Trans-Pcog-Alkaloids PDF

VOLATILE OILS – PCOG LEC ALKALOIDS Alkaloidal Reagents Alkaloids Mayer’s Potassium mercuric Iodide Cream ppt...

VOLATILE OILS – PCOG LEC ALKALOIDS Alkaloidal Reagents Alkaloids Mayer’s Potassium mercuric Iodide Cream ppt Alkaline Potassium mercuric Basic nitrogenous plant cons)tuent – physiologically ac)ve Nessler’s Brown ppt Iodide - Most of them ends with “-ine” Reddish brown Wagner’s Iodine in KI Nomenclature ppt Generic Name Hydrasta)ne and Atropine Bouchardat’s Iodine in KI Brown ppt Specific Name Cocaine and Belladonine Reddish brown Common Name Ergotamine Dragendorff’s Potassium Bismuth Iodide ppt Physiologic AcCvity Eme)ne and Morphine Valser’s Mercuric Iodide White ppt Discoverer Pelle)ne All Alkaloids are solid except: Marmer’s Potassium Cadmium Iodide White ppt 1. Coniine Sonnenschein’s Phosphomolybdic Acid Ppt - Poison hemlock – Conium maculatum 2. Arecoline Scheiber’s Phosphotungs?c Acid Ppt - Betel nut – Areca catechu Hager’s Picric Acid Yellow ppt 3. NicoCne - Tobacco – Nico1ana tabacum Gold Ppt 4. Sparteine Compounds Can precipitate Proteins, Ppt - Scotch broom – Cys1cus coparius Tannic Acid Alkaloids, and Glycosides - Lupin – Lupinus mutabilis Ppt Ecolle’s Chemical Structure Heterocyclic Non-Heterocyclic Note: Methylxanthines does not react with alkaloidal reagents Typical Atypical Has N-ring No N-ring Biosynthesis of Alkaloids Divided based on Ring Biological Amines (Epinephrin Pyridine-Piperidine Ornithine System & Norepinephrine) Tropane or Solanaceous Tropic acid, Phenylalanine, Ornithine with 3-acetate ExtracCon of Alkaloids derived carbon Quinoline (W) Tryptophan A. Process A Isoquinoline (Y) Tyrosine - Acid Treated Imidazole His)dine - Treated with lime to neutralize acids and phenolics Steroidal CPPP and liberate free base Indole (W) Tryptophan - Free base is extracted with petroleum ether Alkaloidal amines Phenylalanine, (Y) Tyrosine, - Treated with aqueous acid to precipitate the free (W) Tryptophan base as salts Purine or Glycine, Glutamine, B. Process B Methylxanthines Asparagine, CO2, - Base Treated Tetrahydrofolate - Treated with aqueous acids - Other components are removed by chloroform - Treated with base (NaHCO3/Na2CO3/ NH3) to liberate free-base Espinosa, Ayee | 2B VOLATILE OILS – PCOG LEC 1 Pyridine-Piperidine 2 Tropane 3 Quinoline 1. Areca or Betel Nut 1. Belladona or Deadly Nightshade 1. Cuprea Source: Areca catechu Source: Atropa belladona Source: Remijia purdieana and pedunculata AC: Arecoline AC: Atropine AC: Quinidine (Commercial Source) Use: Anthelminthic 2. Hyoscyamus or Henbane Prepara)on: Punsupari (Areca, Lime, Leaves of Piper 2. Cinchona or Peruvian Bark or Jesuit’s Bark betle) – s)mulant mas)catory Source: Hyoscyamus niger Source: Cinchona succirubra (Red) Cinchona calisya (Yellow) Has a tannin component but reported as a cause of AC: Scopolamine and Hyoscyamine (0.04% alkaloid) AC: Quinidine (An)-arrhythmic) Esophageal Cancer in South Africa and India 3. EgypCan Henbane AC: Quinine (An)malarial for pregnant) Source: Lobelia inflata Analogs: Cinchonine – Quinidine 2. Lobelia and Indian Tobacco AC: Scopolamine and Hyoscyamine (1.5% alkaloid) AnalogsMa: Cinchonidine – Quinine Source: Lobelia inflata Toxicity: Cinchonism AC: Lobeline 4. Stramonium or Jimson/Jamestown Weed Use: CNS S)mulant, Smoking Deterrent (discourage Source: Datura stramonium smoking) AC: Scopolamine and Hyoscyamine Available Brand: Bantron – tablet Talumpay or Thorn Apple - Datura metel 3. Tobacco Vapor is used for asthma treatment Source: Nico1ana tabacum 4. Winthania AC: NicoCne Source: Winthania somnifera Use: CNS S)mulant, Smoking Deterrent (discourage AC: Atropine (Chief source for commercial) smoking) Atropine source before: EgypCan Henbane Available Brand: Nicore[e 5. Duboisia Source: Duboisia myroporoides AC: Atropine (Chief source for commercial) 6. Pituri or Australian Tobacco Source: Duboisia hopwoodii Use: CNS s)mulant 7. Mandragora or European mandrake Source: Mandragora officinarum AC: Mandragorine (Use: Eme)c) Datura fastousa – commercial source of scopolamine 8. Coca or Divine Plant of Incan Huánuco: Erythroxylum coca Peruvian: Erythroxylum spruceanum Truxillo: Erythroxylum novogranatense v. truxillense AC: Cocaine (aka: Crack or Coke) Brompton’s Cocktail – analgesic for cancer pain o Cocaine + Morphine + Chlorpromazine + 90% EtOH Use: Psychomotor s)mulant with a strong abuse poten)al, euphoric, vasoconstrictor, seda)ve Espinosa, Ayee | 2B VOLATILE OILS – PCOG LEC 4 Isoquinoline Opioids 7 Indole Formed from condensa)on of 1. Ipecac Apomorphine morphine with HCI 1. Rauwolfia Brazilian: Cephalis ipecacuanha Use: Eme)c Source: Rauwolfia serpen1na Panama: Cephalis acuminata Heroin or AC: Reserpine – Hypotensive, Tranquilizer, Depressant More pronounced effect than AC: EmeCne or Methylcephaeline Diacetylmorphine Morphine AC: Rescinnamine – Hypotensive Use: Ipecac Syrup – eme)c or Diamorphine AC: Deserpidine – Hypotensive, Lesser Side Effects Use: Ipecac Fluidextract – 14x more potent More potent narco)c analgesic, less Alseroxylon FracCon – basic powdered alkaloidal Hydromorphone Use: Dover’s Powder (Ipecac + Opium) – Diaphore)c cons)pa)ve and habit-forming extract without toxicity in long term use Original use: An)-amoeba Hydrocodone An)tussive 2. Catharanthus or Chichirica or Periwinkle 2. HydrasCs or Golden Seal Opiate Source: Catharanthus roseus (Vinca rosea) Source: Hydras1s canadensis Morphine Analgesic AC: VinblasCne/VincaleukoblasCne – for Hodgkin's AC: HydrasCne and Berberine Codeine or and other lymphomas Analgesic, An)tussive Use: Astringent Methylmorphine AC: Vinleurosine/Leurosine – for lymphosarcoma, Papaverine Smooth muscle relaxant, An)tussive sarcomas, blastomas 3. Sanguinaria or Blood Root Thebaine Precursor of Naloxone AC: Vinrosidine /Leurosidine Source: Sanguinaria canadensis AC: VincrisiCne/LeucocrisCne AC: Sanguinarine 5 Imidazole Use: An)neoplas)c Use: Expectorant and Eme)c 1. Pilocarpus 3. Nux vomica 4. Curare or South American Arrow Poison Pernambuco jaborandi: Pilocarpus jaborandi Source: Styrchnos nuxvomica Source: Styrchnos castelpei, S. toxifera, and Chondrodendo Maranham jaborandi: Pilocarpus microphyllus AC: Strychnine – CNS S)mulant, Vermin Killer, tomentosum Paraguay jaborandi: Pilocarpus pina1folius Neurotronic Research AC: Tubocurarine AC: Pilocarpine AC: Brucine (Dimethoxystrychnine) – Alcohol Types: Calabash – in a gourd Use: Cholinergic for glaucoma (Mio)c), constricts denaturant Types: Tube – in a bamboo ciliary muscles to improve ouilow of aqueous humor Types: Pot – in a clay pot 4. St. IgnaCus Bean or IgnaCa Use: Skeletal muscle relaxant (curariform effect), 6 Steroidal Source: Styrchnos Igna1i an)convulsant in strychnine poisoning AC: Same with Nux vomica Side Effect: Anaphylactoid Reac)on 1. American Hellebore or Green Hellebore Use for commercial source Standardiza)on: Head drop crossover test Source: Veratum viride Animal Test: Rabbit and Rat AC: Group I (Esters of Steroidal Base) 5. Ergot or Rye Ergot or Secale cornutum o Germidine and Germitrine Source: Claviceps purpurea (Parasi)c) C. paspali (Saprophy)c) 5. Opium or Stone of Immortality AC: Group II (Glucosides) Toxicity: Decreases blood into the extremi)es causing Source: Papaver sominferum (Poppy seed/maw seed) o Pseudojervine and Veratrosine a gangrenous ergo)sm (St. Antony’s Fire) From the milky exudate of unripe capsule AC: Group III (Alkamines) AC: Meconic Acid (found only in opium – forms red o Germine, Jervine, Rubijervine, 6. PhysosCgma or Calabar or Esere or Ordeal Bean color with Ferric Chloride) Veratramine Only legal in India Source: Physos1gma venenosum Use: Hypotensive, Cardiac depressant, Insec)cide Powdered opium – 10 to 10.5% morphine AC: PhysosCgmine/Eserine Paregoric – Camphorated O. Tincture – an)-peristal)c 2. European Hellebore or White Hellebore Use: Mio)c Agent Laudanum – Deodorized O. Tincture (an)-peristal)c) Source: Veratum album DOC for atropine and neos)gmine toxicity Sydenham's laudanum – Wine of Opium AC: Same with American Hellebore Toxicity: Cholinergic crisis Use: Hypotensive, Cardiac depressant, Insec)cide An)dote: Atropine Espinosa, Ayee | 2B VOLATILE OILS – PCOG LEC 8 Ergot 10 Purine Alkaloids Ergonovine or Theobromine 3,7-dimethylxanthine Oxytocic Ergometrine Theophylline 1,3-dimethylxanthine Oxytocic Caffeine 1,3,7-trimethylxanthine Methylergonovine (More potent and longer ac)ng) Methysergide Prophylaxis for: Migraine Headache 1. Cola or Kola Nuts Analgesic for migraine with caffeine, Source: Cola ni1da Ergotamine AC: Caffeine, Theobromine, Kolacatechin Vasoconstrictor Dihydroergotamine More potent and longer ac)ng Use: CNS S)mulant Ergotoxine Vasorelaxant Psychomime)c ac)vity, most potent 2. Coffee LSD Source: Coffee arabica var. robusta and liberica hallucinogen AC: Caffeol – Vola)le Oil Present 9 Alkaloidal Amines AC: Caffeine & Trigonelline – CNS s)mulant, inotropic, chronotropic, diure)c 1. Ephedra or Ma Huang Caffeine is bound to chlorogenic acid – releases upon roas)ng Source: Ephedra sinica Decaffeinated Coffee – less than 0.08% caffeine, more AC: Ephedrine expensive 2. Colchicum 3. Mate or Paraguay Tea Source: Colchicum Source: Ilex paraguariensis AC: Colchicine AC: Caffeine and Tannins TX for: Acute Gout Use: Laxa)ve, purga)ve, diure)c diaphore)c, CNS s)mulant, astringent 3. Khat or Abyssinian Tea Source: Cantha edulsis 4. Theobroma, Cacao, Food for the Gods AC: Cathinone Source: Theobroma cacao Use: Alleviate sensa)on of hunger or fa)gue AC: Theobromine Use: CNS s)mulant, smooth muscle relaxant for 4. Peyote or Mescal Buions angina, diure)c for cardiac edema Source: Lophophora williamsi AC: Mescaline (3,4,5-trimethoxy-beta- 5. Tea phenylethylamine) Source: Camelia sinensis Use: Hallucinogen AC: Theophylline and Thein Green Tea – Fresh Leaves, Dried on Mild Heat 5. Psilocybe (China and Japan) Source: Psilocybe mexicana Black Tea – Fermented leaves, dried over rapid heat AC: Psilocybin (India and Lanka) Use: Hallucinogen Use: Bronchodilator and Diure)c Espinosa, Ayee | 2B