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1. Among the outstanding alkaloid yielding plants are Leguminosae, Papaveracae, Renunculaceae, Rubiaceae,
Solanaceae and Berberidaceae
2. Primary amine (RNH2), Secondary amine (R2NH), Tertiary amine (R)
3. Liquid Alkaloids: CONIINE, NICOTINE, SPARTEINE; lacks oxygen
Names of alkaloids are obtained in various ways:
1. Generic name of plant yielding them (hydrastine, atropine)
2. Specific name of plant yielding them (cocaine, belladonnine)
3. Common name of drug yielding them (ergotamine)
4. Physiologically active (emetine, morphine)
5. Discoverer (pelleterine)
Classification based on the ring structure or nucleus of the chief alkaloid group in the plant drug
1. Pyridine & Piperidine (arecoline, lobeline, nicotine)
2. Tropane – condensation product of pyrrolidine & piperidine (atropine, hyoscine, hyoscyamine)
3. Quinoline – (cinchona, quinine, quinidine, cinchonine & cinchondine)
4. Indole – (ergonovine, reserpine, strychnine)
5. Imidazole – (pilocarpine)
6. Purine – (caffeine & theobromine)
7. Steroidal – (protoveratrine)
8. Purine bases – (caffeine & theobromine)
Alkaloidal reagents:
Wagner’s Iodine in Potassium Iodide Reddish-brown ppt.
Mayer’s Potassium in Mercuric Iodide Cream/white ppt.
Dragendorff’s Potassium Bismuth Iodide Orange ppt.
Valser’s Mercuric Iodide White ppt.
Marme’s Cadmium in Potassium Iodide
Scheibler Phospotungstic
Sonneschein Phospomolybdic
Pyridine – tertiary base; upon reduction it is converted into 2ndary base, piperidine
Most important alkaloids in this group are: areca, arecoline HBR, lobelia, lobeline, nicotine
3 subgroups:
1. Piperidine – lobeline and lobelia
2. Nicotinic acid – arecoline and areca
3. Pyridine and pyrrolidine - nicotine
QUINOLINE ALAKALOIDS – includes those obtained from cinchona, QUININE, QUINIDINE, CINCHONINE,
CINCHONIDINE
- TRYPTOPHAN – is a precursor of quinine in cinchona
- Appears to be a cleavage of the benzopynole ring of the tryptophan moiety
ISOQUINOLINE ALKALOIDS - important drugs are: IPECAC, EMETINE, HYDRASTIS, HYDRASTINE, SANGUINARIA,
CURARE, TUBOCURARINE, BERBERINE & OPIUM
- Derived from phenylalanine or tyrosine
ALKALOIDS OF OPIUM
CODEINE Obtained from opium Most widely used opium Narcotic analgesic
or synthetically by alakaloid Antitussive
demethylation Sedative in cough
DIACETYLMORPHINE OR Phenolic and acetyl group are replaced by acetyl More pronounced than
HEROIN groups morphine
(ANALGESIC)
PAPAVERINE Occurs naturally in opium by 1%
PAPAVERINE HCl Smooth muscle relaxant
Relief of cerebral and peripheral ischemia
HYDROMORPHONE Reducing morphine in Well known by trade Narcotic analgesic
HYDROCHLORIDE or HCl sol’n name DILAUDID
Dihydromorphinone
HYDROCODONEBITARTRAT/ antitussive
Dihydrocodeinone Bitartrate
INDOLE AKALOIDS
Botanical Source Constituents/Description Uses
RAUWOLFIA Rauwolfia serpentine Reserpine Hypotensive
SERPENTINA FN: Apocynaceae 3 series of alkaloids: Sedative and
a. Weakly basic indole tranquilizing effect
(reserine)
b. Indoline alkaloids of
intermediate basicity
c. Strong anyhydronium bases
Powdered Rauwolfia Reserpine – chief alkaloid with hypotensive and sedative activity
Serpentina - Antihypertensive & antipsychotic agent
RESCINNAMINE Methyl reserpate ester of 3,4,5-trimethoxycinnamic acid Used to treat mild
hypertension
DESERPIDINE Rauwolfia canescens Canescine, recanescine hypotensive
11-desmethoxyreserpine
YOHIMBINE Pausinystalia yohimbe Yohimbine Tx of impotence
FN: Rubiaceae ↑cholinegic activity;
↓penile blood outflow
CATHARANTHUS or Catharanthus roseus Four Bisindole: vinblastine,
Oral hypoglycemic
Vinca; Periwinkle; vinleurosine, vinrosidine,
Chichirica vincristine
CATHARANTHUS ALKALOIDS
VINBLASTINE SO4 Catharanthus N-methyl group Tx for neoplasms
Vincaleukoblastine Tx for Hodgkin’s dse
Sulfate VLB Antineoplastic
VINCRISTINE SO4 Catharanthus N-formyl group Tx for acute lymphocytic
Leurocristine SO4 leukemia
VCR or LCR
VINDESINE Semisynthetic derivative Antineoplastic activity
of vinblastine
VINORELBINE Semi synthetic derivative 3-noranhydrovinblastine First line of Tx of non
TARTRATE of vinblastine small cell lung cancer
NUX VOMICA Strychnos nux vomica Strychnine & brucine
STRYCHNINE & Nux vomica/ignatia by Brucine – less toxic than Central stimulant
BRUCINE extraction with dilute strychnine; alcohol Vermin killer
(Dimethoxystrychnine) Sulfuric acid denaturant
PHYSOSTIGMA, Physostigma venenosum Physostigmine/serine Reversible
CALABAR BEAN, FN: Fabaceae cholinesterase inhibitor
ORDEAL BEAN Tx of Glaucoma
Physostigmine/eserine Cholinergic (ophthalmic) applied topically to the conjunctiva
salicylate Antidote in poisonings caused by anticholinergic agents
Physostigmine/serine Cholinergic (ophthalmic) applied topically to the conjunctiva
sulfate
ERGOT, RYE ERGOT Claviceps purpurea Aka SPURRED RYE
or Secale cornutum
ERGOT ALKALOIDS
ERGONOVINE Ergot Ergometrinine – accepted Oxytocic
MALEATE/ chem.. name of isolysergic
Ergometrine Maleate acid isomer of ergonovine
METHYLERGONOVINE Semi-synthetic homolog White to pinkish tan Oxytocic
MALEATE of ergonovine microcrystalline powder
ERGOTAMINE Oxytocic activity
TARTRATE Used to prevent abort vascular headaches or migraine
(Avamigram) Cerebral vasoconstrictor
Dihydroergotamine Salt of semisynthetic Tx of migraine
mesylate alkaloid
ERGOLOID Relief of symptoms of idiopathic decline in mental capacity in geriartric px
MESYLATE
Methysergide maleate Synthetsis of lysergic Salt of methylergonovine Serotonin antagonist
acid Prophylaxis of vascular
headache
LYSERGIC ACID Most active & most specific psychotomimetic agent
DIETHYLAMIDE (LSD) Central sympathetic stimulant (hallucinogen)
DRUGS RELATED TO ERGOT
Botanical Source Constituents/Description Uses
OLILIUQUI Rivea corymbosa Lysergic acid amide Aztec hallucinogenic drug
(ergine)
Isokysergic amide
(erginine)
PILOCARPINE Pilocarpus jaborandi An acid with glyoxaline Stimulates muscarinic
nucleus receptors
Pilocarine HCl
STEROIDAL ALKALOIDS – derived biosynthetically from 6 isoprene units
- Found in plant families of APOCYNACEAE, BUXACEAE, LILIACEAE, SOLANACEAE
Source Use