ALKALOIDS

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ALKALOIDS:

ALKALOIDS

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naturally occurring chemical compounds containing basic nitrogen atoms Physiologically active Insoluble or sparingly soluble in water Crystalline solids; a few are amorphous Usually classified according to the nature of the basic chemical structures from which they are derived Form double-salts with compounds of Hg, Au, Pt, and other heavy metals. Reagents: Wagner’s (Iodine in Potassium iodide), Mayer’s (Potassium mercuric iodide), Dragendorff’s (Potassium bismuth iodide)

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Named from: the generic name of the plant yielding them the specific name of the plant yielding them the common name of the drug yielding them their physiologic activity the discoverer Possible functions: 1. Poisonous agents protecting the plant against insects and herbivores 2. End products of detoxification reactions representing a metabolic locking up of compounds otherwise harmful to the plant 3. Regulatory growth factors 4. Reserve substances capable of supplying nitrogen or other elements necessary to the plants economy.

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Common amino acid precursors: Phenylalanine Tyrosine Tryptophan Histidine Anthranilic acid Lysine Ornithine Important general reactions involved: Decarboxylation The process of removing a carboxyl group from a chemical compound Transamination The process of transposing an amino group within a chemical compound

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Classification based on the ring structure or nucleus of the chief alkaloid group in the plant drug: Pyridine-Piperidine Tropane Quinoline Isoquinoline Indole Imidazole Steroid Alkaloidal amines Purine

PYRIDINE - PIPERIDINE ALKALOIDS:

PYRIDINE - PIPERIDINE ALKALOIDS

TROPANE ALKALOIDS:

TROPANE ALKALOIDS

QUINOLINE ALKALOIDS:

QUINOLINE ALKALOIDS

ISOQUINOLINE ALKALOIDS:

contain the isoquinoline ring structure ISOQUINOLINE ALKALOIDS Sources: Alkaloid(s) Ipecac emetine hydrastis berberine , hydrastine sanguinaria sanguinarine curare tubocurarine opium morphine, codeine, thebaine

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BIOSYNTHESIS OF OPIUM ALKALOIDS: Tyrosine ------- L Dopa ------ Dopamine + 3,4 – dipydroxyphenylpyruvic acid PAPAVERINE ----------------- norlaudanosoline ( ket intermediate) Reticuline Saluteridine Saluteredinol THEBALNE Codeinone CODEINE MORPHINE

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IPECAC rhizomes and roots of Cephaelis ipecacuanha contains 5 alkaloids 3 principal alkaloids 1.emetine 2. elphaeline 3.psychotrine Ipecac syrup treatment of drug overdose and some poisonings procedure emesis central medullary effect by stimulation of chemoreceptor Ipecac fluidextract 14x stronger than the syrup

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Dover’s powder ipecac + opium Diaphoretic Emetine/ methylcephaeline synthetic methylation product of cephaeline Emetine hydrochloride hydrated hydrochloride of emetine turns yellow when exposed to light Uses: Antiamebic Expectorant Emetic

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HYDRASTIS golderseae dried rhizome and roots of Hydrastis caradensis 3 principal alkaloids 1.hydrastine 2. berberine (astringent in inflammation of mucous membranes) 3. caradine

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SANGUINARIA bloodroot rhizome of Sanguinaria canadensis Other sources: Ranunculaceae Berberidaceae Menispermaceae Papaveraceae Alkaloids (protopine series): sanguinarine chelerythrine protopine allocryptopine sanguinarine

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Alkaloids (protopine series): are colorless but tend to form colored salts: HNO3 sanguinarine--------  reddish salts HSO4 chelerythrine--------  yellowish salts Uses: stimulating expectorant emetic

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CURARE first drug South American arrow poison from bark and stem of Strychnos castelnaei Early preparations: calabash (gournd) tube (bamboo) pot curare (clay pot) -brownish or black, shiny, resinoid mass with a bitter taste Alkaloids: Tubocurarine most important quaternary compound contains b is-benzylisoquinoline structure

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Curariform effect paralyzing effect on voluntary muscle exhibit by the crude extract toxic action blood vessels histamine like effect Tubocurarine Cl salt; white, yellowish white to grayish white, odorless crystalline powder Uses: skeletal muscle relaxant control convulsions of strychnine poisoning and of tetanus adjunct to shock therapy in neuropsyhiatry diagnostic aid in myasthenia gravis

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OPIUM gum opium milky exudate (air-dried) obtained by incising the riped capsule of Papaver somniferum opium poppy – plant source Alkaloids: 1. morphine – 4-12% 2. codeine – 0.8 – 2.5% 3. noscapine (formerly narcotine) – 4- 8% 4. papaverine – 0.5 – 2.5% 5. thebaine – 0.5- 2% 6. meconic acid – 3-5%

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Uses: Stimulant-depressant (first stimulates and then depresses nerve response) analgesic narcotic checks excessive peristalsis miotic Powdered opium used in making Dover’s powder and camphorated opium tincture combined with antidiarrheal preparations Paregoric or camphorated opium tincture antiperistaltic Laudanum, opium tincture, deodorized opium tincture antiperistaltic Maw or poppy seed bluish black or yellowish white contains no significant quantity of alkaloids

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Morphine DIDEHYDROXYEPOXY METHYLMORPHINANDIOL most important of the opium alkaloids narcotic analgesic strongly hypnotic and narcotic induces vomiting, constipation and habit formation structural features CNS acting analgesic: quaternary- central carbon atom with no H substitution a phenyl group or isostere attached to central C atom tertiary nitrogen atom 2 – carbon bridge separating (3) and (1)

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Codeine most widely used opium alkaloid a methylmorphine in which the methyl group replaces the hydrogen of the phenolic hydroxyl group occurs as fine needles or white crystalline powder Uses: Narcotic analgesic Antitussive Sedatives in allaying coughs Less toxic and involves lesser danger of habit formation compared to codeine

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Diacetylmorphine or heroin formed by acetylation of morphine action is similar, yet more pronounced than that of morphine Apomorphine HCl morphine treated with HCl one water molecule is lost emetic; used subcutaneously in cases of poisoning

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Paparavine HCl muscle relaxant antitussive in combination with codeine sulfate Hydromorphone HCl or dihydroxymorphine HCl one of the hydroxyl groups of morphine is replaced by a ketone group; adjacent double bond is removed prepared by reducing morphine in HCl solution with H in the presence of a catalyst powerful narcotic analgesic strongly depresses reeperatory mechanism Hydrocodone bitartrate or dihydrocodeine bitartrate antitussive

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Noscapine commonly called narcotine exists as free base in opium no narcotic properties (anarcotine) antitussive Opioid synthetic morphinelike compounds nonhabit forming others are antitussive

INDOLE ALKALOIDS:

1.Rauwolfia -reserpine -rescinamine -deserpidine 2. Catharanthus (vinca) -vinblastine -vincristine 3. Nux vomica -strychnine -brucine INDOLE ALKALOIDS 4. physostigma -physostigmine 5. Ergot -ergotamine -ergonovine

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Biosynthesis Tryptamine  ajmaline  + Corynanthe-type (monoterpenoid precursor) Serpentine reserpine

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RAUWOLFIA SERPENTINA -dried roots of rauwolfia serpentine ALKALOID SERIES: 1. weakly basic indole alkaloids -reserpine } -rescinamine } PRINcipal alkaloids -desperidine } -8-yohimbine -reserpiline 2.indoline alkaloids of intermediate basicity -ajmaline } -isoajmaline } NO TRANQUILIZING EFFECT -rauwolfinine } 3.strong anhydronium bases -serpentine -serpentinine -alstonine

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USES -hypotensive PACKAGING & STORING must be packaged and stored in a well-closed container in a cool,dry place that is secure against insect attack. RESERPINE – is the chief alkaloid and has a strong hypotensive and sedative activity - white or pale buff to slightly yellow crystalline powder; darkens slowly when exposed to light USES: antihypertensive and tranquilizer

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RESCINNAMINE Methyl reserpate ester of 3,4,5-trimethoxy cinnamic acid Uses: antihypertensive DESERPIDINE: -is an alkaloid from roots of Rauwolfia canescens -11-desmethoxyreserpine USES: -antihypertensive -tranquilizer

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CATHARANTHUS -vinca and periwinkle -dried whole plant of catharanthus rosea -have anticancer potential ALKALOIDS: -ajmalicine,tetrahydroalstonine,serpentine,lochnerine U.S ADOPTED DRUG NAMES Scientific name -Vinblastine Vincaleukoblastine(VLB) -Vinleurosine leurosine -Vinrosidine leurosidine -vincristine leuocristine(LC) = posses demonstrable ancolytic activity

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VINBLASTINE SULFATE -antineoplastic -recommended for generalized Hodgkin’s disease,lymphocytic lymphoma,histiocytic lymphoma,mycosis fungoides,advanced testicular carcinoma,kaposi’s sarcoma,and choriocarcinoma and breast cancer unresponsive to other therapies. VINCRISTINE SULFATE treatment for acute leukemia combination therapy in Hodgkin’s disease,lymphosarcoma,reticulum sarcoma,rhabdomyosarcoma,neuroblastoma,and Wilma’s tumor. VINDESINE -semisynthetic derivative of vinblastine

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NUX VOMICA dried ripe seed of strychnos nux vomica ALKALOIDS; -strychnine -brucine USES: Serve as a commercial source of strychnine and brucine STRYCHNINE: -extremely toxic -CNS stimulant -blocks inhibitory spinal impulses at the postsynaptic level. -results in tonic convulsion USES: vermine killer

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BRUCINE -less toxic -alcohol denaturant PHYSOSTIGMINE -physostigma or calabar bean or ordeal bean -dried ripe seed of physostigma venenosum Alkaloids: -physostigmine(eserine) -eseramine -geneserine -physovenine Physostigmine or eserine -acquires red tint when exposed to heat, light, air or metal

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Uses: -reversible inhibitor of cholinesterase -enhances effects of achetylcholine -used in open-angle glaucoma,decreases intraocular pressure PHYSOSTIGMINE SALICYLATE OR ESERPINE SALICYLATE -it is a white powdered that also acquires a red tint when exposed to the conditions described under physostigmine. -cholinergic (ophthalmic) -IV antidote for poisoning caused by anticholinergic PHYSOSTIGMINE SULFATE -cholinergic -applied topically to conjunctiva -white microcrystalline powder is deliquescent in moist air and acquires the red tint previously described.

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ERGOT -rye ergot or secale cornutum Dried sclerotium of claviceps purpurea developed on plants of rye -not less than 0.15% alkaloids (ergotoxine) -0.01% water soluble (ergonovine) Spurred eye- common name of the drug Mycellium-mass of tissue formed with the hyphae 1.sphacelial stage- asexual stage of the ergot fungi where the spores are being transferred from one plant to the other by insects in honeydew Sclerotium-resting body, hardened ovary 2.ascigerous stage-sexual stage -production of sexual spores or ascospores

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Ergotism-outbreak in old times before moderns agriculture practices a. in France- gangrene -restricted blood flow due to vasoconstricting action of alkaloids -previously called ST.ANTHONY’s FIRE b. in Rhine and Germany- convulsion constituents of ergot: 1.ergonovine-most important 2.ergotoxine- 3.ergoloxine-ergoristine + ergokryptine + ergocornine Lysergic acid-precursor of medicinal useful alkaloids from ergot Derivatives of isolysergic acid-physiologically inert Histamine and tyramine- contribute to physiologic activity of crude drug USES: oxytocic properties

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ERGONOVINE MALEATE OR ERGOMETRINE MALEATE -white or faintly yellow,coloress ,microcrystalline powder Ergobasine- Switzerland -first isolation Uses: oxytocic vasoconstrictor Ergometrinine-isolysergic acid isomer of ergonovine METHLYERGONOVINE MALEATE -semisynthetic homolog of ergonovine -lysergic acid + 2-aminobutanol -white to pinkish tan,microcrystalline powder Uses; oxytocic slightly more active and longer than ergonovine

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ERGOTAMINE TARTRATE -specific analgesic in treatment of migrain by reducing extracranial blood flow and decreases the amplitude of pulsations -enhanced by caffeine HYDROERGOTAMINE MESYLATE -semisynthetic alkaloid ergotamine by hydrogenation -migraine treatment, more effective and tolerated compared to ergotamine ERGOTOXINE -mixture of alkaloid ergocristine ergokyptine ergocornine -formely employed as ergotoxine extranisulfunate Ergoloid-methanisulfonate -for elderly patients -vasorelaxant,increased cerebral blood flow lower BP and causes bradycardia

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METHYsergide maleate -semisynthesized from lysergic acid -serotonin antagonist -for prophylaxis of vascular headache LYSERGIC ACID DIETHYLAMIDE (LSD) produces a predominant central sympathetic stimulation to parallel slight depression most active and specific psychotomemitic agent drugs related to ergot: Ololiuqui -ancient ajtec hallucinogec drug -from seed of rovea corymbosa ipomomea spp and arygyreia

IMIDAZOLE ALKALOIDS:

contain imidazole (glyoxaline) rings PILOCARPINE PILOCARPUS AKA jaborandi Consists of leaflets of: Pilocarpus jaborandi Holmes Pilocarpus microphyllus Stapf Pilocarpus pinatifolius Lamaire Indigenous to Brazil IMIDAZOLE ALKALOIDS

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PILOCARPINE the lactone of pilocarpic acid, an acid with a glyoxaline nucleus Oily, syrupy liquid, though its salts crystallize easily May be obtained by treating the powdered leaves with sodium carbonate Extracting with benzene Shaking the benzene extract with dilute hydrochloric or nitric acid Aqueous solution is made alkaline and shaken with chloroform The chloroform is shaken with acid The alkaloidal salt is allowed to crystallize.

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PILOCARPINE MOA: It directly stimulates the muscarinic receptors in the eye, causing constriction of the pupil and contraction of the ciliary muscle. In narrow-angle glaucoma Miosis opens the anterior chamber angle to improve the outflow of aqueous humor. In chronic open-angle glaucoma The increase in outflow is independent of the miotic effect. Contraction of the ciliary muscle enhances the outflow of aqeous humor via indirect effects on the trabecular system.

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PILOCARPINE Salts Pilocarpine hydrochloride - crystals of the hydrochloride of Pilocarpine Colorless Translucent Odorless faintly bitter Hygroscopic Pilocarpine nitrate – crystals of the nitrate of Pilocarpine Shiny White Stable in air Light-sensitive

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Uses: Ophthalmic drugs for treatment of galucoma Applied topically Dosage: 0.05-0.1mL of a 0.25 to 10% solution of Pilocarpine hyrdochloride OR 0.05-0.1mL of a 0.5 to 6% solution of Pilocarpine nitrate Applied to the conjunctiva, 1-6x a day  Patients should be advised to wash hands immediately after application.

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Isopto-carpine® Pilocar®

STEROIDAL ALKALOIDS:

Characterized by the cyclopentanophenanthrene nucleus either formed from cholesterol or have a common precursor with cholesterol VERATRUM VIRIDE AKA American hellebore or green hellebore Veratum: “vere” = truly, “ater” = black Viride = green Consists of the dried rhizome and roots of Veratum viride Alton STEROIDAL ALKALOIDS

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VERATRUM VIRIDE Grows in wet meadows in the mountainous section of New England and the Eastern United States, North Carolina, Tennessee, and northern Georgia Veratum: “vere” = truly, “ater” = black Obtained by: digging the rhizomes Cleaning Cutting longitudinally drying

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VERATRUM VIRIDE Contains a large no. of alkaloids customarily classified in 3 groups, with their chemical constituents as basis. Group 1 Group 2 Group 3 consists of esters of the steroidal bases ( alkamines ) with organic acids consists of lucosides of of the alkamines Consists of t he alkamines Includes: Cevadine Germidine Germitrine Neogermitrine Neoprotoveratrine Protoveratrine Veratridine Includes: Pseudojervine Veratrosine Includes: Germine Jervine Rubijervine veratramine The ester alkaloids, germidine and germitrine are probably the most important therapeutically.

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VERATRUM VIRIDE Uses: Antihypertensive Small doses principally affect blood pressure without notably changing respiratory or cardiac rate Cardiac-depressant In tincture form Sedative Insecticide VERATRUM ALBUM AKA European hellebore or white hellebore Indigenous to central and southern Europe Similar in appearance and structure with V. viride , though its external color is lighter

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VERATRUM ALBUM Contains a complex mixture of ester alkaloids, grycoalkaloids, and alkamines similar to those occuring in V. viride . Ester alkaloids protoveratrine A and protoveratrine B are the most active Upon hydrolysis, both yield protoverine, acetic acid, methylbutyric acid, and methylhydroxybutyric acid (in protoveratrine A) or methyldihydroxybutyric acid (in protoveratrine B) Uses: Antihypertensive Insecticide

ALKALOIDAL AMINES:

Do not contain heterocyclic nitrogen atoms Mostly are simple derivatives of phenylethylamine EPHEDRINE AKA (-)-erythro- α -[1(methyl-amino)ethyl]benzyl alcohol Obtained from Ephedra or ma huang ( Ephedra sinica Stapf) “ma”=astringent, “huang”=yellow Used as a medicine in China for more than 5000 years ALKALOIDAL AMINES

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EPHEDRINE Produced commercially by: Extraction of the plant material Chemical procedure involving a reductive condensation between L-1-phenyl-1-acetylcarbinol and methylamine Occurs as white, rosette or needle crystals, or as an unctuous mass Soluble in water, alcohol, chloroform, ether, and liquid petrolatum Melts between 33 and 40 0 C, depending on its water content

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EPHEDRINE Uses: Sympathomimetic (stimulates α , β 1, & β 2 adrenergic receptors) Salts Ephedrine Sulfate – crystals of the sulfate of Ephedrine Fine, white, odorless Darkens when exposed to light Used to combat hypotensive states, for allergic disorders, and for nasal decongestion Usual dose is: 25-50mg, 6-8x a day as necessary (oral & parenteral) 0.1-0.15mL of a 1-3% solution, 2-3x a day (intranasal) Readily soluble in water and in hot alcohol but not in ether

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EPHEDRINE Ephedrine hydrochloride – crystals of the hydrochloride of Ephedrine Fine, white, odorless Affected by light Used as a symphatomimetic Usual dose is 25-50mg, every 3-4 hrs Readily soluble in water and in hot alcohol but not in ether

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Dainite KI, Quadrinal, Tedral, Bronkotabs, Bronkaid

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COLCHICINE - extracted from plants belonging to the Colchicum genus - has one amino nitrogen atom - lacks pronounced basicity and does not form a well-defined series of salts - pale yellow, amorphous scales or powder that gradually turns darker when exposed to light - soluble in water and ether; freely soluble in alcohol and chloroform - inhibits leukocyte migration and reduces lactic acid production by leukocytes, resulting in a decreased deposition of uric acid - causes reduction in phagocytosis which decreases inflammatory response Colchicum seed - dried, ripe seed of C. autumnale Colchicum corm – dried corm (stalk) of C. autumnale

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Use: -suppressant for gout Dosage: -500-650µg, 1-3x a day (oral) -500µg-1mg, 1-2x a day (intravenous)

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KHAT AKA Abyssinian tea Extracted from the fresh leaves of Catha edulis Considered narcotic in France Contains a potent phenylalkylamine alkaloid called (-)-cathinone. properties and potency analogous to those of amphetamine MOA: Induction of catecholamine release from storage sites

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PEYOTE AKA mescal buttons Extracted from dried tops of Lophophora williamsii Disturbs normal mental function and causes concomitant hallucinations and euphoria Ingestion results in mydriasis, accompanied by unusual and bizarre color perception Alkaloids: Mescaline (most active) Anhalanine Anhalamine Anhalidine Mescaline first of a series of hallucinogens or psychotomimetics used in psychiatry

PURINE BASES:

Derivatives of a heterocyclic nucleus consisting of the 6-memebered pyrimidine ring fused to the 5-membered imidazole ring Does not occur in nature, but numerous derivatices are biologically significant Xanthine – source of the most important purine bases eg caffeine (1,3,7-trimethylxanthine), theophylline (1,3-dimethylxanthine), & theobromine (3,7-dimethylxanthine) MOA: The methylxanthines competitively inhibit phosphodiesterase, which results in an increase of cyclic adenosine monophosphate with a subsequent release of endogenous epinephrine. This results in a direct relaxation of the smooth muscles of the bronchi and pulmonary vessels, a stimulation of the CNS, an induction of diuresis, an increase in gastric acid secretion, an inhibition of uterine contractions, and a weak positive inotropic effect on the heart. PURINE BASES

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Caffeine-containing drugs Kola AKA cola or kolanuts Dried cotyledon of Cola nitida or other sp. of Cola Yields not less than 1% of anhydrous caffeine Impt. because of its caffeine content and flavor Contains up to 3.5% caffeine, and less than 1% theobromine Bound to the tannin kolacatechin in fresh nuts Uses: Stimulant Ingredient in several carbonated beverages

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Coffee bean AKA coffee seed Dried, ripe seed of Coffea arabica or C. liberica Contains about 1-2% caffeine, 0.25% trigonelline, 3-5% tannin, about 15% glucose and dextrin, 10-13% fatty oil (mainly olein and palmitin), and 10-13% proteins. Roasted coffee – coffee roasted until it acquires a dark brown color and develops the characteristic aroma Caffeol – oil that causes the aroma - consists about 50% furfurol with traces of valerianic acid, phenol, and pyridine -produced during the roasting process

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Decaffeinated coffee – prep. by extracting the most of the caffeine from the coffee bean, yet retaining the pleasant characteristic aroma -contain up to 0.08% caffeine Methods of freeing the seeds from the parchmentlike endocarp: The fruits are allowed to dry and are then broken The wet method in which the sarcocarp is removed by means of a machine, and the 2 seeds with the parchmentlike endocarp are allowed to dry in such a manner as to undergo a fermentation. After drying, the endocarp is removed.

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Caffeine content comparison: A cup of brewed coffee : 100-150mg instant coffee : 85-100mg tea: 60-75mg cocoa: 5-40mg 12oz cola drink: 40-60mg Est. max. daily dose: 1.5g Uses: Dietetic Stimulant Diuretic

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Guarana Dried paste composed chiefly of the crushed seed of Paullinia cupana Contains 2.5-5% caffeine, and 25% cathechutannic acid Uses: Stimulant Astringent Maté AKA Paraguay tea Consists of the leaves of Ilex paraguariensis Contains 2% caffeine and tannin Uses: Stimulant Laxative/purgative Diaphoretic Diuretic

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Caffeine 1,3,7-trimethylxanthine Usually prep. from tea, tea dust, or tea sweeping, or recovered from coffee roasters Anhydrous or contains 1 molecule of water of hydration White powder or white glistening neededs matted together in fleecy masses Bitter May be sublimed without decomposition when heated Uses: CNS stimulant Caffeine and sodium benzoate for IM inj. as an analeptic in the treatment of poisoning Stimulant in acute circulatory failure diuretic

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Tea AKA thea Consists of leaves and leaf buds of Camellia sinensis Occurs as more or less crumpled, bright green or blackish green masses Smells agreeable and aromatic Tastes pleasantly astringent and bitter Contains 1-4% caffeine (theine) and small amounts of adenine, theobromine, theophylline, and xanthine Green tea – prep. by rapidly drying the freshly-picked leaves in copper pans over a mild artificial heat. The leaves are often rolled in the palm of the hand as they dry. Black tea – prep. by heaping the fresh leaves until fermentation has begun. They are then rapidly dried artificially with heat. Uses: Stimulant (due to caffeine) Astringent (due to the tannin)

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Theophylline Isomeric with theobromine White, odorless, bitter crystalline powder Soluble in about 120 parts of water, rendered more soluble in basic compounds Uses: Smooth muscle relaxants for the symptomatic relief or prevention of bronchial asthma and treatment of reversible bronchospasm associated with chronic bronchitis and emphysema Diuretic Aminophylline - valuable diuretic - exhibits dilating action on the pulmonary vessels in relieving asthma and can lower venous pressure in certain cases of heart failure

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Theobromine 3,7-dimethylxanthine Prep from the dried, ripe seed of Theobroma cacao White, crystalline powder with bitter taste and sublimes at about 260 0 C. Uses: Diuretic Smooth muscle relaxant Preferred over caffeine in the treatment of cardiac edema and angina pectoris, since it has little stimulant action

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