Amerigen Ex. 1044, p. 1
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`TH E
`
`MERCK INDEX
`
`.
`
`.
`
`AN ENCYCLOPEDIA OF
`
`CHEMICALS, DRUGS, AND BIOLOGICALS
`
`
`
`
`
`ELEVENTH EDITION
`
`Susan Budavari, Editor
`Maryadele I. O’Neil, Associate Editor
`Ann Smith, Assistant Editor
`Patricia E. Heckelman, Editorial Assistant
`
`Paiaiished by '
`MERCK & CO., INC.
`HAHWAY. N.J., U.S..A.
`
`1989
`
`
`
`Amerigen Ex. 1044, p. 2
`
`

`
`Copyright ® 1939 by Merck & Co.. Inc.
`Previous Editions
`Copyright @ 1940, 1952, 1960, 1963,
`by Merck & Co., Inc.
`reserved under
`the
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`rights
`All
`conventions. Copyright under
`the Universal Copyright
`Convention.
`
`l9'r'6, 1983
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`"The Merck Index is published on a non—profit basis as a
`service to the scientific community.
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`Merck 3. co.,"Inc.
`Rahway. New Jersey, USA.
`MERCK SHARP & DOHME
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`lst Editiun—lBB9
`2nd Edition—~l396
`3rd Edition—19{)’i'
`4th Edition—l93O
`5th Edition——l94O
`6th Edition—1952
`7th" Edition~—l960
`Bth Edition—l968
`9th Edition—197r'6
`10th Edition/1933
`11th Edition—19B9
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`Library of Congress Catalog
`Card Number 89-6000!
`ISBN Number 91 l9l0~2B—X
`
`Printed in the U.S.A
`First Printing—November 1989
`Second Printing——February 1990
`Third PI'II]I.'.II]g4e]3tCI'.I1. ber 1991
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`Amerigen Ex. 1044, p. 3
`Amerigen Ex. 1044, p. 3
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`

`
`613
`
`Amphecloral
`
`at-M'ethyt-N«(2,2,2-»trichioroeth_yii~
`613. Amphettlural.
`(fem!) hen zeneethariamine; 0: -methyl -N—(2,2.2 —trich1or0ethyli—
`dene)P1'Ienethy1amine; N—{2—(1~phenylpropyll]—2,2,2 -triclllo —
`methylidenimine; amfecloi-a.1; Acutran. C,,H,,Cl3N; mol wt
`264.60. C 49.93%. H 4.57%. C140.20%. N 5.29%. Prepn:
`Cavallito, U.S. pat. 2,923,661 (1960 to Irwin. Neisler).
`
`pharmtzcci. 11, 1-93 (1973). Review of use and abuse; I. P_
`Morgan. Substance Abuse: Ciinicai Pmbiems and Perspec.
`tives, J. H. Lowinson. P. Ruiz. Eds. (Williams &. Wilkins,
`Baltimore. 1981) pp l6T—l34. Books: C. D. Leake, The
`Amphetamines: Their Actions and Uses (Thomas. Springfield,
`1953) 167 p; 0. I. Kalant, The Amphetamines:
`'I'o:ttI:iiy and
`Addiction
`homas, Springfield. 1966) 151 pp.
`
`‘rs
`
` *CHZCI’-'N=CHDC13
`
`<}°"=r““aFII2
`
`1.255 1.530.
`d1‘-Forim, 1:9,, '95".
`d—Fonn. {.:x],,_+49.9"i(}.3° (e = 5 in dioxane).
`‘IHERAP CAT: Anorexia.
`-
`
`l-(3-Arninopiienyth2(IHJ-pyi'idiri-
`61-1-. Amphenidone.
`one; I-(m-amirtopitenyi)-ZIIH}-pyridone; Domwal. C, H",-
`N,o; mol wt 136.21. c 70.95%, H 5.41%, N 15.05%, 0
`8.59%. Prepn: Scudi at cti., U.S. pat. 2,947,754 (1960 to
`Wallace 81: Tiernan).
`.
`
`.mlz
`
`11
`
`,0
`
`1
`
`/
`
`L135" orally in mice. rats:
`Crystals. mp 182.5-184.5“.
`1300, 3200 mgtkg, Plekss er at, Fed. Proc. 19, 390 (1960).
`THERAP cm‘: Sedative; hypnotic.
`615.
`'Amphenone B.
`3,3-Bis[4-amittopitenyi]-2-buttim
`one; amphenone; 2—oxo-3,3-bis[p-aminopheny1]butane. C“-
`H,sN,_0; mol wt 254.32. C 15.56%. H 7.13%, N 11.02%, 0
`6.29%. Prepn: Allen, Corwin. J. Am. Chem. Soc.
`'72, 11'!
`(1950); US. pat. 2,539,388 (1951).
`Structure: Bencze.
`Allen. J’. Org. Chem. 22, 352 (19511). Shows antiestrogenic
`activity in the chick oviduct test: Hertz et cti., Recent Progr.
`Horm. Res. 11, 119-147 (1955). Decreases adrenal action.
`Review.‘ Subsidia. Median 11}, 99-102 (1958).
`'
`
`n»@.:<}»«.
`
`Crystals, mp 1315-138‘.
`Dihydroehloride. CW!-I,,,Cl,N,O, crystals from ethanol,
`dec 272-275°. Soluble in water.
`Note: Formerly a pinacolone structure was assigned to
`amphenone B:
`I,2-Bisfp-urninopitenyt]-2-me£ityi—1-pro-
`pan-‘me.
`'
`use:
`In biological research.
`616. Amphetamine.
`(ill-at-Methyibenzeneethartunliue;
`cit-a-metityipitenetityiamErie; 1-phenyl-2-aminopropanei
`(phenylisopropyl)amine; fhaminopropylbenzeneg racemio
`destnty -norwephedrine; Actedron; Allodene; Adipan; Sym-
`patedrine; Psychedrine; Isomyn; Isoamyne; Mecodi-in;
`Norephedrane; Novydrine; Elastonon; Ortedrine: Phene-
`drine; Profamina; Propisaminc: Sympamine; Simpatedrin.
`C‘.,H,3N; mol wt 135.20. C 19.95%. H 9.69%. N 10.36%»
`Prepn: U.S. pats. 1,879,003 (1932); 1,921,424 (1933);
`2,015,408 (1935); Hartung, Munch. J. Am. Chem. Soc. 53.
`1875 (1931). Demonstration of stereospecific binding sites
`for (+)-3!-I-a.n1phetamine in hypothalarnic membranes and
`correlations with anorexic potency of henylethylamines: S.
`M. Paul et 111.. Science 218, 487 (1982 . Toxicity data: M.
`R. Warren, H. W. Werner. J. Ptmrmacot. Exp. Ther. 85, 119
`(1945); W. A. Behrendt. R. Deininger, Amieiminel-Forscit.
`13, 711 (1963). Series of articles on the biochemical and
`behavioral effects of amphetamines in man and animals:
`Hamil). Exp. Pharmcticoi. 45, 3-304 (l9'i'il; Hcmdbt Psycho-
`
`Mobile liquid. Amine odor. Acrid, burning taste. Vela.
`tilizes slowly at room temp.
`cl§5 0.913. bpm 200-203°; bp
`82-85“. Slightly soluble in water: sol in atc, ether; readily so
`in acids. Aq solns are alkaline to litmus.
`L135“ in rats
`180 s.c. (Warren. Werner).
`_ ongrkg):
`Sulfate, Cml-I,3N2O4S. Atentoi, Bertzedrirte, Psycitotou,
`. Simpamina.
`Crystals. Slightly bitter taste followed by a
`sensation of numbness. mp above 300” (dec). One part;
`dissolves in 8.8 parts water, 515 parts 95% alc. A soln of 1
`gt 10 ml water has a pH 5-6. LD in mice, rats (niglkg);
`24.2, 55 orally (Behrendt, Deiningelg.
`Phosphate, C.,H,6NO,,P. Actemtn, Aktedron, Monophag,
`Profetamine Phosphate, Racepiten, Raphetamine'Pi1osphm¢_
`Crystals. bitter taste. Sinters at about 150". Dec around
`300"’. More sol in water than amphetamine sulfate. Slightly
`sol in alcohol. Practically insoi in benzene, chloroform, eth.
`er. The pH of a 10% soin is about 4.6. Prepn: Goggin, I‘J_S,
`pat. 2,507,468 (1950 to Clark\&. Clark).
`d—Fonn tannatc. tartpitetamin, Synatau. Prepn: Cavallito.
`U.S. pat. 2,95l},3t19 (1960 to Irwin. Neisler and Co).
`d—Form sulfate, see Dextroampluztamine Sulfate.
`i—Form, ievampitetamiue, ievamfetamine.
`l—Fonn succinate. Cydrii.
`Note.‘ This is a controiled substance (stimulant) listed in
`198‘? .
`Ehe USS. Code of Federal Regulations. Title 21 Part 1303.12
`THEM? cA'l‘:_ CNS stimulant; anorexic.
`TH!-:11.-tr CAT (VET): CNS stimulant.
`in narcotic poisoning,
`anesthetic collapse. in depression from encephalitis.
`617. Amphetaminil.
`ct—[(1-Methyl-2-phenyIcti1yi)ami-
`nolbenzeneacetonitrite; N-(at-methylphenethyl)—2—phen3,-lgly.
`cinonitrile; ac-p11eJ1y1-at-(13 -phenylisopr0py1a.minolaceton.i-
`trile; crphenyl -c:—(1-methyl-2-phenyllethylaminoacetoni.
`trile; at-phenyi-at—N-«(I-phenylisopropy1)aminoaceton.itr1le;
`AN 1; Aponeuron. C,.,I-INN}; mol wt 250.33. C 31.56%, H
`17.25%, N 11.19%.
`Prepd by reaction of DL—fi-pheny1iso-
`propylamine with sodium cyanide and berizaldehyde or with
`at-phenyt-oi-bromoacetonitrile: Klosa. Ger. pat. 1,112,981
`(1959), CA. 56, 34-09d (I962); idem. J. Pmict. Chem. 20, 2'15
`(1963). Pharmacology: Dominok. Oelssner, Acta Bfoi. Med
`Ger. 20, 625 (1968); Beyer e: 111., Dent Apoth-Ztg. 111, 6'17.
`680 (1971). Nletabolic studies: Remherg et ai.. Amit. Toxi-
`coi. 29, 153 (1972). Chemistry: Beyrich et at. Piiorrrglzie 27,
`28 (1972); Gloeckl. Beyrich. ibfd. 95.
`-
`
`Crystals from ethanol-water, mp 85-81“.
`Hydrochloride. CHI-I,,ClN,, sinters at 100-104’. mp 13-1--
`136°.
`1'1'1eR.u- cu: Psychotropic.
`
`613. Arnphomycin. Arnfomycin; glumamycin. C“H,',-
`NHOM; mol wt 1290.46. C 33.98%, H 7.11%. N 14.11%, 0
`24.80%. Polypeptide antibiotic active against gram positive
`bacteria. Produced. by'Streptom_vces ctmus from soil collec-
`ted near Syracuse. N.Y.: B. Heinemann et at, A iibioi. u’:
`Chemother. 3, 1239 (1953). Production:
`eidem.
`.S. pat.
`3,126,317-(1964 to Bristol-Myers). Structure and identity
`with glumamycin: M. Bodanszky er at, J. Am. Chem.-She.
`95, 2352-(1973). Pharmacology and toxicity: D. E. Tisch et
`at, Antibiot. Ann. 1954-1955, 1011. Mechanism of action:
`H. Tanaka.et'ui., Biocitem. Biophys. Res. Commtm. 86, 902
`
`Page 92
`
`Commit the cross index before using this section.
`
`Amerigen Ex. 1044, p. 4
`Amerigen Ex. 1044, p. 4