The Results of a Search for A.Pinner in the CHEM4 Data Base of Dialog (Merck Index Online) Now in CHEMISTRY (CHEM) Section (CHEM4) Database DISCLAIMER: see HELP CHEM The Merck Index Online(SM)/1996S1 (c) 1996,1996 Merck & Co. Inc. S1 6 PINNER 1/L/1 DIALOG(R)File 304:The Merck Index Online(SM)/1996S1 (c) 1996,1996 Merck & Co. Inc. All rts. reserv. 09545 Monograph Name: .alpha.,.alpha.,.beta. -Trichloro-n-butyraldehyde CAS REGISTRY NUMBER: 76-36-8 MOLECULAR FORMULA: C4H5Cl3O MOLECULAR WEIGHT: 175.44 MOLECULAR COMPOSITION: C 27.38%, H 2.87%, Cl 60.62%, O 9.12% LINEAR FORMULA: CH3CHClCCl2CHO C.A. CHEMICAL NAME(s): 2,2,3-Trichlorobutanal SYNONYMS: butylchloral; anhydr butylchloral; butyrchloral; crotonchloral LITERATURE REFERENCES: Prepd by the action of chlorine on acetaldehyde: Kramer, Pinner, Ber. 3, 883 (1870); Pinner, Ann. 179, 24 (1875); on paraldehyde: idem; on crotonaldehyde after saturation with gaseous HCl: High, U.S. pat. 2,280,290 (1942); Brown, Plump, U.S. pat. 2,351,000 (1944). From crotonaldehyde and chlorine: Ropp et al., Org. Syn. coll. vol. IV, 130 (1963). See also Butylchloral Hydrate. PATENT INFORMATION: US 2280290; US 2351000 PHYSICAL DATA: Oily liquid. Pungent, disagreeable odor; d420 1.3956; bp760 164.5-165.5 degrees ; bp25 57-60 degrees. nD20 1.47554. Freely sol in water forming butylchloral hydrate; sol in alcohol forming an alcoholate; sol in ether. Polymerizes. PHYSICAL DATA: BOILING POINT: (760) 164.5-165.5 degrees; (25) 57-60 degrees REFRACTIVE INDEX: n(20/D) 1.47554 DENSITY: (20/4) 1.3956 REFERENCE KEYS PRESENT: Patent number; Prepd DATA KEYS PRESENT: Molecular weight; Patent number; Density; Boiling point; Refractive index 1/5/2 DIALOG(R)File 304:The Merck Index Online(SM)/1996S1 (c) 1996,1996 Merck & Co. Inc. All rts. reserv. 06434 Monograph Name: Nicotine CAS REGISTRY NUMBER: 54-11-5 MOLECULAR FORMULA: C10H14N2 MOLECULAR WEIGHT: 162.23 MOLECULAR COMPOSITION: C 74.03%, H 8.70%, N 17.27% C.A. CHEMICAL NAME(s): (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine SYNONYMS: 1-methyl-2-(3-pyridyl)pyrrolidine; .beta. -pyridyl-.alpha.-N-methylpyrrol idine BRAND NAME (and COMPANY): Habitrol (Ciba-Geigy); Nicabate (Marion Merrell Dow); Nicoderm (Alza; Marion Merrell Dow); Nicolan (Elan); Nicopatch (Fabre); Nicotell TTS (Ciba-Geigy); Nicotinell (Geigy); Tabazur (Theraplix) LITERATURE REFERENCES: From the dried leaves of Nicotiana tabacum and N. rustica where it occurs to the extent of 2 to 8%, combined with citric and malic acids. Commercial nicotine is entirely a byproduct of the tobacco industry. Extraction procedure: Gattermann, Wieland, Laboratory Methods of Organic Chemistry (New York, 24th ed., 1937); Schwyzer, Die Fabrikation pharmazeutischer und chemisch-technischer Produkte (Berlin, 1931). Purification through the zinc chloride double salt: Ratz, Monatsh. 26, 1241 (1905). Structure and synthesis: Pinner, Ber. 26, 294 (1893); Pictet, Rotschy, Ber. 37, 1225 (1904); Craig, J. Am. Chem. Soc. 55, 2854 (1933). Recent synthesis: M. Nakane, C. R. Hutchinson, J. Org. Chem. 43, 3922 (1978). Conformation in soln: T. P. Pitner et al., J. Am. Chem. Soc. 100, 246 (1978). HPLC determn in plasma: M. Harlharan et al., Clin. Chem. 34, 724 (1988). Toxicity data: R. B. Barlow, L. J. McLeod, Brit. J. Pharmacol. 35, 161 (1969). Review and bibliography: Jackson, Chem. Rev. 29, 123 (1941). Review of pharmacology: R. W. Ryall in Neuropoisons: Their Pathophysiological Actions vol. 2, L. L. Simpson, D. R. Curtis, Eds. (Plenum, New York, 1974) pp 61-97; N. L. Benowitz, Ann. Rev. Med. 37, 21-32 (1986). PHYSICAL DATA: Colorless to pale yellow, oily liq; very hygroscopic; turns brown on exposure to air or light. Acrid burning taste. Develops odor of pyridine. bp745 247 degrees (partial decompn); bp17 123-125 degrees. Volatile with steam. nD20 1.5282. d420 1.0097. (.alpha.)D20 -169 degrees. pK1 (15 degrees ) 6.16; pK2 10.96. pH of 0.05M soln: 10.2. Forms salts with almost any acid and double salts with many metals and acids. Absorption spectrum: Purvis, J. Chem. Soc. 97, 1035 (1910); Dobbie, Fox, ibid. 103, 1194 (1913). Misc with water below 60 degrees ; on mixing nicotine with water the volume contracts. Very sol in alc, chloroform, ether, petr ether, kerosene, oils. Distribution of nicotine between water and petroleum oils: Norton, Ind. Eng. Chem., Ind. Ed. 32, 241 (1940). LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow, McLeod). PHYSICAL DATA: BOILING POINT: (745) 247 degrees (partial decompn); (17) 123-125 degrees OPTICAL ROTATION: (.alpha. D): -169 degrees REFRACTIVE INDEX: n(20/D) 1.5282 DENSITY: (20/4) 1.0097 LD50: LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow, McLeod) DERIVATIVE INFORMATION: SUBSTANCE: Nicotine Hydrochloride DERIVATIVE CAS RN: 21361-93-3 DERIVATIVE MOL. FORMULA: C10H14N2.HCl DERIVATIVE PHYSICAL DATA: deliquesc crystals. (.alpha.)D20 +104 degrees (p = 10). OPTICAL ROTATION: (.alpha. D): +104 degrees (p = 10) SUBSTANCE: Nicotine Dihydrochloride DERIVATIVE CAS RN: 6019-02-9 DERIVATIVE MOL. FORMULA: C10H14N2.2HCl DERIVATIVE PHYSICAL DATA: deliquesc crystals, very sol in water and alcohol. Nearly insol in ether. SUBSTANCE: Nicotine Sulfate DERIVATIVE CAS RN: 65-30-5 DERIVATIVE MOL. FORMULA: (C10H14N2)2.H2SO4 DERIVATIVE SYNONYMS: nicotine neutral sulfate DERIVATIVE PHYSICAL DATA: six-sided tablets. (.alpha.)D20 +88 degrees (p = 70). Sol in water, alcohol. OPTICAL ROTATION: (.alpha. D): +88 degrees (p = 70) SUBSTANCE: Nicotine Bitartrate DERIVATIVE CAS RN: 65-31-6 DERIVATIVE MOL. FORMULA: C10H14N2.2C4H6O6 DERIVATIVE SYNONYMS: nicotine tartrate DERIVATIVE PHYSICAL DATA: dihydrate, crystals. mp 90 degrees. (.alpha.)D20 +26 degrees (c = 10). Very sol in water or alcohol. MELTING POINT: 90 degrees OPTICAL ROTATION: (.alpha. D): +26 degrees (c = 10) SUBSTANCE: Nicotine Zinc chloride double salt monohydrate DERIVATIVE MOL. FORMULA: C10H16Cl4N2Zn.H2O DERIVATIVE PHYSICAL DATA: also with 4H2O. Very sol in water; sparingly sol in abs alcohol and ether. SUBSTANCE: Nicotine Salicylate DERIVATIVE CAS RN: 29790-52-1 DERIVATIVE MOL. FORMULA: C17H20N2O3 DERIVATIVE BRAND NAME (COMPANY): Eudermol DERIVATIVE PHYSICAL DATA: Six-sided plates, mp 118 degrees. (.alpha.)D20 +13 degrees (c = 9). Freely sol in water or alcohol. MELTING POINT: 118 degrees OPTICAL ROTATION: (.alpha. D): +13 degrees (c = 9) SUBSTANCE: Nicotine Polacrilex DERIVATIVE CAS RN: 96055-45-7 DERIVATIVE BRAND NAME (COMPANY): Nicorette (Lundbeck; Merrell Dow) NOTES: Caution: Nicotine can be absorbed from the alimentary canal, the respiratory tract and intact skin. Percutaneous absorption of the free alkaloid is much more rapid than the acid salts. Local effects due to overexposure are burning sensation in mouth and throat, salivation, nausea, abdominal pain, vomiting and diarrhea. GI reactions are less severe but do occur after cutaneous and respiratory exposure. The major systemic effects are a transient stimulation and subsequent depression or paralysis of the CNS. Symptoms include agitation, headache, sweating, dizziness, auditory and visual disturbances, confusion, weakness and incoordination. At first respirations are deep and rapid, the blood pressure is high and the pulse is slow. CNS excitation may be evidenced by tremors or clonic-tonic convulsions. As depression develops, the pupils dilate, the blood pressure falls, and the pulse becomes rapid and irregular. Faintness, prostration, cyanosis and dyspnea progress to collapse. Death from paralysis of respiratory muscles usually follows shortly after collapse. See: Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 311-314. USE: Insecticide; fumigant. In the U.S. a 40% soln of nicotine sulfate, Black Leaf 40, was the commonly used form. As a contact poison it is most effective as soap, i.e., as the laurate, oleate, or naphthenate. As a stomach poison a combination with bentonite has come into use. THERAPEUTIC CATEGORY: Treatment of smoking withdrawal syndrome. THERAPEUTIC CATEGORY VET: Ectoparasiticide. Has been used as an anthelmintic. REFERENCE KEYS PRESENT: Conformation; Extraction; HPLC; Pharmacology; Purification; Review; Structure; Synthesis; Toxicity DATA KEYS PRESENT: Caution; Molecular weight; Uses; Therap. Cat.; Therap. Cat. Vet.; Density; Boiling point; Refractive index; Optical rotation; Lethal dose DATA KEYS PRESENT IN DERIVATIVE: Melting point; Optical rotation ?t 1/5/3 DIALOG(R)File 304:The Merck Index Online(SM)/1996S1 (c) 1996,1996 Merck & Co. Inc. All rts. reserv. 06026 Monograph Name: 3-Methyl-5-phenylhydantoin CAS REGISTRY NUMBER: 6846-11-3 MOLECULAR FORMULA: C10H10N2O2 MOLECULAR WEIGHT: 190.20 MOLECULAR COMPOSITION: C 63.15%, H 5.30%, N 14.73%, O 16.82% C.A. CHEMICAL NAME(s): 3-Methyl-5-phenyl-2,4-imidazolidinedione BRAND NAME (and COMPANY): Norantoin; Nuvarone LITERATURE REFERENCES: Prepn: Pinner, Ber. 21, 2325 (1888); Kjaer, Acta Chem. Scand. 4, 892 (1950); Klosa, Arch. Pharm. 285, 274 (1952). PHYSICAL DATA: Fine needles from aq ethanol, mp 162-163 degrees. PHYSICAL DATA: MELTING POINT: 162-163 degrees THERAPEUTIC CATEGORY: Anticonvulsant. REFERENCE KEYS PRESENT: Prepn DATA KEYS PRESENT: Molecular weight; Therap. Cat.; Melting point ?t 1/5/4 DIALOG(R)File 304:The Merck Index Online(SM)/1996S1 (c) 1996,1996 Merck & Co. Inc. All rts. reserv. 03705 Monograph Name: Ethotoin CAS REGISTRY NUMBER: 86-35-1 MOLECULAR FORMULA: C11H12N2O2 MOLECULAR WEIGHT: 204.23 MOLECULAR COMPOSITION: C 64.69%, H 5.92%, N 13.72%, O 15.67% C.A. CHEMICAL NAME(s): 3-Ethyl-5-phenyl-2,4-imidazolidinedione; 3-ethyl-5-phenylhydantoin SYNONYMS: 1-ethyl-2,5-dioxo-4-phenylimidazolidine BRAND NAME (and COMPANY): Peganone (Abbott) LITERATURE REFERENCES: Prepd by heating the potassium salt of 5-phenylhydantoin with ethyl bromide in alc at 100 degrees in a sealed tube: Pinner, Ber. 21, 2320 (1888). Use as anticonvulsant: W. J. Close, U.S. pat. 2,793,157 (1957 to Abbott Labs.). Metabolism: Dudley et al., J. Pharmacol. Exp. Ther. 175, 27 (1970). PATENT INFORMATION: US 2793157 PHYSICAL DATA: Stout prisms from water, mp 94 degrees. Sparingly sol in cold water, more sol in hot water. Freely sol in alcohol, ether, benzene, dil aq solns of alkali hydroxides. PHYSICAL DATA: MELTING POINT: 94 degrees THERAPEUTIC CATEGORY: Anticonvulsant. REFERENCE KEYS PRESENT: Patent number; Prepd; Use DATA KEYS PRESENT: Molecular weight; Patent number; Therap. Cat.; Melting point ?t 1/5/5 DIALOG(R)File 304:The Merck Index Online(SM)/1996S1 (c) 1996,1996 Merck & Co. Inc. All rts. reserv. 02552 Monograph Name: Cotinine CAS REGISTRY NUMBER: 486-56-6 MOLECULAR FORMULA: C10H12N2O MOLECULAR WEIGHT: 176.22 MOLECULAR COMPOSITION: C 68.16%, H 6.86%, N 15.90%, O 9.08% C.A. CHEMICAL NAME(s): 1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone SYNONYMS: N-methyl-2-(3-pyridyl)-5-pyrrolidone LITERATURE REFERENCES: Nicotine metabolite first described by Pinner, Arch. Pharm. 231, 378 (1893). Isolated from autoxidized nicotine, nicotine treated with hydrogen peroxide, from nicotine irradiated with ultraviolet light: Frankenburg, Vaitekunas, J. Am. Chem. Soc. 79, 149 (1957). PHYSICAL DATA: Viscous oil, bp6 210-211 degrees. Absorption spectra: Frankenburg, Vaitekunas, loc. cit. PHYSICAL DATA: BOILING POINT: (6) 210-211 degrees DERIVATIVE INFORMATION: SUBSTANCE: Cotinine Fumarate DERIVATIVE CAS RN: 5695-98-7 DERIVATIVE MOL. FORMULA: (C10H12N2O)2.C4H4O4 DERIVATIVE BRAND NAME (COMPANY): Scotine (Unimed) THERAPEUTIC CATEGORY: Antidepressant. DATA KEYS PRESENT: Molecular weight; Therap. Cat.; Boiling point ?t 1/5/6 DIALOG(R)File 304:The Merck Index Online(SM)/1996S1 (c) 1996,1996 Merck & Co. Inc. All rts. reserv. 00037 Monograph Name: Acetamidine Hydrochloride CAS REGISTRY NUMBER: 124-42-5 MOLECULAR FORMULA: C2H7ClN2 MOLECULAR WEIGHT: 94.54 MOLECULAR COMPOSITION: C 25.41%, H 7.46%, Cl 37.50%, N 29.63% C.A. CHEMICAL NAME(s): Ethanimidamide hydrochloride SYNONYMS: ethanamidine hydrochloride; .alpha.-amino-.alpha.-iminoethane hydrochlori de; ethenylamidine hydrochloride; acediamine hydrochloride DRUG CODES: SN-4455 LITERATURE REFERENCES: Prepd by passing HCl into a soln of acetonitrile in abs alcohol, then passing NH3 into the reaction mixture: Pinner, Ber. 16, 1654 (1883); 17, 178 (1884); Dox, Org. Syn., coll. vol. I, 5 (New York, 2nd ed., 1941). See also Fargher, J. Chem. Soc. 117, 674 (1920). Review: Shriner, Neumann, Chem. Rev. 35, 351-425 (1944). PHYSICAL DATA: Long prisms from alcohol, somewhat deliquescent, mp 174 degrees (Fargher); mp 164-166 degrees (Dox). Very sol in water. Sol in alcohols. Practically insol in acetone, ether. Should be stored in a closed container and in a cool place. If alkali is added to an aq soln, the free base is liberated. PHYSICAL DATA: MELTING POINT: 174 degrees (Fargher); 164-166 degrees (Dox) DERIVATIVE INFORMATION: SUBSTANCE: Acetamidine Hydrochloride Free base DERIVATIVE MOL. FORMULA: C2H6N2 DERIVATIVE PHYSICAL DATA: uv max: 224 nm (.epsilon. 4000). pK1 (25 degrees ): 12.1. Has a strong alkaline reaction and on slight warming dissociates into ammonia and acetic acid. UV MAX: uv max: 224 nm (.epsilon. 4000) NOTES: Caution: Irritates mucous membranes, skin. Avoid tasting, swallowing, inhalation of the dust, skin contact. USE: In the synthesis of imidazoles, pyrimidines, triazines. REFERENCE KEYS PRESENT: Prepd; Review DATA KEYS PRESENT: Caution; Molecular weight; Uses; Melting point DATA KEYS PRESENT IN DERIVATIVE: UV Max