pcog alkaloids

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