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ALKALOIDS
One or more rings of carbon atoms, usually with a nitrogen atom in the ring
Characteristics of alkaloids
MOST ALKALOIDS ARE CRYSTALLINE SOLIDS
COLORLESS
SOLUBLE IN ORGANIC SOLVENTS AND INSOLUBLE IN WATER
BITTER IN TASTE
Crystaline solid
Conine
Nicotinr
Spartene
Liquid alkaloid
Yellow alkaloids
Colchicine
Berberine
Methyl Red Alkaloids
salt of saguinarine
Function
Source of nitrogen
Final products of detoxification
Growth regulators
Protection
Source of energy
TRUE ALKALOIDS
from amino acid and they share a heterocyclic ring with nitrogen
Potent
TRUE ALKALOIDS examples
Cocaine
Quinine
Dopamine
Morphine
Atropine.
PROTOALKALOIDS
which the N atom derive from an amino acid is not a part of the heterocyclic
PROTOALKALOIDS Examples
ephedrine
Mescaline
Yohimbine
PSEUDOALKALOIDS
not derived from amino acids but have nitrogen in a heterocyclic ring.
PSEUDOALKALOIDS Examples
Caffeine
Theobromine
PYRIDINE- PIPERIDINE
from the amino acid Lysine/Ornithine
Tobacco
sc: Nicotiana tobacum
fam: Solanaceae
cons: Nicotine
use: CNS stimulant, ganglionic (nicotinic) cholinergic receptor agonist, and smoking deterrent (Nicorette®)
Nicorette
product temporary nicotine
ARECA/ARECA NUT/BETEL NUT
sc: Areca catechu
fam: Arecaceae
cons: Arecoline, arecaidine, and guvacoline
use: Vermicide and taenifuge
Areca Masticatory stimulant
agents salivation
LOBELIA/INDIAN TOBACCO
sc: Lobelia inflata
fam: Lobeliaceae
cons: Lobeline
use: CNS stimulant, ganglionic (nicotinic) cholinergic receptor agonist, and smoking deterrent
TROPANE
A dicyclic compound formed by the condensation of a pyrolidine precursor (ornithine)
3 acetate derived carbon atoms
BELLADONNA/DEADLY NIGHTSHADE
sc: Atropa belladonna
fam: Solanaceae
cons: Atropine
use: Parasympathetic depressant, Anticholinergic properties, Antidote for cholinesterase inhibitors, antisialogogue
HYOSCYAMUS/HENBANE
sc: Hyoscyamus niger
Hyoscyamus muticus (Egyptian henbane)
fam: Solanaceae
cons: Hyoscyamine and scopolamine
use: treat motion sickness and anticholinergic
STRAMONIUM/JIMSON WEED/JAMESTOWN WEED
sc: Datura stramonium
fam: Solanaceae
cons: Hyoscyamine and scopolamine
use: Anticholinergic and relief of asthma
WITHANIA
sc: Withania somnifera
fam: Solanaceae
cons: Tropine and pseudotropine
DUBOISIA
sc: Duboisia myoporoides
fam: Solanaceae
cons: Hyoscyamine and scopolamine
use: Treatment of motion sickness, stomach disorder, side effects of cancer therapy, and antispasmodic
MANDRAGORA/EUROPEAN MANDRAKE
sc: Mandragora officinarum
fam: Solanaceae
cons: Hyoscyamine, scopolamine, and mandragorin
use: Emetic
Mandragorin
Elicit emetic property
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
Brompton's cocktail
Cocaine
Morphine/ Methadone
analgesic for terminal ill px - cancer
QUINOLINE
Alkaloids containing quinoline as their basic nucleus obtained from cinchona.
Tryptophan is a precursor of quinine in cinchona
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
Cinchonism
overdose toxicity
hallmark
tinnitus
temporary loss of hearing and impaired sight
CUPREA BARK
sc: Remijia purdieana /pedunculata
fam: Rubiaceae
cons: Quinidine
use: Cardiac depressant
ISOQUINOLINE
largest single group of plant alkaloids.
Exhibit a phenanthrene nucleus
Morphine, codeine, thebaine
Sanguinaria
another member of the Papaveraceae
contains isoquinoline alkaloids
IPECAC
sc: Cephaelis ipecacanhua
fam: Rubiaceae
cons: emetine, cephaeline, and psychotrine
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
EMELINE OR METHYLCEPHAELIN
obtained from ipecac or prepared synthetically by methylation of cephaeline
not orally
it can cause nausea and vomiting
EMETINE HYDROCHLORIDE
salt form
Antiamebic
amebic dysenttery
antiprotozoan
HYDRASTIS/GOLDENSEAL
sc: Hydrastis canadensis
fam: Ranunculaceae
cons: hydrastine, berberine, and canadine
use: astringents in inflammation of the mucous membranes (125mg)
SANGUINARIA/BLOOD ROOT
sc: Sanguinaria canadensis
fam: Papaveraceae
cons: sanguinarine
use: stimulating expectorant and emetic properties
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)
Head drop rabbit
curare
ear rabbit
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
POWDERED OPIUM
products obtained from ipecac
making Dover's powder and camphorated opium tincture and is combined with other agents in antidiarrheal preparations.
analgesic
PAREGORIC/CAMPHORATED OPIUM TINCTURE
products obtained from ipecac
Antiperistaltic
LAUDANUM, OPIUM TINCTURE, OR DEODORIZED OPIUM TINCTURE
products obtained from ipecac
Antiperistaltic
POPPY SEED/MAW SEED
products obtained from ipecac
Parenteral formulations
Salad dressings
OPIATES
natural occuring
MORPHINE
OPIATES
Most important
Narcotic analgesic
Strongly hypnotic
Induce nausea, vomiting, constipation, and habit formation.
addictive
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.
NOSCAPINE
OPIATES
narcotine/anarcotine
Antitussive.
The usual dose is 15 mg, up to 4 times a day
available in syrup and chewable tablets
PAPAVERINE
OPIATES
Smooth muscle relaxant
Antitussive in combination with codeine (15mg)
oral 150 mg
IM 30 mg
OPIOIDS
synthetic
HEROIN
OPIOIDS
Diacetylmorphine
Formed by the acetylation of morphine
Increased danger of habit formation, very potent.
most addictive
HYDROMORPHONE
OPIOIDS
Dihydromorphinone hydrochloride
Powerful narcotic analgesic
tends to strongly depress the respiratory mechanism
Less frequent SE (constipation
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
APOMORPHINE
OPIOIDS
Condensation of morphine + HCl and one molecule of water is lost
Emetic
100mg/ 1 kg
max 6g
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
RAUWOLFIA SERPENTINA
sc: Rauwolfia serpentina
fam: Apocynaceae
cons: reserpine
use: Treatment of snakebites to insanity, antihypertensive and tranquilizer
Mood swings
CATHARANTHUS/VINCA
sc: Catharanthus roseus
fam: Apocynaceae
cons: vinblastine, vinleurosine, vinrosidine and vincristine
use: Antineoplastic
anticancer
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
VINCRISTINE SULFATE
n-formly
Acute leukemia and in combination therapy in Hodgkin's disease, lvmphosarcoma, reticulum cell sarcoma, rhabdomyosarcorna, neuroblastoma, and Wilms' tumor.
YOHIMBINE
sc: Pausinystalia yohimbe
fam: Rubiaceae
cons: yohimbine
use: Treatment of impotence/erectile dysfunction, aphrodisiac
alpha 2 antagonist
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
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
ERGOT/RYE ERGOT/SECALE CORNUTUM
sc: Secale cereale
fam: Clavicipitaceae
cons: ergotamine
treatment for migraine
use: oxytocic properties
ERGONOVINE MALEATE
ERGOT ALKALOIDS
Ergometrine maleate (labor)
An oxytocic and produces much faster stimulation of the uterine muscles than do other ergot alkaloids
Methylergonovine maleate
ERGOT ALKALOIDS
Semisynthetic homolog of ergonovine
Oxytocic lightly more active and longer acting than ergonovine
ERGOTAMINE TARTRATE
ERGOT ALKALOIDS
Specific analgesic in treatment of migraine
METHYLSERGIDE MALEATE
ERGOT ALKALOIDS
Prophylaxis of vascular headache
salt of methyl ergotrovine
prophylaxis for headache
LYSERGIC ACID DIETHYLAMIDE/LSD
ERGOT ALKALOIDS
Most active and most specific psychomimetic drug
Hallucinogenic agent
Dangerous
IMIDAZOLE
Monoacidic tertiary base containing a lactone group as well as the imidazole nucleus
histidine
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
STEROIDAL
cyclopentanophenanthrene nucleus
They apparently are either formed from cholesterol, or they and cholesterol have a common precursor
GREEN HELLEBORE/AMERICAN HELLEBORE
sc: Veratrum viride
fam: Liliaceae
cons: veratrosine, veratrine, and veratridine
use: hypotensive, cardiacdepressant, and sedative properties
decrease contraction - inotropy
WHITE HELLEBORE/EUROPEAN HELLEBORE
sc: Veratrum album
fam: Liliaceae
cons: protoveratrine A and B
use: insecticide
ALKALOIDAL AMINES
do not contain heterocyclic nitrogen atoms.
Derivatives of phenylethvlamin and derived from the common amino acids, phenylalanine or tyrosine
EPHEDRA/ MA HUANG
sc: Ephedra sinica
fam: Gnetaceae
cons: Ephedrine
use: Nasal decongestant, bronchodilator
COLCHICINE
sc: Colchicum autumnale
fam: Liliaceae
cons: Colchicine
use: suppressant for gout
uric
KHAT/ABYSSINIAN TEA
sc: Catha edulis
fam: Celastraceae
cons: cathinone
use: mimic methamphetamine
PEYOTE/MESCAL BUTTONS
sc: Lophophora williamsii (Lemaire)
fam: Cactaceae
cons: mescaline
use: Hallucinogenic & euphoric agent
PURINE
heterocyclic nucleus consisting of the 6-membered pyrimidine ring fused to the 5-membered imidazole ring.
CAFFEINE
1,3,7-trimethylxanthine
THEOPHYLLINE (neo)
1,3- dimethylxanthine
THEOBROMINE
3,7-dimethylxanthine
KOLA/COLA/KOLANUTS
sc: Cola nitida
fam: Sterculiaceae
cons: caffeine and theobromine
use: ingredient in carbonated drinks stimulant
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
THEA/TEA
sc: Camelia sinensis
fam: Theaceae
cons: theophylline
use: : bronchial asthma
Aminophylline
reversible broncho spasm associated with chronic bronchitis emphysenia (COPD)
THEOBROMINE
sc: Theobroma cacao
fam: Sterculiaceae
cons: theobromine
use: diuretic and a smooth muscle relaxant
METHOD I
powder is treated with alkalis to liberate the free bases that can then be extracted with water immiscible organic solvents
METHOD II
powdered material is extracted with water or aqueous alcohol containing dilute acids.
METHOD III
powder is extracted with water soluble organic solvents which are good solvents for both salts and free bases
Wagners Test (WIKI)
reagent: Potassium Triiodide
res: reddish-brown precipitate
Mayers Test (MANEKI)
reagent: Potassium-Mercuric Iodide
res: creamy-white precipitate
Valsers Test
reagent: Mercuric iodide
Dragendorff Test (Dr. KBIO)
reagent: Potassium bismuth iodide
res: Orangish red colour
Bouchdart Test
reagent: Iodine in KI, most sensitive
Marme Test
reagent: Potassium cadmium iodide
res: White precipitate
Sonnencheim Test ( SON in PMA)
reagent: Phosphomolybdic acid