Alkaloids Flashcards
10 pages
Organic nitrogenous compounds with varied pharmacologic actions
ALKALOIDS
Only liquid alkaloids (CNSA)
Coniine, Nicotine, Sparteine, Arecoline
Characteristics of Alkaloids
Basic pH, bitter taste; usually crystalline or amorphous
t/f Majority of the activities of plants is due to alkaloids
true
t/f To be a true alkaloid, it should be derived from amino acids.
true
Secondary amine: R2NH
ephedrine
Primary amine: RNH2
Mescaline
Alkaloids are generally white solid substance except _____________ (yellow) & ________________ (colorless, yields red salts)
berberine (yellow)
sanguinarine (colorless, yields red salts)
known as blood root, used by Indians
to color their faces. Colorless when its still in the plant, but when cut and exposed to oxygen, it becomes red.
Sanguinaria
Rich in berberine which undergoes extraction then evaporation, its extract will turn to brownish-yellow.
Makabuhay
Tertiary amine: R3N
atropine
Alkaloids derived from Lysine
Connine, Lobeline
Alkaloids derived from L-tryptophan
Strychnine, LSD
Quaternary amine
tubocurarine
Alkaloids derived from L-tyrosine
Morphine, Papaverine
Alkaloids derived from Ornithine Aspartate
Nicotine
Alkaloids derived from Ornithine
Cocaine, atropine, hyoscyamine, scopolamine
Alkaloids derived from Tyrosine
Morphine, Berberine, hydrastine, emetine, sanguinarine, opium alkaloids
Alkaloids derived from Tryptophane
Quinine
Alkaloids derived from Purine (Aspartate, Glycine, Glutamine)
Caffeine, Theobromine, theophylline
Remedy for alkaloid’s insolubility in water, soluble in organic solvents (fat soluble)
Convert them into salts to be soluble in water
Known as free alkaloids
ALKALOIDAL BASE
t/f Alkaloids are soluble in ether, chloroform, and other non-polar solvents <isolation></isolation>
true
freely soluble in water
ALKALOIDAL SALTS
Alkaloidal base (Free alkaloids) + inorganic acid
Alkaloidal salts
Alkaloidal salts + inorganic base
Alkaloidal base (Free alkaloids)
narcotine without narcotic effect
anarcotine
narcotine (1803)
Derosne
most important opium alkaloid
Morphine
Serturner
morphine
Pelletier and Caventou
BESPQCCC
brucine, emetine, strychnine, piperine, quinine, caffeine, colchicine, coniine
coniine
Schiff
first alkaloid with established structure
coniine
t/f True alkaloids are rare occurrence in other organisms
true
lysergic acid derivatives and sulfurcontaining alkaloids are best known in ?
fungi
t/f alkaloids are present in amphibians (many are antimicrobial)
true
Pteridophytes
Ephedra, Taxus
plant with Paclitaxel as chemotherapeutic agen
taxus
ephedra
source of Ephedrine
It is onsidered the heart of universal antidote because its mechanism is by precipitation. It inhibits further absorption of alkaloid in the stomach.
Tannic acid
Rgt: Potassium mercuric iodide
(+) result: Cream/yellowish ppt
Mayer’s rgt
Rgt: Potassium bismuth iodide
(+) result: Orange ppt
Dragendroff’s rgt
Rgt: Iodine in potassium iodide
(+) result: Reddish brown ppt
Wagner’s rgt
Rgt: Cadmium in potassium iodide
(+) result: Cream/yellowish ppt
Marme’s rgt
Rgt: Mercuric iodide
(+) result: White ppt
Valser’s rgt
Rgt: Phosphotungstic acid
(+) result: Reddish brown ppt
Scheibler’s rgt
Rgt: Phosphomolybdic acid
(+) result: Amorphous yellow white ppt
Sonnenchein’s rgt
Mahogany red
Picric acid
Buff color ppt
Tannic acid
Ppt
Gold salt test
Marquis: Marquis rgt, (+) blue
Codeine
Hasseman: Ferric Chloride, (+) Blood red
Codeine
Codeine Tests
Marquis, Hasseman
Atropine Test
Vitali, Gulielmo, Gerard’s
__________: Nitric acid, (+) gray ppt
Vitali
Gulielmo: Sulfuric acid, (+) ___________
Red with flower odor
___________: Ethanol, mercuric chloride, (+) yellow
Gerard’s
(+) Fine blue fluorescence, then green ppt with ammonia
Thalleoquin test for Quinine
Strychnine Test
Mandelin tets
Mandelin: Mandelin rgt, (+) violet
Strychnine
(+) purple color
(+) pink on paper chrom
Murexide test for Caffeine
emits a different color under UV (e.g., chlorophyll)
Fluorescence
substance emit color/light in the absence of light (glow in the dark)
Phosphorescence
t/f Almost all compounds considered to be alkaloids have their nitrogen atoms enclosed within a ring system
true. these are called TRUE alkaloids
not derived from AA and are sometimes called pseudoalkaloids
Heterocyclic “alkaloids”
protoalkaloids
do not have nitrogenous alkaloids (ex. ephedrine)
Non-heterocyclic ring
protoalkaloids
lacks one or more properties of alkaloids in that they are feeble bases.
Non-heterocyclic ring
contain nitrogen in a side chain
non-heterocyclic ring / protoalkaloids
t/f Protoalkaloids are alkaloids due to their physiological action rather than their chemical nature
true
alkaloid products from shikimic acid pathway
Chorismate : CAPA
Prephenate : PALF
Chorismate products
Anthraquinone, Phenol, Alcohol
Prephenate products
Aldehyde, Lactone, Flavonoid
Quaternary amine + carbanion
Mannich-type condensation, which produces alkaloid
true alkaloids or typical alkaloids
Heterocyclic
Traditionally called pyridine-piperidine alkaloids
“P” ALKALOIDS
Pyridine - from ______
Piperidine - from _____
Pyrrolidine - from _____
Pyrrolizidine - from _____
Pyridine - from ornithine or aspartate
Piperidine - from lysine
Pyrrolidine - from ornithine or aspartate
Pyrrolizidine - from ornithine
Pyridine-Piperidine Alkaloids
NiCo SpaLo
Nicotine (pyri)
Coniine (piper)
Sparteine (piper)
Lobeline (piper)
Scientific Name: Nicotiana tabaccum
Derivative of pyrrolidone
NICOTINE
Use: smoking deterrent, CNS stimulant, cholinergic neurotransmitter
NICOTINE
t/f Nicotine is addictive, can increase tolerance
true
Scientific Name: Areca catechu
Constituent: arecoline
ARECA NUT / BETEL NUT / NGANGA
areca nut tox/ high tannin content
risk of mouth / esophageal cancer
Use: masticatory (betel chewing), taenicide, anthelmintic (veterinary)
ARECA NUT / BETEL NUT / NGANGA
anti-taenia specie (tapeworm)
Taenicide
Scientific Name: Lobelia inflata
Constituent: lobeline
LOBELIA / INDIAN TOBACCO
less addictive than nicotine
lobeline
Use: smoking deterrent (ingredient in tablets and lozenges), resuscitation of newborn infants
LOBELIA / INDIAN TOBACCO
toxic effect of Lobelia
Paralytic
Scientific Name: Conium maculatum
Family: Apiaceae
Constituents: Coniine
POISON HEMLOCK
KOH allows coniine to develop strong, mouse-like odor due for the ____________
liberation of coniine
Used by Greeks for preparing draught by means of which criminals were put to death
poison hemlock / coniine
lethal injection of the Greeks
POISON HEMLOCK
Chief source of atropine
DUBOISIA
Scientific Name: Duboisia myoporoides
Chief: source of atropine; also has hyoscyamine,
scopolamine
DUBOISIA
Scientific Name: Duboisia hopwoodii
Constituents: nicotine, nornicotine
Use: Used like tobacco
PITURI / AUSTRALIAN TOBACCO
Hepatotoxic alkaloids
PYRROLIZIDINE ALKALOIDS
t/f Besides hepatotoxicity, pyrrolizidine alkaloids are also carcinogenic and mutagenic
true
(pyrrolizidine) used to treat hypertension without extensive studies, causing people to have hepatic necrosis and problems
Comfrey
(pyrrolizidine) Indicine use
antitumor
(pyrrolizidine) has glycosidase inhibitory activity which reduce postprandial increase in blood sugar
Australine
hepatotoxic properties of pyrrolizidine alkaloids are from
breakdown to alkylating pyrrole esters
Tropic acid fragment is derived from
phenylalanine
bicyclo [3.2.1] structure (encircled)
Tropane
tropane precursors
Ornithine, putrescine, and acetate
Scientific Name: Atropa belladonna
Constituents: hyoscyamine, atropine
BELLADONNA / DEADLY NIGHTSHADE
atropine is from
racemization of hyoscyamine
main uses of belladonna/atropine
antidote for organophosphate poisoning, anticholinergic
used for pupil dilation (mydriasis) to look beautiful
Sap of belladonna
antidote for organophosphate and carbamate poisoning
Atropine
muscarinic symptoms DUMBBELLS
Diarrhea, Urination, Miosis, Bronchoconstriction, Bradycardia, Emesis, Lacrimation, Salivation
mechanism of atropine as antidote
antimuscarinic; reverse the muscarinic effects
second stage of organophosphate poisoning involves nicotinic symptoms which is reversed by
pralidoxime
atropine : ____________
pralidoxime : ____________
physiologic antidote, antimuscarinic
chemical antidote, antinicotinic
Scientific Name: Datura stramonium
Constituents: Hyoscyamine, scopolamine
Use: anticholinergic
STRAMONIUM / JIMSON WEED / JAMESTOWN WEED
main use of stramonium
vapor is used to relieve ASTHMA. vapor is burnt and smoke is inhaled as bronchodilator
Scientific Name: Hyoscyamus niger
Constituents: Hyoscyamine, scopolamine
Use: anticholinergic
HYOSCYAMUS / HENBANE
Scientific Name: Hyoscyamus muticus
Constituent: Hyoscyamine
Egyptian Henbane
Scientific Name: Datura metel and Datura fastuosa
Constituent: Rich source of scopolamine (“hyoscine”)
TALUMPUNAY / THORNAPPLE
Buscopan (Hyoscine butylbromide) use
antispasmodic
Side effect: constipation (GIT muscle relaxation)
Buscopan
Scopolamine + Morphine
Twilight sleep (anesthesia)