Alkaloids, Acanthicifoline to Hypaconitine¶

Last updated 2026-01-24 by Dr John Elfick

9.2.0 Caffeine¶

9.2.1 Caffeine¶

Caffeine, (C₈H₁₀N₄O₂), guaranine, (1,3,7-Trimethylxanthine), (3-Methyltheobromine), purine derivative alkaloid, methylxanthine alkaloid, methylated purine source

It is an odourless white powder or white glistening needles, usually melted together, bitter taste, solutions neutral to litmus.

It is a xanthosine, weak stimulant, diuretic, CNS stimulant, causes wakefulness and increased mental activity, diuretic, cardiac and respiratory stimulant.

It may block absorption of calcium, (fatal dose is about 10 mg, but not from tea, coffee, or other beverages), included in proprietary analgesics.

Caffeine is used to treat apnea and bronchopulmonary dysplasia in premature infants.

It occurs in Camellia, Coffee, Cola, Ilex, Paullinias, and in Yerba Mate (Ilex paraguariensis).

Coffee, coffee tins, Use, (Experiments)

See diagram: Caffeine Theobromine, Theophylline

9.2.2 Approximate caffeine content of beverages, mg /cup¶

Brewed coffee 40-180 mg/cup, depends on length of time brewed.

Percolated coffee cup 150 mL, Caffeine content 100 mg

Drip coffee cup 150 mL, Caffeine content 80 to 200 mg

Instant coffee cup 150 mL, Caffeine content 60 to 70 mg (30 to 120 mg)

Energy drink with caffeine, e.g. Red Bull, Caffeine content 80 mg / can

Cocoa cup 150 mL, Caffeine content 4-5 mg

Dark chocolate bar 100 g Caffeine content 20-25 mg

Milk chocolate bar, Caffeine content 3-6 mg

Kola, Cola drink-can 375 mL, Caffeine content 35 to 55 mg

Tea cup 150 mL, Caffeine content 50 mg (20-90 mg depends on length of time brewed)

Decaffeinated tea cup 150 mL, Caffeine content 2 mg

Coffee beans (green), Caffeine content 0.8 to 1.8% mg

Tea leaves (undried), Caffeine content 0.8 to 2.1% mg

In some countries, the legal limit for caffeine content is 55 mg / 375 mL (cola drink-can).

The fatal dose of caffeine is about 10 mg.

Caffeine is in analgesic preparations containing Ergotamine for the relief of migraine headaches.

Caffeine is found in coffee Coffea arabica, tea Camellia sinensis, yerba mate Ilex paraguariensis, guarana Paullinia cupana Cola Cola nitida

Theobromine is found in chocolate Theobroba cacao.

9.2.3 Caffeine, extraction with supercritical carbon dioxide, critical point¶

Materials can exist in three states: solid, liquid and gas.

You can change from one to another by altering temperature and / or pressure.

If you increase temperature and pressure enough, the distinction between liquid and gas will disappear at the critical point.

No phase boundary between liquid and gas exists, because at extremely high temperatures and pressures, the liquid and gaseous phases become indistinguishable.

The critical point of water is 374 o C, 218 atmospheres of pressure.

At above 31.1 o C and 72.9 atmospheres of pressure carbon dioxide behaves like liquid and like a gas.

It spreads out like a gas to fill the available space and can dissolve substances as if it was a liquid.

The low temperature is convenient, because it can be used with substances that would be damaged by the high temperature.

Supercritical carbon dioxide is used to remove caffeine from tea and coffee, an extract substances from hops, essential oils, and environmental pollutants.

It is also used for dry cleaning.

Supercritical carbon dioxide is used to extract caffeine from coffee beans, extract nicotine from tobacco, extract oil from oilseeds, e.g. soy bean and sunflower, extract the natural insecticide pyrethrins from the perennial plant pyrethrum, (Chrysanthemum cinerariaefolium).

9.2.4 Extraction of caffeine and benzoic acid from soft drinks¶

Extraction of caffeine and benzoic acid from soft drinks, e.g. cola and lemonade

See diagram 16.21.10: Purines (See: Caffeine)

9.2.5 Isolation of caffeine in cola (kola), soft drink¶

Add 2 g of sodium carbonate to 50 mL of a cola (kola) drink in a 1 litre conical flask.

Add 50 mL of dichloromethane (methylene chloride) and swirl gently for 5 minutes.

Do not shake.

Transfer into a separating funnel and leave to settle for 10 minutes.

Drain the lower methylene chloride layer into a 250 mL conical flask.

Add 50 mL more dichloromethane to the separating funnel and enclose with a stopper.

Carefully invert the separating funnel 3 times to allow any remaining caffeine to be extracted into the dichloromethane layer.

Again drain the lower methylene chloride layer into the 250 mL conical flask.

Add 5 g of anhydrous magnesium sulfate to remove the water when it forms insoluble hydrated magnesium sulfate.

Filter the now clear dichloromethane through cotton wool pad into a 250 mL beaker.

Evaporate the dichloromethane on a water bath in a fume cupboard or distil it off to recover the solvent.

Weigh the remaining precipitate.

Test the precipitate by putting a small amount on a watch glass and mix with 3 drops of concentrated hydrochloric acid.

Be careful! Add small crystals of potassium chlorate.

Mix with a glass rod and evaporate to dryness on a water bath in a closed fume cupboard.

Leave the watch glass to cool then moisten the residue with 2 drops 2 M ammonia solution.

The residue turns purple.

16.6.17 Unclassified alkaloids¶

| Colchicine

| Elaeocarpine

| Ficine

Candicine, (C11H18NO+), Unclassified Alkaloid¶

Candicine, (C₁₁H₁₈NO⁺), Unclassified Alkaloid source

C₁₁H₁₈NO⁺, HOC₆H₄(CH₂)₂N(CH₃)₃⁺, has N + in its molecular structure, so it is classed as an Alkaloid source

Candicine, Candicin, primary amine, 4-Hydroxy-N,N,N-trimethylbenzeneethanaminium, action like nicotine, hypertension

It occurs in root of Trichocereus, Fagara, Philodendron, Magnolia, and in Lysichitum.

Cannabisativine, (C21H39N3O3), Unclassified Alkaloid¶

Cannabisativine, (C₂₁H₃₉N₃O₃), Unclassified Alkaloid source

Cannabisativine, (azamacrocycle, so has N in a ring of 12 or more atoms), lactam

It occurs in roots and leave of (Cannabis sativa).

Cryptopleurine, (C24H27NO3), Unclassified Alkaloid¶

Cryptopleurine, (C₂₄H₂₇NO₃), Unclassified Alkaloid source

Cryptopleurine, organic heteropentacyclic compound, aromatic ether, alkaloid antibiotic, protein synthesis inhibitor, antineoplastic, antiviral against herpes

It occurs in Cryptocarya, Boehmeria, and in Cissus.

Acanthicifoline, (C10H12N2O2), Monoterpenoid and Sesquiterpenoid Alkaloid¶

Acanthicifoline, (C₁₀H₁₂N₂O₂), Monoterpenoid and Sesquiterpenoid Alkaloid source

Acanthicifoline is a derivative of 2,7-naphthyridine, C₈H₆N₂, a naphthyridine. source

The traditional use in India and China is to treat dyspepsia, paralysis, asthma, headache, rheumatism.

It occurs in (Acanthus ilicifolius).

Aconine, (C25H41NO9)¶

Aconine, (C₂₅H₄₁NO₉) source

Aconine, jesaconine, main constituent of aconitine, amorphous alkaloid with a polycyclic molecule, polyether, tertiary amino compound

It is used for research only, not for human or veterinary use.

It inhibits osteoclast differentiation and bone resorption, induces flaccid paralysis, and is toxic to rats and mice.

It occurs in Aconitum.

Aconitine, (C34H47NO11), Diterpenoid Alkaloid¶

Aconitine, (C₃₄H₄₇NO₁₁), Diterpenoid Alkaloid source

Aconitine, Acetylbenzoylaconitine, too dangerous to use internally

It is very poisonous and can be absorbed by skin, slows heart and lowers blood pressure, acute toxic, neurotoxin, anti-inflammatory, antineuralgic

It blocks neurotransmitters release, blocks norepinephrine (noradrenaline) uptake, causes ventricular tachycardia

It occurs in Aconitum.

Acronidine, (C18H17NO4), Quinoline Alkaloid¶

Acronidine, (C₁₈H₁₇NO₄), Quinoline Alkaloid source

Acronidine, organic heterotetracyclic compound, is an aromatic ether.

It occurs in Acronychia.

Acronycine, (C20H19NO3), Quinoline Alkaloid¶

Acronycine, (C₂₀H₁₉NO₃), Quinoline Alkaloid source

Acronycine, Acronine, Acromycine, Pyriproxyfen, pyrano-acridone alkaloid, carcinogenic, is possibly antitumour agent, broad spectrum of activity.

It occurs in Acronychia.

Actinidine, (C10H13N), Monoterpenoid and Sesquiterpenoid Alkaloid¶

Actinidine, (C₁₀H₁₃N), Monoterpenoid and Sesquiterpenoid Alkaloid source

Actinidine, pyridine derivative, cyclopentapyridine, pyridine alkaloid, (derived from pyridine), pheromone, attracts cats, in Actinidiaceae, Actinidia polygama, in Valerian, and in Tecoma stans leaves.

Affinine, (C21H24N2O2), Indole Alkaloid¶

Affinine, (C₂₁H₂₄N₂O₂), Indole Alkaloid source

Affinine, 17-Hydroxyvobasan-3-one, psychoactive.

It occurs in (Tabernaemontana catharinensis).

Affinisine, (C₂₀H₂₄N₂O) source

Agroclavine, (C16H18N2), Indole Alkaloid¶

Agroclavine, (C₁₆H₁₈N₂), Indole Alkaloid source

Agroclavine, tetracyclic indole alkaloid, ergot alkaloid, (based on ergoline), is used for ergot-based drug synthesis.

It occurs in fungus (Claviceps purpurea), (Rivea bernoulliana), and in (Jacquemontia tamnifolia).

Ergoline, C₁₄H₁₆N₂, structurally-related alkaloids which bind to neurotransmitter receptors, e.g. dopamine, noradrenaline and serotonin receptors source

Ajaconine, (C22H33NO3), Diterpenoid Alkaloid¶

Ajaconine, (C₂₂H₃₃NO₃), Diterpenoid Alkaloid source

Ajaconine, organic heterohexacyclic compound, tertiary amino compound, cyclic ether, olefin compound, poisonous, is insecticidal.

It occurs in Delphinium.

Ajmalicine, (C21H24N2O2), Indole Alkaloid¶

Ajmalicine, (C₂₁H₂₄N₂O₂), Indole Alkaloid source

Ajmalicine, Raubasine, a methyl ester indole derivative alkaloid, corynanthe type alkaloid, pentacyclic indole alkaloid, anti-hypertensive and sedative.

It is used to treat circulatory disorders, antimicrobial activity, used to study effects as antagonist of adrenergic and nicotinic receptors.

It occurs in (Rauwolfia sepentina), and in (Catharanthus roseus).

Allocryptopine, (C21H23NO5), dibenzazecine Alkaloid¶

Allocryptopine, (C₂₁H₂₃NO₅), dibenzazecine Alkaloid source

Allocryptopine, a cyclic ketone, cyclic acetal, aromatic ether

It occurs in (Glaucium arabicum), (Zanthoxylum beecheyanum), (Berberis integerrima) and in the Papaveraceae family.

Alpinine, (C23H29NO6), Isoquinoline Alkaloid¶

Alpinine, (C₂₃H₂₉NO₆), Isoquinoline Alkaloid source

Alpinine, rhoeadine alkaloid, methylalpinigenine

It occurs in Papaver.

Amaranthin, (C30H34N2O19), Betalain Alkaloid¶

Amaranthin, (C₃₀H₃₄N₂O₁₉), Betalain Alkaloid source

Amaranthin, Amaranthin betacyanin, Amarantin, Betanidin 5-O-sophorobiuronic acid, disaccharide derivative of betanidin, biological pigment

It occurs in (Atriplex hortensis), Amaranthus, (Celosia cristata), and in (Chenopodium album).

Ambelline, (C18H21NO5), Amaryllidaceae Alkaloid¶

Ambelline, (C₁₈H₂₁NO₅), Amaryllidaceae Alkaloid source

Ambelline, isoquinoline derivative, amaryllis alkaloid, analgesic but too toxic

It occurs in Amaryllis, (Crinum × powellii), and in Hippeastrum.

Amurensine, (C19H19NO4), Isoquinoline Alkaloid¶

Amurensine, (C₁₉H₁₉NO₄), Isoquinoline Alkaloid source

Amurensine, pavine alkaloid, xanthopetaline, is used for pain relief, expectorant, tranquilliser.

It occurs in Papaver.

Amurine, (C19H19NO4), Isoquinoline Alkaloid¶

Amurine, (C₁₉H₁₉NO₄), Isoquinoline Alkaloid source

Amurine, a morphinan alkaloid

It occurs in Papaver.

Anabasine, (C10H14N2), Pyrrolidine and Piperidine Alkaloid¶

Anabasine, (C₁₀H₁₄N₂), Pyrrolidine and Piperidine Alkaloid source

Anabasine, Neonicotine, pyridine derivative, teratogenic agent, nicotine analog so is chemically similar to nicotine.

It is a skeletal muscle relaxant, and was formerly used as industrial piperidine botanical insecticide.

It occurs in tobacco smoke and is used as test of smoking.

It occurs in (Nicotiana acuminata), and in (Anabasis phylla).

Anagyrine, (C15H20N2O), Quinolzidine Alkaloid¶

Anagyrine, (C₁₅H₂₀N₂O), Quinolzidine Alkaloid source

Anagyrine, Monolupine, Rhombinine, Anagyrine, highly toxic, teratogenic, causes "crooked calf's disease, cardiotonic.

It occurs in (Anagyris foetida), (Ulex europaeus), Thermopsis, (Cystisus scoparius), Genista, Lupinus, Sophora, Ammodendron, (Ormosia cocconia), and in (Viscum cruciatum).

Anatabine, (C12H10N2), Pyrrolidine and Piperidine Alkaloid¶

Anatabine, (C₁₂H₁₀N₂), Pyrrolidine and Piperidine Alkaloid source

Anatabine, (polycyclic noncondensing pyridine derivative), bipyridine, Nicotine-related tobacco alkaloid, in urine, inhibitor of human cytochrome.

It occurs in Nicotiana.

Anisodamine, (C17H23NO4), Tropane Alkaloid¶

Anisodamine, (C₁₇H₂₃NO₄), Tropane Alkaloid source

Anisodamine, 6-Hydroxyhyoscamine, a monocarboxylic acid, anticholinergic

It is Chinese medicine, used to treat circulatory shock, possible treatment of intestinal diseases.

It occurs in (Duboisia myoporoides), (Hyoscyamus albus), and in (Anisodus tanguticus).

Anisodine, (C17H21NO5), Tropane Alkaloid¶

Anisodine, (C₁₇H₂₁NO₅), Tropane Alkaloid source

Anisodine, Daturamine, alpha-Hydoxyscolopamine, antispasmodic, anticholinergic, is used to treat circulatory shock.

It occurs in (Anisodus tanguticus).

Annolobine, (C17H15NO3), Isoquinoline Alkaloid¶

Annolobine, (C₁₇H₁₅NO₃), Isoquinoline Alkaloid source

Annolobine, Anolobine, Anolobin, aporphine alkaloid, an alkaloid antibiotic

It occurs in (Asimina triloba), and in (Goniothalamus amuyon).

Annonaine, (C17H15NO2), Isoquinoline Alkaloid¶

Annonaine, (C₁₇H₁₅NO₂), Isoquinoline Alkaloid source

Annonaine, Anonaine, Anonain, aporphine alkaloid, oxacycle, organic heteropentacyclic compound, insecticidal, antimicrobial, anticancer, antiplasmodial

It occurs in Annona, (Nelumbo nucifera), and in (Xylopia aethiopica).

Annotine, (C16H21NO3)¶

Annotine, (C₁₆H₂₁NO₃) source

Annotine, an azaspiro compound, is used to treat skin disorders.

It occurs in Icelandic club moss (Lycopodium annotinum), Chinese herbal medicine.

Apodine, (C21H22N2O4), Indole Alkaloid¶

Apodine, (C₂₁H₂₂N₂O₄), Indole Alkaloid source

Apodine, hexacyclic indole alkaloid, methyl ester

It occurs in Tabernaemontana.

Apohyoscine, (C17H19NO3), Tropane Alkaloid¶

Apohyoscine, (C₁₇H₁₉NO₃), Tropane Alkaloid source

Apohyoscine, Aposcopolamine, Aposcopolamin, epoxyatropyloxytropane, monocarboxylic acid

It occurs in Hyoscyamus, Datura, and in (Duboisia hopwoodii).

Apparicine, (C18H20N2), Indole Alkaloid¶

Apparicine, (C₁₈H₂₀N₂), Indole Alkaloid source

Apparicine, Gomezine, Pericalline, Tabernoschizine, monoterpenoid indole alkaloid, antimicrobial, stimulates central nervous system, analgesic.

It occurs in (Aspidosperma quebracho-blanco), Tabernaemontana, and in (Ochrosia illiptica).

Arecaidine, (C7H11NO2), Pyrrolidine and Piperidine Alkaloid¶

Arecaidine, (C₇H₁₁NO₂), Pyrrolidine and Piperidine Alkaloid source

Arecaidine, methylguvacine, N-methylguvacine, mildly toxic, astringent, causes sweating, folk medicine

It occurs in (Areca catechu).

Arecoline, (C8H13NO2), Pyrrolidine and Piperidine Alkaloid¶

Arecoline, (C₈H₁₃NO₂), Pyrrolidine and Piperidine Alkaloid source

Arecoline, Arecaline, Arecholine, Methylarecaiden

It stimulates muscarinic and nicotinic receptors, toxic may cause convulsions and paralysis.

The seeds used medically for parasympathetic stimulant action, used as euphoriant, used in various salts to stimulate the parasympathetic nervous system.

Also, it is used as a veterinary vermifuge.

It occurs in (Areca catechu).

Arenaine, (C11H17N3O), Monoterpenoid and Sesquiterpenoid Alkaloid¶

Arenaine, (C₁₁H₁₇N₃O), Monoterpenoid and Sesquiterpenoid Alkaloid source

Arenaine, aliphatic heteropolycyclic compound, a pyrimidine

It occurs in seeds of the sand plantain (Plantago arenaria).

Argentine, (C23H26N4O3), Quinolzidine Alkaloid¶

Argentine, (C₂₃H₂₆N₄O₃), Quinolzidine Alkaloid source

Argentine, Carbonylbiscytisine

It occurs in Sophora, Thermopsis, and in (Dermatophyllum secundiflorum).

Armepavine, (C190H23NO3), Isoquinoline Alkaloid¶

Armepavine, (C₁₉₀H₂₃NO₃), Isoquinoline Alkaloid source

Armepavine, benzylisoquinoline alkaloid, convulsions, irritation, irregular cardiac action

It occurs in Papaver, (Euonymus europaeus), Rhamnus, Nelumbo, and in (Berberis integerrima).

Atropine, (C17H23NO3), Tropane Alkaloid¶

Atropine, (C₁₇H₂₃NO₃), Tropane Alkaloid source

Atropine, dl-Hyoscyamine, Tropine tropate, poisonous, highly toxic, lethal dose for humans 100 mg

It blocks the action of the neurotransmitter acetylcholine C₇H₁₆NO₂⁺, the major transmitter at neuromuscular junctions. source

Like curare on poison-tipped arrows, causing blurred vision, suppressed salivation, vasodilation, delirium.

It is generally not used as an administered drug because it is broken down very rapidly by cholinesterases, but it is useful in some ophthalmological applications.

Atropine sulfate is used in anticholinergic medicines, to treat cardiac arrest, dilate pupils for eye examination, relax muscles, inhibit secretions.

Atropine occurs in (Atropa belladonna), Datura, (Cyphanthera tasmanica), and (Anthocercis ilicifolia).

Baptifoline, (C15H20N2O2), Quinolzidine Alkaloid¶

Baptifoline, (C₁₅H₂₀N₂O₂), Quinolzidine Alkaloid source

Baptifoline, Hydroxyanagyrene, Argentamin, occurs in coffee and coffee products.

It occurs in (Baptisia tinctoria), Sophora, (Caulophyllum thalictroides), (Thermopsis chinensis), and in (Thermopsis lanceolata).

Belladine, (C19H25NO3), Amaryllidaceae Alkaloid¶

Belladine, (C₁₉H₂₅NO₃), Amaryllidaceae Alkaloid source

Belladine, N-Benzylphenethylamine, acetylcholinesterase and cholinesterase inhibitor

It occurs in (Amaryllis belladonna), (Crinum powelli), and in Nerium.

Bellendine, (C12H15NO2), Tropane Alkaloid¶

Bellendine, (C₁₂H₁₅NO₂), Tropane Alkaloid source

Bellendine, (10-methylpyranotropane), oxacycle

It occurs in (Bellendena montana), and in (Darlingia darlingiana).

Berberine, (C20H18NO4), Isoquinoline Alkaloid¶

Berberine, (C₂₀H₁₈NO₄), Isoquinoline Alkaloid source

Berberine, Berberin, Umbellatine, isoquinoline derivative, protoberberine alkaloid, bitter, yellow, used to treat bacillary dysentery.

It occurs in barberry Berberis, (Coptis chinensis), (Evodia rutaecarpa), Mahonia, Nandina, and in Thalictrum.

It occurs in Goldenseal (Hydrastis canadensis), and in Oregon grape (Berberis aquifolium).

Berberine chloride, (C₂₀H₁₈ClNO₄), occurs in Chinese herbs, and is antifungal, antiviral, and anticancer. source

Berberine hemisulfate, (C₂₀H₁₈NO₄.1/2SO₄), anti-inflammatory, fluoresces under UV light, and occurs in Hydrastis. source

Berberine chloride hydrate, (C₂₀H₁₈NO₄.H₂O), Natural Yellow 18 hydrate, is used to treat intestinal infections. source

Betalamic acid, (C₉H₉NO₅), Betalain Alkaloid source

Betalamic acid, dicarboxylic acid, betalain

It occurs in beetroot (Beta vulgaris), (Celosia cristata), Cistanthe, and in Portulaca.

Betanidin, (C18H16N2O8), Betalain Alkaloid¶

Betanidin, (C₁₈H₁₆N₂O₈), Betalain Alkaloid source

Betanidin, (2,6-Pyridinedicarboxylic acid), non-proteinogenic alpha-amino acid

Betanidin, purple pigment, (aglycone of betanin)

It occurs in Mesembryanthemum, Portulaca, and in (Ullucus tuberosus).

Betanin, (C24H26N2O13), Betalain Alkaloid¶

Betanin, (C₂₄H₂₆N₂O₁₃), Betalain Alkaloid source

Betanin, betanine, betacyanin, betanidin 5-O-beta-glucoside, a red-violet betacyanin, purple pigment, a cyanogenic glycoside

Purple pigment, E162 Beetroot Red, from beet, food additive, colorant used in cosmetics and pharmaceuticals.

Betanin, Red beef extract diluted with dextrin, Food dye, cosmetic and pharmaceutical colorant

Betanin may not broken down in the body so can cause temporary red urine (beeturia and red faeces).

The appearance of red urine may cause distress, but the patient is not suffering haematuria, (blood in the urine).

Betalains: indole-derived glycoside pigments, contain nitrogen.

Betanin aglycone is betanidin, (C₁₈H₁₆N₂O₈) source

Betanin occurs in (Beta vulgaris), Carpobrotus, Drosera, Mesembryanthemum, Opuntia, and in Portulaca.

.
See diagram: Betanin — . See diagram: Betanin

Betonicine, (C7H13NO13), Pyrrolidine and Piperidine Alkaloid¶

Betonicine, (C₇H₁₃NO₁₃), Pyrrolidine and Piperidine Alkaloid source

Betonicine, Achillein, amino-acid betaine, secondary alcohol,br> It is a zwitterion, an acid that loses a proton from its -NH₃⁺ group to form an anion, both hydrogens attached to the nitrogen replaced by methyl groups. source

It occurs in herbs and spices, and in Yarrow (Achillea millefolium).

Bocconine, (C21H161NO5) + Isoquinoline Alkaloid¶

Bocconine, (C₂₁H₁₆₁NO₅) + Isoquinoline Alkaloid source

Bocconine, benzophenanthridene alkaloid, chelirubine, local anaesthetic, kills nematode worms.

It occurs in Bocconia, and in Papaver.

Boldine, (C19H21NO4), Isoquinoline Alkaloid¶

Boldine, (C₁₉H₂₁NO₄), Isoquinoline Alkaloid source

Boldine, uniboldina, boldin, an aporphine alkaloid, antioxidant, hepatoprotective, cytoprotective, antipyretic, anti-inflammatory

It is used in laxatives, to increase bile secretion and treat gallstones It occurs in Peumus, root of (Lindera umbellata), (Boldea fragrans), Peumus, Monimia, Litsea, Sassafras, Desmos, Liriodendron, Retanilla, and in (Damburneya salicifolia).

Boschniakine, (C10H11NO), Monoterpenoid and Sesquiterpenoid Alkaloid¶

Boschniakine, (C₁₀H₁₁NO), Monoterpenoid and Sesquiterpenoid Alkaloid source

Boschniakine, indicaine

It occurs in (Boschniakia rossica), Tecoma, Plantago, and in Pedicularis.

Bracteoline, (C19H21NO4), Isoquinoline Alkaloid¶

Bracteoline, (C₁₉H₂₁NO₄), Isoquinoline Alkaloid source

Bracteoline, aporphine alkaloid

It occurs in Papaver and in (Licaria armeniaca).

Brucine, (C23H16N2O4), Indole Alkaloid¶

Brucine, (C₂₃H₁₆N₂O₄), Indole Alkaloid source

Brucine, Brucinum, monoterpenoid indole alkaloid, acute toxic, white crystalline solid, is combustible but hard to ignite.

It has a toxic vapour or dust by inhalation and ingestion.

It occurs in (Strychnos axillaris), and in (Strychnos ignatii).

Bufotenine, (C₁₂H₁₆N₂O), Tryptamine alkaloid and tertiary amine source

Indole derivative alkaloid, Non-isoprene indole alkaloid, dimethyl serotonin, in skin of toads, in psychedelic compounds, illegal in USA

It occurs in Arundo reed, (Anadenanthera colubrina), and in Piptadenia.

Bulleyaconitine A, (C35H43NO9), Alkaloid¶

Bulleyaconitine A, (C₃₅H₄₃NO₉), Alkaloid source

Bulleyaconitine, Bulleyanum, analgesic, anti-inflammatory, formerly used for the treatment of chronic pain and rheumatoid arthritis

It occurs in Aconitum.

Calafatimine, (C38H40N2O7)¶

Calafatimine, (C₃₈H₄₀N₂O₇) source

Calafatimine, an isoquinoline, a bisbenzylisoquinoline alkaloid, Chinese medicine, weakly antineoplastic

It occurs in (Berberis vulgaris).

Calebassine, (C40H48N4O4 +2 ), Indole Alkaloid¶

Calebassine, (C₄₀H₄₈N₄O₄ +2 ), Indole Alkaloid source

Calebassine, toxiferine IV, C-Alkaloid A, highly toxic, neuromuscular blocker, arrow poison

It was called "calabash curare", because it was formerly packed into hollow gourds.

It occurs in Strychnos.

Calystegin, Tropane Alkaloid¶

Calystegin, Tropane Alkaloid

Calystegin A3, (8-Azabicyclo[3.2.1]octane-1,2,3-triol), Trihydroxynorpropane, (C₇H₁₃NO₃), inhibits glucosidases, livestock nerve disorder if eating bindweed source

It occurs in alcoholic beverages.

It occurs in Calystegia, Convolvulus, and in Solanum.

Camptothecin, (C20H16N2O4), Quinoline Alkaloid¶

Camptothecin, (C₂₀H₁₆N₂O₄), Quinoline Alkaloid source

Camptothecin, Camptothecine, pyranoindolizinoquinoline, tertiary alcohol, delta-lactone, antitumour activity, inhibits nuclear enzyme topoisomerase

It is used for research into apoptosis - a form of programmed cell death in multicellular organisms.

It occurs in (Camptotheca acuminata).

Cancentrine, (C36H33N2O7), Isoquinoline Alkaloid¶

Cancentrine, (C₃₆H₃₃N₂O₇), Isoquinoline Alkaloid source

Cancentrine, morphinan alkaloid, ibenzooxazepine alkaloid, bisbenzylisoquinoline alkaloid, bright yellow

It occurs in (Dicentra canadensis).

Candimine, (C18H19NO6), Amaryllidaceae Alkaloid¶

Candimine, (C₁₈H₁₉NO₆), Amaryllidaceae Alkaloid source

Candimine, Maltotoxin, toxic

It occurs in (Hippeastrum morelianum).

Cantleyine, (C11H13NO3), Monoterpenoid and Sesquiterpenoid Alkaloid¶

Cantleyine, (C₁₁H₁₃NO₃), Monoterpenoid and Sesquiterpenoid Alkaloid source

Cantleyine, aromatic carboxylic acid, a pyridine

It occurs in tree bark of (Cantleya corniculata), Dipsacus, and in (Strychnos nux-vomica).

Capsaicin, (C18H27NO3)¶

Capsaicin, (C₁₈H₂₇NO₃) source

Capsaicin is a Protoalkaloid

It occurs in chilli peppers, Capsicum.

Caranine, (C16H17NO3), Amaryllidaceae Alkaloid¶

Caranine, (C₁₆H₁₇NO₃), Amaryllidaceae Alkaloid source

Caranine, (2-Deoxylycorine), indolizidine alkaloid, organic heteropentacyclic compound, secondary alcohol, toxic to animals

It occurs in (Amaryllis belladonna), (Clivia miniata), and in (Crinum bulbispermum).

Carboxystrictosidine, (C28H34N2O4), Gluco Indole Alkaloid¶

Carboxystrictosidine, (C₂₈H₃₄N₂O₄), Gluco Indole Alkaloid source

5-Carboxystrictosidine, (5α-Carboxy-3-isovincoside), anti-inflammatory

It occurs in (Uncaria tomentosa), and in (Sinoadina racemosa).

Carnegine, (C13H19NO2), Isoquinoline Alkaloid¶

Carnegine, (C₁₃H₁₉NO₂), Isoquinoline Alkaloid source

Carnegine, carnegin, Pectenin, simple isoquinoline

It occurs in Carnegiea, Cereus, and in Haloxylon.

Carpaine, (C27H50N2O4), Pyrrolidine and Piperidine Alkaloid¶

Carpaine, (C₂₇H₅₀N₂O₄), Pyrrolidine and Piperidine Alkaloid source

Carpaine, macrocyclic lactone, cardiovascular drug, affects myocardium, decreases blood pressure, amoebicide

It occurs in Papaya (Carica papaya), Vasconcellea, and in many seeds.

Cassine, (C18H35NO2), Pyrrolidine and Piperidine Alkaloid¶

Cassine, (C₁₈H₃₅NO₂), Pyrrolidine and Piperidine Alkaloid source

Cassine is a citraconoyl group, C₅H₄O₂. source

It occurs in Cassia, Prosopis, (Senna spectabili)s, and in (Elaeodendron matabelicum).

Cassythicine, (C19H19NO4), Isoquinoline Alkaloid¶

Cassythicine, (C₁₉H₁₉NO₄), Isoquinoline Alkaloid source

Cassythicine, aporphine alkaloid, methylacinodaphnine, antimicrobial, cytotoxic

It occurs in (Cassytha filiformis), (Annona glabra), and in (Neolitsea sericea).

Castanospermine, (C8H15NO4), Pyrrolidine and Piperidine Alkaloid¶

Castanospermine, (C₈H₁₅NO₄), Pyrrolidine and Piperidine Alkaloid source

Castanospermine, tetrahydroxyindolizidine alkaloid, inhibits glucosidases, causes severe gastrointestinal irritation and perhaps death to animals.

It may be useful in HIV/AIDS prevention research.

Castanospermine derivative "celgosivir" possible antiviral drug to treat hepatitis C virus

It occurs in (Castanospermum australe), (Alexa grandiflor), and in (Alexa wachenheimii).

Catharine, (C₄₆H₅₄N₄O₁₀), alkaloid, a natural product source

It occurs in (Catharanthus lanceus) and (Catharanthus roseus).

Caulophylline, (C₁₂H₁₆N₂O), Quinolzidine Alkaloid source

Caulophylline, Methylcytisine, (12-Methylcytisine), toxic, repels snails

It occurs in (Caulophyllum thalictroides), (Cytisus laburnum), (Spartium junceum), (Thermopsis lanceolata), and in (Sophora chrysophyll).

Celosianin, (C₄₀H₄₂N₂O₂), Betalain Alkaloid source

Celosianin, Betacyanin, Celosianin II, monoferulylamaranthin, glycoside, (derives from betanidin), purple pigment

It occurs in (Chenopodium rubrum).

Cephaeline, (C₂₈H₃₃N₂O₄), alkaloid in (Cephaelis ipecacuanha), Isoquinoline Alkaloid, formerly used in commercial medicine "syrup of ipecac". and is used to treat poisoning. source

Cepharanthine, (C₃₇H₃₈N₂O₆), Isoquinoline Alkaloid source

Cepharanthine, Cepharanthin, O-Methylcepharanoline, alkaloid, (CEP)

Japanese medicine, antitumour, anti-allergic, anti-inflammatory, immunimo-modulatory and antineoplastic alkaloid

It inhibits efflux transporter multidrug-resistant protein in cancer cells by preventing the intracellular accumulation of certain antitumour drugs.

It inhibits the entry of HIV-1 by reducing plasma membrane fluidity.

It stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.

It occurs in (Stephania cepharantha), and in (Stephania sinica).

Cevadine, (C₃₂H₄₉NO₉), mixture of alkaloids source

Cevadine, Veratrine, poisonous, irritates skin and mucous membranes, highly toxic to insects, less toxic to mammals

It occurs in (Schoenocaulon officinale) and in (Veratrum oblongum).

Chaconine, (C₄₅H₇₃NO₁₄), Steroidal Alkaloid source

Chaconine, glycoalkaloid, poison, in green potato skins, in Potato, (Solanum tuberosum), Solanaceae, insecticidal, fungicidal, a-chaconine more toxic

Potato tubers in sunlight form glycoalkaloids when amyloblasts change to chloroplasts, but cooking does not destroy the glycoalkaloids.

Pregnant women should especially avoid eating damaged potatoes to avoid possible birth defects due to glycoalkaloids.

Toxicity is caused by anticholinesterase activity on the central nervous system and membrane disruption, which irritates the gastro-intestine of the digestive system.

Store potatoes in cool dark places where air circulates, but not in a refrigerator.

Do not purchase green, bruised, insect-damaged or cut potatoes, do not display potatoes under strong fluorescent lights.

Irradiate potatoes to delay sprouting and prevent greening, but not prevent the production of a-solanine.

Chelerythrine, (C₂₁H₁₈NO₄) + Benzophenanthridine alkaloid source

Chelerythrine, Toddalin, Cheleritrine, Broussonpapyrine, benzophenanthridine alkaloid, organic cation, enzyme inhibitor, antibacterial, antineoplastic

It occurs in Zanthoxylum simulans root, and in Chelidonium majus, (greater celandine).

Chelerythrine chloride, (C₂₁H₁₈ClNO₄), benzophenanthridine alkaloid, irritant, is a salt of an unstable naturally fluorescent material. source

It is anti-inflammatory, and anti-tumour.

It occurs in (Chelidonium majus).

Cinchonidine, (C₁₉H₂₂N₂O), Cinchona Alkaloid source

Cinchonidine, Cinchovatine, (derived from a hydride of Cinchonan), diasteroisomer of cinchonine, antimalarial

It occurs in (Cinchona officinalis), and in (Cinchona calisaya).

Cinchonine, (C₁₉H₂₂N₂O), Cinchona Alkaloid source

Cinchonine, irritant, occurs in the bark of most varieties of Cinchona shrubs

It occurs in (Cinchona calisaya), and in (Neolamarckia cadamba).

Cinegalline, (C₂₃H₃₀N₂O₆), Quinolzidine Alkaloid source

Cinegalline is a quinolizidine alkaloid

It occurs in Genista.

Clivorine, (C₂₁H₂₇NO₇), Pyrrolizidine Alkaloid source

Clivorine, Senecionanium, heptacarcinogenic

It occurs in Anchusa, and in Ligularia.

Cocaine¶

Cocaine, C₁₇H₂₁ON₄, benzoylmethylecgonine, alkaloid ester, benzoic acid ester, local aneasthetic, vasoconstrictor, has powerful CNS effects like amphetamines. source

It is a drug of abuse, causes inhibition of dopamine uptake, high doses mood elevating effects and toxic reactions, in the cocoa plant (Erythroxylum coca).

Cobalt (II) thiocyanate, Co(SCN)₂, Harmful, Environment danger, in Scott's reagent test for cocaine source

Copolymer, Polymer from linking different monomer types, e.g. cocaine, curare, caffeine, piperine

See diagram, 16.20.0 Caffeine, cocaine, coniine, heroin, LSD

See diagram 16.21.7, Mescaline, dopamine, psilocybin, serotonin, ergine, LSD, tropane

It occurs in Cocoa (Erythroxylon coca), Erythroxylaceae.

Codeine, (C₁₈H₂₁NO₃), Isoquinoline Alkaloid source

Codeine, isoquinoline derivative, morphinan alkaloid, 3-methylmorphine

It is an opioid analgesic related to morphine, but with less potent analgesic properties and mild sedative effects.

It is used to treat moderate pain and cough, not linked to liver injury.

It occurs in Papaver.

Codeine, heroin, methadone, abuse

Codonopsine, (C₁₄H₂₁NO₄), Pyrrolidine and Piperidine Alkaloid source

Codonopsine, may decrease blood pressure.

It occurs in (Codonopsis clematidea), and in (Averrhoa bilimbi).

Colchicine, (C₂₂H₂₅NO₆), Unclassified Alkaloid source

Colchicine, an alkaloid with nitrogen in the side chain, (protoalkaloid), yellow, irritant, carcinogen, extremely toxic by all routes

It inhibits cell division, because is a mitosis spindle poison at metaphase.

It is used for laboratory investigation of mitosis and in plant breeding to induce polyploidy mutations.

It is anti-inflammatory so used in treatment of gout and Mediterranean fever (Periodic disease). possibly anticancer.

Colchicine, Solution < 0.1% Not hazardous, is not associated with liver injury except overdoses.

It occurs in meadow saffron, (Colchicum autumnale).

Coniceine, (C₈H₁₅N), Pyrrolidine and Piperidine Alkaloid source

Coniceine, beta-Coniceine, piperidine derivative, extremely toxic, mouse-like odour, can be reduced to dl-coniine, causes abnormal embryos

It occurs in (Conium maculatum), and in Aloe.

Coniine, (C₈H₁₇N), Pyrrolidine and Piperidine Alkaloid source

Coniine, piperidine derivative, 2-propyl-piperidine, volatile, oily, extremely toxic, paralyses nerve endings, neurotoxic toxic principle, mouse smell

It is used to paralyse insect prey.

It occurs in (Conium maculatum), (Sarracenia flava), and in Black Elderberry (Amorphophalus rivieri).

Conium maculatum was used to cause the death of Socrates.

Convolvine (C₁₆H₂₁NO₄), Tropane Alkaloid source

Convolvine, O-Veratroylnortropine, (8-Azabicyclo[3.2.1]oct-3-yl 3,4-dimethoxybenzoate), a methoxybenzoic acid, acutely toxic, irritant

It occurs in Convolvulus, Datura, Physalis, Salpichroa, and in Bruguiera.

Coptisine, (C₁₉H₁₄NO₄) + Alkaloid source

Coptisine, Coptisin, cytotoxic alkaloid, related to Berberine

It occurs in opium, bitter taste, Chinese medicine for digestive disorders caused by bacteria, cytotoxic agent in heptoma and leukemic cells.

It occurs in Coptis chinensis, Chelidonium majus> and in Fumaria.

Corynoline, (C21H21NO5), Benzophenanthridine Alkaloid¶

Corynoline, (C₂₁H₂₁NO₅), Benzophenanthridine Alkaloid source

Corynoline, acetylcholinase inhibitor, hepatoproactive

It occurs in Chinese goldthread Coptis, and in (Corydalis incisa).

Crassicauline A, (C35H49NO10), Diterpenoid Alkaloid¶

Crassicauline A, (C₃₅H₄₉NO₁₀), Diterpenoid Alkaloid source

Crassicauline A, in human urine, xenobiotic, acetate ester, aromatic ether, benzoate ester

It is an analgesic drug, which is clinically used in China.

It occurs in Aconitum.

Cucurbitine, (C5H10N2O2), Pyrrolidine and Piperidine Alkaloid¶

Cucurbitine, (C₅H₁₀N₂O₂), Pyrrolidine and Piperidine Alkaloid source

Cucurbitine is a non-proteinogenic alpha-amino acid

Cucurbitine, [3-amino-beta-proline], used to treat Schistosoma japonica infection.

It occurs in (Cucurbita moschat).

Cularidine, (C19H21NO4), Isoquinoline Alkaloid¶

Cularidine, (C₁₉H₂₁NO₄), Isoquinoline Alkaloid source

Cularidine, Demethylcularine, cularine alkaloid, cytotoxic

It occurs in (Corydalis claviculata), (Dicentra cucullaria), (Sarcocapnos baetica), and in (Sarcocapnos saetabensis).

Cularimine, (C19H21NO4), Isoquinoline Alkaloid¶

Cularimine, (C₁₉H₂₁NO₄), Isoquinoline Alkaloid source

Cularimine, cularine alkaloid, alkaloid F30, kills malignant cells

It occurs in (Dicentra eximia).

Cularine, (C20H23NO4), Isoquinoline Alkaloid¶

Cularine, (C₂₀H₂₃NO₄), Isoquinoline Alkaloid source

Cularine, isoquinoline derivative, cularine group, stimulates uterus, increases heart tone and contractions, antispasmotic activity on human airways, cytotoxic

It occurs in (Corydalis claviculata), (Dicentra cucullaria), Berberis, and in (Sarcocapnos saetabensi)s.

Curarine, (C38H44N2O6), Indole Alkaloid¶

Curarine, (C₃₈H₄₄N₂O₆), Indole Alkaloid source

Curarine, Dimethylbebeerinium, very toxic neuromuscular blocking agent, arrow poison, in calabash curare It is used as a muscle relaxant or paralysant in general anaesthesia called tubocurarine.

It competes with acetylcholine where motor nerves stimulate muscle fibres.

It is obtained from curare paralysing poison.

It occurs in Strychnos.

Tubocurarine, toxic benzylisoquinoline alkaloid, chief active constituent of curare, used as an hydrated hydrochloride (C₃₇H₄₁ClN₂O₆.HCl.5H₂O) It is a skeletal muscle relaxant, adjunct to surgical anesthesia, neuromuscular blocker. source

Tubocurarine chloride, chloride salt form of tubocurarine, muscle relaxant, (inhibits action of acetylcholine) naturally occurring curare alkaloid

It occurs in the bark and stem of (Chondodendron tomentosum).

Cuscohygrine, (C13H24N2O), Pyrrolidine and Piperidine Alkaloid¶

Cuscohygrine, (C₁₃H₂₄N₂O), Pyrrolidine and Piperidine Alkaloid source

Cuscohygrine, Cuskhygrine, Hellaridine, folk medicines, used as sedatives or narcotics

It occurs in (Hyoscyamus niger), roots of (Atropa belladonna), Datura, Scopolia, Convolvulus, (Erythroxylum argentinum), and in (Physalis peruviana).

Cyclovirobuxine, (C₂₆H₄₆N₂O) source

Steroidal Alkaloid

Cyclovirobuxine, Bebuxine, Cyclovirobuxin D, acutely toxic, anti-arrhythmic, purgative It occurs in Buxus.

Cytisine, (C₁₁H₁₄N₂O), Quinolzidine Alkaloid source

Cytisine, Sophorine, Baptitoxine, quinolizidine, organic heterotricyclic compound, secondary amino compound, lactam, cytisine group, phytotoxin

It is a nicotinic acetylcholine agonist used to treat smokers to stop smoking.

It occurs in Laburnum, and in Golden Rain (Cytisus laborinum).

Darlingine, (C13H17NO2), Tropane Alkaloid¶

Darlingine, (C₁₃H₁₇NO₂), Tropane Alkaloid source

Darlingine, oxacycle

It occurs in (Darlingea ferruginea).

Delcosine, (C24H39NO7), Diterpenoid Alkaloid¶

Delcosine, (C₂₄H₃₉NO₇), Diterpenoid Alkaloid source

Delcosine, Delphamine, Lucaconine, Delcosin, Iliensine, poisonous, insecticidal

It occurs in Aconitum and in (Delphinium consolida).

Delphinine, (C33H45NO9), Diterpenoid Alkaloid¶

Delphinine, (C₃₃H₄₅NO₉), Diterpenoid Alkaloid source

Delphinine, diterpene alkaloid, lycoctonine type, cardiovascular toxicity, dangerous herbal medicine, causes low blood pressure

It is used to treat disordered heart rhythms.

It occurs in Delphinium, and in (Staphisagria macrosperma).

Deltaline, (C27H41NO8), Diterpenoid Alkaloid¶

Deltaline, (C₂₇H₄₁NO₈), Diterpenoid Alkaloid source

Deltaline, Delphelatine, eldeline, tertiary alcohol, acetate ester, cyclic acetal, organic polycyclic compound, (derived from an aconitane hydride)

It occurs in (Delphinium cheilanthum), and in (Delphinium andersonii).

Demecolcine, (C21H25NO5), Colchicine Alkaloid¶

Demecolcine, (C₂₁H₂₅NO₅), Colchicine Alkaloid source

Demecolcine, Colcemid, Colchamine, Demecolcin, antineoplastic, arrests white blood cells in metaphase, mitosis spindle poison at metaphase, antitumour agent

It is less toxic than colchicine, and is used to inhibit growth of malignant cells.

It occurs in (Colchicum autumnal), (Colchicum alpinum), and in (Colchicum arenarium).

Demecolcine

Demethylcoclaurine, (C16H17NO3), Isoquinoline Alkaloid¶

Demethylcoclaurine, (C₁₆H₁₇NO₃), Isoquinoline Alkaloid source

Demethylcoclaurine, bisbenzylisoquinoline alkaloid, cardiac stimulant, "Higenamine", in coffee and coffee products.

It occurs in Aconitum, (Nelumbo nucifera), (Delphinium caeruleum), and in (Berberis beale).

Dendrobine, (C16H25NO2), Monoterpenoid and Sesquiterpenoid Alkaloid¶

Dendrobine, (C₁₆H₂₅NO₂), Monoterpenoid and Sesquiterpenoid Alkaloid source

Dendrobine, antiviral, antitumour, lowers blood pressure, may cause death by convulsions.

It occurs in Dendrobium.

Denudatine, (C22H33NO2), Diterpenoid Alkaloid¶

Denudatine, (C₂₂H₃₃NO₂), Diterpenoid Alkaloid source

Denudatine, acute toxic, effects on action potential of ventricular fibres, inhibits arrhythmogenic action of aconitine

It occurs in Delphinium.

Deserpidine, (C32H38N2O8), Indole Alkaloid¶

Deserpidine, (C₃₂H₃₈N₂O₈), Indole Alkaloid source

Deserpidine, Raunormine, Recanescin, alkaloid ester, methyl ester, benzoate ester, yohimban alkaloid, anti-hypertensive, causes decrease in blood pressure.

It has been used for the control of high blood pressure and for the relief of psychotic behavior, and as a tranquillizer.

It occurs in Rauvolfia canescens, Apocynaceae.

Diethanolamine, Secondary Amine¶

Diethanolamine, Secondary Amine

Diethanolamine, [HN(CH₂CH₂OH)₂], DEA, secondary amineweak base, oily colourless liquid or white crystals, fish smell, denser than water source

It is sometimes called "dialcohol", because two OH group.

It is used to make soaps, surfactants, dishwashing detergents, and as an anticorrosion agent.

Diethanolamine (photography developer), irritates skin and eyes.

Diethanolamine, Solution < 10%, Not hazardous

Diethanolamine bisulfite (photography developer), Irritates skin and eyes

Diethylamine, (C4H11N), Secondary Amine¶

Diethylamine, (C₄H₁₁N), Secondary Amine source

Diethylamine, (CH₃-CH₂-NH-CH₂-CH₃), diethyl amine, toxic, irritant and corrosive to eyes and skin, strongly alkaline, flammable, volatile source

It mixes with water and ethanol, a colourless liquid if pure, strong unpleasant odour, during combustion forms dangerous nitrogen gases.

Diethylamine, Solution <2%, Not hazardous

Dihydrosanguinarine, (C20H15NO4), Isoquinoline Alkaloid¶

Dihydrosanguinarine, (C₂₀H₁₅NO₄), Isoquinoline Alkaloid source

Dihydrosanguinarine, Dihydroavicine, benzophenanthridine alkaloid, dihydroavicine, benzophenanthrodine

It is an antifungal agent, antiseptic, and anti-inflammatory.

It occurs in Fumaria, Corydalis, Eschscholzia, Pteridophyllum, (Sarcocapnos baetica), and in (Sarcocapnos saetabensis).

Dimethylamine, (C2H7N), Secondary Amine¶

Dimethylamine, (C₂H₇N), Secondary Amine source

Dimethylamine, [C₂H₇N(CH₃)₂NH], DMA, [NH = imino group], colourless, flammable gas, fish odour source

It increases in human urine after fish diet, and is used in tanning dyes, soaps, fungicides.

Long exposure to fire or intense heat may cause the containers to rupture violently.

Dimethylamine salts are the active ingredients in commercial weedicides.

Dioscorine, (C13H19NO2), Pyrrolidine and Piperidine Alkaloid¶

Dioscorine, (C₁₃H₁₉NO₂), Pyrrolidine and Piperidine Alkaloid source

Dioscorine, opalescent (yellow-red to blue), molecule, contains a non-aromatic pyran ring, neurotoxin, convulsant, arrow poison

It occurs in (Dioscorea hispids), (Dioscorea dregeana), and in yams (Dioscorea bulbifera).

Ecgonine, (C9H15NO3), Tropane Alkaloid¶

Ecgonine, (C₉H₁₅NO₃), Tropane Alkaloid source

Ecgonine, tropaine derivative, cocaine group, 2-hydroxy monocarboxylic acid

It is a precursor to cocaine, and a controlled substance.

It occurs in leaves of (Erythroxylum coca).

Echimidine, (C₂₀H₃₁NO₇), Pyrrolizidine Alkaloid source

Echimidine, 2-Butenoic acid, pyrrolizine, acute toxic, heptatonic

It occurs in honeys produced in Australia and New Zealand.

It occurs in (Echium plantagineum), (Echium pininanam), and in (Symphytum officinale).

Echinopsine, (C₁₀H₉NO), Quinoline lkaloid source

Echinopsine, (1-Methyl-4-quinolone), simple quinoline structure

It occurs in (Echinops niveus), (Echinops ritro), and (Echinops echinatus).

Elaeocarpine, (C₁₆H₁₉NO₂), Unclassified Alkaloid source

Elaeocarpine, Isoelaeocarpine, indolizidine alkaloid

It occurs in leaves of (Elaeocarpus polydactylus).

Elatine, (C₃₈H₅₀N₂O₁₀), Diterpenoid Alkaloid source

Elatine, Elatin, dicarboximide, pyrrolidinone, benzoate ester, folk medicine is used for neurological disorders.

It occurs in (Delphinium shawurense).

Emetine, (C₂₉H₄₀N₂O₄), Isoquinoline Alkaloid source

Emetine, Emetin, Cephaeline methyl ether, Methyl cephaeline, ipecacuanha alkaloid

It is the principal alkaloid of ipecac from Cephaelis ipecacuanha, which contains emetic alkaloids emetine and cephaeline, C₂₈H₃₈N₂O₄. source

(Ipecac as an ingredient may be old over the counter for emergency use to cause vomiting in poisoning).

Emetine is used as amoebicide (antiprotozoal), and emetic.

It inhibits protein synthesis by blocking ribosome movement along the mRNA, strand and may cause cardiac, hepatic, or renal damage, violent diarrhea, omiting.

It occurs in Ipecac (Carapichea ipecacuanha), (Hedera helix), and in (Alangium longiflorum).

Ephedrine, (C₁₀H₁₅NO), Protoalkaloid source

Ephedrine, alkaloid with nitrogen in the side chain (protoalkaloid), beta-phenylethylamine derivative alkaloid, hydroxylated form of phenethylamine

It is sympathomimetic, bronchodilatory and anti-hypertensive, activates post-synaptic noradrenergic receptors, alpha-adrenergic agonist, and beta-adrenergic agonist.

It may increase release of norepinephrine (noradrenaline), used to treat asthma, heart failure, rhinitis, and urinary incontinence, and depression.

It has been less used with use of more selective agonists.

It occurs in (Ephedra sinica).

Pseudoephredine is an isomer of ephedrine.

Ergine, (C₁₆H₁₇N₃O), Indole Alkaloid source

Ergine, Lysergic acid amide, Lysergamide, (LSA), ergoline alkaloid, (derived from a hydride of an ergoline), South American folk medicine, hallucinogen.

It occurs in fungi, in seeds of (Rivea corymbosa, Ololiuhqui (Turbina corymbosa), Hawaiian baby woodrose (Argyreia nervosa), and in (Ipomoea ricolo).

Ergocristine, (C₃₅H₃₉N₅O₅), Indole Alkaloid source

Ergocristine, acute toxic, natural ergot alkaloid, (derived from a hydride of an ergotaman), prevents implantation and lactation.

It occurs in Ergot (Claviceps purpurea), (Scolochloa festucacea), and in (Calamagrostis arundinacea).

Ergometrine, (C₁₉H₂₃N₃O₂), Indole Alkaloid source

Ergometrine, Ergonovine, Ergobasine, Ergotocine, Ergometrin, ergot alkaloid, monocarboxylic acid amide, (derived from lysergamide), primary alcohol.

Ergometrine causes contraction of uterine and vascular smooth muscles, used to cause contractions of uterus if vaginal bleeding after childbirth Ergometrine is made from rye ergot fungus or lysergic acid, can be used to make lysergic acid diethylamide (LSD) so it is a regulated substance.

It occurs in (Jacquemontia tamnifolia), and in Acremonium.

Ergotamine, (C₃₃H₃₅N₅O₅), Indole Alkaloid source

Ergotamine, C₃₃H₃₅N₅O₅, gynergen, ergomar, ergotaminum, ergonsvine, ergopeptine, semiterpenoid indole alkaloid, ergot alkaloid, vasoconstrictor, analgesic source

Ergotamine is used as oxytocic agent and in treatment of migraine disorders, activates serotonin receptors on intracranial blood vessels causing vasoconstriction.

Ergotamine reduces blood flow in cerebral arteries, binds to alpha-adrenergic receptors to stimulate vascular smooth muscle and cause vasoconstriction.

Ergotamine inhibits pro-inflammatory neuropeptide release, used to treat bleeding after childbirth.

It occurs the ergot fungus of Central Europe (Claviceps purpurea).

Erythroidine, (C₁₆H₁₉NO₃), Isoquinoline Alkaloid source

Erythroidine, isoquinoline derivative, erythrina alkaloid, alpha-Erythroidine, neuromuscular blocker like curare, beta-Erythroidine, delta-lactone

Erythroidine is a neuromuscular blocker, hypnotic, respiratory depressant, muscle relaxant, organic heterotetracyclic indole alkaloid.

It occurs in the coral tree, Erythrina.

Dihydro-Beta-Erythroidine, (DHbetaE), (C₁₆H₂₁NO₃), organic heterotetracyclic compound, alkaloid like curare, nicotinic antagonist source

Dihydro-Beta-Erythroidine occurs in sseds of Erythrina.

Ethanolamine, (NH₂CH₂CH₂OH), Primary Amine + Primary Alcohol source

Ethanolamine, (NH₂CH₂CH₂OH) (usually called monoethanolamine, MEA) (2-aminoethanol). source

Ethanolamine is a toxic, flammable, corrosive, colourless, viscous liquid, odour like ammonia, weak base.

Ethanolamine is harmful by ingestion, inhalation or if absorbed through the skin, corrosive eye, skin and respiratory irritant.

Ethanolamine is used to produce detergents and many other chemical products.

Monoethanolamine is head group for phospholipids in biological membranes, formed by decarboxylation of serine.

[HOCH₂CH(CO₂H)NH₂] → (NH₂CH₂CH₂OH) + (CO₂) source

serine → monoethanolamine + carbon dioxide source

Evodiamine, (C₁₉H₁₇N₃O), Indole Alkaloid source

Evodiamine, anti-inflammatory, interferes with metastasis formation of new blood vessels.

It occurs in (Tetradium ruticarpum), (Vepris soyauxii), and in Cryptocarya.

Febrifugine, (C₁₆H₁₉N₃O₃), Quinoline Alkaloid source

Febrifugine, quinazoline derivative, (3,4-Dihydro-4-quinazolone derivative), antimalarial.

It occurs in (Dicrroa febrifuga), (Hydrangea febrifuga), and in (Hydrangea macrophylla).

Ficine, (C₂₀H₁₉NO₄), Unclassified Alkaloid source

Ficine, dihydroxyflavone, N-alkylpyrrolidine.

It occurs in the wild fig (Ficus pantoniana).

Frangulanine, (C₂₈H₄₄N₄O₄), Peptide and Cyclopeptide Alkaloid source

Frangulanine, Ceanothamine A, Peptide alkaloids with a 14-membered cycle, Frangulanine type, frangula bark used as a purgative, weak antibiotic.

It occurs in Ramnus, Waltheria, root bark of New Jersey tea (Ceanothus americanus), raisin tree (Hovenia dulcis), and in (Zizyphus jujuba).

Galanthamine, (C₁₇H₂₁NO₃), Amaryllidaceae Alkaloid source

Galanthamine, Lycoremin, Benzazepine, Amaryllis alkaloid, oral cholinesterase inhibitor

It is used to treat Alzheimer's disease, analgesic, inhibits cholinesterase activity, and a herbal medicine used to treat nervous diseases It is used to reverse the effects of gallamine triethiodide (C₃₀H₆₀N₃O₃) and tubocurarine (C₃₇H₄₁N₂O₆⁺), synthetic drugs that block the cardiac vagus nerve. source

It occurs in Galanthus, (Amaryllis belladonna), (Hymenocallis leucojum), (Lycoris squamigera), Narcissus, Pancratium, Ungernia, and in (Galanthus nivalis).

Gelsemicine, (C₂₀H₂₆N₂O₄), Indole Alkaloid source

Gelsemicine, very toxic, stimulates central nervous system, may cause respiratory paralysis.

It occurs in (Gelsemium supervirens), (Gelsemium elegans), and in (Mostuea brunonis).

Gentianadine, (C₈H₇NO₂), Monoterpenoid and Sesquiterpenoid Alkaloid source

Gentianadine, [3,4-dihydropyrano[3,4-c]pyridin-1-one], a pyranopyridine, mildly toxic, anti-inflammatory, hypothermic, hypotensive muscle relaxant

It occurs in the aerial parts of Gentiana.

Gentianaine, (C₆H₇NO₃), Monoterpenoid and Sesquiterpenoid Alkaloid source

Gentianaine, Gentiocrucine, low inflammatory activity

It occurs in Gentiana, Causasa, and in Enicostemma.

Gentianine, (C₁₀H₉NO₂), Monoterpenoid and Sesquiterpenoid Alkaloid source

Gentianine, Pyridine derivative, polycyclic condensed pyridine derivative, pyranopyridine, polycyclic aromatic compound

The bitter tasting Gentian liqueur, Gentian schnapps, is made from the roots of the gentian plant and is used as a hypotensive medicine.

It occurs in fenugreek Trigonella, and the large leaf gentian, (Gentiana macrophylla)

Gentioflavine, (C₁₀H₁₁NO₃), Monoterpenoid and Sesquiterpenoid Alkaloid source

Gentioflavine

It occurs in Gentiana, Erythrea, and in Swertia.

Glaucine, (C₂₁H₂₅NO₄), Isoquinoline Alkaloid source

Glaucine, iquinoline derivative, aporphine alkaloid, bronchiodilator, anti-inflammatory, antitussive.

It occurs in (Galucium flavum), (Sarcocapnos baetica), and in (Sarcocapnos saetabensis).

Glaziovine, (C₁₈H₁₉NO₃), Isoquinoline Alkaloid source

Glaziovine, isoquinoline derivative, proaporphine alkaloid, antidepressant

It occurs in (Octea glaziovii), (Hypserpa nitida), (Litsea cubeba), and in (Annona cherimola).

Guvacine, Tetrahydronicotinic acid, Hydrogenated nicotinic acid, Alpha, beta-unsaturated monocarboxylic acid, pyridine alkaloid, It inhibits 4-aminobutanoic acid, but has no known uses.

It occurs in Areca.

Harmaline, (C₁₃H₁₄N₂O), Indole Alkaloid source

Harmaline, Dihydroharmine, Harmalol methyl ether, beta-carboline alkaloid, fluorescent

It is a psychoactive, central nervous system stimulant, and acetylcholinesterase inhibitor.

It occurs in Syrian rue (Peganum harmala), (Passiflora pilosicorona), and in (Passiflora boenderiin).

It occurs in the hallucinogenic beverage ayahuasca brewed from Banisteriopsis caapi.

The active chemical in ayahuasca is DMT (dimethyltryptamine), C₁₂H₁₆N₂, a hallucinogenic substance with no medical use. source

Tetrahydroharmine, C₁₃H₁₆N₂O, UNII-AF812R7053, AF812R7053, C09243, a harmala alkaloid source

Harman, (C₁₂H₁₀N₂), Indole Alkaloid source

Harman, indole derivative, Non-isoprene indole alkaloid

Harmala alkaloid, inhibits monoamine oxidase A, and is an anti-HIV agent.

It occurs in (Sickingia rubra), (Symplocus racemosa), (Passiflora incarnata), (Peganum harmala), (Banisteriopsis caapi), (Tribulus terrestris), and in (Cichorium intybus)>

It also occurs in tobacco smoke.

Harmine, (C₁₃H₁₂N₂O), Indole Alkaloid source

Harmine, Aribine, Loturine, Methyl carboline, Passiflorine, (derivative of beta-carboline), beta-Carboline alkaloid, in folk medicine ayahuasca, used for treating nervous disorders, diabetes

Harmala alkaloids: Harmine (C₁₃H₁₂N₂O), Harmaline (C₁₄H₁₄N₂O), Harmalol ((C₁₂H₁₂N₂O), can be used to affect nervous system, but prohibited in Australia. source

It occurs in (Thalictrum foetidum), and in (Acraea andromacha)

Harzianopyridone, (C₁₄H₁₉NO₅), Pyrrolidine and Piperidine Alkaloid source

Harzianopyridone, phytotoxin, blocks electron transfer in oxidative phosphorylation, potential and antibacterial uses.

It occurs in (Trichoderma harzianum), and in Mays (Zea mays).

Heliosupine, Cynoglossophine, heptatoxic

It occurs in (Cynoglossum officinale), Echium, Heliotrope, and in (Symphytum officinale).

Heliotridine, (C₈H₁₃NO₂), Pyrrolizidine Alkaloid source

Heliotridine, pyrolizidine derivative, non-ester, heptatoxic

It occurs in Heliotropium, and in Cynoglossum.

Heliotrine, (C₁₆H₂₇NO₅), Pyrrolizidine Alkaloid source

Heliotrine, 9-Heliotrylheliotridine, Pyrrolizine, heptatoxic, mutagenic

It occurs in (Heliotropium arborescense).

Humilixanthin, (C₁₄H₁₈N₂O₇), Betalain Alkaloid source

Humilixanthin, a betaxanthin, yellow pigment, alpha amino acid

It occurs in Phytolacca, Delosperma, Lampranthus, Portulaca, and in eetroot (Beta vulgaris subsp. vulgaris).

Huperzine B, (C₁₆H₂₀N₂O), Lycopodium Alkaloid source

Huperzine, Fordine, Selagine, anticholinesterase, in Lycopodium, Chinese medicine, neuroprotective, possibly used to treat Alzheimer’s disease.

It occurs in the water tassel-fern, Huperezia.

Huperzine A, is a sesquiterpene alkaloid, a neuroprotective, acetylcholinesterase inhibitor, and an organic heterotricyclic compound

It occurs in Huperzia serrata Huperzine B, is a phenanthrol, novel acetylcholinesterase inhibitor.

Hydrastine, (C₂₁H₂₁NO₆), Isoquinoline Alkaloid source

Hydrastine, isoquinoline derivative, phthalideisoquinoline alkaloid, astringent, alkaloid hydrastinine, (C₁₁H₁₃NO₃), haemostatic drugs source

It occurs in goldenseal, Hydrastis, and in Fumaria.

Hydroxylupanine, (C₁₅H₂₄N₂O₂), Quinolzidine Alkaloid source

Hydroxylupanine, 3-Hydroxylupanine, Jamaidine, Luparine, Oxylupanine, Octalupine, anti-arrhythmic, hypotensive

It occurs in Cyrtisus, Genista, Thermopsis, and in Lupinus.

Hydroxystachydrine, (C₇H₁₃NO₃), Pyrrolidine and Piperidine Alkaloid source

Hydroxystachydrine, 4-Hydroxystachydrine, urine biomarker citrus consumption, 3-Hydroxystachydrine

It occurs in (Boscia augustifolia), and in Capparis.

Hygrine, (C₈H₁₅NO), Pyrrolidine and Piperidine Alkaloid source

Hygrine, pyrrolidine derivative, pungent taste, pungent odour, yellow liquid

It occurs in (Picea breweriana), and in (Erythroxylum argentinums).

Hyoscyamine, (C₁₇H₂₃NO₃), Tropane Alkaloid source

Hyoscyamine, toxic, laevorotatory isomer, anticholinergic with both central and peripheral nervous system actions, It is used to treat motion sickness and pre-operative medication for sedation and to induce anaesthesia.

Its weak poisoning causes rapid breathing, nervousness, frequent urination.

Its fatal poisoning is preceded by weak pulse, irregular breathing, coma, convulsions.

It occurs in (Hyoscyamus niger.

Hyoscine, (Scopolamine), is less toxic than hyoscyamine.

Hypaconitine, (C₃₃H₄₅NO₁₀), Diterpenoid Alkaloid source

Hypaconitine, causes neuromuscular blocking action of aconite root.

It occurs in Aconitum.

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