6,7-Benzomorphan Derivatives as Antagonists of the NMDA Receptor-Channel Complex
Grauert, M.; Bechtel, W. D.; Ensinger, H. A.; Merz, H.; Carter, A. J.;,
J. Med. Chem.; (Article); 1997; 40(1; 2922-2930.
PDF
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Antipodal .alpha.-N-(Methyl through Decyl)-N-normetazocines (5,9.alpha.-Dimethyl-2'-hydroxy-6,7-benzomorphans): In vitro and In vivo Properties
Everette L. May, Mario D. Aceto, Edward R. Bowman, Christine Bentley, Billy R. Martin, Louis S. Harris, Fedor Medzihradsky, Mariena V. Mattson, Arthur E. Jacobson;,
J. Med. Chem.; 1994; 37(20); 3408-3418.
PDF
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Syntheses, analgetic activity and physical dependence capacity of 5-phenyl-6,7-benzomorphan derivatives
Naokata Yokoyama, Prabodh I. Almaula, Fred B. Block, Frank R. Granat, Norman Gottfried, Ronald T. Hill, Elihu H. McMahon, Walter F. Munch, Howard Rachlin, et al.;,
J. Med. Chem.; 1979; 22(5); 537-553.
PDF
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Synthesis of pentazocine
Noel F. Albertson, William F. Wetterau;,
J. Med. Chem.; 1970; 13(2); 302-303.
PDF
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Structures Related to Morphine. IX. Extension of the Grewe Morphinan Synthesis in the Benzomorphan Series and Pharmacology of Some Benzomorphans
Nathan B. Eddy, James G. Murphy, Everette L. May;
J. Org. Chem.; 1957; 22(11); 1370-1372.
PDF
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Synthesis of 6,7-benzomorphan from 4-phenylpyridine
Ken Kanematsu, Robert T. Parfitt, Arthur E. Jacobson, J. Harrison Ager, Everette L. May;
J. Am. Chem. Soc.; 1968; 90(4); 1064-1065.
PDF
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Rearrangement Products of 9-Acetoxy- and 9-Hydroxy-2,5,9-trimethyl-6,7-benzomorphans
Robert T. Parfitt, E. M. Fry, Everette L. May;
J. Org. Chem.; 1966; 31(3); 903-905.
PDF
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Synthesis of Analgesics with Benzomorphane Structure. A Possible Intermediate: 1-Methyl-2-benzyl-4-piperidol
U. M. Teotino;
J. Org. Chem.; 1962; 27(5); 1906-1908.
PDF
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Structures Related to Morphine. XXI. An Alternative Synthesis of Diastereoisomeric 2'-Hydroxy-2,5,9-trimethyl-6,7-benzomorphans
Seiichi Saito, Everette L. May;
J. Org. Chem.; 1962; 27(3); 1087-1089.
PDF
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Structures Related to Morphine. XIX. Benzomorphans from 3,4-Diethylpyridine
J. Harrison Ager, Everette L. May;
J. Org. Chem.; 1962; 27(1); 245-247.
PDF
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Structures Related to Morphine. XII. (±)-2'-Hydroxy-5,9-dimethyl-2-phenethyl-6,7-benzomorphan (NIH 7519) and Its Optical Forms
Everette L. May, Nathan B. Eddy;
J. Org. Chem.; 1959; 24(10); 1435-1437.
PDF
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Structures Related to Morphine. XIII. 2-Alkyl-2'-hydroxy-5,9-dimethyl-6,7-benzomorphans and a More Direct Synthesis of the 2-Phenethyl Compound (NIH 7519)
J. Harrison Ager, Everette L. May;
J. Org. Chem.; 1960; 25(6); 984-986.
PDF
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Improved synthesis of a 9-oxo-6,7-benzomorphan and its homolog. Novel rearrangement of heterocyclic enamines via bromination
Mikio Takeda, Hirozumi Inoue, Mikihiko Konda, Seiichi Saito, Hiroshi Kugita;
J. Org. Chem.; 1972; 37(17); 2677-2679.
PDF
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Structures Related to Morphine. XIV. 2'-Hydroxy-5-methyl-2-phenethyl-6,7-benzomorphan, the 9-Demethyl Analog of NIH 7519 (Phenazocine) from 3,4-Dihydro-7-methoxy-2(1H)naphthalenone
James G. Murphy, J. Harrison Ager, Everette L. May;
J. Org. Chem.; 1960; 25(8 ); 1386-1388.
PDF
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Structures Related to Morphine. VIII. Further Syntheses in the Benzomorphan Series
Everette L. May, Edward M. Fry;
J. Org. Chem.; 1957; 22(11); 1366-1369.
PDF
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Synthesis of 2,9.beta.-dimethyl-6,7-benzomorphan
Tokuro Ohishi, Arthur E. Jacobson, Raymond S. Wilson, Herman J. C. Yeh, Everette L. May;
J. Org. Chem.; 1974; 39(10); 1347-1349.
PDF
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Structures Related to Morphine. XI. Analogs and a Diastereoisomer of 2'-Hydroxy-2,5,9-trimethyl-6,7-benzomorphan
Everette L. May, J. Harrison Ager;
J. Org. Chem.; 1959; 24(10); 1432-1435.
PDF
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Structure Related to Morphine. XXVI. Cyclization Experiments with 2-Benzyl-1,3,4-trialkyl-1,2,5,6-tetrahydropyridines. Improved Yields of -5,9-Dialkyl-6,7-benzomorphans
J. Harrison Ager, S. E. Fullerton, E. M. Fry, Everette L. May;
J. Org. Chem.; 1963; 28(9); 2470-2472.
PDF
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Structures Related to Morphine. XXIII. Stereochemistry of 5,9-Dialkyl-6,7-benzomorphans
S. Edward Fullerton, Everette L. May, Edwin D. Becker;
J. Org. Chem.; 1962; 27(6); 2144-2147.
PDF
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Structures Related to Morphine. XX. Stevens Reaction in the Synthesis of 5-Ethyl-2'-hydroxy-2-methyl-(or phenethyl)-6,7-benzomorphan
Seiichi Saito, Everette L. May;
J. Org. Chem.; 1962; 27(3); 948-951.
PDF
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Structures Related to Morphine. XXIV. Further Application of the Stevens Rearrangement in the Synthesis of Diastereoisomeric 6,7-Benzomorphans from 3-Ethyl-4-methyl- and 4-Ethyl-3-methylpyridines
S. E. Fullerton, J. H. Ager, E. L. May;
J. Org. Chem.; 1962; 27(7); 2554-2557.
PDF
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New Benzomorphan Ring Closure in the Synthesis of 5-Phenylbenzomorphans
Gordon N. Walker, David Alkalay;
J. Org. Chem.; 1966; 31(6); 1905-1911.
PDF
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Meta bridging reactions of electron-deficient aromatics. I. One-step synthesis of the 6,7-benzomorphan ring system. Facile preparation of potential narcotic antagonists
Raymond R. Bard, Michael J. Strauss;
J. Am. Chem. Soc.; 1975; 97(13); 3789
PDF
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6,7-Benzomorphans. Stereospecific synthesis of 2,9.alpha.- and 2,9.beta.-dimethyl-2'-methoxy-6,7-benzomorphans
Richard D. Gless, Henry Rapoport;
J. Org. Chem.; 1979; 44(8 ); 1324-1336.
PDF
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Benzomorphans: synthesis, stereochemistry reactions, and spectroscopic characterizations
David C. Palmer, Michael J. Strauss;
Chem. Rev.; 1977; 77(1); 1-36.
PDF
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A novel cleavage of aryl benzyl ethers and allyl aryl ethers by sodium bis(2-methoxyethoxy)aluminum hydride. An alternative synthesis of pentazocine
Tetsuji Kametani, Shyh-Pyng Huang, Masataka Ihara, Keiichiro Fukumoto;
J. Org. Chem.; 1976; 41(15); 2545-2548.
PDF
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Studies on the synthesis of heterocyclic compounds. 726. Thermal rearrangement of aminomethyl cyclopropyl ketones and a novel synthesis of pentazocine
Tetsuji Kametani, Hideharu Seto, Hideo Nemoto, Keiichiro Fukumoto;
J. Org. Chem.; 1977; 42(22); 3605-3608.
PDF
Last edited by java on Thu May 12, 2005 7:44 pm; edited 1 time in total |
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LSD and structural analogs: pharmacological evaluation at D1
Tue May 03, 2005 3:27 am |
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LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors
Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB
Psychopharmacology (Berl). 1995 Apr;118(4):401-9
Abstract
The hallucinogenic effects of lysergic acid diethylamide (LSD) have been attributed primarily to actions at serotonin receptors. A number of studies conducted in the 1970s indicated that LSD also has activity at dopamine (DA) receptors. These latter studies are difficult to interpret, however, because they were completed before the recognition of two pharmacologically distinct DA receptor subtypes, D1 and D2. The availability of subtype-selective ligands (e.g., the D1 antagonist SCH23390) and clonal cell lines expressing a homogeneous receptor population now permits an assessment of the contributions of DA receptor subtypes to the DA-mediated effects of LSD. The present study investigated the binding and functional properties of LSD and several lysergamide and analogs at dopamine D1 and D2 receptors. Several of these compounds have been reported previously to bind with high affinity to serotonin 5HT2 (i.e., 3H-ketanserin) sites in the rat frontal cortex (K0.5 5-30 nM). All tested compounds also competed for both D1-like (3H-SCH 23390) and D2-like (3H-spiperone plus unlabeled ketanserin) DA receptors in rat striatum, with profiles indicative of agonists (nH < 1.0). The affinity of LSD and analogs for D2 like receptors was similar to their affinity for 5HT2 sites. The affinity for D1 like receptors was slightly lower (2- to 3-fold), although LSD and several analogs bound to D1 receptors with affinity similar to the prototypical D1 partial agonist SKF38393 (K0.5 ca. 25 nM). A second series of experiments tested the binding and functional properties of LSD and selected analogs in C-6 glioma cells expressing the rhesus macaque D1A receptor.(ABSTRACT TRUNCATED AT 250 WORDS)
DJVU
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Alcohol Oxidation Articles
Tue May 03, 2005 5:00 am |
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Alcohol Oxidation Articles
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Stereo specific synthesis of (-)-cathinone from norephedrine, characterization as HCl salt
B. D. Berrang et al.
J. Org. Chem. 47, 2643 (1982)
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Alumina As a Triphase Catalyst'
Quici S., Regen S.L.
J. Org. Chem. vol.44, 3436, 1979
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(This article discusses oxidation of cyclododecanol with Al2O3/KMnO4 in PhMe
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Activation of Manganese Dioxide by Azeotropic Removal of Water
Goldman I.M.
J. Org. Chem. 34, 1979 (1969)
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(This article discusses oxidation of a sec alcohol with MnO2)
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Study of Synthesis and Cardiovascular Activity of some Furox
Sat May 14, 2005 6:24 am |
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Study of Synthesis and Cardiovascular Activity of some Furoxan Derivatives as Potential NO-Donors
Mu, Li; Feng, Si-shen; Go, Mei Lin
]Chem. Pharm. Bull.; 48; 6; 2000; 808 - 816.
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Sat May 14, 2005 6:44 am |
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Requested by Sandmeyer
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EINE NEUE DARSTELLUNGSWEISE VON AMINEU AUS ALPHA-AMINOCARBONSAUREN
Dose K.,
Ber., 1957, 90, 1251
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Note: thanks to Lugh for securing the citation
Last edited by java on Sat May 14, 2005 7:44 pm; edited 2 times in total |
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Studies and Reactions between Aromatic Aldehydes and .....
Sat May 14, 2005 6:56 am |
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Requested by Sandmeyer
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Studies and Reactions between Aromatic Aldehydes and alpha-amino Acids I. New Facts on Akabori Reaction
Takagi; Yakugaku Zasshi;]
The Pharmaceutical Society of Japan Study #185,vol. 71, no. 7, pg 648, 1951
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re: Archives of Journal Articles
Mon May 16, 2005 9:58 pm |
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Requested by Klot
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The serotonin transporter (SLC6A4) is present in B-cell clones of diverse malignant origin: probing a potential antitumor target for psychotropics
Elizabeth J. Meredith, Michelle J. Holder, Anita Chamba, Anita Challa, Adrian Drake Lee, Christopher M. Bunce, Mark T. Drayson, Geoffrey Pilkington, Randy D. Blakely, Martin J. S. Dyer, Nicholas M. Barnes, and John Gordon
The FASEB Journal Express Article doi:10.1096/fj.04-3477fje
Published online May 3, 2005
Abstract
Following our previous description of the serotonin transporter (SERT) acting as a conduit to 5-hydroxytryptamine (5-HT)-mediated apoptosis, specifically in Burkitt's lymphoma, we now detail its expression among a broad spectrum of B cell malignancy, while exploring additional SERT substrates for potential therapeutic activity. SERT was readily detected in derived B cell lines with origins as diverse as B cell precursor acute lymphoblastic leukemia, mantle cell lymphoma, diffuse large B cell lymphoma, and multiple myeloma. Concentration and timecourse kinetics for the antiproliferative and proapoptotic activities of the amphetamine derivatives fenfluramine (an appetite suppressant) and 3,4-methylenedioxymethamphetamine (MDMA; "Ecstasy") revealed them as being similar to the endogenous indoleamine. A tricyclic antidepressant, clomipramine, instead mirrored the behavior of the selective serotonin reuptake inhibitor fluoxetine, both being effective in the low micromolar range. A majority of neoplastic clones were sensitive to one or more of the serotonergic compounds. Dysregulated bcl-2 expression, either by t(14;1(q32;q21) translocation or its introduction as a constitutively active transgene, provided protection from proapoptotic but not antiproliferative outcomes. These data indicate a potential for SERT as a novel anti-tumor target for amphetamine analogs, while evidence is presented that the seemingly more promising antidepressants are likely impacting malignant B cells independently of the transporter itself.
Direct Link URL: http://home.ripway.com/2005-1/247174/Theserotonintransporter(SLC6A4).pdf
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Tue May 31, 2005 10:04 pm |
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The Direct Synthesis of Trifluoronitromethane, CF3 NO2
N. Lu, J. S. Thrasher
J. Fluorine Chem., 117(2), 181-184 (2002).
Abstract
Trifluoronitromethane, CF3 NO2 , can be prepared in one step in about 35% yield from the direct photolysis of iodotrifluoromethane, CF3 I, and nitrogen dioxide, NO2 , with diazo (superblue) light (?max = 420 nm).
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Tue May 31, 2005 11:30 pm |
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Synthesis and 5-HT2A Radioligand Receptor Binding Assays of DOMCl and DOMOM, Two Novel 5-HT2A Receptor Ligands
Antje Harms, Ernst Ulmer, Karl-Artur Kovar
Archiv der Pharmazie, Volume 336, Issue 3, 155-158 (2003)
Abstract
A synthesis of two new active substances, DOMCl (1-(4-chloromethyl-2,5-dimethoxyphenyl)-2-propanamine (2) and DOMOM (1-(2,5-dimethoxy-4-methoxymethylphenyl)-2-propanamine (3), was developed. Unexpectedly, the Blanc reaction permitted successful synthesis of 2,5-dimethoxyphenylpropylamine derivatives having a substituted methyl group in position 4 since solvation of the reactant occurs during the reaction. Afterwards, their affinities towards the 5-HT2A receptor were examined in 5-HT2A radioligand receptor binding assays. The study of these substances is of considerable interest because they were predicted, by preliminary molecular modeling studies based on mescalin units, to be potential new hallucinogens that should be added to the list of substances prohibited by law. It was assumed that DOMCl would be 82 times more potent as a hallucinogen than mescalin, and DOMOM would be 94 times more potent. The 5-HT2A radioligand receptor binding studies showed that the affinities of DOMCl and DOMOM for the 5-HT2A receptor are less than expected but are nevertheless 1.6 and 8.7 times higher, respectively, than that of mescalin. Therefore, scheduling these substances as potential drugs of abuse might be considered.
pdf
Note: thanks to mk-1 for securing citation for demerol |
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java
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Tue May 31, 2005 11:40 pm |
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Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate
Daniel Trachsel
Helv. Chim. Acta, Vol. 85, Issue 9, 3019-3026 (2002)
Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, 2, 3.
trachsel1.pdf
Abstract
The synthesis and the spectroscopic data of 14 novel 4-substituted mescaline derivatives are reported. Starting from syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde), several ethers were obtained from reaction with a series of corresponding saturated and unsaturated alkyl- and fluoroalkyl halides. Henry-reaction with MeNO2 or EtNO2 followed to afford the nitro-olefines, which were then reduced with AlH3 to the desired 2-phenylethyl- and 1-methyl-2-phenylethylamine derivatives.
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Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen. Mitteilung 2
Daniel Trachsel
Helv. Chim. Acta, Vol. 86, Issue 7, 2610-2619 (2003)
trachsel2.pdf
Abstract
The 4-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (2,5-dimethoxybenzeneethanamines) and its -methyl analogs are known to act as potent 5-HT2A/C ligands, which have, depending on their 4-substituent, agonistic or antagonistic character. Generally, compounds with a small lipophilic substituent typically are agonists and those with a larger lipophilic substituent predominantly antagonists or at least partial agonists. Since little is known about the transition and more information is needed about the structural requirements of the 4-substituent to control the functional activity, 12 novel 4-thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines were synthesized and spectroscopically characterized. Thus 2,5-dimethoxybenzenethiol (7) was converted to the thioether derivatives 8a-l with several alkyl, fluoroalkyl, alkenyl, and benzyl halides. Subsequent Vilsmeier-formylation afforded the benzaldehydes 9a-l, condensation with MeNO2 the nitroethenyl derivatives 10a-l, and reduction with AlH3 the desired (2-phenylethyl)amines 11a-l.
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Synthesis of Novel (Phenylalkyl)amines for the Investigation of StructureActivity Relationships, Part 3
Daniel Trachsel
Helv. Chim. Acta, Vol. 86, Issue 8, 2754-2759 (2003)
trachsel3.pdf
Note : thanks to namgramk foe aquiring the citations for demoral |
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re: Archives of Journal Articles
Wed Jun 15, 2005 9:34 pm |
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Synthesis of Novel (Phenylalkyl)amines for the Investigation of StructureActivity Relationships, Part 3
4-Ethynyl-2,5-dimethoxyphenethylamine (=4-Ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN)
Daniel Trachsel
Helvetica Chimica Acta, 2003, 86(8 ), 2754 - 2759
full article from helvetica chemica
this is the ChemInform page, detailing the sonogashira coupling
Abstract
An easy and efficient pathway for the preparation of 4-ethynyl-2,5-dimethoxyphenethylamine (4-ethynyl-2,5-dimethoxybenzeneethanamine; 2C-YN; 1) was developed, an ethynyl analogue of the potent 5-HT2A/C agonists, e.g., 4-iodo-2,5-dimethoxy-amphetamine (DOI; 2b). The ethynyl moiety was introduced by a Pd-catalyzed Sonogashira reaction of (trimethylsilyl)ethyne with N-(trifluoroacetyl)-protected 4-iodo-2,5-dimethoxyphenethylamine (7) in almost quantitative yield within only 1 h. Removal of the Me3Si group was accomplished with Bu4NF. Final N-deprotection by NaOH treatment afforded the novel phenethylamine 1 in an overall yield of 88%.
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Note: thanks to mk-1 for securing the citation for Demerol |
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re: Archives of Journal Articles
Wed Jun 15, 2005 9:43 pm |
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An Improved Synthesis of Hydroxyindoles
Lena Lermana, Marta Weinstock-Rosinb, Abraham Nudelman
SYNTHESIS 2004, No. 18, pp 3043–3046x.x.204
pdf
Abstract
An improved synthetic procedure for the synthesis of 6- and 7-hydroxyindoles is described. In this method, the addition of two chlorine atoms in 1-benzyloxy-4,5-dichloro-2-nitrobenzene (3) and 1-benzyloxy-2,6-dichloro-3-nitrobenzene (9) facilitated the subsequent cyanomethylation step to give substituted cyanomethyl-dichloronitrobenzenes 4 and 10, leading to an overall increase in the yield of the hydroxyindoles 6 and 12.
Note: thanks to Demorol for the citation acquired for mk-1 |
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java
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re: Archives of Journal Articles
Sat Jul 16, 2005 7:22 am |
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Chemical Engineering Magazin June 2005.PDF
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http://rapidshare.de/files/2925755/Chemical.Engineering.Magazine.June.2005.PDF.eBook-YYePG.rar.html
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Note : thanks to ayush for his contribution |
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java
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re: Archives of Journal Articles
Sat Jul 16, 2005 7:33 pm |
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Alloy electrodes with high hydrogen overvoltage for analytical use in voltammetry. Some preliminary results.
Mikkelsen O, Schroder KH.
Analyst. 2000 Dec ; 125 (12): 2163-5
http://rapidshare.de/files/3102918/Alloy_electrodes_with_high_hydrogen_overvoltage_for_....pdf.html
Abstract
Liquid mercury and liquid diluted mercury amalgams have been the major electrode systems employed in voltammetry and related methods. This is mainly due to their high overvoltage to hydrogen, which enables the determination of heavy metals (zinc, nickel, cobalt, etc.) and other species with high negative half-wave potentials; the toxicity of mercury and liquid diluted mercury leads to ever increasing restrictions in their use. The use of such systems may even be forbidden in the future, at least in online systems for work in the field. Recent work, carried out in our laboratory, has demonstrated that a non-toxic solid dental amalgam may be used as the electrode material, conveniently replacing mercury. An extension of this work has shown that electrode materials comprising a metal or a compound with low hydrogen overvoltage change their hydrogen overvoltage properties substantially when contaminated with even small amounts of metals or compounds which show high hydrogen overvoltage. This extends greatly the range of potentially available electrode systems and thereby analytical possibilities of voltammetry. This new discovery also makes it possible to produce solid electrodes that have high overvoltage to hydrogen without any use of mercury.
Note: article aquired for Vitus |
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java
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re: Archives of Journal Articles
Sat Jul 16, 2005 10:47 pm |
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Functionalized Polymers - Emerging Versatile Tools for Solution-Phase Chemistry and Automated Parallel Synthesis
Andreas Kirschning, Holger Monenschein, Rüdiger Wittenberg
Angewandte Chemie International Edition
Volume 40, Issue 4, 2001. Pages 650-679
http://rapidshare.de/files/3104706/AngChemieIntl_v40_i4_p650-679.pdf.html
Note: thanks to spicybrown for securing the citation for java |
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