SYNTHESIS OF THE INDIVIDUAL, PHARMACOLOGICALLY DISTINCT, ENANTIOMERS OF A TETRAHYDROCANNABINOL DERIVATIVE

被引:101
作者
MECHOULAM, R
LANDER, N
BREUER, A
ZAHALKA, J
机构
[1] Department of Natural Products, Hebrew University Medical Faculty, Jerusalem
关键词
D O I
10.1016/S0957-4166(00)86322-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The individual enantiomers of the 1,1-dimethylheptyl homolog of 7-hydroxy- Δ6-tetrahydrocannabinol, (1) and (2a), which exhibit distinct pharmacological profiles, have beenobtained with very high e.e. by synthesis from the antipodes of myrtenol. © 1990.
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页码:315 / 318
页数:4
相关论文
共 10 条
[1]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[2]  
FEIGENBAUM J, 1989, P NAT ACAD SCI, V169, P159
[3]   STEREOCHEMICAL EFFECTS OF 11-OH-DELTA-8-TETRAHYDROCANNABINOL-DIMETHYLHEPTYL TO INHIBIT ADENYLATE-CYCLASE AND BIND TO THE CANNABINOID RECEPTOR [J].
HOWLETT, AC ;
CHAMPION, TM ;
WILKEN, GH ;
MECHOULAM, R .
NEUROPHARMACOLOGY, 1990, 29 (02) :161-165
[4]  
JARBE TUC, 1989, J PHARMACOL EXP THER, V250, P1000
[5]   STEREOCHEMICAL EFFECTS OF 11-OH-DELTA-8-THC-DIMETHYLHEPTYL IN MICE AND DOGS [J].
LITTLE, PJ ;
COMPTON, DR ;
MECHOULAM, R ;
MARTIN, BR .
PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1989, 32 (03) :661-666
[6]  
Mechoulam R, 1987, NIDA Res Monogr, V79, P15
[7]   SYNTHESES OF DELTA-TETRAHYDROCANNABINOL AND RELATED CANNABINOIDS [J].
MECHOULAM, R ;
BRAUN, P ;
GAONI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6159-+
[8]   ENANTIOMERIC CANNABINOIDS - STEREOSPECIFICITY OF PSYCHOTROPIC ACTIVITY [J].
MECHOULAM, R ;
FEIGENBAUM, JJ ;
LANDER, N ;
SEGAL, M ;
JARBE, TUC ;
HILTUNEN, AJ ;
CONSROE, P .
EXPERIENTIA, 1988, 44 (09) :762-764
[9]  
RAZDAN RK, 1986, PHARMACOL REV, V38, P75
[10]   AN OPTICALLY-ACTIVE TERPENIC SYNTHON FOR DELTA-9-CANNABINOIDS - SYNTHESIS OF (-)-11-HYDROXY-DELTA-9-TETRAHYDROCANNABINOL (THC) AND ITS 1',1'-DIMETHYLHEPTYL ANALOG [J].
SIEGEL, C ;
GORDON, PM ;
RAZDAN, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5428-5430