pcog alkaloids

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ALKALOIDS

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103 Terms

1

ALKALOIDS

  • One or more rings of carbon atoms, usually with a nitrogen atom in the ring

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Characteristics of alkaloids

  • MOST ALKALOIDS ARE CRYSTALLINE SOLIDS

  • COLORLESS

  • SOLUBLE IN ORGANIC SOLVENTS AND INSOLUBLE IN WATER

  • BITTER IN TASTE

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Crystaline solid

  • Conine

  • Nicotinr

  • Spartene

  • Liquid alkaloid

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Yellow alkaloids

  • Colchicine

  • Berberine

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Methyl Red Alkaloids

  • salt of saguinarine

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Function

  • Source of nitrogen

  • Final products of detoxification

  • Growth regulators

  • Protection

  • Source of energy

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TRUE ALKALOIDS

  • from amino acid and they share a heterocyclic ring with nitrogen

  • Potent

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TRUE ALKALOIDS examples

  • Cocaine

  • Quinine

  • Dopamine

  • Morphine

  • Atropine.

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PROTOALKALOIDS

  • which the N atom derive from an amino acid is not a part of the heterocyclic

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PROTOALKALOIDS Examples

  • ephedrine

  • Mescaline

  • Yohimbine

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PSEUDOALKALOIDS

  • not derived from amino acids but have nitrogen in a heterocyclic ring.

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PSEUDOALKALOIDS Examples

  • Caffeine

  • Theobromine

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PYRIDINE- PIPERIDINE

  • from the amino acid Lysine/Ornithine

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Tobacco

  • sc: Nicotiana tobacum

  • fam: Solanaceae

  • cons: Nicotine

  • use: CNS stimulant, ganglionic (nicotinic) cholinergic receptor agonist, and smoking deterrent (Nicorette®)

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Nicorette

  • product temporary nicotine

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ARECA/ARECA NUT/BETEL NUT

  • sc: Areca catechu

  • fam: Arecaceae

  • cons: Arecoline, arecaidine, and guvacoline

  • use: Vermicide and taenifuge

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Areca Masticatory stimulant

  • agents salivation

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LOBELIA/INDIAN TOBACCO

  • sc: Lobelia inflata

  • fam: Lobeliaceae

  • cons: Lobeline

  • use: CNS stimulant, ganglionic (nicotinic) cholinergic receptor agonist, and smoking deterrent

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TROPANE

  • A dicyclic compound formed by the condensation of a pyrolidine precursor (ornithine)

  • 3 acetate derived carbon atoms

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BELLADONNA/DEADLY NIGHTSHADE

  • sc: Atropa belladonna

  • fam: Solanaceae

  • cons: Atropine

  • use: Parasympathetic depressant, Anticholinergic properties, Antidote for cholinesterase inhibitors, antisialogogue

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HYOSCYAMUS/HENBANE

  • sc: Hyoscyamus niger

  • Hyoscyamus muticus (Egyptian henbane)

  • fam: Solanaceae

  • cons: Hyoscyamine and scopolamine

  • use: treat motion sickness and anticholinergic

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STRAMONIUM/JIMSON WEED/JAMESTOWN WEED

  • sc: Datura stramonium

  • fam: Solanaceae

  • cons: Hyoscyamine and scopolamine

  • use: Anticholinergic and relief of asthma

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WITHANIA

  • sc: Withania somnifera

  • fam: Solanaceae

  • cons: Tropine and pseudotropine

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DUBOISIA

  • sc: Duboisia myoporoides

  • fam: Solanaceae

  • cons: Hyoscyamine and scopolamine

  • use: Treatment of motion sickness, stomach disorder, side effects of cancer therapy, and antispasmodic

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MANDRAGORA/EUROPEAN MANDRAKE

  • sc: Mandragora officinarum

  • fam: Solanaceae

  • cons: Hyoscyamine, scopolamine, and mandragorin

  • use: Emetic

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Mandragorin

  • Elicit emetic property

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COCA/DIVINE PLANT OF INCAS

  • sc: Erythroxylon coca

  • fam: Erythroxylaceae

  • cons: Cocaine, cinnamylocaine, and α- and βtruxilline

  • use: local anesthetic, psychomotor stimulant, analgesic, and ingredient in Brompton's cocktail

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Brompton's cocktail

  • Cocaine

  • Morphine/ Methadone

  • analgesic for terminal ill px - cancer

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QUINOLINE

  • Alkaloids containing quinoline as their basic nucleus obtained from cinchona.

  • Tryptophan is a precursor of quinine in cinchona

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CINCHONA/CINCHONA BARK/PERUVIAN BARK

  • sc: Cinchona succirubra

    • Cinchona ledgeriana (Howard)

    • Cinchona calisaya

  • fam: Rubiaceae

  • cons: quinine

    • quinidine

    • chonine

    • cinchonidine

  • use: Malaria and to treat various cardiac arrhythmias

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Cinchonism

  • overdose toxicity

  • hallmark

  • tinnitus

    • temporary loss of hearing and impaired sight

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CUPREA BARK

  • sc: Remijia purdieana /pedunculata

  • fam: Rubiaceae

  • cons: Quinidine

  • use: Cardiac depressant

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ISOQUINOLINE

  • largest single group of plant alkaloids.

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Exhibit a phenanthrene nucleus

  • Morphine, codeine, thebaine

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Sanguinaria

  • another member of the Papaveraceae

  • contains isoquinoline alkaloids

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IPECAC

  • sc: Cephaelis ipecacanhua

  • fam: Rubiaceae

  • cons: emetine, cephaeline, and psychotrine

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USES OF IPECAC

  • Emetic

  • Dover's powder (Ipecac mixed with opium) acts as a diaphoretic

    • Post poison emetic property

  • Ipecac syrup should not be confused with ipecac fluidextract, which is 14 times stronger

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EMELINE OR METHYLCEPHAELIN

  • obtained from ipecac or prepared synthetically by methylation of cephaeline

  • not orally

  • it can cause nausea and vomiting

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EMETINE HYDROCHLORIDE

  • salt form

  • Antiamebic

    • amebic dysenttery

  • antiprotozoan

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HYDRASTIS/GOLDENSEAL

  • sc: Hydrastis canadensis

  • fam: Ranunculaceae

  • cons: hydrastine, berberine, and canadine

  • use: astringents in inflammation of the mucous membranes (125mg)

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SANGUINARIA/BLOOD ROOT

  • sc: Sanguinaria canadensis

  • fam: Papaveraceae

  • cons: sanguinarine

  • use: stimulating expectorant and emetic properties

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CURARE/SOUTH AMERICAN ARROW POISON

  • sc: Strychnus castelnaei

  • fam: Loganiaceae

  • cons: tubocurarine

  • use: skeletal muscle relaxant and a diagnostic aid in myasthenia gravis.

  • Assay: by the head drop cross over test in rabbits (ear)

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Head drop rabbit

  • curare

  • ear rabbit

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OPIUM/GUM OPIUM

  • sc: Papaver somniferum

  • fam: Papaveraceae

  • cons: morphine, codeine, noscapine, papaverine, and thebaine

  • use: analgesic and hypnotic and a narcotic and checks excessive peristalsis and contracts the pupil of the eye

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POWDERED OPIUM

  • products obtained from ipecac

  • making Dover's powder and camphorated opium tincture and is combined with other agents in antidiarrheal preparations.

  • analgesic

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PAREGORIC/CAMPHORATED OPIUM TINCTURE

  • products obtained from ipecac

  • Antiperistaltic

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LAUDANUM, OPIUM TINCTURE, OR DEODORIZED OPIUM TINCTURE

  • products obtained from ipecac

  • Antiperistaltic

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POPPY SEED/MAW SEED

  • products obtained from ipecac

  • Parenteral formulations

  • Salad dressings

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OPIATES

  • natural occuring

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MORPHINE

  • OPIATES

  • Most important

  • Narcotic analgesic

  • Strongly hypnotic

  • Induce nausea, vomiting, constipation, and habit formation.

  • addictive

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CODEINE

  • OPIATES

  • Most widely used

  • Methylmorphine

  • Obtained from methylation of morphine

  • Narcotic analgesics

  • Antitussives (10- 20 mg Q4 prn)

  • Sedative

  • Analgesic(15- 60mg Q4 prn)

  • Less toxic and involves much less danger of habit formation.

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NOSCAPINE

  • OPIATES

  • narcotine/anarcotine

  • Antitussive.

  • The usual dose is 15 mg, up to 4 times a day

  • available in syrup and chewable tablets

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PAPAVERINE

  • OPIATES

  • Smooth muscle relaxant

  • Antitussive in combination with codeine (15mg)

  • oral 150 mg

  • IM 30 mg

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OPIOIDS

  • synthetic

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HEROIN

  • OPIOIDS

  • Diacetylmorphine

  • Formed by the acetylation of morphine

  • Increased danger of habit formation, very potent.

  • most addictive

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HYDROMORPHONE

  • OPIOIDS

  • Dihydromorphinone hydrochloride

  • Powerful narcotic analgesic

  • tends to strongly depress the respiratory mechanism

  • Less frequent SE (constipation

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HYDROCODONE BITARTRATE

  • OPIOIDS

  • dihydrocodeinone bitartrate

  • Bears the same relation to codeine as dihydromorphinone does to morphine

  • Antitussive

    • excellent troublesome cough

    • 5-10mg 3-4x a day

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APOMORPHINE

  • OPIOIDS

  • Condensation of morphine + HCl and one molecule of water is lost

  • Emetic

    • 100mg/ 1 kg

    • max 6g

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INDOLE

  • amino acid tryptophan (serotonin)

  • Some indole alkaloids don’t come from the amino acid tryptophan it is believe that non tryptophan portions of the alkaloids are derived from the monoterpenoid precursor

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RAUWOLFIA SERPENTINA

  • sc: Rauwolfia serpentina

  • fam: Apocynaceae

  • cons: reserpine

  • use: Treatment of snakebites to insanity, antihypertensive and tranquilizer

    • Mood swings

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CATHARANTHUS/VINCA

  • sc: Catharanthus roseus

  • fam: Apocynaceae

  • cons: vinblastine, vinleurosine, vinrosidine and vincristine

  • use: Antineoplastic

    • anticancer

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VINBLASTINE SULFATE

  • ALKALOIDS OF CATHARANTHUS

  • Hodgkin's disease

  • lymphocytic lymphoma

  • histiocytic lymphoma

  • mycosis fungoides

  • advanced testicular carcinoma, Kaposi's sarcoma

  • and choriocarcinoma, and breast cancer unresponsive to other therapies.

  • 2nd line

  • effective in single dose

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VINCRISTINE SULFATE

  • n-formly

  • Acute leukemia and in combination therapy in Hodgkin's disease, lvmphosarcoma, reticulum cell sarcoma, rhabdomyosarcorna, neuroblastoma, and Wilms' tumor.

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YOHIMBINE

  • sc: Pausinystalia yohimbe

  • fam: Rubiaceae

  • cons: yohimbine

  • use: Treatment of impotence/erectile dysfunction, aphrodisiac

    • alpha 2 antagonist

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NUX VOMICA

  • sc: Strychnos nux-vomica

    • Strychnos ignatii Bergius (St. Ignatius bean)

  • fam: Loganiaceae

  • cons: strychnine and brucine

  • use: Brucine - alcohol denaturant

  • Strychnine - toxic central stimulant

    • excite all parts of the CNS- block post synaptic inhibitory spinal impulse

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PHYSOSTIGMINE/CALABAR BEAN/ORDEAL BEAN

  • sc: Physostigma venenosum

  • fam: Fabaceae

  • cons: physostigmine, eseramine, geneserine, and physovenine

  • use: glaucoma, and inhibits acetylcholinesterase

    • decrease iop increase outflow

    • myasthenia gravis

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ERGOT/RYE ERGOT/SECALE CORNUTUM

  • sc: Secale cereale

  • fam: Clavicipitaceae

  • cons: ergotamine

    • treatment for migraine

  • use: oxytocic properties

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ERGONOVINE MALEATE

  • ERGOT ALKALOIDS

  • Ergometrine maleate (labor)

  • An oxytocic and produces much faster stimulation of the uterine muscles than do other ergot alkaloids

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Methylergonovine maleate

  • ERGOT ALKALOIDS

  • Semisynthetic homolog of ergonovine

  • Oxytocic lightly more active and longer acting than ergonovine

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ERGOTAMINE TARTRATE

  • ERGOT ALKALOIDS

  • Specific analgesic in treatment of migraine

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METHYLSERGIDE MALEATE

  • ERGOT ALKALOIDS

  • Prophylaxis of vascular headache

  • salt of methyl ergotrovine

  • prophylaxis for headache

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LYSERGIC ACID DIETHYLAMIDE/LSD

  • ERGOT ALKALOIDS

  • Most active and most specific psychomimetic drug

  • Hallucinogenic agent

  • Dangerous

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IMIDAZOLE

  • Monoacidic tertiary base containing a lactone group as well as the imidazole nucleus

  • histidine

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PILOCARPUS/JABORANDI

  • sc: Pilocarpus jaborandi

  • fam: Rutaceae

  • cons: pilocarpine

  • use: Narrow-angle glaucoma • Pilocarpine nitrate and Pilocarpine hydrochloride

  • opens the anterior chamber angle to improve the outflow - miosis

  • eyedrops

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STEROIDAL

  • cyclopentanophenanthrene nucleus

  • They apparently are either formed from cholesterol, or they and cholesterol have a common precursor

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GREEN HELLEBORE/AMERICAN HELLEBORE

  • sc: Veratrum viride

  • fam: Liliaceae

  • cons: veratrosine, veratrine, and veratridine

  • use: hypotensive, cardiacdepressant, and sedative properties

    • decrease contraction - inotropy

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WHITE HELLEBORE/EUROPEAN HELLEBORE

  • sc: Veratrum album

  • fam: Liliaceae

  • cons: protoveratrine A and B

  • use: insecticide

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ALKALOIDAL AMINES

  • do not contain heterocyclic nitrogen atoms.

  • Derivatives of phenylethvlamin and derived from the common amino acids, phenylalanine or tyrosine

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EPHEDRA/ MA HUANG

  • sc: Ephedra sinica

  • fam: Gnetaceae

  • cons: Ephedrine

  • use: Nasal decongestant, bronchodilator

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COLCHICINE

  • sc: Colchicum autumnale

  • fam: Liliaceae

  • cons: Colchicine

  • use: suppressant for gout

    • uric

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KHAT/ABYSSINIAN TEA

  • sc: Catha edulis

  • fam: Celastraceae

  • cons: cathinone

  • use: mimic methamphetamine

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PEYOTE/MESCAL BUTTONS

  • sc: Lophophora williamsii (Lemaire)

  • fam: Cactaceae

  • cons: mescaline

  • use: Hallucinogenic & euphoric agent

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PURINE

  • heterocyclic nucleus consisting of the 6-membered pyrimidine ring fused to the 5-membered imidazole ring.

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CAFFEINE

  • 1,3,7-trimethylxanthine

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THEOPHYLLINE (neo)

  • 1,3- dimethylxanthine

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THEOBROMINE

  • 3,7-dimethylxanthine

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KOLA/COLA/KOLANUTS

  • sc: Cola nitida

  • fam: Sterculiaceae

  • cons: caffeine and theobromine

  • use: ingredient in carbonated drinks stimulant

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COFFEE BEAN/COFFEE

  • sc: Coffea arabica

  • fam: Rubiaceae

  • cons: caffeine and theobromine

  • use:dietetic, stimulant, and a diuretic, and CNS poisoning

  • Decaffeinated coffee is prepared by extracting most of the caffeine from the coffee bean

  • aroma of caffeine - caffeol

  • usual cup (100mg - 150mg)

  • max- 1.5g daily dose

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THEA/TEA

  • sc: Camelia sinensis

  • fam: Theaceae

  • cons: theophylline

  • use: : bronchial asthma

  • Aminophylline

    • reversible broncho spasm associated with chronic bronchitis emphysenia (COPD)

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THEOBROMINE

  • sc: Theobroma cacao

  • fam: Sterculiaceae

  • cons: theobromine

  • use: diuretic and a smooth muscle relaxant

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METHOD I

  • powder is treated with alkalis to liberate the free bases that can then be extracted with water immiscible organic solvents

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METHOD II

  • powdered material is extracted with water or aqueous alcohol containing dilute acids.

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METHOD III

  • powder is extracted with water soluble organic solvents which are good solvents for both salts and free bases

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Wagners Test (WIKI)

  • reagent: Potassium Triiodide

  • res: reddish-brown precipitate

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Mayers Test (MANEKI)

  • reagent: Potassium-Mercuric Iodide

  • res: creamy-white precipitate

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Valsers Test

  • reagent: Mercuric iodide

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Dragendorff Test (Dr. KBIO)

  • reagent: Potassium bismuth iodide

  • res: Orangish red colour

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Bouchdart Test

  • reagent: Iodine in KI, most sensitive

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Marme Test

  • reagent: Potassium cadmium iodide

  • res: White precipitate

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Sonnencheim Test ( SON in PMA)

  • reagent: Phosphomolybdic acid

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