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Alkaloids.Tarek Kakhia.Pdf ADANA UNIVERSTY – INDUSTRY JOINT RESEARCH CENTER ALKALOIDS & ALKALOIDS PLANTS By TAREK ISMAIL KAKHIA 1 2 INDEX Itam Page Itam No 1 - Alkaloids : 1 Alkaloids 2 Atropine 3 Caffeine 4 Cocaine 5 Codaine 6 Heroine 7 Lidocaine 8 Morphin 9 Nicotine 10 Papaverine 11 Solanine 2 - Alkaliod Plants 1 Belladonna 2 Cannabis 3 Cannabis ( Drug ) 4 Cannabis ( Altivation ) 5 Coca 6 Coffee 7 Datura Stramonium 8 Datura 9 Hashish 10 Khat 11 Opium 12 Opium Poppy 3 13 Tea 14 Tobacco 15 Yerba Mate 3 - Alkaliod Plants Time Line 1 Time Line of Cannabis 1 2 Time Line of Cannabis 2 3 Time Line of Coca 4 Time Line of Coffee 5 Time Line of Datura 6 Time Line of Hashish 7 Time Line of Khat 8 Time Line of Poppy & Opium 9 Time Line of Tea 10 Time Line of Tobacco 11 Time Line of Yerba Mat 12 Time Line of 4 - Extension and Supplements 1 Night Shade Alkaloid Toxins Atropine , Scopolamine and Solanine 2 Hyoscyamus Niger 3 Nerium Oleander 4 PART – 1 ALKALOIDS 5 6 Alkaloid Chemical structure of ephedrine, a phenethylamine alkaloid Contents : 1 Introduction 2 Alkaloid Classifications 3 Physicochemical Properties 4 Category : Alkaloids 1 – Introduction : Alkaloids are naturally occurring chemical compounds containing basic nitrogen atoms . The name derives from the word alkaline and was used to describe any nitrogen - containing base. Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals and are part of the group of natural products (also called secondary metabolites ) . Many alkaloids can be purified from crude extracts by acid - base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications, as recreational drugs, or in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine, the stimulant caffeine, nicotine, the analgesic morphine, or the antimalarial drug quinine. Some alkaloids have a bitter taste . Caffeine 7 2 - Alkaloid classifications : The classification of the alkaloids is complex and may be guided by a set of rules that take into account the structure and other chemical features of the alkaloid molecule, its biological origin, as well as the biogenetic origin where known.[2][3] For example, where the biosynthesis pathway of an alkaloid is unknown, it may be grouped based on structural similarities with known compounds, including non-nitrogenous compounds, or by the organism (s) from which the alkaloid was isolated . Pyridine group : piperine , coniine , trigonelline , arecoline , arecaidine , guvacine, cytisine , lobeline , nicotine , anabasine , sparteine , pelletierine . Pyrrolidine group : hygrine , cuscohygrine , nicotine . Tropane group : atropine , cocaine , ecgonine , scopolamine , catuabine . Indolizidine group : senecionine , swainsonine . Quinoline group : quinine , quinidine , dihydroquinine, dihydroquinidine , strychnine , brucine , veratrine , cevadine . Isoquinoline group : opium alkaloids ( papaverine , narcotine , narceine ) , pancratistatin , sanguinarine , hydrastine , berberine , emetine , berbamine , oxyacanthine . Phenanthrene alkaloids : opium alkaloids ( morphine , codeine , thebaine , oripavine ) Phenethylamine group : mescaline , ephedrine , dopamine . 8 Indole group : Tryptamines : serotonin , bufotenine , psilocybin Ergolines : ergine , ergotamine , lysergic acid Beta - carbolines : harmine , harmaline , tetra hydro harmine Yohimbans : reserpine, yohimbine . Vinca alkaloids : vinblastine, vincristine . Kratom) alkaloids : mitragynine , 7- hydroxy mitragynine . Tabernanthe iboga : ibogaine , voacangine , coronaridine . Strychnos nux-vomica : strychnine , brucine . Purine group : Xanthines , caffeine , theobromine , theophylline . Terpenoid group : Aconitum alkaloids : aconitine . Steroid alkaloids : ( containing a steroid skeleton in a nitrogen containing structure) : Solanum alkaloids ( e.g. potato and tomato ) : ( solanidine , solanine , chaconine ) . Veratrum alkaloids : ( veratramine , cyclo pamine , cycloposine , jervine , muldamine ) .. Fire Salamander alkaloids : ( samandarin ) . thers : conessine . Quaternary ammonium compounds : muscarine , choline , neurine . Miscellaneous : capsaicin , cynarin , phytolaccine , phytolaccotoxin . 3 - Physicochemical properties : Low - molecular weight alkaloids without hydrogen bond donors such as hydroxy groups are often liquid at room temperature , examples are nicotine , sparteine , coniine , and phenethylamine . The basicity of alkaloids depends on the lone pairs of electrons on their nitrogen atoms. As organic bases, alkaloids form salts with mineral acids such as hydrochloric acid and sulfuric acid and organic acids such as tartaric acid or maleic acid. These salts are usually more water-soluble than their free base form . 9 4 - Category : Alkaloids : An alkaloid is a naturally occurring nitrogenous organic molecule that has a pharmacological effect on humans and other animals. The name derives from the word alkaline; originally, the term was used to describe any nitrogen - containing base (an amine in modern terms). Alkaloids are found in plants (e.g., in potatoes and tomatoes), animals (e.g., in shellfish) and fungi (e.g., in mushrooms), and can be extracted from their sources by treatment with acids ( usually hydrochloric acid or sulfuric acid, though organic acids such as maleic acid and citric acid are sometimes used ) . A : Acetylpsilocin . Aconitine . Ageliferin . Ajmalan . Ajmaline . Akuammine . Allopumiliotoxin . Allopumiliotoxin 267A . Anabasine . Anatoxin - a . Apomorphine . Aporphine B : Batrachotoxin . Benzyl isoquinoline . Berberine . Brucine . Bulbocapnine C : Calligonine . Camptothecin . Carpaine . Castanospermine . Cathinone . Chaconine . Chavicine . Chelerythrine . Cinchonidine . Cinchonine . Colchicine . Conessine . Conhydrine . Coniine . Coptisine . Coramsine . Cordycepin . Cryogenine . Cuscohygrine . Cylindrospermopsin . Cytisine . D : Dehydro emetine . Delphinine . Demecolcine . Dihydro ergocornine . Dihydro ergocristine . Dihydro quinidine . Dihydro quinine . Docetaxel E : Eletefine . Emetine . Epibatidine . Ergine E cont . Ergoline . Ethocybin . G : Glaucine . Glycoalkaloid . H : Harmine . Hasubanan . Hasubanonine . Himbacine . Histrio nicotoxin . Hodgkinsine . Horsfiline . Huperzine A . Hydrastine . Hydrastinine . Hygrine . I : Imidazole . Isovaleramide 10 L : Lennoxamine . Leonurine . Lobeline . Loline alkaloids . Lupinine . Lycorine . Lysergic acid hydroxy ethylamide . M : Methcathinone . Methoxy methyl enedioxy amphetamine . Methoxy coronaridine . 1-Methyl - 2,3,4,9 – tetra hydro -1H – pyrido - 3,4 – b - indole . Methyl benzo dioxolyl butanamine . N –Methyl coniine . Methyllycaconitine . Methylone . N : Nantenine . Narcotoline . Neurine . Nicotine . Norzoanthamine . O : Orellanine P : Paclitaxel . Pancratistatin . Pericine . Phenyl propanol amine . Phenyl tropane . Physostigmine . Piperine . Prajmaline . Pseudo aconitine . Pseudo pelletierine . Pukateine P cont . Pumiliotoxin . Pumiliotoxin 251D . Pyrrolizidine alkaloid . R : Rhynchophylline . Rodiasine . Ryanodine . S : Samandaridine . Samandarin . Sanguinarine . Saxitoxin . Scoulerine . Senecionine . Sinomenine . Solamargine . Solanine . Solanocapsine . Solasodamine . Solasodine . Solasonine . Solauricidine . Solauricine . Solenopsin . Sparteine . Spirotryprostatin. Staurosporine . Stepholidine . Strychnine . Swainsonine . T : Tetra hydro harman . Tetra hydro palmatine . Thebaine . Tri gonelline . Tri methoxy amphetamine . Tropane . Tropane alkaloid . Tropinone . Tryptoline . Tubocurarine V : Veracevine . Veratridine . Vinblastine . Vinburnine . Vincristine . Vindesine . Vinflunine . Vinorelbine . Voacangine . Y : Yuremamine 11 Atropine Contents : 1 Introduction 2 Physiological effects and uses o 2.1 Ophthalmic use o 2.2 Resuscitation o 2.3 Secretions and bronchoconstriction o 2.4 Treatment for organophosphate poisoning o 2.5 Optical penalization o 2.6 Side - effects and overdose 3 Chemistry and pharmacology 4 History 5 Natural sources 1 – Introduction : Atropine is a tropane alkaloid extracted from deadly nightshade ( Atropa belladonna ) , jimsonweed ( Datura stramonium ) , mandrake ( Mandragora officinarum ) and other plants of the family Solanaceae . It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects. It is a competitive antagonist for the muscarinic acetylcholine receptor. It is classified as an anti cholinergic drug. Being potentially deadly, it derives its name from Atropos, one of the three Fates who, according to Greek mythology, chose how a person was to die. Atropine is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic health care system . 12 Systematic (IUPAC) name ( 8 – methyl – 8 – azabicyclo [ 3.2.1 ] oct – 3 – yl ) 3 – hydroxyl – 2 – phenyl propanoate Formula C17H23NO3 Mol Mass 289 Pharmacokinetic data Bioavailability 25 % Metabolism 50 % hydrolyzed to tropine and tropic acid Half life 2 hours Excretion 50 % excreted unchanged in urine 2 - Physiological effects and uses Atropine increases firing of the sinoatrial node (SA) and conduction through the atrioventricular node (AV) of the heart, opposes the actions of the vagus nerve , blocks acetylcholine receptor sites, and decreases bronchial secretions. In general, atropine lowers the parasympathetic activity of all muscles and glands regulated by the parasympathetic nervous system. This occurs because atropine is a competitive antagonist of the muscarinic acetylcholine
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