pcog alkaloids

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