alkaloids & alkaloids plants · low - molecular weight alkaloids without hydrogen bond donors such...
TRANSCRIPT
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ADANA UNIVERSTY – INDUSTRY JOINT RESEARCH CENTER
ALKALOIDS
& ALKALOIDS
PLANTS
By
TAREK ISMAIL KAKHIA
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INDEX
Itam
No
Page Itam
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
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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
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PART – 1
ALKALOIDS
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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
http://en.wikipedia.org/wiki/Ephedrinehttp://en.wikipedia.org/wiki/Alkaloid#Alkaloid_classificationshttp://en.wikipedia.org/wiki/Alkaloid#Physicochemical_propertieshttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Alkalinehttp://en.wikipedia.org/wiki/Bacteriahttp://en.wikipedia.org/wiki/Fungushttp://en.wikipedia.org/wiki/Planthttp://en.wikipedia.org/wiki/Animalhttp://en.wikipedia.org/wiki/Natural_productshttp://en.wikipedia.org/wiki/Secondary_metabolitehttp://en.wikipedia.org/wiki/Acid-base_extractionhttp://en.wikipedia.org/wiki/Toxicityhttp://en.wikipedia.org/wiki/Pharmacologyhttp://en.wikipedia.org/wiki/Medicationhttp://en.wikipedia.org/wiki/Recreational_drughttp://en.wikipedia.org/wiki/Entheogenichttp://en.wikipedia.org/wiki/Local_anesthetichttp://en.wikipedia.org/wiki/Stimulanthttp://en.wikipedia.org/wiki/Cocainehttp://en.wikipedia.org/wiki/Caffeinehttp://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/Analgesichttp://en.wikipedia.org/wiki/Morphinehttp://en.wikipedia.org/wiki/Antimalarial_drughttp://en.wikipedia.org/wiki/Quininehttp://en.wikipedia.org/wiki/Bitter_(taste)#Bitternesshttp://en.wikipedia.org/wiki/Caffeine
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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 .
http://en.wikipedia.org/wiki/Chemical_structurehttp://en.wikipedia.org/wiki/Biosynthesishttp://en.wikipedia.org/wiki/Alkaloid#cite_note-Rogers.26Wink-1http://en.wikipedia.org/wiki/Alkaloid#cite_note-Rogers.26Wink-1http://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/Piperinehttp://en.wikipedia.org/wiki/Coniinehttp://en.wikipedia.org/wiki/Trigonellinehttp://en.wikipedia.org/wiki/Arecolinehttp://en.wikipedia.org/w/index.php?title=Arecaidine&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Guvacine&action=edit&redlink=1http://en.wikipedia.org/wiki/Cytisinehttp://en.wikipedia.org/wiki/Lobelinehttp://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/Anabasinehttp://en.wikipedia.org/wiki/Sparteinehttp://en.wikipedia.org/w/index.php?title=Pelletierine&action=edit&redlink=1http://en.wikipedia.org/wiki/Pyrrolidinehttp://en.wikipedia.org/wiki/Hygrinehttp://en.wikipedia.org/wiki/Cuscohygrinehttp://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/Tropanehttp://en.wikipedia.org/wiki/Atropinehttp://en.wikipedia.org/wiki/Cocainehttp://en.wikipedia.org/wiki/Ecgoninehttp://en.wikipedia.org/wiki/Scopolaminehttp://en.wikipedia.org/wiki/Catuabinehttp://en.wikipedia.org/w/index.php?title=Indolizidine&action=edit&redlink=1http://en.wikipedia.org/wiki/Senecioninehttp://en.wikipedia.org/wiki/Swainsoninehttp://en.wikipedia.org/wiki/Quinolinehttp://en.wikipedia.org/wiki/Quininehttp://en.wikipedia.org/wiki/Quinidinehttp://en.wikipedia.org/wiki/Dihydroquininehttp://en.wikipedia.org/wiki/Dihydroquinidinehttp://en.wikipedia.org/wiki/Strychninehttp://en.wikipedia.org/wiki/Brucinehttp://en.wikipedia.org/wiki/Veratrinehttp://en.wikipedia.org/w/index.php?title=Cevadine&action=edit&redlink=1http://en.wikipedia.org/wiki/Isoquinolinehttp://en.wikipedia.org/wiki/Opiumhttp://en.wikipedia.org/wiki/Papaverinehttp://en.wikipedia.org/wiki/Narcotinehttp://en.wikipedia.org/w/index.php?title=Narceine&action=edit&redlink=1http://en.wikipedia.org/wiki/Pancratistatinhttp://en.wikipedia.org/wiki/Sanguinarinehttp://en.wikipedia.org/wiki/Hydrastinehttp://en.wikipedia.org/wiki/Berberinehttp://en.wikipedia.org/wiki/Emetinehttp://en.wikipedia.org/wiki/Phenanthrenehttp://en.wikipedia.org/wiki/Morphinehttp://en.wikipedia.org/wiki/Codeinehttp://en.wikipedia.org/wiki/Thebainehttp://en.wikipedia.org/wiki/Oripavinehttp://en.wikipedia.org/wiki/Phenethylaminehttp://en.wikipedia.org/wiki/Mescalinehttp://en.wikipedia.org/wiki/Ephedrinehttp://en.wikipedia.org/wiki/Dopamine
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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 .
http://en.wikipedia.org/wiki/Indolehttp://en.wikipedia.org/wiki/Tryptaminehttp://en.wikipedia.org/wiki/Serotoninhttp://en.wikipedia.org/wiki/Bufoteninehttp://en.wikipedia.org/wiki/Psilocybinhttp://en.wikipedia.org/wiki/Ergolinehttp://en.wikipedia.org/wiki/Erginehttp://en.wikipedia.org/wiki/Ergotaminehttp://en.wikipedia.org/wiki/Lysergic_acidhttp://en.wikipedia.org/wiki/Beta-carbolinehttp://en.wikipedia.org/wiki/Harminehttp://en.wikipedia.org/wiki/Harmala_alkaloidhttp://en.wikipedia.org/wiki/Tetrahydroharminehttp://en.wikipedia.org/wiki/Reserpinehttp://en.wikipedia.org/wiki/Yohimbinehttp://en.wikipedia.org/wiki/Catharanthus#Vinca_alkaloidshttp://en.wikipedia.org/wiki/Vinblastinehttp://en.wikipedia.org/wiki/Vincristinehttp://en.wikipedia.org/wiki/Kratomhttp://en.wikipedia.org/wiki/Mitragyninehttp://en.wikipedia.org/wiki/7-hydroxymitragyninehttp://en.wikipedia.org/wiki/Tabernanthe_ibogahttp://en.wikipedia.org/wiki/Ibogainehttp://en.wikipedia.org/wiki/Voacanginehttp://en.wikipedia.org/w/index.php?title=Coronaridine&action=edit&redlink=1http://en.wikipedia.org/wiki/Strychnos_nux-vomicahttp://en.wikipedia.org/wiki/Strychninehttp://en.wikipedia.org/wiki/Brucinehttp://en.wikipedia.org/wiki/Purinehttp://en.wikipedia.org/wiki/Xanthinehttp://en.wikipedia.org/wiki/Caffeinehttp://en.wikipedia.org/wiki/Theobrominehttp://en.wikipedia.org/wiki/Theophyllinehttp://en.wikipedia.org/wiki/Terpenoidhttp://en.wikipedia.org/wiki/Aconitumhttp://en.wikipedia.org/wiki/Aconitinehttp://en.wikipedia.org/wiki/Steroidhttp://en.wikipedia.org/wiki/Solanumhttp://en.wikipedia.org/wiki/Potatohttp://en.wikipedia.org/wiki/Tomatohttp://en.wikipedia.org/w/index.php?title=Solanidine&action=edit&redlink=1http://en.wikipedia.org/wiki/Solaninehttp://en.wikipedia.org/wiki/Chaconinehttp://en.wikipedia.org/wiki/Veratrumhttp://en.wikipedia.org/w/index.php?title=Veratramine&action=edit&redlink=1http://en.wikipedia.org/wiki/Cyclopaminehttp://en.wikipedia.org/w/index.php?title=Cycloposine&action=edit&redlink=1http://en.wikipedia.org/wiki/Jervinehttp://en.wikipedia.org/w/index.php?title=Muldamine&action=edit&redlink=1http://en.wikipedia.org/wiki/Fire_Salamanderhttp://en.wikipedia.org/wiki/Samandarinhttp://en.wikipedia.org/wiki/Conessinehttp://en.wikipedia.org/wiki/Ammoniumhttp://en.wikipedia.org/wiki/Muscarinehttp://en.wikipedia.org/wiki/Cholinehttp://en.wikipedia.org/wiki/Neurinehttp://en.wikipedia.org/wiki/Capsaicinhttp://en.wikipedia.org/w/index.php?title=Cynarin&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Phytolaccine&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Phytolaccotoxin&action=edit&redlink=1http://en.wikipedia.org/wiki/Hydrogen_bondhttp://en.wikipedia.org/wiki/Hydroxy_grouphttp://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/Sparteinehttp://en.wikipedia.org/wiki/Coniinehttp://en.wikipedia.org/wiki/Phenethylaminehttp://en.wikipedia.org/wiki/Lone_pairhttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Mineral_acidhttp://en.wikipedia.org/wiki/Hydrochloric_acidhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Organic_acidhttp://en.wikipedia.org/wiki/Organic_acidhttp://en.wikipedia.org/wiki/Tartaric_acidhttp://en.wikipedia.org/wiki/Maleic_acidhttp://en.wikipedia.org/wiki/Solubilityhttp://en.wikipedia.org/wiki/Free_base
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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
http://en.wikipedia.org/wiki/Moleculehttp://en.wikipedia.org/wiki/Pharmacologyhttp://en.wikipedia.org/wiki/Humanhttp://en.wikipedia.org/wiki/Animalhttp://en.wikipedia.org/wiki/Alkalihttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Planthttp://en.wikipedia.org/wiki/Potatohttp://en.wikipedia.org/wiki/Tomatohttp://en.wikipedia.org/wiki/Shellfishhttp://en.wikipedia.org/wiki/Fungushttp://en.wikipedia.org/wiki/Mushroomhttp://en.wikipedia.org/wiki/Acidhttp://en.wikipedia.org/wiki/Hydrochloric_acidhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Maleic_acidhttp://en.wikipedia.org/wiki/Citric_acidhttp://en.wikipedia.org/wiki/Citric_acidhttp://en.wikipedia.org/wiki/O-Acetylpsilocinhttp://en.wikipedia.org/wiki/Aconitinehttp://en.wikipedia.org/wiki/Ageliferinhttp://en.wikipedia.org/wiki/Ajmalanhttp://en.wikipedia.org/wiki/Ajmalinehttp://en.wikipedia.org/wiki/Akuamminehttp://en.wikipedia.org/wiki/Allopumiliotoxinhttp://en.wikipedia.org/wiki/Allopumiliotoxin_267Ahttp://en.wikipedia.org/wiki/Anabasinehttp://en.wikipedia.org/wiki/Anatoxin-ahttp://en.wikipedia.org/wiki/Apomorphine_(data_page)http://en.wikipedia.org/wiki/Aporphinehttp://en.wikipedia.org/wiki/Batrachotoxinhttp://en.wikipedia.org/wiki/Benzylisoquinolinehttp://en.wikipedia.org/wiki/Berberinehttp://en.wikipedia.org/wiki/Brucinehttp://en.wikipedia.org/wiki/Bulbocapninehttp://en.wikipedia.org/wiki/Calligoninehttp://en.wikipedia.org/wiki/Camptothecinhttp://en.wikipedia.org/wiki/Carpainehttp://en.wikipedia.org/wiki/Castanosperminehttp://en.wikipedia.org/wiki/Cathinonehttp://en.wikipedia.org/wiki/Chaconinehttp://en.wikipedia.org/wiki/Chavicinehttp://en.wikipedia.org/wiki/Chelerythrinehttp://en.wikipedia.org/wiki/Cinchonidinehttp://en.wikipedia.org/wiki/Cinchoninehttp://en.wikipedia.org/wiki/Colchicinehttp://en.wikipedia.org/wiki/Conessinehttp://en.wikipedia.org/wiki/Conhydrinehttp://en.wikipedia.org/wiki/Coniinehttp://en.wikipedia.org/wiki/Coptisinehttp://en.wikipedia.org/wiki/Coramsinehttp://en.wikipedia.org/wiki/Cordycepinhttp://en.wikipedia.org/wiki/Cryogeninehttp://en.wikipedia.org/wiki/Cuscohygrinehttp://en.wikipedia.org/wiki/Cylindrospermopsinhttp://en.wikipedia.org/wiki/Cytisinehttp://en.wikipedia.org/wiki/Dehydroemetinehttp://en.wikipedia.org/wiki/Delphininehttp://en.wikipedia.org/wiki/Demecolcinehttp://en.wikipedia.org/wiki/Dihydroergocorninehttp://en.wikipedia.org/wiki/Dihydroergocorninehttp://en.wikipedia.org/wiki/Dihydroergocristinehttp://en.wikipedia.org/wiki/Dihydroquinidinehttp://en.wikipedia.org/wiki/Dihydroquininehttp://en.wikipedia.org/wiki/Dihydroquininehttp://en.wikipedia.org/wiki/Docetaxelhttp://en.wikipedia.org/wiki/Eletefinehttp://en.wikipedia.org/wiki/Emetinehttp://en.wikipedia.org/wiki/Epibatidinehttp://en.wikipedia.org/wiki/Erginehttp://en.wikipedia.org/wiki/Ergolinehttp://en.wikipedia.org/wiki/Ethocybinhttp://en.wikipedia.org/wiki/Glaucinehttp://en.wikipedia.org/wiki/Glycoalkaloidhttp://en.wikipedia.org/wiki/Harminehttp://en.wikipedia.org/wiki/Hasubananhttp://en.wikipedia.org/wiki/Hasubanoninehttp://en.wikipedia.org/wiki/Himbacinehttp://en.wikipedia.org/wiki/Histrionicotoxinhttp://en.wikipedia.org/wiki/Histrionicotoxinhttp://en.wikipedia.org/wiki/Hodgkinsinehttp://en.wikipedia.org/wiki/Horsfilinehttp://en.wikipedia.org/wiki/Huperzine_Ahttp://en.wikipedia.org/wiki/Hydrastinehttp://en.wikipedia.org/wiki/Hydrastininehttp://en.wikipedia.org/wiki/Hygrinehttp://en.wikipedia.org/wiki/Imidazolehttp://en.wikipedia.org/wiki/Isovaleramide
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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
http://en.wikipedia.org/wiki/Lennoxaminehttp://en.wikipedia.org/wiki/Leonurinehttp://en.wikipedia.org/wiki/Lobelinehttp://en.wikipedia.org/wiki/Loline_alkaloidshttp://en.wikipedia.org/wiki/Lupininehttp://en.wikipedia.org/wiki/Lycorinehttp://en.wikipedia.org/wiki/Lysergic_acid_hydroxyethylamidehttp://en.wikipedia.org/wiki/Methcathinonehttp://en.wikipedia.org/wiki/Methoxymethylenedioxyamphetaminehttp://en.wikipedia.org/wiki/18-Methoxycoronaridinehttp://en.wikipedia.org/wiki/18-Methoxycoronaridinehttp://en.wikipedia.org/wiki/(1S)-1-Methyl-2,3,4,9-tetrahydro-1H-pyrido-3,4-b-indolehttp://en.wikipedia.org/wiki/(1S)-1-Methyl-2,3,4,9-tetrahydro-1H-pyrido-3,4-b-indolehttp://en.wikipedia.org/wiki/Methylbenzodioxolylbutanaminehttp://en.wikipedia.org/wiki/N-Methylconiinehttp://en.wikipedia.org/wiki/N-Methylconiinehttp://en.wikipedia.org/wiki/Methyllycaconitinehttp://en.wikipedia.org/wiki/Methylonehttp://en.wikipedia.org/wiki/Nanteninehttp://en.wikipedia.org/wiki/Narcotolinehttp://en.wikipedia.org/wiki/Neurinehttp://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/Norzoanthaminehttp://en.wikipedia.org/wiki/Orellaninehttp://en.wikipedia.org/wiki/Paclitaxelhttp://en.wikipedia.org/wiki/Pancratistatinhttp://en.wikipedia.org/wiki/Pericinehttp://en.wikipedia.org/wiki/Phenylpropanolaminehttp://en.wikipedia.org/wiki/Phenyltropanehttp://en.wikipedia.org/wiki/Physostigminehttp://en.wikipedia.org/wiki/Piperinehttp://en.wikipedia.org/wiki/Prajmalinehttp://en.wikipedia.org/wiki/Pseudaconitinehttp://en.wikipedia.org/wiki/Pseudaconitinehttp://en.wikipedia.org/wiki/Pseudopelletierinehttp://en.wikipedia.org/wiki/Pukateinehttp://en.wikipedia.org/wiki/Pumiliotoxinhttp://en.wikipedia.org/wiki/Pumiliotoxin_251Dhttp://en.wikipedia.org/wiki/Pyrrolizidine_alkaloidhttp://en.wikipedia.org/wiki/Rhynchophyllinehttp://en.wikipedia.org/wiki/Rodiasinehttp://en.wikipedia.org/wiki/Ryanodinehttp://en.wikipedia.org/wiki/Samandaridinehttp://en.wikipedia.org/wiki/Samandarinhttp://en.wikipedia.org/wiki/Sanguinarinehttp://en.wikipedia.org/wiki/Saxitoxinhttp://en.wikipedia.org/wiki/Scoulerinehttp://en.wikipedia.org/wiki/Senecioninehttp://en.wikipedia.org/wiki/Sinomeninehttp://en.wikipedia.org/wiki/Solamarginehttp://en.wikipedia.org/wiki/Solaninehttp://en.wikipedia.org/wiki/Solanocapsinehttp://en.wikipedia.org/wiki/Solasodaminehttp://en.wikipedia.org/wiki/Solasodinehttp://en.wikipedia.org/wiki/Solasoninehttp://en.wikipedia.org/wiki/Solauricidinehttp://en.wikipedia.org/wiki/Solauricinehttp://en.wikipedia.org/wiki/Solenopsinhttp://en.wikipedia.org/wiki/Sparteinehttp://en.wikipedia.org/wiki/Spirotryprostatin_Ahttp://en.wikipedia.org/wiki/Staurosporinehttp://en.wikipedia.org/wiki/Stepholidinehttp://en.wikipedia.org/wiki/Strychninehttp://en.wikipedia.org/wiki/Swainsoninehttp://en.wikipedia.org/wiki/Tetrahydroharmanhttp://en.wikipedia.org/wiki/Tetrahydropalmatinehttp://en.wikipedia.org/wiki/Thebainehttp://en.wikipedia.org/wiki/Trigonellinehttp://en.wikipedia.org/wiki/Trigonellinehttp://en.wikipedia.org/wiki/Trimethoxyamphetaminehttp://en.wikipedia.org/wiki/Tropanehttp://en.wikipedia.org/wiki/Tropane_alkaloidhttp://en.wikipedia.org/wiki/Tropinonehttp://en.wikipedia.org/wiki/Tryptolinehttp://en.wikipedia.org/wiki/Tubocurarinehttp://en.wikipedia.org/wiki/Veracevinehttp://en.wikipedia.org/wiki/Veratridinehttp://en.wikipedia.org/wiki/Vinblastinehttp://en.wikipedia.org/wiki/Vinburninehttp://en.wikipedia.org/wiki/Vincristinehttp://en.wikipedia.org/wiki/Vindesinehttp://en.wikipedia.org/wiki/Vinfluninehttp://en.wikipedia.org/wiki/Vinorelbinehttp://en.wikipedia.org/wiki/Voacanginehttp://en.wikipedia.org/wiki/Yuremamine
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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 .
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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 receptors ( Acetylcholine is the main
neurotransmitter used by the parasympathetic nervous system ) .
Therefore, it may cause swallowing difficulties and reduced secretions
2 -1 : Ophthalmic use
Topical atropine is used as a cyclo plegic, to temporarily paralyze
the accommodation reflex, and as a mydriatic, to dilate the pupils.
Atropine degrades slowly, typically wearing off in 7 to 14 days, so it
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is generally used as a therapeutic mydriatic , whereas tropicamide ( a
shorter - acting cholinergic antagonist ) or phenyl ephrine (an α-
adrenergic agonist) is preferred as an aid to ophthalmic examination.
Atropine induces mydriasis by blocking contraction of the circular
pupillary sphincter muscle, which is normally stimulated by
acetylcholine release, thereby allowing the radial pupillary dilator
muscle to contract and dilate the pupil. Atropine induces cycloplegia
by paralyzing the ciliary muscles, whose action inhibits
accommodation to allow accurate refraction in children, helps to
relieve pain associated with iridocyclitis, and treats ciliary block
(malignant) glaucoma. Atropine is contraindicated in patients pre-
disposed to narrow angle glaucoma . Atropine can be given to patients
who have direct globe trauma .
2 – 2 : Resuscitation
Injections of atropine are used in the treatment of bradycardia (an
extremely low heart rate), asystole and pulseless electrical activity
(PEA) in cardiac arrest. This works because the main action of the
vagus nerve of the parasympathetic system on the heart is to decrease
heart rate. Atropine blocks this action and, therefore, may speed up the
heart rate. The usual dosage of atropine in bradyasystolic arrest is 0.5
to 1 mg IV push every three to five minutes, up to a maximum dose of
0.04 mg/kg. For symptomatic bradycardia, the usual dosage is 0.5 to
1.0 mg IV push, may repeat every 3 to 5 minutes up to a maximum
dose of 3.0 mg .
Atropine is also useful in treating second-degree heart block
Mobitz Type 1 (Wenckebach block), and also third-degree heart block
with a high Purkinje or AV-nodal escape rhythm. It is usually not
effective in second - degree heart block Mobitz type 2, and in third-
degree heart block with a low Purkinje or ventricular escape rhythm.
Atropine is contraindicated in ischemia-induced conduction block,
because the drug increases oxygen demand of the AV nodal tissue,
thereby aggravating ischemia and the resulting heart block.
One of the main actions of the parasympathetic nervous system is
to stimulate the M2 muscarinic receptor in the heart, but atropine
inhibits this action.
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2 – 3 : Secretions and broncho constriction
Atropine's actions on the parasympathetic nervous system inhibits
salivary, sweat, and mucus glands. This can be useful in treating
hyperhidrosis, and can prevent the death rattle of dying patients. Even
though atropine has not been officially indicated for either of these
purposes by the FDA, it has been used by physicians for these
purposes .
2 – 4 : Treatment for organophosphate poisoning
Atropine is not an actual antidote for organophosphate poisoning.
However, by blocking the action of acetylcholine at muscarinic
receptors, atropine also serves as a treatment for poisoning by
organophosphate insecticides and nerve gases, such as Tabun (GA),
Sarin (GB), Soman (GD) and VX. Troops that are likely to be attacked
with chemical weapons often carry autoinjectors with atropine and
obidoxime, which can be quickly injected into the thigh. Atropine is
often used in conjunction with Pralidoxime chloride.
Atropine is given as a treatment for SLUDGE (Salivation,
Lacrimation, Urination, Diaphoresis, Gastrointestinal motility,
Emesis) symptoms caused by organophosphate poisoning .
Some of the nerve agents attack and destroy acetyl cholin
esterase , so the action of acetylcholine becomes prolonged. Therefore
atropine can be used to reduce the effect of acetylcholine .
2 – 5 : Optical penalization :
In refractive and accommodative amblyopia , when occlusion is not
appropriate sometimes atropine is given to induce blur in the good eye
2 – 6 : Side - effects and overdose
Adverse reactions to atropine include ventricular fibrillation,
supra ventricular or ventricular tachycardia, dizziness, nausea, blurred
vision, loss of balance, dilated pupils, photophobia, and, possibly,
notably in the elderly, extreme confusion, extreme dissociative
hallucinations, and excitation. These latter effects are because atropine
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is able to cross the blood - brain barrier. Because of the hallucinogenic
properties, some have used the drug recreationally, though this is
potentially dangerous and often unpleasant.
In overdoses, atropine is poisonous. Atropine is sometimes added
to other potentially addictive drugs, particularly anti-diarrhea opioid
drugs such as diphenoxylate or difenoxin, wherein the secretion-
reducing effects of the atropine can also aid the anti-diarrhea effects.
Although atropine treats bradycardia ( slow heart rate ) in
emergency settings, it can cause paradoxical heart rate slowing when
given at very low doses, presumably as a result of central action in the
CNS. The antidote to atropine is physostigmine or pilocarpine .
A common mnemonic used to describe the physiologic
manifestations of atropine overdose is: "hot as a hare, blind as a bat,
dry as a bone, red as a beet, and mad as a hatter".[6]
These associations
reflect the specific changes of warm, dry skin from decreased
sweating, blurry vision , decreased sweating / lacrimation ,
vasodilation, and central nervous system effects on muscarinic
receptors, type 4 and 5 . This set of symptoms is known as anti
cholinergic toxidrome , and may also be caused by other drugs with
anti cholinergic effects, such as diphenhy dramine , phenothiazine
antipsychotics and benztropine .
3 - Chemistry and pharmacology
Atropine is a racemic mixture of D - hyoscyamine and L -
hyoscyamine , with most of its physiological effects due to L –
hyoscyamine . Its pharmacological effects are due to binding to
muscarinic acetylcholine receptors. It is an antimuscarinic agent.The
most common atropine compound used in medicine is atropine sulfate
( C17H23NO3 )2 · H2SO4 ·H2O, the full chemical name is 1α H , 5α H –
Tropan – 3 - α ol (±) – tropate (ester) , sulfate mono hydrate .
4 - History
Mandragora (mandrake) was described by Theophrastus in the
fourth century B.C. for treatment of wounds, gout, and sleeplessness,
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and as a love potion. By the first century A.D. Dioscorides recognized
wine of mandrake as an anaesthetic for treatment of pain or
sleeplessness, to be given prior to surgery or cautery . The use of
Solanaceae containing tropane alkaloids for anesthesia, often in
combination with opium, persisted throughout the Roman and Islamic
Empires and continued in Europe until superseded by the use of ether,
chloroform, and other modern anesthetics.
Atropine extracts from the Egyptian henbane were used by
Cleopatra in the last century B.C. to dilate her pupils, in the hope that
she would appear more alluring. In the Renaissance, women used the
juice of the berries of Atropa belladonna to enlarge the pupils of their
eyes, for cosmetic reasons; " bella donna " is Italian for "beautiful
lady".[8]
This practice resumed briefly in the late nineteenth - and early
twentieth - century in Paris .
The mydriatic effects of atropine were studied among others by
the German chemist Friedrich Ferdinand Runge (1795–1867). In
1831, the pharmacist Mein succeeded the pure crystalline isolation of
atropine. The substance was first synthesized by German chemist
Richard Willstätter in 1901.
Atropinic shock therapy, also known as atropinic coma therapy, is
an old and rarely - used method. It consists of induction of atropinic
coma by rapid intravenous infusion of atropine. Atropinic shock
treatment is considered safe with careful monitoring and preparation,
but it entails prolonged coma (between four and five hours), and it has
many unpleasant side-effects, such as blurred vision .
5 - Natural sources
Atropine is found in many members of the Solanaceae family.
The most commonly-found sources are Atropa belladonna, Datura
inoxia, D. metel, and D. stramonium. Other sources include members
of the Brugmansia and Hyoscyamus genera . The Nicotiana genus
( including the tobacco plant, N. tabacum ) is also found in the
Solanaceae family, but these plants do not contain atropine or other
tropane alkaloids .
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Caffeine
Contents :
1 Introduction
2 Occurrence
3 History
4 Synthesis and properties
5 Pharmacology
o 5.1 Metabolism and half-life
o 5.2 Mechanism of action
o 5.3 Effects when taken in moderation
o 5.4 Tolerance and withdrawal
o 5.5 Overuse
5.5.1 Caffeine intoxication
5.5.2 Anxiety and sleep disorders
o 5.6 Effects on memory and learning
o 5.7 Effects on the heart
o 5.8 Effects on children
o 5.9 Caffeine intake during pregnancy
o 5.10 Genetics and caffeine metabolism
o 5.11 Intraocular Pressure and caffeine
6 Decaffeination
o 6.1 Water extraction
o 6.2 Supercritical carbon dioxide extraction
o 6.3 Extraction by organic solvents
7 Religion
1 – Introduction :
Caffeine is a bitter , white crystalline xanthine alkaloid that is a
psychoactive stimulant drug . Caffeine was discovered by a German
chemist , Friedrich Ferdinand Runge , in 1819 . He coined the term
kaffein , a chemical compound in coffee , which in English became
caffeine . Caffeine is also part of the chemical mixtures and insoluble
complexes guaranine found in guarana , mateine found in mate , and
theine found in non - herbal tea ; all of which contain additional
alkaloids such as the cardiac stimulants theophylline and theobromine,
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and often other chemicals such as polyphenols which can form
insoluble complexes with caffeine .
Caffeine is found in varying quantities in the beans , leaves , and
fruit of some plants , where it acts as a natural pesticide that paralyzes
and kills certain insects feeding on the plants . It is most commonly
consumed by humans in infusions extracted from the cherries of the
coffee plant and the leaves of the tea bush , as well as from various
foods and drinks containing products derived from the kola nut . Other
sources include yerba mate , guarana berries, and the Yaupon Holly .
In humans , caffeine is a central nervous system ( CNS ) stimulant
having the effect of temporarily warding off drowsiness and restoring
alertness . Beverages containing caffeine , such as coffee , tea , soft
drinks , and energy drinks enjoy great popularity . Caffeine is the
world's most widely consumed psychoactive substance , but unlike
many other psychoactive substances it is legal and unregulated in
nearly all jurisdictions . In North America , 90 % of adults consume
caffeine daily . The U.S . Food and Drug Administration lists caffeine
as a " multiple purpose generally recognized as safe food substance ".
Caffeine has diuretic properties, at least when administered in
sufficient doses to subjects who do not have a tolerance for it .
Regular users , however , develop a strong tolerance to this effect ,
and studies have generally failed to support the common notion that
ordinary consumption of caffeinated beverages contributes
significantly to dehydration .
Other Names
1,3,7- Tri methyl xanthine ,
Tri methyl xanthine ,
Theine ,
Methyl theo bromine
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Molecular Formula C8 H10 N4 O2
Molar Mass 194 g / mol
Appearance Odorless , white needles or powder
Density 1.23 g /cm3 , solid
Melting Point 227 – 228 °C ( anhydrous) ,
234 – 235 °C ( monohydrate )
Boiling Point 178 °C subl .
Solubility in Water
2.17 g / 100 ml ( 25 °C )
18.0 g / 100 ml ( 80 °C )
67.0 g / 100 ml ( 100 °C )
Acidity ( pKa ) − 0.13 – 1.22
Dipole Moment 3.64 D ( calculated )
EU classification Harmful ( Xn )
LD50 192 mg / kg ( rat , oral )
2 - Occurrence :
Roasted coffee beans, a common source of caffeine
Caffeine is found in many plant species , where it acts as a natural
pesticide , with high caffeine levels being reported in seedlings that
are still developing foliages, but are lacking mechanical protection ;
caffeine paralyzes and kills certain insects feeding upon the plant .
High caffeine levels have also been found in the surrounding soil of
coffee bean seedlings. It is therefore understood that caffeine has a
natural function as both a natural pesticide and as an inhibitor of seed
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germination of other nearby coffee seedlings thus giving it a better
chance of survival .
The most commonly used sources of caffeine are coffee, tea , and
to a lesser extent cacao . Less commonly used sources of caffeine
include the yerba maté and guarana plants,[15]
which are sometimes
used in the preparation of teas and energy drinks . Two of caffeine's
alternative names, mateine and guaranine , are derived from the
names of these plants . Some yerba mate enthusiasts assert that
mateine is a stereoisomer of caffeine , which would make it a different
substance altogether . This is not true because caffeine is an achiral
molecule , and therefore has no enantiomers ; nor does it have other
stereoisomers . The disparity in experience and effects between the
various natural caffeine sources could be due to the fact that plant
sources of caffeine also contain widely varying mixtures of other
xanthine alkaloids , including the cardiac stimulants theophylline and
theobromine and other substances such as polyphenols which can
form insoluble complexes with caffeine .
One of the world's primary sources of caffeine is the coffee bean
( which is the seed of the coffee plant ) , from which coffee is brewed .
Caffeine content in coffee varies widely depending on the type of
coffee bean and the method of preparation used ; even beans within a
given bush can show variations in concentration . In general, one
serving of coffee ranges from 40 milligrams , for a single shot ( 30
milliliters ) of arabica - variety espresso, to about 100 milligrams for
a cup ( 120 milliliters ) of drip coffee . Generally , dark - roast coffee
has less caffeine than lighter roasts because the roasting process
reduces the bean's caffeine content . Arabica coffee normally contains
less caffeine than the robusta variety . Coffee also contains trace
amounts of theophylline , but no theobromine .
Tea is another common source of caffeine. Although tea contains
more caffeine than coffee , a typical serving contains much less , as
tea is normally brewed much weaker. Besides strength of the brew ,
growing conditions , processing techniques and other variables also
affect caffeine content . Certain types of tea may contain somewhat
more caffeine than other teas . Tea contains small amounts of
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theobromine and slightly higher levels of theophylline than coffee.
Preparation and many other factors have a significant impact on tea,
and color is a very poor indicator of caffeine content . Teas like the
pale Japanese green tea gyokuro , for example , contain far more
caffeine than much darker teas like lapsang souchong , which has very
little .
Caffeine content of select common food and drugs :
Product Serving size
Caffeine
per serving
(mg)
Caffeine per
litre (mg)
Caffeine tablet
( regular strength ) 1 tablet 100 —
Caffeine tablet
( extra strength ) 1 tablet 200 —
Excedrin tablet 1 tablet 65 —
Hershey's Special
Dark ( 45 % cacao
content )
1 bar (43 g; 1.5 oz) 31 —
Hershey's Milk
Chocolate ( 11 %
cacao content )
1 bar (43 g; 1.5 oz) 10 —
Percolated coffee 207 mL ( 7 U.S. fl oz) 80 – 135 386 - 652
Drip coffee 207 mL ( 7 U.S. fl oz) 115 – 175 555–845
Coffee,decaffeinated 207 mL ( 7 U.S. fl oz) 5 - 15 24 - 72
Coffee , espresso 44–60 mL ( 2 U.S. fl oz ) 100 1691- 2254
Coffee , Starbucks ( Tall 12 U.S. fl oz ) 240 650 - 700
Black tea 177 mL (6 U.S. fl oz) 50 282
Green tea 177 mL ( 6 U.S. fl oz ) 30 169
Coca - Cola Classic 355 mL ( 12 U.S. fl oz ) 34 96
Caffeine is also a common ingredient of soft drinks such as cola ,
originally prepared from kola nuts. Soft drinks typically contain about
10 to 50 milligrams of caffeine per serving. By contrast , energy
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drinks such as Red Bull can start at 80 milligrams of caffeine per
serving . The caffeine in these drinks either originates from the
ingredients used or is an additive derived from the product of
decaffeination or from chemical synthesis. Guarana, a prime
ingredient of energy drinks , contains large amounts of caffeine with
small amounts of theobromine and theophylline in a naturally
occurring slow-release excipient .
Chocolate derived from cocoa contains a small amount of
caffeine. The weak stimulant effect of chocolate may be due to a
combination of theobromine and theophylline as well as caffeine . A
typical 28 - gram serving of a milk chocolate bar has about as much
caffeine as a cup of decaffeinated coffee .
In recent years various manufacturers have begun putting caffeine
into shower products such as shampoo and soap , claiming that
caffeine can be absorbed through the skin . However, the effectiveness
of such products has not been proven, and they are likely to have little
stimulatory effect on the central nervous system because caffeine is
not readily absorbed through the skin .
Various manufacturers market caffeine tablets , claiming that
using caffeine of pharmaceutical quality improves mental alertness .
These effects have been borne out by research that shows that caffeine
use ( whether in tablet form or not ) results in decreased fatigue and
increased attentiveness . These tablets are commonly used by students
studying for their exams and by people who work or drive for long
hours .
3 - History :
Humans have consumed caffeine since the Stone Age . Early
peoples found that chewing the seeds , bark , or leaves of certain
plants had the effects of easing fatigue , stimulating awareness , and
elevating one's mood . Only much later was it found that the effect of
caffeine was increased by steeping such plants in hot water. Many
cultures have legends that attribute the discovery of such plants to
people living many thousands of years ago .
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A coffeehouse in Palestine , circa 1900
According to one popular Chinese legend, the Emperor of China
Shennong , reputed to have reigned in about 3000 BC , accidentally
discovered that when some leaves fell into boiling water , a fragrant
and restorative drink resulted . Shennong is also mentioned in Lu Yu's
Cha Jing , a famous early work on the subject of tea . The history of
coffee has been recorded as far back as the ninth century . During that
time, coffee beans were available only in their native habitat , Ethiopia
A popular legend traces its discovery to a goatherder named Kaldi ,
who apparently observed goats that became elated and sleepless at
night after grazing on coffee shrubs and , upon trying the berries that
the goats had been eating, experienced the same vitality. The earliest
literary mention of coffee may be a reference to Bunchum in the
works of the 9th century Persian physician al - Razi. In 1587 , Malaye
Jaziri compiled a work tracing the history and legal controversies of
coffee, entitled " Undat al safwa fi hill al - qahwa ". In this work ,
Jaziri recorded that one Sheikh , Jamal – al - Din al – Dhabhani , mufti
of Aden , was the first to adopt the use of coffee in 1454 , and that in
the 15th century the Sufis of Yemen routinely used coffee to stay
awake during prayers .
Towards the close of the 16th century , the use of coffee was
recorded by a European resident in Egypt , and about this time it came
into general use in the Near East . The appreciation of coffee as a
beverage in Europe, where it was first known as "Arabian wine," dates
from the 17th century . During this time " coffee houses " were
established , the first being opened in Constantinople and Venice . In
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Britain , the first coffee houses were opened in London in 1652 , at St
Michael's Alley , Cornhill . They soon became popular throughout
Western Europe, and played a significant role in social relations in the
17th and 18th centuries .
The kola nut , like the coffee berry and tea leaf , appears to have
ancient origins . It is chewed in many West African cultures,
individually or in a social setting, to restore vitality and ease hunger
pangs . In 1911 , kola became the focus of one of the earliest
documented health scares when the US government seized 40 barrels
and 20 kegs of Coca - Cola syrup in Chattanooga , Tennessee , lleging
that the caffeine in its drink was " injurious to health ".[34]
On March
13 , 1911 , the government initiated The United States v. Forty Barrels
and Twenty Kegs of Coca - Cola, hoping to force Coca - Cola to
remove caffeine from its formula by making claims, such as that the
excessive use of Coca - Cola at one girls' school led to " wild
nocturnal freaks , violations of college rules and female proprieties,
and even immoralities." Although the judge ruled in favor of Coca-
Cola, two bills were introduced to the U.S. House of Representatives
in 1912 to amend the Pure Food and Drug Act, adding caffeine to the
list of " habit - forming " and "deleterious" substances which must be
listed on a product's label .
The earliest evidence of cocoa use comes from residue found in
an ancient Mayan pot dated to 600 BC. In the New World, chocolate
was consumed in a bitter and spicy drink called xocoatl, often
seasoned with vanilla, chile pepper, and achiote. Xocoatl was believed
to fight fatigue , a belief that is probably attributable to the
theobromine and caffeine content . Chocolate was an important luxury
good throughout pre - Columbian Mesoamerica, and cocoa beans were
often used as currency .
Xocoatl was introduced to Europe by the Spaniards and became a
popular beverage by 1700 . They also introduced the cacao tree into
the West Indies and the Philippines. It was used in alchemical
processes, where it was known as Black Bean .
The leaves and stems of the Yaupon Holly (Ilex vomitoria) were
used by Native Americans to brew a tea called Asi or the Black Drink
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the use of which among Native American groups archaeologists have
demonstrated to stretch back far into antiquity, possibly dating to Late
Archaic times.
4 - Synthesis and properties :
In 1819, the German chemist Friedrich Ferdinand Runge isolated
relatively pure caffeine for the first time. According to Runge , he did
this at the behest of Johann Wolfgang von Goethe . In 1827 , Oudry
isolated " theine " from tea, but it was later proved by Mulder and
Jobat that theine was the same as caffeine . The structure of caffeine
was elucidated near the end of the 19th century by Hermann Emil
Fischer , who was also the first to achieve its total synthesis . This was
part of the work for which Fischer was awarded the Nobel Prize in
1902 . The nitrogen atoms are all essentially planar ( in sp 2
orbital
hybridisation ) , resulting in the caffeine molecule having aromatic
character . Being readily available as a byproduct of decaffeination,
caffeine is not usually synthesized . If desired, it may be synthesized
from dimethylurea and malonic acid .
5 - Pharmacology :
Global consumption of caffeine has been estimated at
120,000 tonnes per year , making it the world's most popular
psychoactive substance. This number equates to one serving of a
caffeine beverage for every person, per day . Caffeine is a central
nervous system and metabolic stimulant , and is used both
recreationally and medically to reduce physical fatigue and restore
mental alertness when unusual weakness or drowsiness occurs.
Caffeine and other methylxanthine derivatives are also used on
newborns to treat apnea and correct irregular heartbeats. Caffeine
stimulates the central nervous system first at the higher levels,
resulting in increased alertness and wakefulness, faster and clearer
flow of thought , increased focus, and better general body
coordination, and later at the spinal cord level at higher doses.[28]
Once
inside the body, it has a complex chemistry, and acts through several
mechanisms as described below.
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5 – 1 : Metabolism and half-life
Caffeine is metabolized in the liver into three primary metabolites :
paraxanthine ( 84 % ) , theobromine ( 12 % ) , and theophylline (4 %).
Caffeine from coffee or other beverages is absorbed by the
stomach and small intestine within 45 minutes of ingestion and then
distributed throughout all tissues of the body.[41]
It is eliminated by
first-order kinetics.[42]
Caffeine can also be ingested rectally,
evidenced by the formulation of suppositories of ergotamine tartrate
and caffeine ( for the relief of migraine ) and chlorobutanol and
caffeine ( for the treatment of hyperemesis ) .
The half-life of caffeine — the time required for the body to
eliminate one-half of the total amount of caffeine — varies widely
among individuals according to such factors as age, liver function,
pregnancy, some concurrent medications, and the level of enzymes in
the liver needed for caffeine metabolism. In healthy adults, caffeine's
half-life is approximately 4.9 hours. In women taking oral
contraceptives this is increased to 5 – 10 hours , and in pregnant
women the half-life is roughly 9 –1 1 hours . Caffeine can accumulate
in individuals with severe liver disease , increasing its half-life up to
96 hours . In infants and young children, the half - life may be longer
than in adults; half-life in a newborn baby may be as long as 30 hours.
Other factors such as smoking can shorten caffeine's half - life .
Fluvoxamine reduced the apparent oral clearance of caffeine by
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91.3 % , and prolonged its elimination half - life by 11.4 - fold ( from
4.9 hours to 56 hours ) .
Caffeine is metabolized in the liver by the cytochrome P450
oxidase enzyme system ( specifically , the 1A2 isozyme ) into three
metabolic dimethylxanthines , which each have their own effects on
the body :
Paraxanthine ( 84 % ) : Has the effect of increasing
lipolysis, leading to elevated glycerol and free fatty acid levels in
the blood plasma.
Theobromine (12 % ) : Dilates blood vessels and increases
urine volume. Theobromine is also the principal alkaloid in
cocoa, and therefore chocolate.
Theophylline ( 4 % ) : Relaxes smooth muscles of the
bronchi, and is used to treat asthma. The therapeutic dose of
theophylline, however, is many times greater than the levels
attained from caffeine metabolism.
Each of these metabolites is further metabolized and then
excreted in the urine.
5- 2 : Mechanism of action
Caffeine's principal mode of action is as an antagonist of
adenosine receptors in the brain .
Like alcohol and nicotine, caffeine readily crosses the blood–
brain barrier that separates the bloodstream from the interior of the
brain. Once in the brain, the principal mode of action is as an
antagonist of adenosine receptors . The caffeine molecule is
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structurally similar to adenosine, and binds to adenosine receptors on
the surface of cells without activating them ( an " antagonist "
mechanism of action ). Therefore, caffeine acts as a competitive
inhibitor .
Adenosine is found in every part of the body, because it plays a
role in the fundamental ATP - related energy metabolism, but it has
special functions in the brain. There is a great deal of evidence that
concentrations of brain adenosine are increased by various types of
metabolic stress including anoxia and ischemia. The evidence also
indicates that brain adenosine acts to protect the brain by suppressing
neural activity and also by increasing blood flow through A2A and
A2B receptors located on vascular smooth muscle . By counteracting
adenosine, caffeine reduces resting cerebral blood flow between 22%
and 30%.[53]
Caffeine also has a generally disinhibitory effect on
neural activity. It has not been shown, however, how these effects
cause increases in arousal and alertness.
Adenosine is released in the brain through a complex
mechanism.[52]
There is evidence that adenosine functions as a
synaptically released neurotransmitter in some cases, but stress-related
adenosine increases appear to be produced mainly by extracellular
metabolism of ATP. It is not likely that adenosine is the primary
neurotransmitter for any group of neurons, but rather that it is released
together with other transmitters by a number of neuron types. Unlike
most neurotransmitters, adenosine does not seem to be packaged into
vesicles that are released in a voltage - controlled manner, but the
possibility of such a mechanism has not been completely ruled out.
Several classes of adenosine receptors have been described, with
different anatomical distributions. A1 receptors are widely distributed,
and act to inhibit calcium uptake. A2A receptors are heavily
concentrated in the basal ganglia, an area that plays a critical role in
behavior control, but can be found in other parts of the brain as well,
in lower densities. There is evidence that A 2A receptors interact with
the dopamine system , which is involved in reward and arousal. ( A2A
receptors can also be found on arterial walls and blood cell
membranes ) .
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Beyond its general neuroprotective effects, there are reasons to
believe that adenosine may be more specifically involved in control of
the sleep-wake cycle. Robert McCarley and his colleagues have
argued that accumulation of adenosine may be a primary cause of the
sensation of sleepiness that follows prolonged mental activity, and that
the effects may be mediated both by inhibition of wake-promoting
neurons via A1 receptors, and activation of sleep-promoting neurons
via indirect effects on A2A receptors.[54]
More recent studies have
provided additional evidence for the importance of A2A , but not A1 ,
receptors . Some of the secondary effects of caffeine are probably
caused by actions unrelated to adenosine. Caffeine is known to be a
competitive inhibitor of the enzyme cAMP - phosphodiesterase
( cAMP – PDE ) , which converts cyclic AMP (cAMP) in cells to its
noncyclic form, thus allowing cAMP to build up in cells. Cyclic AMP
participates in activation of protein kinase A (PKA) to begin the
phosphorylation of specific enzymes used in glucose synthesis. By
blocking its removal caffeine intensifies and prolongs the effects of
epinephrine and epinephrine-like drugs such as amphetamine,
methamphetamine, or methylphenidate. Increased concentrations of
cAMP in parietal cells causes an increased activation of protein kinase
A (PKA) which in turn increases activation of H+ / K+ ATPase ,
resulting finally in increased gastric acid secretion by the cell. Cyclic
AMP also increases the activity of the funny current, which directly
increases heart rate. Caffeine is also a structural analogue of
strychnine and like it ( though much less potent ) a competitive
antagonist at ionotropic glycine receptors .
Metabolites of caffeine also contribute to caffeine's effects.
Paraxanthine is responsible for an increase in the lipolysis process,
which releases glycerol and fatty acids into the blood to be used as a
source of fuel by the muscles. Theobromine is a vasodilator that
increases the amount of oxygen and nutrient flow to the brain and
muscles. Theophylline acts as a smooth muscle relaxant that chiefly
affects bronchioles and acts as a chronotrope and inotrope that
increases heart rate and efficiency .
Caffeine has a significant effect on spiders , which is reflected in
the construction of their webs.
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5 – 3 : Effects when taken in moderation :
Over view of the more common side effects of caffeine, possibly
appearing even at levels below overdose .
The precise amount of caffeine necessary to produce effects
varies from person to person depending on body size and degree of
tolerance to caffeine. It takes less than an hour for caffeine to begin
affecting the body and a mild dose wears off in three to four hours.[28]
Consumption of caffeine does not eliminate the need for sleep, it only
temporarily reduces the sensation of being tired throughout the day. In
general, 25 to 50 milligrams of caffeine is sufficient for most people
to report increased alertness and arousal as well as subjectively lower
levels of fatigue.
With these effects, caffeine is an ergogenic, increasing a person's
capability for mental or physical labor. A study conducted in 1979
showed a 7 % increase in distance cycled over a period of two hours
in subjects who consumed caffeine compared to control subjects.[60]
Other studies attained much more dramatic results; one particular
study of trained runners showed a 44 % increase in "race-pace"
endurance, as well as a 51 % increase in cycling endurance, after a
dosage of 9 milligrams of caffeine per kilogram of body weight.[61]
Additional studies have reported similar effects. Another study found
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5.5 milligrams of caffeine per kilogram of body mass resulted in
subjects cycling 29 % longer during high intensity circuits .
Caffeine citrate has proven to be of short and long term benefit in
treating the breathing disorders of apnea of prematurity and
bronchopulmonary dysplasia in premature infants . The only short
term risk associated with caffeine citrate treatment is a temporary
reduction in weight gain during the therapy , and longer term studies
(18 to 21 months ) have shown lasting benefits of treatment of
premature infants with caffeine .
Caffeine relaxes the internal anal sphincter muscles and thus
should be avoided by those with fecal incontinence .
While relatively safe for humans, caffeine is considerably more
toxic to some other animals such as dogs, horses, and parrots due to a
much poorer ability to metabolize this compound. Caffeine has also a
pronounced effect on mollusks and various insects as well as spiders.
5 – 4 : Tolerance and with drawal :
Because caffeine is primarily an antagonist of the central nervous
system's receptors for the neurotransmitter adenosine, the bodies of
individuals who regularly consume caffeine adapt to the continual
presence of the drug by substantially increasing the number of
adenosine receptors in the central nervous system. This increase in the
number of the adenosine receptors makes the body much more
sensitive to adenosine, with two primary consequences . First, the
stimulatory effects of caffeine are substantially reduced, a
phenomenon known as a tolerance adaptation. Second, because these
adaptive responses to caffeine make individuals much more sensitive
to adenosine, a reduction in caffeine intake will effectively increase
the normal physiological effects of adenosine, resulting in unwelcome
withdrawal symptoms in tolerant users .
Other research questions the idea that up-regulation of adenosine
receptors is responsible for tolerance to the locomotor stimulant
effects of caffeine, noting, among other things, that this tolerance is
insurmountable by higher doses of caffeine (it should be surmountable
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