pcog alkaloids

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103 Terms

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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