MONOGRAPHSTHE MERCK INDEX OF CHEMICALS, DRUGS, AND BIOLOGICALS A Averimeetia Hy, 3-O-temethyliver- S-Oedemethiyl 25-eL-merdyytpropy 0-25- overmua GoD MK 846. Affi. Agnmicki Avorcec, Verimec Mixture of avermechins. @.¥~ conbsiwirg at least 80% of averneectin B, el thm 20% of uvermectin By (Cy Teo fron Sireptompees avcrmiahs. Allies t Ger. pul 2.1780, exdem, US, pot 4 SULSI9 UISTT, 1982 both to Merck & Co.) Scparotion cf components. TW. Miller ot ub, Anmricra). Ag. Chernother. 1S, 366 (979). by kemni-propurnive HPTC: CC Kparal J. 7 2005 ration J.P Springer et cl. ibid 4221 Partral synthesis of KC. Riusloou et al, ibid. 106, $169 (1984) Tet! 5S Hanessiun ef ob, dhol WOH, 2776 (1986), Ant netnnty maul, 1S Bias, WoC Campbell, 5 Parexital 64, 1032 (978), J. RE Egerton et al Antumucrob Ag, Chemother 15, 372 (1979, KS Todd ex all. Anu. J. Vet Rex 45, 976 (1989). Pedunlal cetivity, WL Putler otal, b perentts 37, 963 (SKI) RA Dytus, &. Si. J. Groen. Bra Chip. Prot Conf - Fess Dx 1984, 947 Comtech of red. amported fire arty, JA. Greenblut et ol, J. Agr Enromol 3,233 (1980), Interaction with GABA receptors: SS. Poug 4. Neurachor. 34, 351 (1980). TN. Mellin «f ol. Neurspharmocol, 22, 89 (1953). receptor binding studies, S Pang, C.C Wang, did 10, 11 UKO), G Drala, W. Seghurl, Eur J Pharmaca! 99, 269 (19a) Fate in weal nd Jute. D. L. Bull of cl. J. Agr Food Chem 32, 94 (1984), A, Moye ot ck iid, 35, #89 (1OR7E: M.S. Moyne i a ibid 37.19% 181 19K), Renew, JR Babu, “Avermenine: Biohyuat and Pesiqulal Acuwinus” mn Blalogicully Active Nowral Produces, ACS Symp. Senes 380, 1G Cutler, Hd (Amencan Chemical Society Waxlaugion, DC. 188) pp I-08. Kenacws nf maces of Ce Win compere 8 component Big RCH | Pony. Prog Clin Biol Res 97, ¥14.495 (1929, DJ Wang " Biochem Soo Trans 18, 65-67 (ORT) Rewew of msec adsl uenynies end axe “T Steong. 1 A Beowe. Bull Era Res, 77, 487-380 (1987). Chlorlens, ulf-wlale fal, 85-7" yellow etystals front methanol. mp Tate = O87 w CHC) uv 337, 245, 258 nm fing «4.4K, 499.4 UD 15 210 S1aer Soly at 27 Get water acetone 10, r-butnnol 10. chlereierm 25. sydlulecxune 6, hase 20, beprepanol 70, kerosene 0.3, methainal 19 5, toluene $80 Hydrolyni does cu ectir We se] soln et PH 3.3.7) LDg, (eeuhinical grade) rally m sexame ojo muuse nd 134" 100 mgfke deruuilly an cablot +2000 mg/kg Lx, in mall K. bobwhitc quuil M4 6, 2200 ng tke EC oe (96 hich ia agmbow traut. bluegal 3. 96 BFL, LG yp G8 BED in Duphrig maxna 0 54 yg/t (Merck Techmeal Date Sheci) Use Acuricide: inseutlotde IMuRA® Cal OEY Anithelmorte 2, Abiotic Acid, [1R+4..tusi-thagt h.3.n,10.1Ne-Decabyaro-t tems AS0-I58 Glee) H YO OID SH feud prepared hy women: ‘A Sully svulluble organic cm il casey Hares, Sanulerso, 1963, Plescr, Fiese sural Pruduces Related to Pheaenthrs 1 jon J, Airy Chee Seg 83, (1961. ED Wenkert et af thik HO, 203% (1908 C hres sapluc study: AG Douglas, 1G Powell, 2, Ciu 93,241 (1969). Metabolism ut rabhas Y Asakawa er al Xenvbiostea 16 753 (1980) ry of! Mowvchume plates fem alcohol — water, mp 172-175" fe tes abs al) uy man 23 (¢ 19500, 22000, 14100) insol un water Sod im ke, busrzem na, wher acetone uurbon disulfide. dil NUOH solu Commercul ablutic 201d made by neunng rose olowe or «ab: y be glassy or panty. cr} Meihyl ester sce methyl abilare USF Manufacture of esters (ester Bums), © 2 methyl, v1 uyl and plycoryt esters for use an Imcquers and varnish “mictal reainatis™, soaps, Plastics and p ef aca cunt butgrie 2. Abikaviremyem, 7-Brhylrdene-to,2,1,7errahy- drocyclopentfhfostrenofsfprridune, 4 asepuxy A-cibyhcee= 2 ddgacrahydro-SH-l-pynidinc abicowironycmt. Consult the cross index before using this section,4 Abrin cidin, CH, NOs mol we 16120. € 74.51% H 6.88% N 8.69%, O'9.98%, Antiviral antibiotic produced by Sirepio- mec abitaensis and Streptomyces rubetcen®. Chromatogra- [hic isoln from broth culeures: Uimerawn et af, Japan. Med J.4.33) C951: CA. 46, 7167 (1952, Umezawa, Japan. pat. ‘S200 54) (10 Nippon). Identity with tatumeicin:, Sakeaeeni ‘ial J. Antibior 1A, 23) (1958). Structare: Gurevich of ft, Towrahadrom Latter: 1968, 2208. Sierenehemisiry Kono tt al, 1 Antibiot. 23, 572 (4970); Gurevich et al, Khon. Priv Soedin. 7, 104 (1971), C.A. 75, 5752¢ (971). Crystal and molecular stcuciure of the selénate: Y. Kono ¢ al, Aci Crystaliog. Sect. By 27, 2341 (I9T1). dn vitro antiviral act ty) VM. Roikbel, N! A. Zeitlenok, Ansihiokt (Moscow) 14, 969 (£969), C4. 72, 19394q (1969). cajcw a Highly unstable and potymerizes promptly on isolation even a — 50°, however, it can be handled in dilure solutions and in the form of its salts, uv max (neutral ethanol or O.1N KOM): 218, 244, 289 nm Gog € 3.83, 3.99, 3.94), (O.EN HOD 236, 34) nm (log € 3.99, 4.05). 4, Abrin, Agglutinin; toxatburnin. A toxic lectin and hemagglutinin obtained rom seeds of jequérity, Abrus Precatorius L., Leguminosae, a common vine of tropical ‘countries, also found jn cenfra| and southern Florida. Isoln and purification: J. ¥. Lin er al, J. Formosan Med. Assoc 68, 518 (1969), C.A. 72, 98695 (1970); eidem, Toxicon 9, 97 G91. The high toxicity of abrin was originally belicved to result from its hemagglutmating activity, but subsequent ‘studies Aaye shown that separate proteins are responsible for the toxicity and agglusination: $8. Olsnes, A. Pik, Eur. J. iochom. 35, 179 (1973). Five glycoproteins have been puri- fied from the seeds of 4. precalorius: Abrus agglutinin and Ihe toxic principles, abrins ad. Abrus agglutinin is a tetra- mer of 134,900 Day is non-toxic to animal cells and a potent hemaggludnator. Abring 2 through d (mol wt 63,000- 67,000 Da) are composed of 1wo disulfide-linked polypep- fide chains. ‘The smaller A-chain inhibits protein synthesis and causes cel! death; the larger B-chain binds to the cell plasma membrane. Purification of major components: | C. H. Wei et al, J. Biol Chem. 289, 3061 (1974). Crystallo- graphic study: CH. Wei, J. R. Einstein, ibid. 2985. Im. Proved purification, propesties, crystallography of Abrus agglutinin: C. H. Wei ef al. ibid. 280, 4790 (1975). Physical properties of the tonie principles: M. S. Hermann, W. D. Behnke. Biochim. Biophys. Acts 621, 43 (1980); etdam, ibid 667, 397 (1981). Isoln and purification of all five proceins: JY Lin et ab, Toxicon 19, 410981). Amino acid sequence of the A-chain of abrina and comparison with ricin: |G. Funatsu et af, Agr Biol Chem $2, 1095 (1988). Antitumor effects in animals: V. V. 8. Reddy, M. Sirsi, Cancer Res. 29, 14a7 (1969). J. Y. Lin et at, Narre 227, 292 (1970); 0. Fodstad et af, Cancer Res 39, 4559 (1977). Irnmunoetcc~ tron microscopy studies of abrin toxic action on tumor cells: C.T, Lin ef af, J. Ultrastruc. Res. 73, 110 (1980). Seudies on toxicity and binding kinetics: _M. Witten et al, Exp. Celt Biol, 49, 306 (1981); C.F. Bennett er af, thi 319. Use of A-chain in cell-type-specific cytotoxic agents known as. “immmunotoxins”: A. 5. Cumber 2 al, Methods in Enzymol. egy 112, 207 (1985). See also Ricin, Lectins. ‘Yellowish white powder. Sol in solns of sodium ohloride, usually with turbidity. The joaie portion js heat-stable 10 incubation ay 60° for 40 min; at 80", most of the toxicity is fost in 30 min. LDyg isp. in mice: 0.020 mg/kg. J. Y. Lin er ah, J. Formosan Med. Assoc. 68, 322 (1969), CAT, 124926 (1369, Caution: Seeds of A. precatorius are extremely toxic; one seed, if thoroughly masticaied, can cause fatal poisoning, of. JM. Kingsbury, Potionous Plans of the United States and Canada (Prentice-Hall. New Jersey, 1964) p 303: K. Genest etal, Arzuolmitel-Forsch. 21, #88 (1971) Nove: “Do nol confuse with sbring, gv. USE: Exptly in cancer research. Page 2 8, Abrine, NeMethyl-. tryptophan: a-methylamino-i- (G-indoledpropionic acid. CpH,N,O,; mol wt 218.25. 66.03%, H6.47% N 12.64%, 0 4.06% Nol 10 be confused, with the slbuminous substance abrin, gv. Oblained from the seeds of Abrus precatorius L.. Leguminesae Gequirity): Hoshino, Arm. 529, 31 (1935). Synthesis: Miller. Robson, J. Chem. Soe. 1988, 1910. Configuration: Cahill Jackson, J. iol Chem, 126, 28 (1938). Piss from water, de 205%, lf) +4" (0.28 g in 10 ml O5N Hep. One pram dissolves on about 100 mt meshonot shghtly sol in waicr, insol in ether. Sol in dit acids, alkalics. Hydrochloride, C3HyN;O,HCh needles, mp 222" sol - vole in water Nitra, gH NO, HINO, Aecgt detalles a Se on mr GIN NSO, 6. Abscisic Acid. (S4(Z,E))-S(l-Hydroxy.2,6,6-tri~ methyld-oxo-2-cyclohexen-t-yf)-S-methyl-2, d-penadienoic ‘abscisin IL; dormia; ABA. CyFly0y: mol wi 264.31 € 68.16% H 7.63%, O 24.21%, An abscission-aecelerating plant hormone. Presence of the naturally occurring (4)- Cis,troms-form (also designated as (S)-abscisic acid) in syca- more, birch, rose leaves, cabbage, potato, lemon, avocado: Corntorth ef at.. Narure 210, 627; 211, 743 (1966), Identity with dormin: “Cornforth ef at. Narire 208, 1269 (1965): idem, Tetrahedron, Suppl. No. 8, Part If, 603 (1967). Isoin from’ young cotton fruit: Obkuma et a2. Science 142, 1592 (1963). Identification of (+)-abscisie acid in rat. pig brain: M.Th. Le Page-Degivry ef al, Proc. Nat. Acad. Sci USA 83, 155 (1986). Synthesis of Ci)-cixtraastorms: Comforth et ah. Nature 206, 715 (1968); of G)-cis,trans. and (—)- ciswans-forms: F. Kienale ef al. Hels. Chim. Acta 6f, 2616 (1978); of Cby-trons.clssform: Obkumna, gr Biel. Chem, 28, 962. (1965): 30, 434 (1966); Findlay, MacKay. Can, J. Chern. 49, 2369 (1971), Structure: Cornforth ei ab, Nature 206, 715 (1965): Ohkuma et at, Tetrahedron Letters 1965, 2529. Absolute configuration of G+)-cis,trans-form: Cornfarth et at, Chem. Commun. 1967, $142 revised stereochemistry: Ryback, ibid. 1972, 1190; Koreeda et ai, J. dm. Chem, Soc. 95, 259 (1973). Crystal and motccular structure: HW, Sciumalle ef al, Acie Crystaliogr. B33, 2218 (1977). Effect On seed Set in Wheat: J. M. Morgan, Nature 285, 655 (1980) Reviews Addicott, Lyon, Ann Rev. Plant Physiol 20, 139 (1968). Review of role in ract growth regulation: P. E. Pi. kt, P. W. Bartow, Plant Growth Regul. 6, 217-265 (1987 of nyctabolism: J. A. D. Zeevaar, R. A. Creclman, Ant. Rev. Plane Physiol Plant Mok Biol 39, 439-473 (1988). Book: “Abscisic Acid, F. T. Addicoue, ES. Praeger, New York, 1983) ‘08 pp. needles, dec 143° O,. mp 176 (akf — bak ony chy Coon (4) -cis trans-Form, crystals from ethyl acetate + hexane, emp 161-163", Sublimes at 120. aie +a = 1 in ethanoD. Tel? +426.5° (= 1 in 0.005N methanolic H,- S0,). Sot in aq NaHCO,, chloroform, acetone, ethyl acetate, ether: slightly sol in benzene. water: sparingly sol in petr eter. uv max (methanol): 252 nm [e 25200). () cistrans.Form, mp 162-163". Jal —426.2" (© in 0008N H,S00. B-cis trahs-Foem, crystals. mp 188-190. Note Abseisin 7, an abscission accelerating substance. Nomenctanire Ohkuma et ab, Science 142, 1592 (1963). Isola from mature fruit walls of cotton: Liv, Cars, Science 434, 384 (L961). Crystals. mp 197-198", wy max (meiha- nol}: 250 nm, Acidic reaction. Sol in chloreformn. dil Consult the cross index before using this section.Acacic Acid u NuOHL shahily rol in drmethyl ether Practically wnsol ie ali in, [38-1 2e, Yee 607 tbune. Obi, Ze, Zar fe the Fa), MS 3 304, 5.6.60, 60.7. 70,8, 10 Hin Die Vie bth Hexndecobdent 14.1 Shexameihy 49602 © 7255. 812% 0 193% Chef biter pnn- aple of warmwood, Arterusig afvuntuuen Ly Campostey raphy Herout cb ad. Call Cz. € hon Commas 2H, VARS H19%6). see ako Chem & Ind (Lonctey 1955, 569. Structural stucies Newoiny et ut. sbid 1958, 865. Coll, Ceocl. Chuan, Cumann. 25, 1492 (1960) Vokue of al, Petrahedron Leuers 1962, 3855 Strocture J. Beaultarre otal, thud, 21, 3191 9x0). ne ¥ " oy, oy Very bitter orange needles from abs ether, mp 179-180" (ed = Solvated crystals from benzene. decump 165° felt! HIROUr (= 1.9 in CHOL). Bitterness tiireshoid 170,00 8. Absinthium, Wormseud: Abunthe Armore Ded leaves andl Mnwerng tops of.Arremusic absintirawmh Componter, Habit Grows rape, US, Cubads, North o Used ny stomuchic trl and anthelmintic thn anatsinthin, dark green or brown volatile © thigane), EC. Guenther, The Ewentual Oits, V, 487 (sie Notion, New York 1952} Isaluiwe of voriius va vols Geka. Herout, Coff Caveh Chem Commun. 956%, Meru ef gf, roid. 4X8 Chureterzauioy of oT Sacco. F Chiatvn, Plame Med 54,91 (1988) Very irons aur, aerd tante Ast As Tinvonng. an sleohol: beverges. eg vermmuth, sehich #0 blewd of white wares, conIg srnees of abstr, nd other flavers. Ceadron” Ingestion af th volatile cil oF of Siqueur. abet Hess, slupar. centva 9, Acacetin. Sr rere genin4’-merhyl ether Cyl Og mat wi 78d 26 C Ohh HL a 20e OF TILIA MEME glycan, of marin, gv and of acacun soln from liaunn Zenplén, Hogar, Ber Jam, XIE C41) Front aceciin Huhori Acta Phycokin 2,105 (1925) soln from Robaila prysutozcaeia L, Legg fonge Nakazawa, Matspea, J. Pharm Sor Sopon 73, 4X1 (195) Steuamre Baker ef at, L Chart, Sic 1954, 601 Robmacn, Venkatarinmn. chi 1926, 244%, Hogar, Aer 76B, 452 (1943), Nurasamhachars, Sexhudn. Proc Indian Acad. Sel 30A, 131 (194). Sinupscn, Sik Proc Roy, Dublin Soe. 27, 111 (9860, C4 SH, Wiis 957) on ¥atlaw wescles from 9% Moab mp 26% Sol an be practically imal ir ether. Sal in alkalice wich yellow c Diacceme, CHC; lustewus ncedles eam at, mp 207 7-Rhamnogiowle. Cyl gy, acaciin, From Robinia Prudururia t Legvonmosae. “Tetaxlunberp, Hurinionn, Arn 587, 20711953) Sinuctule Zempten, Mester, Maxvur Kena Consult the cow index bafare using, this section. Folyourat 6, 2 (195). © 4. 45, 7O77L ULSI) Newelhes frome pyndine | wuler, mp 268 [a] — 8S ¥ apyridinel; 99 (cial scene nad) Sparmgly suloble ut eal, mere sol in boakung water: slightly sol in orgerac sclventy, 10, Acacia, range: 136 (1539), Corny Res 3, 308 467) “According 1e the ENP. acacia e the dred Burry exudation from the stores and branches of Aeuca Senegal (1) Volld « Lexuer scr Ayan species of Acum According to © 1 Free Wieser Sols Guins (New Vork, 1987) Kerdolune pura (hishsb gencins), the gum from Acacia verck Call # Perr feean poate the Kordofan proce (Soden? is conmdcred the bes! commercil winety. Tirade af Kotaku geen whieh ore Hout, wine Gum blercltec) inet tauelest ue preferred for food pri pm nl phurmacectwals (There 0 alos eur ship berwcen color and Meor duc ty the pescuce thine) Acacus was originally thought to be empesed © Facabinose, (1) -ealachoss, © D-tlumamoss. C7 )-slyau~ rome et). Revised c@mposatton Ul s€eticiulal SuLtoS Anderun #8 aft Chem Sac (C) 1966, 1950 Sew Sweuson er ot Potvin Sct Part 4-26, 1593 (1968). Gen cral review Anderson Dea. J Suc Cosmet Chem 22, 61- TOAISTY Review nf uve ax ford abi: DOM W An sextet, Fond Adllt Cenitm 3, 725-24 (1996 Gccamrs ir xplweunlal iets up 16 32 resin dumseter Aino Rakes ind powder olny a pn fram Acacia veruh ure Ievorotatory. other acacia species are deatror Hamy. Fudd. Sex. Phureurgh, 354 521 QU28) Sywealec exavily 1.33 TAY tsamples dried ul TU are heavsce) Massie ut usually vines From 11218) USP. lima 13 Matural Containing Less aban 12) chips canlly nnd peoduces dual luring transportation. Insol in alcohol. Almost completely Sol i toner ts es 10 ram sate sila outuuey 37 Bat 29 Scr 40 ae SO" tay Tham Kam "atu Sar 82,29 (1020) Ag sain mal wor, Also sol an xlyceral ine an propylere glyco but pro= Tonge heating (severa} days) may be necessary for complete solutiwn Gabou! 9) Ineornpat Pccapuiater or yellnes resalt ups ude a soln of ferne silts, borax. base lead wee Mead subs tate, but net pevteal lead ueetate. kaha, sedbue sibeu Selalin, ainmomiated wneture of snioKRe Use As mmucilage, racaaeit ine tublets, nats musi shuckewer, afra nt cau, thee Hood, os colle In the munufietmre al spray dried “hee” Muvcrs powdered flavors used in packaged dry min products (y things. slewserts. cake muxes? where favor smbillty and Jone Stell hfe ore mpertnt Ti, Aescle Auld, iste. 2113-Frironvseun enczheie ack aifty Tool wi AK OR CC TRTE H Sao fostire fel Hom rece of eae conctnna DC Legurnnnsee | Vershiney, Shalwoein, Terrebedron Letters 3. frat bork wf A rommrs DOR tank § K. Nigam, J dnd Chew Soc ST, 1044 (19K0) _‘Sicuctore atid nlerecclaumstiy Varsbey et af, bid 0965, 1187 Re- weed steuure: A. K Frun of af,” frum. Din Res. Ens), Cotourta 39, 61 (1928), CA B7, 84h C1977 Gum Arabic. Needles from methanol mp 280-21" Methyl estas. CyyHyO,, needles from methan ne ‘Dutvatyt lucwre, mp 222 HHO, ceystate, mp 295-2806 Page 312 Acarbose 12, Acarbose, 0-4,6-Dideory-defff1S-(1a,f0,58,60)}> 4,5, 6rihydroxy-3-(hydroxpmeth yi)-2-cycToherened-ytfami> noj-a-D-glucopyranosyi-(? =4}-O--D-glucopyranosyl {4-0 glucose: Hay-g-5421; Glucobay. CH gO: mol Wt 645.63. C 46.51%, H 6.71%, N 2.17%, O 44.61%. Pou doterrasaccharide containing am unsaturated cyctitol moiety. An a-slucosidase inhibitor that reduces suger absorption in the gastrointestinal tract. Isoin from strains of Aetinaplanes: W. Frommer et ai, Ger. pat. 2,347,782; eidem, U.S, pat. 4,062,980 (1975, 197 both (0 Bayer}, Total synthesis: S. ‘Ogawa, ¥. Shibata, Chem. Commun. 4988, 605. Biosynthe- fic studies: U, Degwert er af, J. Antibiot. 40, 855 987). Giucosidase inhibition studies: "DD, Schmidt et af, Naewr wiss. $4, 535 (1977); W. Puls et af. ibid 536. Use in treat ment of diabetic aduits: D, Sailor, G. Roder, Arcneimittel- Forsch, 30, 2182 (1980), H. Laube et ef, ibid. 1134. Long- term study in sutfonyturea-treated diabetics: H. Vierhapper et al, Diabecolegia 2, 586 (1981), Potential use in prophy fans of dental caries.” N. E. Fichn, D. Moe, Seand. J. Der Res, ®, 124 (1982). Review of pharmacodynamics, phar- macokinetics and therapeutic potential: S. P. Clissold, C. Edwards, Drugs 35, 214-243 (1988). Iolif +165 (waren) AWERAP ca Antidia 13, Acebutolol, N-{3-Acetyl4-2-hydrexy-3-Il- methylethylaminolproporyiphensloutanaraide: 3'-ace! 4 -{2-hydroxy-3-cisopropylaminoypropoxypburyraniide; 1 Gonecety| 300" THERA? car. Durreve; curdkotonic; breachoaitator ‘19. Acetylling Pipererine. #,2,3,6-Tetrahydro-t 3-di- amethyl-2,6-dioxo-7#-purine-7-acetic ecid compd with piper- ‘azine; acepiiviline, Piperazine theophylhne-7-ovetate, 7 Meophythneacatic acd piperazme salt, piperazine theophyl fine enfunoate, Dynaphylline. Eimphyuet, Etaphylline: Eta Filine; Fuophylate. CjsHagN,O¢ mol wi 324.34 C 48.14%. H 6.22%, N 259%, © 19 73% Us ined mixture of the I] and 2-1 salts which contains 73-24% theophyllme acetic aid and 22-25% anhydrous piperazine, Active melsbohte ts scelyiline, g» Prepon Bamse. Bull Soc Chim. France 1088, 769° Pharmecchanerior J-Zuwdema, F. WH Merkus, Pharm. Weckbl 113, 605 (1978), § Sved et ab, Biopharm. Drug Dépos 2, 177 (1981). HPLC deter an serum: 7. Zuideraa, F.W. H. Merkus, J. Chromatog. 143, 489 (1978). GC dete un ering: I Zeideme, He Hilbert 182,405 15 C0008 OO |-Q a, nal or? ‘aegap cat Bronchodilator 20, Aceglatone, D-Glucarie acid di-y-tactone dace rate, 2,5-d1-O-acetyl-p-ghicaro-1,66,5-dilactone, 2,3-ci-O- acetyl -D-glucosscchara -1,4:6,3-dilactone; Acegleton. Ghi- caron jgO MO! wt 258.19. C 46.52%, H 3.90% © 49.58%. Prepn and structure Hirasaka, Umemoto, Chem. Pharm. Bull. 13, 325 (1965). CA 63, 3024h (1965); Ishudate et ol, Japan, pat. 24,956; 67) (1967 10 Tokyo Biochem. Res. Com), CA 68, 78558 (1968). Pharmacological studies: ida ef of, Japan. J Phormacol. 15, 88 (1965), CA 63, 59613 See Ree ait chem ata! sere. sce 0) 15 1971 ‘White, odorless ana tasteless erysialline powder, mp 185- 186° (Hurasaka): from 2-1 ethanol-etbyl acetate 192° (dec) Gopan Med. Gor} Solin dimnetbylformaiude, speringly sot ip acetone. sghtly so) in dioxane. methanol’ and ethanol Practically unsol an water. LDg ami mice, rats (g/ka > 20, Consult the evoss index before using this section > Worally, +20, > 10 s.c., 580-6 35. 6.10-6.15 ip Jopon. Med. Gaz}. THERAP CAT: Antineoplaanc 2A. Aceglutumide.N2—Acetyft-pfutamine: «-Nesce~ tyl-Lglotamme: Acuti-S. GHyNjOp mol wr TRE IB. C 44 68%, H 6.42%, N 1488, O SCI Prep. PB Karrer gt al, Hels, Chur. Acta 9, 301 (1926). Brit, pot 792,576 {41958 to Merck & Co}. CA, 53, 2405a (1959), 1. 1. Masch- fer, No Lach Bioctim, Biophys Avia ST, 252 (192) Stabibty study G. Sckules. G. Guadagnimi. Furmaco Ed Prat, 21, 22 (1965) NMR study. W. Voclier et cl. Z, Ne- tufarsch. B 26, 213 (1971), Fermentunion siady T Naka- sushi, J. Ferment. Technol. 56, 573 (1978) oof the alumioum complex: T Kagana ef af, Ger. pat 2827176 ccorresp to US, par_ 3,787,466 (1971. 1974 both to Kyowa) Physico-chematal properties E. Hayakawa et af, Yakuguku Zashi 97, 7M (1977), CA. B7, 141198 (ISTP) Effect on exptl chrom gasinc ulcer: H_ Tanskn et al, Oyo Yakuri 7, 1035 (1973), CA, 81, 33283v (1974) Cytoprotecwve effect H Tanaka. Arsneimiuel-Forsch 36, 1483 (580) nrcoch, Coastal from ethanchs mp 197 [al8f 12.5" = 2940 water) Alumimim contpler, Cys Al Ng Oz. pentakas (2aceiy!- Loglutaninorotetrabydroxyiriehiminam, acegtutarade al minum. KW-110, Glumal, Winte powder. mp 221° (dec) Solin water. Practically iso] in methunol, cthanel, acetone LD in mole mice, rots @/kg) 14.3, > 16 5 orally. 5.0. 4.2 ip 046, 0.40 Lv (Kagawa). THERAP ca Free acid as nootropic: alumunum complex as ane f-44-Chlorobenzoy}-Somethory-2- mathyliHeindole-3-acetle acid carboxymethyl ester: [TIA chlorobenzoyl)-$-methoxy-2-methylindot3-yljacetony]- acetic ecid. TV 1322. Accmmx, Rantudit, Rheuribis. Cy- HyCINO,, mo! wi 415 83 € 606% H 436%, C18 537, N 3.57%, 023006 Der of indomethacin, g.v. Prepn. KH Boltze er al, Ger. pat 2,234,681 cxsresp to US, pat 3,910,- 952 (1972, i975 both 10 Troponwerke). Series of nrticles an chemistry, analysts, pharmacodynamms, roxicology and clinical tials) Arzseunittel-Forsch. 40, 1313-1468 (1950) Toxicity asta: H. Jaco, H-D. Del, ibid 1398. Very fine pole yellow crystals from per ether. mp 150 133 LD,g tn male, female mice, mule, female rats (mg/kg). 555, 1843, 242, 30.1 arally; 34.1, SUL, 381. 28 Suv. Uae cobr, Dell) THERAP CAT: Anti-anflammatory 23, Acenaphthene, 1,2-Dihydroacenaphihiytene: peri ethylencnaphihalene: 1.8-cihylenenaphihalene | Cyflyg. m0) wr 154.21 € 9346, H 654% Occurs an coal tar ixoln Ges f Teerverwertung, Ger, pot 277110; Chern Zeutr 1914, 11, 597 In peiroleum residues. Orloff et af, CA 34, 28008 (1937). By passmg ethylene and benzene or naphilia~ Tene though a red hot tube: Berthelot. Bull. Soc. Chum. (247, 274, B. 236. 245 (IB6T). Dy heatmeg tetrahydroacenenhthene vath sulfur to BO" Braun et af. Bor $5, 1694 (1922). rom Scenaphthenime or acenaphibenequinone by bigh pressure ydrogenanion qn decaim ‘with mckel at 180-240" Braun, Bayer. Ber. 39, 921. 923 (1926. From oxime Morgan. Stanley. J Soc. Che 4968 (1925).24 Acenocoumarol Orthorhombie bipyramidal necdles from alcohol. ¢ 1.189. mp 95". bp 2797. Uv spectrum: Seaham, Proe. indian cad. Soi, A3, 148 (1938), Factors influencing the uv spectrum: Jones, J. Am. Chem. Soc, 67, 2127 (1945). Insol in water. One gram dissolves in 31 mf alcohol. 56 mi methanol, 25 ml propanol, 2,5 mi chloroform, 5 ml benzene or toluene. 3.2 & fre sol in 100 ml glacial acetic acid. Forms water -s0h, eryst complexes with desoxyeholte acid, containing two molecules of the bile acid 5 a role. The complexes crystallize when concentrated solns of the proper amount of the componcals in atcohot or dioxane aré allowed to cool slowly. User Dye intermediate: manuf plastics: wnssctcidet fungi- side 24, Acenocoumarol. 4-Hydroxy-3-{1-(4-nitrophenyl)> S-oxoburyH-2H-T-bensopyran-2-oue; Pla -acetonylep-titro- bonztl}-s-hydroxyeoumarin: 3-4 athyl)-4-hydroxycoumarin; acenocoumarh G-23580; Sinthrome: Sintrom. CygHygNOg nial wi 353.32, © 64.58%, H 428%, N 3.96%, O 217% Prepn: Stoll, itvan. U.S. pat. 648,682 (1953 to Geigy). Pharmacology: Jindal, Shab, Arzneimittel-Forsch. 16, 878 (1966). 9. Crystals, mp 196-199", Almost insol in water or organic solvents. Forms water sol salt with alkalies, LDgy in mice: 114.7 mg/kg ip. THERAP CAT: Anticoagulant, 25, Aceperone. N-{{t-{4-(4-Fluorophenyl)-4-oxobut- y1]-4-phen yi-4-piperidiny!Imetnyjacetarnide: N-{f1-13-(p- fluorobenzoyi)propyil-4-phenyl-4-piperidylimethy }acce- ‘araide; | -(p-fluorapheny!) 4.(.phen yl -d-acetamidometh- sipiperidino)-Febutanone: 1-Ly-(4sfluorobanzoypropyl] ad acetamidomethyl -4-phenylpiperidines N-[1-13-(p-flaore- benzoyl) propyl] -4-phenylpiperidin-4-vimethylJacetarnides 4’ Shioro-4-(4 -acetamigomethy]-4-phenytpiperidodbutyro- phenone; acctabutone: acetobuton, R 3248. C,HyFN.O,; nol wt 396.5}. C72.70% H 7.39% F 479%, MTom, O 8.08%, Prepd by reacting /-chloro-4-fluorobutyrophenione with 4-acetamidomethyl-4-phenylpiperidine: P. A. J. Jans- sen, Belg. pat, 606,849 (1961), corresp to U.S. pat. 3,083,205 0361, 1963 both to Janssen}. Crystal structure: N. Van Opdenbosch et al, Acta Crysiallogr. 3B, 171 (1977) ° \ clase —or, \ A ate ‘Crystals, mp 97-100", 26. Acephate, Acciy!phosphoramidothivie acid O,Sedi- methyl ester: Ortho 12420; Orthene. C,H yNO;PS: mol wt 183.16. C 26.23%, H. 5.50% N 7.65%, © 26.21% P 16.91% S'17.50% Prepn and activity: Magee, U.S. pats, 3,716,600 and 3,845,172 (1973, 1974, both to Chevron). Co ona ‘scr, s Page 6 ‘White solid, mp 64-68" (impure). Very sol in water; mod rately sol in acetone, alc. Low soly a aromatic solvents LDy orally in rats: 700 mg/kg, Magee, loc. cit. (#973) use. Contact and systemic insecticide. 27, Acepromazine, 1-[10.[3-(Dimethstamino)propyl} 10H-phenothiazin.2aylfethanone; 10-{3-(dimethylamino). propyllphenoihiazin-2-yt methy! ketone: 2-acctyt-10-(3-di- methylaminopropylphenothiazine, 3-acety] -10-(3-dimeth- ylaminopropy)iphenothiazine; 10-(3-dimethylaminopropy!)- phenothiazine -3-eihylone; acelazine: acetopromazine: acet- yipromazine; 1522CB; Vetranquil, CyHN,OS; mol wt 326.47. C 69.90% H 6.7%, N 858%, O 4.90%, S 9.82% Prepni Schmoitt ef ab, Bull, Soo Chim. France 1967, 938. Hae HeHNE yg Coo 8 Orange-colored oil, bpys 220-240". ~, Maleate, CaHgN,O,S. dtravet, Plegicil, Notensit, Soprort- tin, Yetlow crystals from ethyl acetate, mp 135-136. Sol in water. pH of 0.1% ag soin 3.2, LDyy in rats (caled as free base): 130 mg/kg orally; 70 mgfkg tv. THERAP CAT ETI: Tranquilizer. 28, Acerin, An oxtract from the dried fruit of the Norway maple Acer planianoides L., Acensceae. Freshly prepd solutions of acerin destroy F. cati and vaccinia virus in 5 min but are fess effective on the Staphylococcus Twort Virus. Phagicidal action also exists even in the presence of the host cells. Extraction and properties: G. Fischer, Acta Pathol. Microbiol. Scand. 34, 433 (1982); 34, 482 (1954), Fischer et al, Experientia 10, 329 (1954), sally insol in methancl, ethanol, ether, acetone falyze through a cellophane membrane at room, temp But passes through a Seitz filter. Sodium chloride pre- cipitates the active principle ia acerin preparations ae does also normal serum With 1:800 soins of acerin. Strong acerin Preparations acquire reddish-brown color after treaement with alkali and oxidation in air. In generat, the substance behaves similarly to vegetable tannins. It is practically nontoxic 10 rabbits and mice when administered 5.c. 28. Acerala, The tipe {cuit of Malpighia punicifotia 1. ‘Habis Malpighiaceae, also called West Indian Cherry. Contrat America, Puerto Rico. Probably the rich source of ascorbic acid. Analysis of pitted Mui 92.28%, ascorbic acid 1690 mg/100 g: vitamin A 11.0 mg/100 g niacin 407 7/100 g vitamin By 3. Uhlamine-HCI 30.0 %/100 g: fluorine 10/100 g carboby. drates 6.4%, pH of juice 3.3, THe pits comprise 19-25% of the fruit. Ref Derse, Elvehjem, J dim. Med. Assoc 156, #8011930)" Comrocreal aspect: Jr Foe Chem. 2 1155 (1954), Review: Moscoso, Econ. Bor 10, 280 (1956) Method of prepering acerola juice concentrates: Morse, U,S, pats. 3:012942-3 (196] to Nuunlte Products). TTHERAP cat: Nuteient 30. Acesulfame. 6-Meshyl-t,2,3-oxathiazin-4(3H)- one 2,2-dioxide: 6-methy\~J4-dihydro-1.2,3-oxathiezin-@- one 2.3-diorides acetosullam. C,HyNO,S: mol wt 163.15. C 29.48%, HL 3.09%, N 8.59%, O' 38.23%, § 19.63%. Non aurtitive artificial sweetener. K. Clauss, H. Jensen, Ger. pat, 2,001,017; eidem, U.S, pat. 3,689,486 (1971. 1972 to Hochst); K. Clauss et ol, Z. Lebensm.-Uniers. Forsch. 162, 37 (1976), Crystal structure: E. F, Paulus, Acta Crys. tallogr. B31, 1191 (1975). HPLC analysis: H. Grosspietsch, H. Hachenberg, Z Lebensm Unters: Forsch, 171, 41 (1980). H,¢. a ( yo ‘Needles from benzene or chloroform. mp 123-123.5", Consutt the cross index before using this section.