THE
`
`MERCK INDEX
`
`AN ENCYCLOPEDIA OF
`
`CHEMICALS, DRUGS, AND BIOLOGICALS
`
`1v5i'!f‘4".:
`
`FOURTEENTH EDITION
`
`
`
`
`
`.»_-.¢........:-4.~
`
`EDITION
`
`Maryadele J. O’Neil, Editor
`
`Patricia E. Heckelman, Senior Associate Editor
`
`Cherie B. Koch, Associate Editor
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`Kristin J. Roman, Assistant Editor
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`Catherine M. Kenny, Editorial Assistant
`Maryann R. D’Arecca, Administrative Associate
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`Published by
`Merck Research Laboratories
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`Division of
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`MERCK & CO., INC.
`Whitehouse Station, NJ, USA
`
`2006
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`Exhibit 1009A
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`Library of Congress Catalog Card Number 89-6000]
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`ISBN Number O~9l 1910-00-X
`ISBN Number 978-0-9} l9l()-()0-l
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`Copyright © 2006 by MERCK & CO. lNC.. Whitehousc Station. NJ. USA
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`Printed III the USA
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`

`
`6033
`
`Methyl Butyl Ketone
`dar. Ber. 93, 1129 (1960). Toxicity data: Smyth, J. Ind. Hyg.
`224°C. Soly in water: 4.8 g/100 g. Soly of water in methyl I-butyl
`Tr).rir'nl. 23. 259 (1941); Werner. ibid. 25. 157 (1943). Series of
`ether: 1.5 g/100 g. Unstable in acid soln. Volatile: lipophilic.
`articles on toxicology: Environ. Hculrll Pc-r.t-pecr. 57, 1-275 (1984).
`Flammable. LC” in mice (15 min): 1.6 mmol/liter of atmosphere
`(Marsh).
`Liquid. Pai.muou:.I bpm 124.43% bpm 34-41°. di" 0.9663.
`Cumiorl: Potential symptoms of overexposure by inhallation are
`Flash pt 11S"F.
`72%,” 1.4028. Miscible with water. alcohol ether.
`coughing. burning sensation in nose and throat. headache. nausea.
`glycerol. acetone. dimethylfomtamide. LD5" in rats. guinea pigs
`vomiting. dizziness. feeling of spaciness and disorientation (PB97—
`(mg/kg): 2460. 950 orally (Smyth). LC50 (7 hr in air) in mice: 4.6
`121016).
`mg/l (Wemer).
`USE: Octane booster in gasoline. Chromatographic eluent esp in
`Caurirm: Potential symptoms of overexposure are irritation of
`HPLC.
`eyes. nose. throat: headache. drowsiness. weakness: ataxia. tremor.
`THER AP (TAT: Cholclitholytic agent.
`somnolence: anemic pallor. See NIOSH Pocket Guide In Chemical
`Hazards (DHHS/NIOSH 97-140. 1997) p 202. Exerts principle
`toxic effects on brain. blood. kidneys. thymus. testes. Appreciubly
`toxic when inhaled. Absorbed through skin; direct contact may
`cause skin irritation. Embryotoxic and teratogenic in exptl animals.
`See Party's ll1£lll.\‘ll‘l¢ll l'l_V_t{l£’Il(’ and Tn.t'iroIog_v vol. 21), G. D. Clay-
`ton. F. E. Clayton. Eds. (Wiley-lntcrscicnuc, New York, 4th ed..
`1994) pp 2764-2776.
`USE: Solvent for low—viscosity cellulose acetate. natural resins.
`some synthetic resins and some alcohol-soluble dyes: in dyeing
`leather. sealing rnoistureproof cellophane: in nail polishes. quick-
`drying varnishes and enamels. wood stains.
`in modified Karl
`Fischer reagent: Peters. Jungnickel. Anal. Chem. 27. 450 ( 1955).
`
`[591-78-6] 2-Hexanonc. C..-
`6033. Methyl Butyl Ketone.
`H.30:mo1 wt 100.16. C 71.95%. H 12.08%. 0 15.97%. CH_,CO-
`C4 Hg. Toxicity study: H. F. Smyth (‘I al.. Arch. Ind. Hyg. Ocrup.
`Med. 10. 61 (1954). Review of toxicology: P. M. .1. Bos er al.. Am.
`J. Incl. Mal. 20. 175-194 (1991 ); and human exposure: 7'o.rimIog-
`iral Profilrijur 2-H0.\'unum- (P893-1 10773. 1992) 1 16 pp.
`Colorless liquid.
`:1 l).t<l3(l. bp 127°. Slightly soluble in water;
`sol in alcohol. ether. LD.,,, orally in rats: 2.59 g/kg (Smyth).
`Camiml: Potential symptoms 01' overexposure are irritation of
`eyes and nose; peripheral neuropathy; weakness. paresthesia: der-
`matitis; headache: drowsiness. Sec NIOSH Parke! Guide to CItem-
`it'ulHu:urd.\‘(DHHS/NIOSH 97-140. 1997) p 164.
`
`[115-19-5] 2—Hydroxy-2-
`2-Methyl-3-butyn-2-01.
`6034.
`methyl-3-butyne. C,,H,.O; mol wt 84.12. C 71.39%. H 9.59%. O
`19.02%. Toxicity data: W. Kcil ('1 ul.. Arzmrim.-For.rch. 4, 477
`(1954): K. Sochring vi ul.,il7i1l.5. 161 (1955).
`CH;
`
`Hac/)\\\
`
`HO
`
`CH
`
`Liquid. u§:; (l.x(i72. 7.24 lbs/gal. mp 2.6“. bpm, 104-105°;
`bpm, 52°: bp,. 20°. Flush pl 77°F (25°c). nf," 1.4211. Surface
`tension at 25° 2 23.8 dynes/cm: 5% av.) soln = 41.7 dynes/cm.
`Miscible with water. acetone. benzene. carbon tetrachloride. Cello-
`solvc. cyclohexanone. diethylene glycol. ethyl acetate. kerosine.
`ntethyl ethyl ketone. mineral spirits, monnethanolamine. neatsfoot
`oil. petr ether. soybean oil. Stoddard solvent. Azenlrope with water.
`bp 90.7“. contains 28.4% H30.
`l.D5,, in mice (mg/kg): 1800 orally
`(1(eil):23-40 s.c. (Sochring).
`
`I623-42-7] Butanoic acid methyl
`6035. Methyl Butyrate.
`ester. C,H,,,O3; mol wt 102.13. C 58.80%, H 9.87%. O 31.33%.
`CH3(CH3)3COOCH3.
`Colorless liquid.
`:13" 0.898. mp about -95“. bp 102“. Flash pt
`14°C. nf,” 1.3879. Sol in about 60 parts water: miscible with
`alcohol. ether.
`USE: Manufztnilicial rum and fruit essences.
`
`|598-55-0| Urethylane; methyl-
`6036. Methyl Carbamate.
`urelhane. CZH_,NO3; mol wt 75.07. C 32.00%. H 6.71%. N
`18.66%. 0 42.63%. H3 NC()OCH_.. Prcpn from silver or mercu-
`ricyanate with H_,S and methanol: Birkenbach, Kolb. Ber. 68, 901
`(1935). From urea and methanol: DE 753127 (1940 to LG. Far-
`benind.).
`white crystals. mp 52-54”. bp 177°. Freely sublimes even at
`room temp. Freely sol in water. alcohol.
`
`[111-77-3] 2—(2—Mcthoxyeth-
`6037. Methyl Carbitol®.
`oxylcthanol; dicthylcnc glycol monomethyl ether; methyl digol.
`C5H,3O_.: mol wt 120.15. C4998‘/(.. H 10.07%. 0 39.95%. CH,-
`OCH;.CH3OCHzCH3OH. Toxicity data: Smyth er 111., .l. Ind. Hyg.
`T().\'l(‘()l. 23, 259 (1941).
`n,~’,7 1.4264. Flash pl.
`Liquid.
`:13“ 1.035. mp < -84°. bp 193“.
`open cup: 2()0°F (93"C). Miscible with water. ale. glycerol. ether.
`acetone, DMF. LD50 orally in rats: 9.21 g/kg (Smyth).
`USE: Used in the same way as 2-ethoxyethanol where a solvent
`with 11 higher boiling point is required.
`
`(110-49-6] 2-Mcth-
`6039. Methyl Cellosolve® Acetate.
`oxyethanol acetate; ethylene glycol monomethyl ether acetate. C5-
`H”,O3: mol wt 118.13. C 50.84%. H 8.53%. O 40.63%. CH.-
`OCH2CH2OOCcH1- Toxicity data: H. F. Slrlyth et u/.. .l. Ind.
`Hyg. To.\'ir‘nl. 23. 259 (1941). Series of articles on toxicology:
`Environ. Health Pe'r.vper‘l. 57, 1-275 ( 1984).
`77.3,"
`Colorless liquid. dill 1.0067. bp 145°. mp -65. 1°.
`1.4019. Miscible with water. most organic solvents. oils: dissolves
`gums. resins. LD50 orally in rats: 3.4 g/kg (Slnyth).
`Cauliull: Potential symptoms of overexposure are kidney dam-
`age; brain damage. Direct contact may cause eye. nose and throat
`irritation. See NIOSH Parke] Guide to Cherrrirul Huzard.\' (DHHS/-
`NIOSH 97-140. 1997) p 202. See also PuII_v'.t‘ lmllmrrial Hygl(’I1('
`and ‘l‘u.t-it-rilugy vol. 2D, G. D. Clayton. F. E. Clayton. Eds. (Wiley-
`lnlcrscience. New York. 4th ed.. 1994) pp 2918-2921.
`Usl-.':
`lndtlstrial solvent.
`
`[9004-67-51 Cellulose methyl ether;
`6040. Methylcellulose.
`Methocel A; Bcnecel M: Cclcvac: Cellucon; Citrucelz Cologelz
`Tcarisol: Tylose M. Cellulose obtained from librous plant material
`and partially ethcritied with methyl groups. Prepd from cellulose
`fibers heated with caustic solution and treated with methyl chloride.
`Commercial methylccllulosc has (1 mcthoxyl content of 25-33%
`(degree of substitution 1.5 to 2.0). Review ofprepns and properties:
`Olt. C('lluln.\‘e and Celllrlme [)(‘I'l1'llIl\'(’.\' (Wiley-lntcrscience. New
`York. 2nd ed.. 1954/55): 0. K. Gremingcr. A. B. Savage. in Inclus-
`trial Gums. R. L. Whistler. Ed. (Academic Press. New York. 2nd ed..
`1973) pp 619-647. Clinical efficacy as laxative: J. W. Hamilton (-1
`al., Dig. Dis. Sci. 33. 993 (1988). Evaluation in lcns implantation
`surgery:
`.1. R. Rojas er ul._Anr1. Opllrllalmul. 21. 389 (1989).
`Review of production and uses in the food industry: P. de Muriseal.
`D. A‘. Bell in Handbook ofFuI R(’pl0('('l‘.t. S. Roller. S. A. Jones. Eds.
`(CRC Press. Boca Raton FL, 1996) pp 145- 159.
`White granules. Odorless. tasteless. $01 in cold water.
`lnsol in
`hot water. All at; soln is best prepd by dispersing the granules in hot
`(but not boiling) water with stirring and chilling to +5“. The soln is
`then stable at room temp. Presence of inorganic salts increases the
`viscosity. The soly is dependent upon degree of substitution. Clear
`films may be cast from aq soln.
`USE: As a substitute for water-soluble gums; to render paper
`greaseproof. in adhesives. as thickening agent in cosmetics. as
`protective colloid in emulsions. as binder and stabilizer in foods.
`As fat replaeer in the lormulatioll of dietetic foods. Phamluceulic
`aid (suspending agent).
`‘I'll!-LRAP CAT: Laxative: ocular lubricant.
`T1tlF.RAP(‘/\T(Vt£T)I Laxative.
`
`"()5y
`
`ll09—xri—4i 2-Mcthoxyethanol;
`6038. Methyl Cellosolve°9.
`ethylene glycol monomethyl ether. C-.H,.O3: mol wt 76.09. C
`47.35%. H 10.60%. 0 42.05%. HOCH3CH:.OCH3. Prepn from
`ethylene oxide -1- methanol: Finch. Hztgcmeycr. US 2748171 (1956
`to Kodak): from ethylene glycol + diazomcthane: Hesse. Majum—
`
`(74-E7-3| Chlorometltanc; Freon
`6041. Methyl Chloride.
`40. CH,Cl:mo1 wt 50.49. C 23.79%, H 5.99%. Cl 70.22%.
`Known as early as 1835. large scale production started in 1920's.
`Review of mfg processes: Faith, Kr'_vz'.s‘ 6’: Clark's lIl(lll.VIrllll Chem-
`icals. F. A. Lowcnhcim. M. K. Moran, Eds. (Wiley-lnterscience,
`
`Page 1042
`
`Consult the Name Index before using this section.
`
`New York. 4th ed.. 1975) pp 5
`R. Cronn. D. E. Harsch. Anal. 1
`study: D. W. Lindle er al.. Ph_
`T. Holbrook in Kirk-Otllm
`nology vol. 5 (Wiley-lntersci
`1028-1040. Review of toxic
`Crit. Rev. 'l'u.\‘i¢'nl. 6, 283-302
`irolugiral Profllefor Cl1ll)l'UDl(
`Colorless gas of mild odor at
`mp —97.7°: bp -23.7“: no (lit
`water; misc with chloroform. I
`hol. Soly at 20° (ml/100 ml):
`3756; glacial acetic acid 3679:
`0.48.
`Caution: Potential symptt
`nausea and vomiting: visual die
`convulsions. coma: liver and k
`atogenie effects: direct contsl
`Potential occupational CtII’Cl1’|
`Chemical Iluzanls (DHHS/N1
`Patty's Imlllxrrial H_t'gl'¢-nr and
`E. Clayton. Eds. (Wiley-lnters
`34363442.
`USE: Manufof silicones. l(
`butyl rubber. Has been used as
`6042. Methyl Chloroat:
`methyl ester. C_~,H5C1O3C mol
`32.67%. 0 29.49%. CH3C1CC
`Colorless liquid. d;‘,; 1.238
`water: miscible with alcohol. e"
`USE: As solvent.
`
`6043. Methyl Chloroca
`dic acid methyl ester: methyl
`94.50. C 25.42%. H 3.20%.‘
`Made from phosgene and mcth
`Clear liquid. oi" 1.223.
`gradually dec by it; miscible
`ether.
`Crmriml: Vapors strongly ir
`6044.
`3-Methylcholant
`methylbcnzljIaceanlhrylcne: Z
`MC. C,,H,(,; mol wt 268.3.‘
`oxycholic acid: Wicland. Sci‘.
`(1925): Wicland. Wiedcrshei
`Dane. ibid. ZI9. 240 (1933).
`l
`J. Chem. Sol". 1934, 428: Fic:
`2482 (1936): rf. Bachmann.J
`cholanthrene has been produc
`radation of cholesterol deriva
`lich, Angrw. Chem. 70. 190 (l
`Org. Chem. 46. 3429 (1981):
`heclran Len. 22., 1093 (I981).
`t‘£ll'l)()I1.\‘ Vol. I & 2 (Acaclemit
`
`Pale yellow. slender prisms
`up... 230°; <13" 1.28. Absorpt
`Am. Cll(’Il1. Sm‘. 60, 940 (193
`slightly sol in amyl alcohol.
`ll
`USE: Exptlly in cancer reset
`6045. Methylcobalam
`methyl deriv. dihydrogen pho
`5,6-dimelhyl-1-u-D-ribofuran
`dimethylbenzimidazolylcobal
`Bu: MeCbl: Algobaz; Hitoeo
`Cb3H.,,CoN,_1O,,P:mo|wt