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ATP, 489 Absolute Configuration Benzomotphans, 204 Levotphanol

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Index AIDA, 495 Affinity labeling, analogs of (Cont.) cAMP, 409, 489 motphine,448 ATP, 409, 489 naltrexone, 449 [3H] ATP, 489 norlevotphanol,449 Absolute configuration normetazocine, 181 benzomotphans, 204 norpethidine, 232 levotphanol, 115 oripavine, 453 methadone and analogs, 316 oxymotphone, 449 motphine, 86 K-Agonists, 179,405,434 phenoperidine, 234 Aid in Interactive Drug Analysis, 495 piperazine derivatives, 399 [L-Ala2] dermotphin, 363 prodines and analogs, 272 [D-Ala, D-Leu] enkephalin (DADL), 68, 344 sinomenine, 28, 115 [D-Ala2 , Bugs] enkephalinamide, 347, 447 viminol, 400 [D-Ala2, Met'] enkephalinamide, 337, 346, Ac 61-91,360 371,489 Acetylcholine, 5, 407 [D-Ala2]leu-enkephalin, 344, 346, 348 Acetylcholine analogs, 186, 191 [D-Ala2] met-enkephalin, 348 l-Acetylcodeine, 32 [D-Ala2] enkephalins, 347 Acetylmethadols (a and (3) Alfentanil, 296 maintenance of addicts by a-isomer, 304, 309 (±)-I1(3-Alkylbenzomotphans, 167, 170 metabolism, 309 11(3-Alkylbenzomotphans, 204 N-allyl and N-CPM analogs, 310, 431 7-Alkylisomotphinans, 146 stereochemistry, 323 N-Alkylnorketobemidones, 431 synthesis, 309 N-Alkylnorpethidines, 233 X-ray crystallography, 327 N-Allylnormetazocine, 420 6-Acetylmotphine, receptor binding, 27 N-Allylnormotphine, 405 Acetylnormethadol, 323 N-Allylnorpethidine, 233 8(3-Acyldihydrocodeinones, 52 3-Allylprodines (a and (3), 256 14-Acyl-4,5-epoxymotphinans, 58 'H-NMR and stereochemistry, 256 7-Acylhydromotphones, 128 X-ray crystallography, 256 Addiction, 4 N-Allylnormetazocine, 420 Adenylate cyclase, 6, 409, 413, 424, 453, 489- 6-Allyl-ll-oxobenzomotphan, 186 490 N-Allyl-D-Ala2 -metenkephalin, 434 Adrenal medulla, source of opioid peptides, 362 N-Allyl-Ieu-enkephalin, 434 Adrenergic receptors, 454 6-Allylbenzomotphans, 141 Affigel-401, 453 N-Allylcodeine (N-allylnorcodeine), 30, 405 Affinity chromatography, 448 (±)-N-Allylmethoxyhasubanan, 144 Affinity labeling, analogs of, 449 N-Allylnorketobemidone, 275 enkephalins, 348, 454 N-Allylnormetazocine, 176 fentanyl, 453 N-Allylnormotphine, 30 503 504 Index Alvodine, 232 5-Arylmorphans (Cont.) 14-Amidomorphine, 430 pharmacology, 216 Amidone, 303 ( + )-5R-isomers, 226 6-Amino-3,3-diphenylhexan-3-one, 307 stereochemistry, 216 9-Aminoarylmorphans, 219 N-substituted, 218 8-Aminobenzomorphans, 182 synthesis, 215 I-Aminocodeine, 32 3-Arylpiperidines, 432, 433, 468, 474 t-Aminocyclohexanes, 395 4-Arylpiperidines, 299,473,474,476,481- w-Aminohexyl septarose, 448 485 14!3-Aminomorphine, 448 4-alkyl, 432 Aminopeptidases, 337 antagonists, 431 N-p-Aminophenethylnorpethidine, 232 aromatic group variation, 240 Aminotetralins, 396,464 phenolic, 276 Aminotetralins, bridged, 433 3-Arylpyrrolidines, 433, 474 Amitriptyline, 236 2-Arylthiobenzimidazoles, 389 Androcymbine, 145 Aspirin, 1,312 Anileridine, 232, 449 Autoradiography, 446, 490 4-Anilido-I-phenethylpiperidine, 485 Azabicylanes, 483 4-Anilidopiperidines, 466 Azabicyclo [2.2.1] heptanes, 245 4-Anilinopiperidines, 287 2-Azabicyclo [2.2.2] octanes, 298 4-Anilinopiperidines, QSAR, 297 Azabicyclo [3.2.1] nonanes, 215 Animal test procedures, 2 Azacycloalkanes, 251 Antagonists opioid, 405 Azacycloheptan-4-one, 244 basic nitrogen and C-14 substituents, 9-Azamorphinans, 143 424 6-Azido-4,5-epoxymorphinans,92 benzomorphan derivatives, 420, 424 Azidomorphines, 39 K-antagonists, 434 N-!3-(p-Azidophenyl)ethylnorlevorphanol, 119 morphinan derivatives, 416, 427 morphine derivatives, 409 BAM-l2P, 20P, 22P, 362 non-morphine based, 431 BIT, 388,453,492 pure, 412 BSA,446 SARs, 409 Bacitracin, 337, 350 Antinociceptive tests for opioid agonists, 2 Barbiturates, 1, 460 [Arg6]leu-enkephalin, 361 Basic nature of opioid ligands, 460 N-Arginyl-metenkephalin, 180, 372 N-substituent structure, 466 Aromatic features of opioid ligands, 467 Basic propionanilides, 311 4-Aryl-4-alkylpiperidines, 276, 432, 469 conformation (X-ray), 322 synthesis, 279 synthesis, 321 3-Aryl-3-alkylpyrrolidines, 244 Beckett -Casy hypothesis, 471 4-Ary 1-4-dimethy laminocyclohexanols, 391 Beckmann rearrangement, 195, 216 3-Aryl-3-methylpiperidines, 245, 279, 432 Belleau's lone-pair hypothesis, 464 pyrrolidine analogs, 281, 433 Belleau's single receptor theory, 456 synthesis, 380 Bemidone, 239, 241 4-Aryl-4-piperidinols, synthesis, 240 antagonist analog, 431 6-Aryl-2-azabicyclo [4.3.1] decanes, 226 3-Benzazocine-2-carbonitrile, 195 1-Aryl-6-azabicyclo [3.2.1] octanes, 223 Benzethidine, 235 4-Aryl-2-azabicyclo [2.2.2] octanes, 225 Benzimidazoles, 385-389, 470, 475, 485 N-Arylamidinobenzomorphans, 177 Benzitramide, 312 5-Arylazabicyclooctanes, 223 Benzodiazepines, 438 6-Arylbenzomorphans, 160, 162, 184 'Y-Benzomorphan, 166 5-Arylmorphans, 18, 144,215,225,279,431, Benzomorphans, 117, 146, 153,372 481,483 acetylcholine analogs, 186, 191 bridged, 219 amidinium analog, 173 Index 505 Benzomorphans (Cant.) I-Bromocodeine, 32 amino acid derivatives, 180 14-Bromocodeinone, 24, 83 antagonists, 420, 422 (+ )-7-Bromodihydrocodeinone dimethyl ketal, aromatic substitution, 181 413 N-bromoalkyl, 181 N-2-Bromoethylnormetazocine, 449 13C nmr, 204 I-Bromomorphine, 32 4,4-disubstituted, 194 2-Bromopropionyl resin, 342 N-furfuryl, 178 Buprenorphine, 73, 128, 189,406,410-411 'H nmr, 196 pKa' 461 molecular geometry, 205 16,17-Butanomorphinans, 462 ORD/CD, 204, 207 Butorphanol, 110, 132-133, 141, 184,406, parent ring, 183 411,415,418-419,423,427 peptides, 372 antagonist actions, 414 ll-position configuration, 190 19(R)-Butorvinol, 487 quaternary salts, 177 6-t-Butylbenzomorphans, 184 rearrangement products, 194 receptor multiplicity, 353 CAM,416 ring variants, 196 CHAPS, 447, 448 specific receptor sites, 359 CNA,449 spectroscopy, 196 /3-CNA, 450, 451 structure-activity-relationships, 205 /3-COA,450 I-substituted, 190 COAM,416 2-substituted, 191 Capsaicin, 6 4-substituted, 193 N-Carbamoylbenzomorphans, 177 5-substituted, 193 Carboxypeptidase, 337 6-substituted, 183 stable peptides, 352 ll-substituted, 185 Carboxypeptidase-resistant peptides, 349 N-substituted, 206-207 Carfentanil, 296 substitution on nitrogen, 176 /3-Casomorphin, 357-358 synthesis, 155 Cat nictitating membrane, 408, 416 N-tetrahydrofurfuryl, 57, 179, 208 China White, 288 X-ray studies, 203-205 Chlornaltrexarnine, 61, 356,449 Benzomorphan-I-one, 473 /3-Chlornaltrexamine, 439 Benzoquinone, 70 l-Chlorocodeine, 32 2-Benzylbenzimidazoles, 466 a-Chlorocodide, 37, 39 N-[(2-Benzylmethylamino)propyl] a-Chloromorphide, pharmacology, 40 propionanilide, 322 /3-Chloromorphide, pharmacology, 40 I-Benzylnorpethidine, 230 Chloroxymorphamine (/3-COA), 65 I-Benzyltetrahydroisoquinoline alkaloids, 389 Cholinergic receptors, 454 Binding affinity measurements, 2, 3, 333 Chymotrypsin, 371 tests for dualists, 408 Ciramadol, 396, 433 Biochemical pharmacology of opioids, 5 Circular dichroism (CD) Bivalent ligands, 4,5-epoxymorphinans, 67 application to peptide conformation, 370 Blood-brain barrier, 2 of methadone, isomethadone, 327 Boc-Ieu-acyloxymethylphenylacetic acid, 342 Claison-Eschenmoser reaction, 53 Boc-Ieu-enkephalin-OMPA, 342 Clastic binding, 464, 466 Boc-Ieu-resin, 340, 341 Clinical trials, 3 Bradykinin, 407 Codeine, 9, 22-23, 75, 92, 229, 312, 389 Bremazocine, 177,292,438,448 B/C trans-, 24, 27 [3H] analog, 437, 439, 448 C-ring rearrangements, 37 (-)_[3H] analog, 438 clinical, 11 synthesis, 437 GPI responses, 408 14/3-Bromoacetarnidomorphine,448 interconversions, 23 506 Index Codeine (Cont.) DTLET,434 metabolic O-demethylation, 90 Darvon, 312 metabolism, 26, 87 N-Dealkylation, 233, 467 oxidation, 26 Decahydroisoquinolines, 246 phannacology, II ,6.16.17_Dehydroheroinium chloride, 68 synthesis, 14, 22 7,8-Dehydronaltrexone, 430 ( + )-Codeine, 28 15-Dehydrononnorphine, 90 ( - )-Codeine Delta (6) receptors, 354 binding value, 488 adenylate cyclase, 489 biomimetic synthesis, 16 interaction with wreceptors, 490 synthesis, 18 Demerol, 229 Codeine-7,8-oxide, 49, 90 Demethoxydeoxodihydrosinomenine, 144 Codeine derivatives, IH nmr, 84 6-Demethoxythebaine, 75 Codeinone, 22, 24-25 N-Demethylation, 177, 467 Michael-type additions, 52 N-Demethylation procedures, 30 reaction with lithium dialky !cuprates, 50 (±)-3-Deoxy-7,8-dihydromorphine, 125 Codorphone, 52 3-Deoxydihydromorphinan-6-one, 123 Computer graphics, 375, 459, 471, 484, 487, Deoxydihydrothebaine, 126 494,496 I-Deoxyethylketazocine, 435 4-Cyanobenzomorphan, 193 3-Deoxymorphinans, 430 16-Cyanoheroin, 68 3-Deoxymorphines, 430 Cyclazocine, 117, 176-178, 182,413,421, 6-Deoxyorvinols, 80 423,425-426,434 6-Deoxythevinols, 80 GPI responses, 408 Dependence, 4 clinical potency, 407 Dennorphin, 346, 363 pKa' 461 Hyp6-Dennorphin, 363 sodium index, 335 Phel-Dennorphin, 363 (-)-Cyclazocine, binding value, 488 N-Desmethylmethadol,304 Cyclizine, 307 a-( - )-N-Desmethylmethadol, 325 Cyclocodeinone, 138 N-Desmethylmethadone, 304 7,14-Cyclodihydrocodeinone, 49 3-Desmethylprodine, 252, 255 Cyclohexanes, 390 N-Desmethylpropoxyphene, 312 N-Cyclopropylmethyl (CPM), 424 Desomorphine, 37 N-Cyclopropylmethyletorphine, 80 Dextromethorphan, 114, 146 Cyclorphan, 141,417,420,424 Dextromoramide, 297, 307-308, 318-319, 327, clinical potency, 407 459, 470, 479 Cyprenorphine, 409 human phannacology, 308 Cysteine, 451 pKa' 461 Dextropropoxyphene, 312, 319, 327 D' Amour Smith test, 449 Dextrorphan, 119, 145, 333, 454, 489 DADL, 288, 292, 305, 344, 347-348, 356- (+ )-Dextrorphan, binding value, 488 358,371,374,388,435,436,439,451, Dezocine, 397-398, 433 491-492 Diacetylmorphine (heroin), 11 eH]DADL, 448 Diallylnonnorphinan, 335 DAGO, 288, 292, 305, 349, 356, 436, 439, Diaminocyclohexanes, 438 448 Diamorphine (heroin), II DALAMID,
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  • Demonstration and Affinity Labeling of a Stereoselective Binding Site for A

    Demonstration and Affinity Labeling of a Stereoselective Binding Site for A

    Proc. Nati. Acad. Sci. USA Vol. 82, pp. 940-944, February 1985 Neurobiology Demonstration and affinity labeling of a stereoselective binding site for a benzomorphan opiate on acetylcholine receptor-rich membranes from Torpedo electroplaque (cholinergic receptor/ion channel/photoaffinity labeling/N-aliyl-N-normetazocine/phencyclidine) ROBERT E. OSWALD, NANCY N. PENNOW, AND JAMES T. MCLAUGHLIN Department of Pharmacology, New York State College of Veterinary Medicine, Cornell University, Ithaca, NY 14853 Communicated by R. H. Wasserman, October 3, 1984 ABSTRACT The interaction of an optically pure benzo- Benzomorphan opiates have been shown to inhibit the morphan opiate, (-)-N-allyl-N-normetazocine [(-)-ANMC], binding of [3H]PCP to central nervous system synaptic mem- with the nicotinic acetylcholine receptor from Torpedo electro- branes (15, 16) and to modify the activity of serum cholines plaque was studied by using radioligand binding and affinity terase (17). Some opiate derivatives, in particular the benzo- labeling. The binding was complex with at least two specific morphans, can inhibit the binding of [3H]perhydrohistrioni- components having equilibrium dissociation constants of 0.3 cotoxin and [3H]PCP to the Torpedo AcChoR (18, 19). In the jiM and 2 jiM. The affinity of the higher affinity component present studies, a radioactive optically pure benzomorphan, was decreased by carbamoylcholine but not by a-bungaro- (-)-[3H]N-allyl-N-normetazocine {(-)-[3H]ANMC}, was toxin. The effect of carbamoylcholine was not blocked by a- used to measure reversible binding to and affinity labeling of bungarotoxin. In comparison, the affinity of [3Hlphencycli- the Torpedo electroplaque AcChoR. Specific binding was dine, a well-characterized ligand for a high-affinity site for shown to be complex with at least one component having noncompetitive blockers on the acetylcholine receptor, is in- lower affinity in the presence rather than the absence of cho- creased by carbamoylcholine and the increase is blocked by a- linergic effectors.