ALKALOIDS

Bitter, basic nitrogenous compounds, sparingly soluble in water

Most of them end in –ine
All are solids except:
o Coniine
o Nicotine
o Sparteine
Form double salts with compounds of mercury, gold, platinum, and other heavy metals

Alkaloidal reagents/precipitants:
1. Mayer’s Mercuric potassium iodide White or slightly yellow ppt.
2. Marmers Potassium-cadmium iodide White ppt.
3. Dragendorff’s Potassium-bismuth iodide Orange
4. Wagner’s Iodine TS Reddish brown or red brown ppt.
5. Scheibler’s Phosphotungstic acid
6. AuCl
7. Valser’s KI and mercuric iodide White ppt.
8. Tannic acid
9. Hager’s Picric acid Yellow
10. Sonnenscheins Phosphomolybdic acid

CHARACTERISTICS OF ALKALOIDS
1. Free alkaloids - sparingly soluble in H2O
2. + acids --> salts
3. + salts of heavy metals --> highly insoluble precipitates
4. nitrogenous, physiologically active
5. alkaloidal salt + Na2CO3 --> free base
6. Solid alkaloid - white, soluble or slightly soluble in H2O, soluble in organic solvents
7. Pure alkaloids - insoluble in water, soluble in organic solvents
8. alkaloids + acids = alkaloidal salts (soluble in water)

Alkaloid yielding plants: Pharmacologic Action of Alkaloids

1. Leguminosae 1. Analgesic and narcotics -morphine, codeine
2. Solanaceae 2. Central stimulant - strychnine, brucine
3. Rubiaceae 3. Mydriatics - atropine
4. Ranunculaceae 4. Miotics - physostigmine, pilocarpine
5. Papaveraceae 5. Cause a rise in B.P - ephedrine
6. Berberidaceae 6. Excessive hypertension - reserpine

The names of the alkaloids are obtained in various ways:

1. generic name (Hydrastine, Atropine)
2. specific name (Coccaine, Belladona)
3. common name (Ergotamine)
4. physiologic activity (Emetine, morphine)
5. discoverer (Pelletietine)

FUNCTIONS OF ALKALOIDS IN PLANTS

1. poisonous agents – protect plants againts insects & herbivores
2. end products of detox representing metabolic locking up of compounds otherwise harmful to the plant
3. Regulatory growth factor
4. Reserve substance capable of supplying nitrogen or others
PYRIDINE-PIPERIDINE
Origin Use
Nicotine Nicotiana tabacum Nicotine (smoking deterent)
Arecoline Anthelminthic
Areca Betel nut Areca Catechu
Tannin content causes esophageal CA
Lobelia Indian tobacco Lobelia inflata Lobeline (smoking deterent)

TROPANE/SOLANACEOUS
Origin Use
Atropa belladonna Parasympathetic depressant
Belladonna Deadly nightshade
Atropos – fate that cuts the thread of life Adjunct in tx of peptic ulcer

Hyoscyamus Henbane Hyoscyamus niger Hog + Bean toxic to swine

Jimson Weed Datura stramonium

Stramonium Treatment of asthma (vapor)
Jamestown Weed D. metel (Talumpunay/Thorn apple)

Mandragora European mandrake Mandragora officinarum Has folkloric uses

Psychomotor stimulant with a strong

Cocaine Coca Erythroxylum coca
abuse potential, vasoconstrictor

Principal Solanaceous Alkaloids:

1. Atropine
o Antispasmodic
o Antisialogogue – decrease production of secretion
o Mydriatic and cycloplegic
o Antidote for cholinesterase inhibitors

2. Scopolamine or Hyoscine
o Hyoscyamus niger
o Treatment of motion sickness
o Trans-scoop or transderm Scop – 4 hours before anti-emetic effect

QUINOLINE
Cuprea
o Remijia purdieana

Cinchona or Peruvian bark

o Cinchona succirubra (Red cinchona)
Cinchona calisaya (Yellow cinchona)
o Quinidine - anti-arrthythmic
Quinine - antimalarial
o Identification of the quinine /quinidine by Thalleioquin test
ISOQUINOLINE – emerald green color of thalleioquin (Joseph Caventou with Pelltier)
Other Name Origin Constituent Use
Ipecac syrup – emetic
Ipecac Cephalis ipecacuanha Emetine Fluidextract – 14x more potent
Ipecac + Opium - diaphoretic
Sanguinaria Bloodroot Sanguinaria canadensis Sanguinarine Expectorant & emetic

Tubocurarine Curare Strychnus toxifera Tubocurarine Skeletal muscle relaxant

Astringents in inflammation of
Hydrastis Golden seal Hydrastis canadensis Hydrastine
the mucous membrane

Opium Stone of immortality Papaver somniferum Stimulate and depresses CNS

Alkaloids of Opium
1. morphine - most abundant, most important
2. codeine methyl morphine - most widely used; antitussive
3. heroin diacetylmorphine - hallucinogen
4. Papaverine - relief of ischemia & arrhythmias
5. Hydromorphine
6. Hydrocodone
7. Apomorphine - emetic
8. Narcotine/Noscapine - ANARCOTINE, antitussive
9. Paregoric - camphorated opium tincture
10. Dover’s powder - Ipecac + opium

IMIDAZOLE
Pilocarpine (Pilocarpus, Jaborandi)
BO : Pilocarpus jaborandi
Use : Cholinergic drug used in the Tx of glaucoma; miotic

STEROIDAL
Veratum Viride (American or Green hellebore)
BO : Veratrum viride
Uses : hypotension, cardiac depressant, Black hellebore – cardiac stimulant

White Hellebore (European hellebore)

BO : Veratrum album
Use : Hypotensive, Insecticide (crude drug)
INDOLE
Other Name Origin Constituent Use
Rauwolfia Rauvolfia serpentina Reserpine Snake bites
serpentina Insanity
Rescinnamine (Psychotherapy)
Deserpidine (II- Hypotensive
desmethoxyreserpine) Sedative,
Yohimbine - TX: Tranquilizing
impotence (Serpasil)
Catharanthus Vinca Catharanthus roseus Vincristine and Vinblastine -
Chichirica antineoplastic/oncolytic
Nux Vomixa Strychnos nux-vomica Strychnine – toxic central stimulant
Brucine – alcohol denaturant
Physostigmine Calabar bean Physostigma venenosum Physostigmine/Eserine - Tx glaucoma, miotic
Ordeal bean
Ergot Rye ergot Claviceps purpurea Ergonovine – oxytocic
Secale cornutum Ergotamine – migrane
Lysergic acid Diethylamide (LSD)
most specific and most active hallucinogen
discovered by A. Hoffman in 1943

ALKALOIDAL AMINES
Constituent Use
Ephedrine Ephedra, Mahuang Ephedra sinica Sympathomimetic

Plant genetics: doubles the chromosomes

Colchicine Colchicum autumnale
Gout suppressant: Acute

Khat Abyssinian tea Catha edulsis Cathinone - alleviate sensation of hunger and fatigue

Mescaline (3,4,5 trimethoxy-ẞ-phenylethylamine)

Peyote Mescal buttons Lophophora williamsii
Hallucinogen and euphoric

PURINE OR METHYLXANTHINES
1. Caffeine 1,3,7 trimethylxanthine
o Does not react with or ppt with alkaloidal reagnents
o Kola (dried cotyledon of Cola nitida) Caffeine is detected by
o Cofee bean (dried seeds of Coffea arabica) means of a Murexide test
o Guarana (Paullinia cupana) purple color
o Mate/Paraguay tea (Ilex paraguariensis)

2. Theophylline 1,3 dimethylxanthine

o Camella sinensis
o Treatment of bronchial asthma, Tocolytic agent
o Aminophylline – semisynthetic theophylline derivative

3. Theobromine 3,7 dimethyl xanthine

o Theobroma cacao
o Diuretic in cardiac & pulmonary edema (preferred over caffeine - little action on the CNS)
 VITAMINS AND VITAMIN-CONTAINING DRUGS
Vitamins
o Organic substances, not synthesized within the body, that are essential in small amounts for the maintenance of
normal metabolic functions
o Do not furnish energy and are not utilized as building units for cellular structure
o Term was derived in 1911 – vital amine
o Used as special dietary supplements or as drugs
Vit. B2, B3, B5 – coenzymes
Vit. B12, B9 – biosynthetic transfer of 1-C units
Vit. C – biosynthesis of hydroxyproline
Vit. B1, B6 – metabolism of carbohydrates and amino acids
Biotin – metabolic carboxylation
Vit. D, E – influence membrane transport

FAT-SOLUBLE VITAMINS (A, D, E and K)

Absorption from the intestinal tract is associated with that of lipids and a deficiency state may be caused by
conditions that impair fat absorption

Function Source Deficiency

Vitamin A Vision, growth, Tretinoin or all-trans retinoic acid (Retin-A) Fish liver oils Nyctalopia
(β-ionine, Retinol) tissue Highly teratogenic Xeropthalmia
- Most toxic vitamin differentiation Treat acne vulgaris Hyperkeratosis
- Most stable vitamin Isotretinoin or 13-cis retinoic acid (Accutane)
For cystic acne
CI: Pregnancy
B-carotene (Solatene)
Precursor (converted in small intestine)
Vitamin D Ca and PO4 Ergocalciferol/D2 - from ergosterol Fish liver oils Rickets
(Sunshine vitamin) absorption Cholecalciferol/D3 - 7-dehydrocholesterol Osteomalacia
Calcifediol and Calcitriol - hypocalcemia
Dihydrotachysterol - tetany, hypoPTH
Vitamin E Antioxidant green veggies, Neurologic
(α-tocopherol) whole grains, dysfunctions
Test: Further-Meyer yolk, meat (rare)
Synergistic with Se
Vitamin K Prothrombin Vitamin K1 (phytonadione) Leafy veggies Hemorrhage and
(2-methyl-1,4- formation Vitamin K2 (prenylmenaquinone-7) Dairy Capillary fragility
naphthoquinone) Vitamin K3 (menadione, menaquinone) – most
active form
Vitamin K4 (menadiol)
WATER SOLUBLE VITAMINS
Function Deficiency

Beriberi
B1 Thiamine Decarboxylation (CHO, AA)
Wernicke-Korsakoff

Stomatitis
Chelitis
B2 Riboflavin Redox coenzyme, FAD
Glossitis
SE: yellow urine
Pellagra
Niacin/Nicotinic
Dementia
B3 acid/Niacinamide/ Redox coenzyme, NAD
Dermatitis
Nicotinamide
Diarrhea
Paresthesias of the
Pantothenic acid Acetyl CoA
B5 extremities or “burning
“chick antidermatitis factor” Secretion of hormones (cortisone)
foot” syndrome
Transamination, Decarboxylation (CHO, AA), RBC
Pyridoxine
metabolism Peripheral neuropathy
B6 RBC fragility
Pyridoxol – plants
Pyridoxine antagonists: chloramphenicol, Hypochromatic microcytic
Pyridoxal and pyridoxamine –
cycloserine, hydralazine, isoniazid and oral anemia
animals
contraceptives

Folic acid Folate FH2 Tetrahydrofolic acid (liver & Megaloblastic anemia
B9
Pteroylglutamic acid plasma) Macrocytic anemia
Pernicious anemia
Cobalamin
Cyanocobalamin – most active RBC synthesis
Rapidly dividing cells of
B12 Hydroxocobalamin – for CN Metabolism of Folic Acid
the hematopoietic system
toxicity associated with Na
and irreversible
nitroprusside
neurologic damage

B17 Laetrile

B15 Pangamic Acid

Impaired fat and CHO

metabolism, Dermatitis
H D-biotin Carboxylation (gluconeogenesis and FA synthesis)
* Biotin deficiency is
usually caused by avidin
Hydroxylation of pro and lysine (collagen synthesis) Scurvy (impaired wound
C Cevitamic acid Anti-oxidant healing, loss of dental
Enhances Fe absorption cement, SQ hemorrahge)
VITAMIN-RELATED FACTORS
Para-aminobenzoic Acid (PABA)
Precursor of folic acid
Added as an accessory food factor
Used for rheumatic fever and other conditions benefiting from salicylate therapy; UV sunscreen in topical
preparations
Interferes with the antibacterial action of sulfonamides

Choline (B-hydroxyethyltrimethylammonium hydroxide)

Occur in egg yolk, animal organs, fish, milk, cereal grains, fruits and root vegetables
Essential nutrient in certain higher animals
USE: lipotropic agent in conditions such as liver cirrhosis, Huntington’s chorea, presenile dementia and
tardive dyskinesia

Inositol (meso-inositol, myoinositol or cis-1,2,3,5-trans-4,6-cyclohexanehexol)

Dietary sources: legumes, cereal grains, nuts and animal organs
Implicated in membrane transport of amino acids and K and Na ions
Large doses may cause moderate diarrhea

MULTIVITAMIN THERAPY
Inadequate vitamin intake can result not only from a poor diet but also from alcoholism, increased needs during
pregnancy and lactation, prolonged broad-spectrum antibiotic therapy and the course of parenteral nutrition.
 ALKALOIDS

PYRIDINE-PIPERIDINE
1 Areca (Areca Nut, Betel Nut)
2 Lobelia (Indian Tobacco)
3 Nicotine

TROPANE/SOLANACEOUS
1 Belladona (Deadly Nightshade Leaf)
2 Stramonium (Jimson Weed, Jamestown Weed)
3 Cocaine (Coca)

QUINOLINE: Cinchona (Peruvian Bark) QUIN-Chona

IMIDAZOLE: Pilocarpine (pilocarpus , Jaborandi) Si IMILDA walay Piloc

ISOQUINOLINE I-S-O-H
1 Ipecac
2 Hydrastis (Golden Seal)
3 Sanguinaria (Blood Root)
4 Opium (opium Or Gum Opium)

INDOLE Im so Ca-PERN najud

1 Rauwolfia Serpentina Ca-PERN kaayo mag INDOLE (ENROLL)
2 Catharanthus (Vinca)
3 Nux Vomica
4 Physostigma (Physostigma, Calabar Bean, Ordeal Bean)
5 Ergot (rye Ergot, Secale Cornutum)

STEROIDAL
1 Veratum Viride (American Or Green Hellebore)
2 White Hellebore (European Hellebore)
PEYOTE sige ko ug MESCAL ni KHAT kay ABYSSINIAN
ALKALOIDAL AMINES siya ni MAHUANG kay ge arthritis siya
1 Ephedrine (Ephedra, Mahuang)
2 Colchicine (Colchium Seed)
3 Khat (abyssinian Tea) KHA - YOTE ; EPECOL
4 Peyote (mescal Buttons)

PURINE BASES
1 Caffeine (1,3,7 Trimethylxanthine)
2 Theophylline (Thea , Tea , 1,3 Dimethylxanthine)
3 Theobromine (3,7 Dimethyl Xanthine)