Dimemorfan D 661 Dimozole thiozole Reference(s): US 2 578 757 (Hoffmann-La Roche; 1951; prior. 1949). Formulation(s): topical 5 % Tmde Name(s): GB: Aster01 (Roche); wfm J: Aster01 "Roche" (Roche- I: Aster01 (Roche); wfm S hionogi) Diiemorfan ATC: ROSDA11 Use: antitussive, sedative RN: 36309-01-0 MF: C,,H,,N MW: 255.41' EINECS: 252-963-3 CN: (9a,13a,14a)-3,17-dimethylmorphinan phosphate RN: 40678-33-9 MF: C,,H,,N . xH,P04 MW: unspecified pfCH3 + NoBH4 ClMg boronate 2-mothyl-5,6,7,8- 4-methylbenzyl- 2-methyl-1 -(4-methyl- tctrahydroisoquino- mognesium chloride benzyl)-1.2.5.6.7,8- linium bromide hexohydroisoquinoline (+)-2-methyl-1-(4- methylbenzy1)- 1.2.3,4,5,6.7,8-octo- hydroisoquinoline I Dimemorfan D~s 2 128 607 (Yamanouchi; appl. 9.6.1971; J-prior. 20.6.1970, 2.2.197 1,9.2.1971). Formulation(s): drops 5 mglml; cps. 10 mg; syrup 2.5 mglml Tmde Name(s): I: Gentus (Gentili) Tusben (Benedetti) J: Astomin (Yamanouchi) 662 D Dimenhydrinate Dimenhydrinate ATC: A04AD49 Use: anti-emetic RN: 523-87-5 MF: CL7H2,N0. C,H,CIN,O, MW: 469.97 EINECS: 208-350-8 LD,,,: 203 mglkg (M, p.0.); 200 mg/kg (R, i.v.); 1320 mg/kg (R, p.0.) CN: 2-(dipheny1methoxy)-N,N-dimethylethanamine, compd. with 8-chlorotheophylline diphenhydromine 8-chlorotheophylline (4. v.) Dimenhydrinote I Reference(s): US 2 499 058 (Searle; 1950; prior. 1949). US 2 534 813 (Searle; 1950; appl. 1950). Forrnulation(s): drg. 10 mg, 20 mg, 50 mg, 150 mg, 200 mg (s. r. cps.); sol. for inj. 62 mgllO ml (i.v.), 100 mg12 ml (i.m.); suppos.40 mg, 70 mg, 80 mg, 150 mg; tabl. 50 mg Trade' Name(s): D: Arlevert (Hennig)-comb. Dimen (Heumann) Mandros (Dolorgiet) Migraeflux (Henning)- comb. Reisetabletten ratiopharm (ratiopharm) RubieMen (RubiePharm) Superprepl-forte (Hermes) Vertigo-Vomex (Yamanouchi) Vomacur (Hexal) Vomex (Yamanouchi) F: Dramamine (Monsanto) Mercalm (Lab. Phygikne) comb. Nausicalm (Lab. Brother S A) GB: Dramamine (Searle) I: Lomarin (Geymonat) Motozina (Biomedica Foscama) Travelgum (ASTA Medica) Valontan (Recordati) Xamamina (SmithKline Beecham) generics J: Dramamine (Dain~ppon) Vomiles (Fujisawa) USA: Dimenhydrinate (Wyeth- Ayerst) Dimercaprol ATC: V03AB09 (Di thioglycerin) Usc: antidote (heavy metal poisonings) RN: 59-52-9 MF: C,H,OS, MW: 124.23 EINECS: 200-433-7 LD,,: 56 mgkg (M, i.v.); 217 mglkg (M, p.0.) CN: 2,3-dimercapto-1-propanol ollyl alcohol 2,3-dibromo- Dimercoprol 1 -propano1 US 2 402 665 (Du Pont; 1946; appl. 1942). US 2 432 797 (Minister of Supply of the United Kingdom; 1947; GB-prior. 1942). US 2 436 137 (Du Pont; 1948; appl. 1944). Stocken, L.A.; Thompson, R.H.S.: Biochem. J. (BIJOAK) 40,529,535,548 (1946). Dimestrol D 663 ~ynthesis via 2,3-dichloropropanol: Ing, H.R.: J. Chem. Soc. (JCSOA9) 1948, 1393. Fomulation(s): amp. 100 mg Me Name(s): D: Sulfactin Homburg I: B.A.L. Boots (Boots Italia) USA: BAL (Hynson Westcott & (Homburg); wfm J: Bal (Daiichi) Dunning); wfm F: B.A.L (L'Arguenon) Dimestrol (Dimethoxydiethylstilbene) ATC: GO3 Use: estrogen RN: 130-79-0 MF: C2,H,,O2 MW: 296.41 EINECS: 204-994-9 CN: (E)-1,l'-(l,2-dlethyl- l,2-ethenediyl)bis[4-methoxybenzene] diethylstilbestrol methyl iodide L Dimestrol I * '0- mercury(![) - chloride 4'-rnethoxy- pmpiophenone (1) OH ~g. diethy! ether I + H3C Br - H C '0 H& OH \ 0' CH3 phosphorus oxychloride 664 D Dimetacrine Reference(s): a Reid, E.E.; Wilson, E.: J. Am. Chem. Soc. (JACSAT) 64, 1625 (1942). b Sisido, K.; Nozaki, H.: J. Am. Chem. Soc. (JACSAT) 70,776 (1948). c GB 584 253 (B.T. Bush; appl. 1943; USA-prior. 1941). GB 584 705 (B.T. Bush; appl. 1943; USA-prior. 1941). DE 897 559 (Bayer; appl. 1938). alternative synthesis: DE 824 043 (Boehringer Ing.; appl. 1949). review: Solmssen, U.V.: Chem. Rev. (Washington, D. C.) (CHREAY) 36,481 (1945). Trade Name(s): D: Depot-Oestromon (Merck); wfm Dimetacrine ATC: N06AA18 Use: antidepressant, thymoleptic RN: 4757-55-5 MF: C20H2,N2 MW: 294.44 LD,,,: ,39600 ~g/kg (M, i.v.); 1293 mglkg (M, p.0.); 1850 mgkg (R, p.0.) CN: N,N,9,9-tetramethyl- 1 O(9H)-acridinepropanamine tartrate (1:l) RN: 3759-07-7 MF: C20H2,N2.C,H60, MW: 444.53 EINECS: 223-166-8 LD,,,: 40.9 mglkg (M, i.v.); 755 mgkg (M, p.0.); 38 mgkg (R, i.v.); 1671 mglkg (R, p.0.) diphenylomine uNu methylmagnesium uNw bromide H 9-methyl- acridine 9.9-dimethyl- 9,l O-dihydro- ocridine (I) 2. C,-N/CH3 I '3'3 I - 1. sodium omide 2. 3-dimethylomino- I propyl chloride CH3 Rej'erencels): DE 1 224 315 (Kefalas; appl. 7.9.1961; GB-prior. 16.9.1960). GB 933 875 (Kefalas SIA; appl. 16.9.1960; valid from 13.9.1961). US 3 284 454 (Siegfried; 8.1 1.1966; CH-prior. 18.12.1961, 3.8.1962). Molnar, I.; Wagner-Jauregg, T.: Helv. Chim. Acta (HCACAV) 48, 1782 (1965). Fortnulation(s): drg. 100 mg (as hydrochloride) Dimethadione D 665 1 Z'rode Name(s): [ D: Istonil (Siegfried); wfm J: Istonyl (Nippon i Chemiphar) I L j Dimethadione Use: anticonvulsant !. 1 RN: 695-53-4 MF: C,H,NO, MW: 129.12 EINECS: 211-781-4 $ LD,: 850 mag (M, i.p.) ' CN: 5,5-dimethyl-2,4-oxazolidinedione one hydrogen acetone a-hydroxy- a-hydroxy- cyanohydrin isobutyromide isobutyric acid (I) gaseous HCI H3C OH + HO/'CH, - H,C~O"CH~ ethyl a-hydroxy- isobutyrate ATC: A09A Use: antacid, antiflatulant diethoxydimethyl- n=200-350 dimethyldichlorosilane, e. g.: 007 063 (General Electric; appl. 1956; USA-prior. '1955). 2 148 669 (Wacker-Chemie; appl. 29.9.1971). DOS 2 521 742 (Wacker-Chemie; appl. 15.5.1975). 666 D Dimethisterone Forrnulation(s): cream 4 02.; lotion 4 oz. Trade Name(s): D: Absorber HFV (Arteva Pharma) Aegrosan (Opfermann) Busala (Pharma Selz) Ceolat (Solvay Arzneimittel) Dimeticon-ratiopharm (ratiopharm) Espumisan (Berlin- C hemie) ILIO-Funktion Kautabletlen (Robugen) Meteosan (Novartis) sab simplex (Parke Davis) Symadal (Chauvin ankerpharm) F: Castrobul (Lab. Cuerbet)- comb. CB: I: J: Gel de polysilane (Labs. UPSA) Rennie Deflantine (Labs. Roche Nicholas SA)-comb. numerous combination preparations Infacol (Pharmax) numerous combination preparations Mylicon (Parke Davis) Olio Silic (Tariff. Integrative) Polisilon (Midy)-comb. Silisan (Lipha)-comb. Aeropax (Green Cross) Ganatone (Hokuriku) Gasace (Kanto) Gascon (Kissei) USA: Gasless (Hishiyama) Gaspanon (Kotani) Gas tee1 (Fuso) Gaszeron (Nichiiko) Gersmin (Kowa) Harop (Toyo Pharmar) Magarte (Mohan) Poly silo (Toa) Silies (Nippon Shoji) Sili-Met-San S (Nippon Shoji) Spalilin (Maruishi) Eucerin (Beiersdorf) Moisture1 (Westwood- Squibb) Dimethisterone ATC: G03D Use: progestogen RN: 79-64-1 MF: C,,H,202 MW: 340.51 EINECS: 201-215-4 CN: (6a,17~)-17-hydroxy-6-methyl-17-(1-propynyl)androst-4-en-3-one 3,3-ethylenedioxy- 6-rnethd-17-0x0- 5-ondrostene [from 3p.17p-diocetoxy- 5-ondrostene (I)] 17o-ethynyl-68-methyl- 3p.5a.178-trihydroxy- ondrostone [from Jp-hydroxy-17- 0x0-5-androstene (IT)] FH3 + E F MgBr 1 -propynyl- mognesium bromide Dimethinterone u , .$ , PDCI, C Ill 2. H,C-l . Li. NH, 1. CrO,, pyridine 3. (COOH) 2 1. 2.3-dihydropyran, 1. chromium(Vl) phosphorus oxychloride HO oxide 2. methyl iodide. lithium. ammonio 3. oxalic acid a US 2 927 119 (British Drug Houses; 1.3.1960; appl. 15.5.1958; GB-prior. 21.5.1957). Petrov, V. et al.: J. Chem. Soc. (JCSOA9) 1957,4105; 1960, 3676. US 2 939 819 (British Drug Houses; 7.6.1960; GB-prior. 25.1.1957). Petrov, V. et al.: J. Chem. Soc. (JCSOA9) 1959, 1957. Petrov, V. et al.: J. Chem. Soc. (JCSOA9) 1957,4099. Ruzicka, L.; Hofman, K.: Helv. Chim. Acta (HCACAV) 20, 1280 (1937). ' Fbrmulation(s): tabl. 5- 15 mg Eade Namefs): GB: Secrosteron (Duncan, J: Secrosteron (Santen- USA: Oracon (Mead Johnson); 1 Flockhart); wfm Yamanouchi) wfm Dimethoxanate Use: antitussive 1 RN: 477-93-0 MF: C1yH22N203S MW: 358.46 EINECS: 207-520-9 CN: 10H-phenothiazine-10-carboxylic acid 2-[2-(dimethylamino)ethoxy]ethyl ester $ monohydrochloride RN: 518-63-8 MF: ClyH22Nz03S . HCI MW: 394.92 EINECS: 208-255-1 1 LD,,: 580 mgkg (M, p.o.1; 1500 mgkg (R, p.0.) i OYCl pyridine 2-(2-dimethylomino- phenothiozine- ethoxy)ethonol phenothiazine Oirnethoxanate 1 0-corbonyl chloride Referencefs): DE 1 036 259.(Ayerst; appl. 1955; USA-prior. 1955). L ' Formulation(s): syrup 12.5 mg15 ml ! Trade Namefs): i: F: Cotrane (Clin-Midy); wfm I: Cothera (Ayerst); wfm Tussizid (Beolet); wfm Cotrane (Midyfarm); wfm Perlatos (Farm. Mil.); wfm Dimethyltubocurarinium chloride ATC: ~03~~04 (Metocurine chloride) Use: muscle relaxant RN: 33335-58-9 MF: C,,H4,CI2N20, MW: 723.74 EINECS: 25 1-46 1 - 1 CN: 6,6',7',12'-tetramethoxy-2,2,2',2'-tetramethyltubocuraranium dichloride t' iodide $ RN: 7601-55-0 MF: C40H4812NZ06 MW: 906.64 EINECS: 231-510-3 1 LDe: 230 @kg (M, i.v.); 35 ~glkg (R, i.v.) 6 668 D Dimetindene row tubocurore (or tubocurore iodide) H,C-CI or H,C-I, 60 "C b methyl chloride or methyl iodide. fesp. I Dimethyltubocurarinium chloride (or iodide. resp.) I Reference(s): US 2 581 903 (Eli Lilly; 1952; prior. 1949). Formulation(s): vial 2 mg/ml (20 ml) Trade Name(s): D: Methyl Curarin HAF USA: Mecostrin (Squibb); wfm (Ethicon); wfm Metubine Jodide (Lilly) Dimetindene (Dimethindene) ATC: D04AA13; R06AB03 Use: antihistaminic, antipruritic RN: 5636-83-9 MF: C&,N2 MW: 292.43 EINECS: 227-0834 LD,,: 27 mgkg (R, i.v.); 618 mgkg (R, p.0.); 45 mgkg (dog, i.v.) CN: N,N-dimethyl-3-[1-(2-pyridinyl)ethyl]-lH-indene-2-ethanamine maleate (1:l) RN: 3614-69-5 MF: C2,HZ4N2 . C,H404 MW: 408.50 EINECS: 222-789-2 LDSo: 26.8 mglkg (R, i.v.); 618 mglkg (R, p.0.) 1. NOH 2. CI-~/~~, drCH3 C"3 I , 07 1. sodium hydride cH3 2. 2-(dimethylomino) ethyl chloride polyphosphoric acid *I diethyl benzyl- malonate H3C FH3 wN\CH3 H+ 1. phenyllithium or 0 HO 1 \ butyllithium H3C - 2. 2-ethylpyridine 2-(2-dimethylomino- 1 Dimetindene 1 ethyl)-1 4ndanone (I) L l Dimetotiazine D 669 Reference(s): US 2947 756 (Ciba; 2.8.1960; appl. 5.5.1959; prior. 12.8.1958, 3.1 1.1958, 10.2.1959). US2970 149 (Ciba; 31.1.1961; appl. 3.11.1958). Formulation(s): amp. 4 mg; drg. 1 mg; drops 1 mglml; gel 1 mg/g; s. r. drg. 2.5 rng; s. r. tabl. 2.5 mg; syrup 0.122 mg/ml Trade Name(s): D: Fenistil (Zyma-Blaes) Vibrocil (Zyma)-comb.; J: Foristal (Ciba-Geigy- Vibrocil (Zyma)-comb. wfm Takeda) GB: Fenostil (Zyma); wfm I: Fengel (Zyma) USA: Forhistal (Ciba); wfm Fenostil-Retard (Zyma); Fenistil (Zyma) Triten (Marion); wfm wfm Vibrocil (Zyma)-comb. Dimetotiazine (Dimethothiazine; Fonazine) ATC: N02CX05 Use: antiallergic, antihistaminic, antimigraine agent RN: 7456-24-8 MF: C1yH2SN302S2 MW: 391.56 EINECS: 231-229-6 LD,: 100 mg/kg (M, i.v.); 740 mg/kg (M, p.0.) CN: 10-[2-(dimethylamino)propyl]-N,N-dimethyl-lOH-pknothiazine-2-sulfonamide mesylate RN: 7455-39-2 MF: C,,H2,N3O2S, . CH,03S MW: 487.67 1. N0NH2 2. H3C, ,CH, H3C, ,cH3 b 1. sodium omide 2. 2-dimethylomino- propyl chloride 2-dimethylamino- Dimetotiozine sulfonylphenoihiozine Reference(s): GB 814 512 (RhBne-Poulenc; appl. 15.7.1957; F-prior. 1.8.1956, 18.12.1956) FR 1 179 968 (RhBne-Pou1enc;-appl. 1.8.1956). Formulation(s): cps. 20 mg (base); suppos. 50 mg; tabl. 25 mg (mesylate) Trade Name(s): D: Migristene (Rhodia I: Alius (Roussel) Pharma); wfm J: Bistermin (Toyo Shinyaku) F: Migristhe (Specia); wfm Calsekin (Kanto-Isei) GB: Banistyl (May & Baker); Demethotiazine (Mohan) wfm Migristene (Shionogi) Neomestin (Taiyo) Serevirol (Fuji Zoki) Dimoxyline (Dioxyline) ATC: A03 Use: antispasmodic, vasodilator RN: 147-27-3 MF: CZ2H2,NO, MW: 367.45 CN: I-[(4-ethoxy-3-methoxyphenyl)methyl]-6,7-dimethoxy-3-methylisoquinoline phosphate (1:l) RN: 5667-46-9 MF: C2,H2,N0,. H,PO, MW: 449.44 EINECS: 227-126-0 4-(2-aminopropyl)- 1.2-dimethoxybenzene (I) 190-200 OC POCI, ___, n COOH phosphorus oxychloride 4-ethoxy-3- rnethoxyphenyl- ocetic acid Reference(s): US 2 728 769 (Eli Lilly; 1955; prior. 1949). Formulation(s): tabl. 100 mg Trade Namefs): I: Paverona (Lilly); wfm USA: Paveril (Lilly); wfm Dinoprost (Prostagladin F,,) ATC: G02ADOl Use: oxytocic, abortifacient RN: 551-1 1-1 MF: C,,H,,O, MW: 354.49 LD,,,: 56 mgkg (M, i.v.); 1300 mglkg (M, p.0.); 106 mglkg (R, i.v.); 1170 mglkg (R, p.0.); 2.5-5.0 mglkg (rabbit, i.m., i.v.) CN: (5Z,9a,l la,13E,15S)-9,11,15-trihydroxyprosta-5,13-dien-l-oic acid trometharnine salt (1:l) RN: 38562-01-5 MF: C,,H,,O, . C,H,,NO, MW: 475.62 EINECS: 254-002-3 LD,,: 33 1 mglkg (M, i.v.); 71 1 rnglkg (M, p.0.); 101 mglkg (R, i.v.); 665 mglkg (R, p.0.) . 20 1-2 1 5-4 CN: (6a,17~ )-1 7-hydroxy-6-methyl-1 7-( 1-propynyl)androst-4-en-3-one 3,3-ethylenedioxy- 6-rnethd-1 7-0 x 0- 5-ondrostene [from 3p.17p-diocetoxy- 5-ondrostene (I)] 17o-ethynyl-68-methyl-. 2-mothyl-5,6,7, 8- 4-methylbenzyl- 2-methyl-1 -( 4-methyl- tctrahydroisoquino- mognesium chloride benzyl )-1 .2.5.6.7, 8- linium bromide hexohydroisoquinoline (+ )-2 -methyl- 1-( 4- methylbenzy1 )-. 14 7-2 7-3 MF: CZ2H2,NO, MW: 367. 45 CN: I-[(4-ethoxy-3-methoxyphenyl)methyl ]-6 ,7-dimethoxy-3-methylisoquinoline phosphate (1:l) RN: 566 7-4 6-9 MF: C2,H2,N0,. H,PO, MW: 449.44 EINECS: 22 7-1 2 6-0