I
R R 11I s Rz >ID, " C CsH5 "9-210 1 H H 0 > H H 0 4-ClCsH4 226-227 3 H (CH2)oCHa 123-126 H 0 4 H H 123-126 CsHs 1 CH:j H CsHa 146-148 H 0 CsHa 204 6 CH, 7 H H 0 3-023CsHa 236-238 X H H 0 4-C?H;OCsHa 190-1 92 !) H H 0 2-CHzOCaH4 17.5-1 76 10 C1 H 0 CsHj 204-206 11 H CH, 0 CsHj 146-148 a A l , Et,OII; Ac, AcXle; Petr, petr ether (bp 40-70"); €3, P h H ; 11, IIIISO; W, dicated elements are within zt0.37i of the theoretical values. I
After cooling, the reaction mixture was dilut'ed (HZO); the precipitated S-(6-chromanyl)formamide, was filtered, washed (HpO), and then crystallized from EtOH-HSO: yield 8.2 g ( 7 7 C i ) ; mp 93-98". An analytical sample was recrystallized from the ~ ) K. same solvents, mp 98-100". =Inal. ( C ~ O H I ~ NC,OH, A solution of 8.2 g of AY-(6-chromariyl)formamidein 200 ml of anhyd PhH was added dropwise with stirring to a slrury of 2 g of LAH in Et&. After the addition was completed stirring was continued at room temperature for 2 hr and then the mixtiire was refIiixed for an additional 5 hr. The unreacted LA4Hand the formed complex were carefully decomposed with Et20 saturated with HIO. The inorganic salts were filtered off, The evaporated ehereal solutioii left ail oily residiie which was distilled, bp 115' (0.001 mm), yield 5.2 g (605G). To avoid autooxidation t,he com-
CryJtn" solvent
.41
I'orinula
.inalyse~'j
C, H, S A1 C, H, S Ac-Pet r C, H, r\' B-Petr C, H, N, Y B-Petr C, H, S , S .41 C, H, S 1)-W C, H, ?j 1 C, H, ?i B1 C, H, h' B-Pet r C, H, C1, Ti -41-W Ci;Hi$&2 C, H , X HrO. The aiialytical rewlts obtaiiied for the iiiCi,HiJ& CI,jHi,ClS,On Ci4HnoS,O* CisHisNJlS CLTHiSSZOS CnHi,N& ClsHijSiOa CisH~&20a C,iHlux?O, CisHijClS?O%
pouiid was used immediately for the subsequent steps. The picrate melted al 135-137'. .4nal. ( C , G H ~ ~ S , OC,, ) H, S . General Procedure for Compoundsin Table 1.-A PhH solution of the isocyanate or isothiocyanate was added dropwise with stirring t o an equimolar amount of the appropriate chromanylamine dissolved in the same solvent and cooled at 5'. After the addition was completed, the reaction mixture was diluted with petr ether (bp 60-68'). The precipitated solid was filtered and crystallized from appropriate solvent, or solvent mixture.
Acknowledgments.-We
thank Dr. -A. D e Leoriibus
for the microanalyses.
Book Reviews Two Books oa Psychotropic Drugs. I. Neurophysiological and Behavioral Aspects of Psychotropic and W. P . KOELLA. Drugs. Edited by A. G. KARCZMAR Charles C Thomas, Springfield, Illinois. 1969. xviii 199 pp. 18 X 2 3 em. $12.50. 11. Drugs and Youth. Proceedings of the Rutgers Symposium on Drug Abuse. Edited by J. R. WITTENBORK, H . BRILL,J. P . SMITH,and S. A. IViwmBom-. Charles C Thomas, Spring485 pp. 18 X 26 cm. KL2.75. field, Illinois. 1969. xiv
+
+
The two symposia covered in t,hese books complement, each other. Book I is concerned with E E G patterns elicited by LSD, cyclazocine, and Ditran, with physiological responses to such drugs arid to schizophrenic thinking, mid with experimental studies of acquisition, ret,ention, and other learning and memory patterns. Book I1 gives an overview of drug abuse in middle class youth and t,he social problems involved in coping with drug dependence. Special chapters are devoted to morphine, heroin, aiid cocaine, t o t,he amphetamines arid barbiturates, and to marijuana and LSD. For. each of t,hese agents every psychiat,ric aspect is considered, aiid possibilities of therapy- are discussed to break dependence arid treat pharmacologic side effeck. Obviously, the appearanre of dependence and of marly- side eff'ecsts is dose-related, arid the doses leading to these coridit,ions are iiicredible and appalliiig. So simple solutions, eit>hersociologic or punit,ive, are proposed, but, seven papers deal with drug abuse aiid t,he law aiid take, 011 the whole, an eiilight,eried aiid gerierous
att,itude, especially for marijuana which is misclassified by current legal regulations. Other research articles concern themselves with drug abuse specifically among teenagers and college students, and unfold the many unfinished agenda, the implamantation of which baffles sociologists, law enforcement officers, the families of drug abusers, and last but not least, the physicians who see t,he abusers usually when it is too late to reverse the trend which has led to physiologic and psychiatric disaster. Through these pages one gets a glimpse at t,he "now generation" which comprises so many members opposed t,o regular work and jobs, at the youths who purposely beek t,o substitut,e hallucination for "normal" thought processes, and who drift wit,hout. aim into ever increasing abuse of single and combined drugs. The task for chemists should be t,o follow the pattern set by nonaddicting iiarcot,ics, and t,o search for more selective agents which could slowly supplant, at least those compounds which must be manufactured for therapeut,ic purposes but, which at, high dose.* lead 1'0 the array of dependence and abuse potential for which they have become notorious. I t has been the rule rather thaii t,he exception that the pharmaceutical industry has t,urned off their research programs on such drugs as soon as the public image of the drug and its originators has become endangered. Continued researrh iii just these areas should ultimately give the physician those weapotis wit,h which he could begin to combat the ahiise aiid the etisiiiiig phyqiologio damage caiised by at, least. some of the tliugs diwiinsed iii these t,wn voliimes.
