Tropic acid ester

Homatropine (mandelyltropine) being a useful mydriatic it is surprising that of nine esters of mandelic acid tried, none showed mydriatic activity though three were local anaesthetics, two of them being described as good. Only one of the tropic acid esters tried showed local anaesthetic action and that was poor. ... 

O Hagan D and Robins RJ (1998) Tropic acid ester biosynthesis in Datura stramonium and related species. Chem Soc Rev 27, 207-212. 

The alkaloids of this group are derived from a combination of a piperidine and a pyrrolidine ring, designated as tropane (Figure 14.2). The 3-hydroxy derivative of tropane is known as tropine and is the basic component of atropine. When atropine is hydrolyzed, it forms tropine and tropic acid (a-phenyl-p-hydroxy-propionic acid). Atropine is the tropic acid ester of tropine. It has been prepared synthetically. Tropic acid contains an asymmetric carbon atom. The racemic compound (atropine) as obtained naturally or as synthesized may be resolved into its optically active components, d- and /-hyoscyamine. Atropine is racemic hyoscyamine that is, it consists of equal parts of /-hyscyamine and plant cells and also in the process of extraction, so that the relative proportion of the isomers in the plants and in the preparations varies. However, atropine itself does exist in small amounts in the plants, although most of it is formed from the /-hyoscyamine in the process of extraction. 

Diphenyl-methyl-bromide DL-Tropic acid ester of the tropine trans-Tropanol... 

SYNS ATROPIN (GERMAN) EYEULES dl-HYOSCYAMINE 2-PHENYLHYDRACRYLIC ACID-3-a-TROPANYL ESTER P-PHENYL-y-OXYPROPION-SAEURE-TROPYL-ESTER (GERNLAN) l-0-H,5-a-H-TROPAN-3-a-OL ( )-TROPATE (ESTER) dl-TROPAN-YL-2-HYDROXY-1-PHENYLPROPIONATE TROPIC ACID, ESTER with TROPINE TROPIC ACID-3-a-TROPANYL ESTER TROPINE TROPATE dl-TROPYLTROPATE ( )-TROPYL TROPATE... 

HYOSCYAMINE 1-HYOSCYAMINE (-)-TROPIC ACID ESTER with TROPINE... 

SYNS ATROCHIN ATROQUIN 6-P,7-P-EPOXY-3-a-TROPANYL S-(-)-TROPATE EPOXYTROPINE TROPATE HYOSCIN E (-)-HYOSCINE HYOSOL ISOPTO HYOSCINE 9-METHYL-3-OXA-9-AZATRI-CYCLO(3,3.1.o2. )NONAN-7-OL TROPATE (ester) OSCINE SCOPIXE TROPATE (-)-SCOPOLAMINE TROPIC ACID, ESTER with SCOPINE TROPIC ACID, 9-METHYL-3-OXA-9-AZATR1CYCLO(3.3.1.o2" )NON-7-YL ESTER... 

TROPIC ACID. ESTER with SCOPINE see SBGOOO... 

In addition to the effects on the reproductive functions of the female, there has been some study of the effects of tropic acid esters and related compounds on sexual function In che male. One paper on this topic (125) has been mentioned above. Horowitz and Goble (143) have reviewed the literature on drug-induced sexual dysfunction In the male and have concluded chat any drug with acroplne-llke effects may Interfere with penile erection. (They pointed out that Impotence induced by anclmuscarl e drugs may occur without reduction of libido and may thus be particularly frustrating to the male.)... 

The performance of each subject on the Number Facility Test after Injection was compared with his scores on the three validity scales and 10 standard scales of the Minnesota (hiltlphaslc Personality Index (MMPl). The best correlations between performance In the Number Facility Test and scores on scales In the MMPI for the men given atropine at 62 Mg/kg were with those In the h/pochondrlasls and mania scales. The best correlations for the men given atropine at 104 g/kg were with scores In the lie and mania scales. For the men given scopolamine at 11.8 pg/kg, the best correlations were with scores In the hypochondriasis and lie scales. If atropine and scopolamine are taken as representative of the group of tropic acid esters, the best Indexes of performance In the Number Facility Test under the Influence of such esters are the scores In the lie, l pochondrlasls, and mania scales of the MMPI. 

This review of the general literature portrays the tropic acid esters with which this report Is concerned as compounds that are not particularly lethal In single or repeated doses. The members of the group chat are tertiary amines may affect psychic activity In comparatively small doses, but there is fairly rapid adaptation to repeated doses. Removal of the compounds from the body, so far as It has been studied, seems to be comparatively rapid and to occur by a combination of urinary and fecal excretion and metabolic transformation. The... 

Symptoms and signs of the action of the tropic acid esters on human subjects include complaints of mouth dryness and decreased secretion of saliva Increase in heart rate, possibly preceded by a short period of decrease in heart rate dryness and flushing of the skin, particularly in the "blush area" difficult urination ataxia disorientation hallucination delirium dilated pupils, possibly nonreaetlve to light prostration and coma. 

The greatest hazard to life arises from suppression of the ability to secrete sweat, which can give rise to fatal hyperthermia if body temperature is not controlled artificially during hot weather or strenuous activity. Another source of hazard to life arises from the effect of the compounds other than scopolamine and its quaternary form in accelerating heart rate and facilitating Intramural conduction and transmission of Impulses. Ihese actions may result in serious arrhythmias up to and including ventricular fibrillation. The quaternary amine forms of the tropic acid esters in which we are interested are more active in some respects than the tertiary amines, as far as peripheral actions are concerned. This is especially true with respect to actions on nicotinic effectors in ganglia and striated muscles. The quaternary amines penetrate into the central nervous system poorly, but, once there, affect muscarinic effectors in the same way as the tertiary amines. 

Representative LD3qs of Tropic Acid Esters in Laboratory Animals... 

Hyoscyamine and atropine are therefore tropic acid esters of the base tropine. The constitution of tropine according to Willstater is as follows ... 

Tropesin is the tropic acid ester of indometacin, and its adverse effects profile is similar to that of indometacin (SEDA-17,113). 

Tropic acid ester with tropine. 1-Tropine tropate Tropine (-) tropate... 

Tatmnelin. L.-E.. and Fagerlind, L., Organophosphorus analogues of tropic acid esters. Part 1. 2-Phenyl-2-diethoxyphosphoryl ethanol, Acta Chem. Scand., 14, 1353, 1960. 

Three tropic acid esters, ( )-tropoyltropan-3/ -ol (3), ( )-tropoylgranatan-3-/ -ol (4), and its C-3 epimer, have been synthesized and characterized for evaluation as mydriatics and spasmolytics.20 Another group21 has prepared 26 diarylacrylic esters of tropine for pharmacological evaluation all are potent spasmolytics (in mice) but devoid of mydriatic activity. The activities of these esters have been correlated with their structures,22 and a certain degree of success is claimed in this very limited field it may therefore prove possible to predict approximately the activity of hitherto unprepared compounds, and therefore increase the effectiveness of this particular area of pharmaceutical research. 

Amprotropine Phosphate, a. (Hydroxymethyli-benzeneacetie acid 3-ester phosphate 3-diethylamino -2,2-dimethylpropyl tropate phosphate phosphate of the dl-tropic acid ester of 3-dieth-ylamino-2,2-dimethyl-I -propanol Syntropan. Ct(H N OP mol wt 405.42. C 53.32%, H 7.96%, N 3,45%, O 27.62%, P 7.64%, Prepn U.S. pats. 1,932,341 (1933) ... 

Atropine. endo-( )-a-< Hydroxy methyl )benzene-acetic acid 8-methyl-8-azabicyclo[3.2.1 oct 3 yl ester, laH,-SaH-tropan 3a-ol (+)-tropate dj-hyoscyamine tropic acid ester with tropine di-tropyl tropate tropine tropate. C17-HjjNOj mo] wt 289.38, C 70.56%, H 8.01%, N 4.84%. O 16.59%. Parasympatholytic alkaloid isolated from Atropa belladonna L, Datura stramonium L, and other Solanaceae. 

Atropine is the tropic acid ester of tropine and is marketed as the suifate sait. The naturaiiy occurring aikaioid, (-)-hyoscyamine, undergoes base-cataiyzed racemization during isoiation from piants of the Soianaceae to give ( )-hyoscyamine or atropine, it was the first compound shown to biock the effects of eiectricai ... 

Comprehensive reviews have recently appeared on the tropane alkaloids of the Solanaceae and on the biosynthesis and metabolism of the same type of alkaloids. The stereospecific hydroxylation of tropine to 6/3-hydroxytropine and the conversion of its tropic acid ester into 6,7-dehydrohyoscyamine and further into scopolamine have been conclusively proven. Hence, the total synthesis of scopolamine from 6-tropen-3a-yl esters is indeed a biomimetic synthesis. 

A modified technical transesterification method has been elaborated" " for 3-tropanyl and 3-granatanyl tropic acid esters, starting with methyl a-formyl-p-phenylacetate and tropine in toluene (66% yield) followed by reduction of the formyl group over Raney nickel. 

The leaves and roots of Atropa belladonna (Solanaceae) are known as Belladonna leaves and Belladonna roots, and are used as medicine in the form of extracts. These materials are also used as materials for the manufacture of atropine sulfate. Other alkaloids isolated from belladonna include (—)-hyoscyainine and (—)-scopolamine. Atropine is derived from (—)-hyoscyamine by racemization of its tropic acid ester moiety. 

Tropic acid ester B,HBr, cryst from EtOH. M.p. 233°. Sol. HjO, hot EtOH. Becomes yellow on exposure to light. Anasthetic. 

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