Learn about alkaloids, amines and agar in the diet.

School Science Lessons
(appendixF)
2025-02-28

Acanthicifoline, (C10H12N2O2), Monoterpenoid and Sesquiterpenoid Alkaloid
Acanthicifoline is a derivative of 2,7-naphthyridine, C8H6N2, a naphthyridine.
The traditional use in India and China is to treat dyspepsia, paralysis, asthma, headache, rheumatism.
It occurs in Acanthus ilicifolius.
See diagram: Acanthicifoline

Aconine, (C25H41NO9)
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 species.
See diagram: Aconine

Aconitine, (C34H47NO11), Diterpenoid Alkaloid
Aconitine, Acetylbenzoylaconitine, too dangerous to use internally
It isvery 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 species.
See diagram: Aconitine

Acronidine, (C18H17NO4), Quinoline Alkaloid
Acronidine, organic heterotetracyclic compound, is an aromatic ether.
It occurs in Acronychia species.
See diagram: Acronidine

Acronycine, (C20H19NO3), Quinoline Alkaloid
Acronycine, Acronine, Acromycine, Pyriproxyfen, pyrano-acridone alkaloid, carcinogenic, possibly antitumour agent, broad spectrum of activity.
It occurs in Acronychia species.
See diagram: Acronycine

Actinidine, (C10H13N), Monoterpenoid and Sesquiterpenoid Alkaloid
Actinidine, pyridine derivative, cyclopentapyridine, pyridine alkaloid, (derived from pyridine), pheromone, attracts cats, in Actinidiaceae, Actinidia polygama, in Valerian species, and in Tecoma stans leaves.
See diagram: Actinidine

Affinine, (C21H24N2O2), Indole Alkaloid
Affinine, 17-Hydroxyvobasan-3-one, psychoactive.
It occurs in Tabernaemontana catharinensis.
See diagram: Affinine
Affinisine, (C20H24N2O).

Agroclavine, (C16H18N2), Indole Alkaloid
Agroclavine, tetracyclic indole alkaloid, ergot alkaloid, (based on ergoline), used for ergot-based drug synthesis.
It occurs in fungus Claviceps purpurea, Rivea bernoulliana, and in Jacquemontia tamnifolia.
See diagram: Agroclavine
Ergoline, C14H16N2, structurally-related alkaloids which bind to neurotransmitter receptors, e.g. dopamine, noradrenaline and serotonin receptors

Ajaconine, (C22H33NO3), Diterpenoid Alkaloid
Ajaconine, organic heterohexacyclic compound, tertiary amino compound, cyclic ether, olefin compound, poisonous, insecticidal.
It occurs in Delphinium species.
See diagram: Ajaconine

Ajmalicine, (C21H24N2O2), Indole Alkaloid
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.
See diagram: Ajmalicine

Allocryptopine, (C21H23NO5), dibenzazecine Alkaloid
Allocryptopine, Thalictrimine, Allocrytopine, irritant, a dibenzazecine alkaloid, organic heterotetracyclic compound, tertiary amino compound, cyclic ketone, cyclic acetal, aromatic ether, bioactive alkaloid, in Glaucium arabicum, in Papaveraceae family, in Zanthoxylum beecheyanum, in Berberis integerrima.

Alpinine, (C23H29NO6), Isoquinoline Alkaloid
Alpinine, rhoeadine alkaloid, methylalpinigenine.
It occurs in Papaver species.
See diagram: Alpinine

Amaranthin, (C30H34N2O19), Betalain Alkaloid
Amaranthin, Amaranthin betacyanin, Amarantin, Betanidin 5-O-sophorobiuronic acid, disaccharide derivative of betanidin, biological pigment.
It occurs in Atriplex hortensis, Amaranthus species, Celosia cristata, and in Chenopodium album.
See diagram: Amaranthin

Ambelline, (C18H21NO5), Amaryllidaceae Alkaloid
Ambelline, isoquinoline derivative, amaryllis alkaloid, analgesic but too toxic.
It occurs in Amaryllis species, Crinum × powellii, and in Hippeastrum species.
See diagram: Ambelline

Amurensine, (C19H19NO4), Isoquinoline Alkaloid
Amurensine, pavine alkaloid, xanthopetaline, used for pain relief, expectorant, tranquilliser.
It occurs in Papaver species.
See diagram: Amuresine

Amurine, (C19H19NO4), Isoquinoline Alkaloid
Amurine, morphinan Alkaloid
It occurs in Papaver species.
See diagram: Amurine

Anabasine, (C10H14N2), Pyrrolidine and Piperidine Alkaloid
Anabasine, Neonicotine, pyridine derivative, (polycyclic noncondensing pyridine derivative), teratogenic agent, nicotine analog so 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.
See diagram: Anabasine

Anagyrine, (C15H20N2O), Quinolzidine Alkaloid
Anagyrine, Monolupine, Rhombinine, Anagyrine, highly toxic, teratogenic, cause "crooked calf's disease, cardiotonic.
It occurs in Anagyris foetida, Ulex europaeus, Thermopsis species, Cystisus scoparius, Genista species, Lupinus species, Sophora species, Ammodendron species, Ormosia cocconia, and in Viscum cruciatum.
See diagram: Anagyrine

Anatabine, (C12H10N2), Pyrrolidine and Piperidine Alkaloid
Anatabine, (polycyclic noncondensing pyridine derivative), bipyridine, Nicotine-related tobacco alkaloid, in urine, inhibitor of human cytochrome.
It occurs in Nicotiana species.
See diagram: Anatabine

Anisodamine, (C17H23NO4), Tropane Alkaloid
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.
See diagram: Anisodamine

Anisodine, (C17H21NO5), Tropane Alkaloid
Anisodine, Daturamine, alpha-Hydoxyscolopamine, antispasmodic, anticholinergic, used to treat circulatory shock.
It occurs in Anisodus tanguticus.
See diagram: Anisodine

Annolobine, (C17H15NO3), Isoquinoline Alkaloid
Annolobine, Anolobine, Anolobin, aporphine alkaloid, an alkaloid antibiotic.
It occurs in Asimina triloba, and in Goniothalamus amuyon.
See diagram: Annolobine

Annonaine, (C17H15NO2), Isoquinoline Alkaloid
Annonaine, Anonaine, Anonain, aporphine alkaloid, oxacycle, organic heteropentacyclic compound, insecticidal, antimicrobial, anticancer, antiplasmodial.
It occurs in Annona species, Nelumbo nucifera, and in Xylopia aethiopica.
See diagram: Annonaine

Annotine, (C16H21NO3)
Annotine, an azaspiro compound, used to treat skin disorders.
It occurs in Lycopodium annotinum (Icelandic club moss), Chinese herbal medicine.
See diagram: Annotine

Apodine, (C21H22N2O4), Indole Alkaloid
Apodine, hexacyclic indole alkaloid, methyl ester.
It occurs in Tabernaemontana species.
See diagram: Apodine

Apohyoscine, (C17H19NO3), Tropane Alkaloid
Apohyoscine, Aposcopolamine, Aposcopolamin, epoxyatropyloxytropane, monocarboxylic acid.
It occurs in Hyoscyamus species, Datura species, and in Duboisia hopwoodii.
See diagram: Apohyoscine

Apparicine, (C18H20N2), Indole Alkaloid
Apparicine, Gomezine, Pericalline, Tabernoschizine, monoterpenoid indole alkaloid, antimicrobial, stimulates central nervous system, analgesic.
It occurs in Aspidosperma quebracho-blanco, Tabernaemontana species, and in Ochrosia illiptica.
See diagram: Apparicine

Arecaidine, (C7H11NO2), Pyrrolidine and Piperidine Alkaloid
Arecaidine, methylguvacine, N-methylguvacine, mildly toxic, astringent, causes sweating, folk medicine.
It occurs in Areca catechu.
See diagram: Arecaidine

Arecoline, (C8H13NO2), Pyrrolidine and Piperidine Alkaloid
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.
See diagram: Arecoline

Arenaine, (C11H17N3O), Monoterpenoid and Sesquiterpenoid Alkaloid
Arenaine, aliphatic heteropolycyclic compound, a pyrimidine.
It occurs in seeds of Plantago arenaria, sand plantain.
See diagram: Arenaine

Argentine, (C23H26N4O3), Quinolzidine Alkaloid
Argentine, Carbonylbiscytisine.
It occurs in Sophora species, Thermopsis species, and in Dermatophyllum secundiflorum.
See diagram: Argentine

Armepavine, (C190H23NO3), Isoquinoline Alkaloid
Armepavine, benzylisoquinoline alkaloid, convulsions, irritation, irregular cardiac action.
It occurs in Papaver species, Euonymus europaeus, Rhamnusspecies, Nelumbo species, and in Berberis integerrima.
See diagram: Armepavine

Atropine, (C17H23NO3), Tropane Alkaloid
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.
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 species, Cyphanthera tasmanica, and Anthocercis ilicifolia.
See diagram: Atropine

Baptifoline, (C15H20N2O2), Quinolzidine Alkaloid
Baptifoline, Hydroxyanagyrene, Argentamin, in coffee and coffee products.
It occurs in Baptisia tinctoria, Sophora species, Caulophyllum thalictroides, Thermopsis chinensis, and in Thermopsis lanceolata.
See diagram: Baptifoline

Belladine, (C19H25NO3), Amaryllidaceae Alkaloid
Belladine, N-Benzylphenethylamine, acetylcholinesterase and cholinesterase inhibitor
It occurs in Amaryllis belladonna, Crinum powelli, and in Nerium species.
See diagram: Belladine

Bellendine, (C12H15NO2), Tropane Alkaloid
Bellendine, (10-methylpyranotropane), oxacycle.
It occurs in Bellendena montana, and in Darlingia darlingiana.
See diagram: Bellendine

Berberine, (C20H18NO4), Isoquinoline Alkaloid
Berberine, Berberin, Umbellatine, isoquinoline derivative, protoberberine alkaloid, bitter, yellow, used to treat bacillary dysentery.
It occurs in Berberis species, (barberry), Coptis chinensis, Evodia rutaecarpa, Mahonia species, Nandina species, Thalictrum species.
It occurs in Hydrastis canadensis,(goldenseal), and in Berberis aquifolium, (Oregon grape).
Berberine chloride, (C20H18ClNO4), occurs in Chinese herbs, and is antifungal, antiviral, and anticancer.
Berberine hemisulfate, (C20H18NO4.1/2SO4), anti-inflammatory, fluoresces under UV light, occurs in Hydrastis species.
Berberine chloride hydrate, (C20H18NO4.H2O), Natural Yellow 18 hydrate, is used to treat intestinal infections.
See diagram: Berberine
Betalamic acid, (C9H9NO5), Betalain Alkaloid
Betalamic acid, dicarboxylic acid, betalain.
It occurs in Beta vulgaris beetroot, Celosia cristata, Cistanthe species, and in Portulaca species.
See diagram: Betalamic acid

Betanidin, (C18H16N2O8), Betalain Alkaloid
Betanidin, (2,6-Pyridinedicarboxylic acid), non-proteinogenic alpha-amino acid.
Betanidin, purple pigment, (aglycone of betanin).
It occurs in Mesembryanthemum species, Portulacaspecies, and in Ullucus tuberosus.
See diagram: Betanidin

Betanin, (C24H26N2O13), Betalain Alkaloid
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).
Betanin occurs in Beta vulgaris, Carpobrotus species, Drosera species, Mesembryanthemum species, Opuntia species, and in Portulaca species.
. See diagram: Betanin

Betonicine, (C7H13NO13), Pyrrolidine and Piperidine Alkaloid
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.
It occurs in herbs and spices, in Achillea millefolium, (yarrow).

Bocconine, (C21H161NO5) + , Isoquinoline Alkaloid
Bocconine, benzophenanthridene alkaloid, chelirubine, local anaesthetic, kills nematode worms.
It occurs in Bocconia, and in Papaver species.
See diagram: Bocconine

Boldine, (C19H21NO4), Isoquinoline Alkaloid
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 species, (boldo), Lindera umbellata root, Boldea fragrans, Peumus species, Monimia species, Litsea species, Sassafras species, Desmos species, Liriodendron species, Retanilla species, and in Damburneya salicifolia.
See diagram: Boldine

Boschniakine, (C10H11NO), Monoterpenoid and Sesquiterpenoid Alkaloid
Boschniakine, indicaine.
It occurs in Boschniakia rossica, Tecoma species, Plantago species, and in Pedicularis species.
See diagram: Boschniakine

Bracteoline, (C19H21NO4), Isoquinoline Alkaloid
Bracteoline, aporphine alkaloid
It occurs in Papaver species and in Licaria armeniaca.
See diagram: Bracteoline

Brucine, (C23H16N2O4), Indole Alkaloid
Brucine, Brucinum, monoterpenoid indole alkaloid, acute toxic, white crystalline solid, 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.
See diagram: Brucine

Bufotenine, (C12H16N2O), Tryptamine alkaloid and tertiary amine.
Indole derivative alkaloid, Non-isoprene indole alkaloid, dimethyl serotonin, in skin of toads, in psychedelic compounds, illegal in USA.
It occurs in Anadenanthera colubrina, Arundo reed, and in Piptadenia species.
See diagram: Bufotenine

Bulleyaconitine A, (C35H43NO9), Alkaloid
Bulleyaconitine, Bulleyanum, analgesic, anti-inflammatory, formerly used for the treatment of chronic pain and rheumatoid arthritis.
It occurs in Aconitum species.
See diagram: Bulleyaconitine

9.2.0 Caffeine.
9.2.1 Caffeine, (C8H10N4O2).
9.2.2 Approximate caffeine content of beverages, mg /cup.
9.2.3 Caffeine, extraction with supercritical carbon dioxide, critical point.
9.2.4 Extraction of caffeine and benzoic acid from soft drinks.
9.2.5 Isolation of caffeine in cola (kola), soft drink.

9.2.1 Caffeine.
Caffeine, (C8H10N4O2), guaranine, (1,3,7-Trimethylxanthine), (3-Methyltheobromine), purine derivative alkaloid, methylxanthine alkaloid, methylated purine.
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 species, Coffee, Cola species, Ilex species, Paullinias species, and in Ilex paraguariensis, (Yerba mate).
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.

Calafatimine, (C38H40N2O7).
Calafatimine, an isoquinoline, a bisbenzylisoquinoline alkaloid, Chinese medicine, weakly antineoplastic.
It occurs in Berberis vulgaris.

Calebassine, (C40H48N4O4 +2 ), Indole Alkaloid
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 species.
See diagram: Calebassine

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
It occurs in alcoholic beverages.
It occurs in Calystegia species, Convolvulus species, and in Solanum species.
See diagram: Calystegin

Camptothecin, (C20H16N2O4), Quinoline Alkaloid
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.
See diagram: Camptothecin

Cancentrine, (C36H33N2O7), Isoquinoline Alkaloid
Cancentrine, morphinan alkaloid, ibenzooxazepine alkaloid, bisbenzylisoquinoline alkaloid, bright yellow.
It occurs in Dicentra canadensis.
See diagram: Cancentrine

Candicine, (C11H18NO+), Unclassified Alkaloid
C11H18NO+, HOC6H4(CH2)2N(CH3)3+, has N + in its molecular structure, so it is classed as an Alkaloid
Candicine, Candicin, primary amine, 4-Hydroxy-N,N,N-trimethylbenzeneethanaminium, action like nicotine, hypertension.
It occurs in Trichocereus species root, Fagara species, Philodendron species, Magnolia species, and in Lysichitum species.
See diagram: Candicine

Candimine, (C18H19NO6), Amaryllidaceae Alkaloid.
Candimine, Maltotoxin, toxic.
It occurs in Hippeastrum morelianum.
See diagram: Candimine

Cannabisativine, (C21H39N3O3), Unclassified Alkaloid
Cannabisativine, (azamacrocycle, so has N in a ring of 12 or more atoms), lactam
It occurs in Cannabis sativa, roots and leaves.
See diagram: Cannabisativine

Cantleyine, (C11H13NO3), Monoterpenoid and Sesquiterpenoid Alkaloid
Cantleyine, aromatic carboxylic acid, a pyridine.
It occurs in Cantleya corniculata tree bark, Dipsacus species, and in Strychnos nux-vomica.
See diagram: Cantleyine

Capsaicin, (C18H27NO3)
Capsaicin Protoalkaloid
It occurs in Capsicum species, (chilli peppers).
See diagram: Capsaicin

Caranine, (C16H17NO3), Amaryllidaceae Alkaloid
Caranine, (2-Deoxylycorine), indolizidine alkaloid, organic heteropentacyclic compound, secondary alcohol, toxic to animals.
It occurs in Amaryllis belladonna, Clivia miniata, and in Crinum bulbispermum.
See diagram: Caranine

Carboxystrictosidine, (C28H34N2O4), Gluco Indole Alkaloid
5-Carboxystrictosidine, (5α-Carboxy-3-isovincoside), anti-inflammatory.
It occurs in Uncaria tomentosa, and in Sinoadina racemosa.
See diagram: Carboxystrictosidine

Carnegine, (C13H19NO2), Isoquinoline Alkaloid
Carnegine, carnegin, Pectenin, simple isoquinoline.
It occurs in Carnegiea species, Cereus species, and in Haloxylon species.
See diagram: Carnegine

Carpaine, (C27H50N2O4), Pyrrolidine and Piperidine Alkaloid
Carpaine, macrocyclic lactone, cardiovascular drug, affects myocardium, decreases blood pressure, amoebicide.
It occurs in Carica papaya, (papaya), Vasconcellea species, and in many seeds.
See diagram: Carpaine

Cassine, (C18H35NO2), Pyrrolidine and Piperidine Alkaloid
Cassine is a citraconoyl group, C5H4O2.
It occurs in Cassia species, Prosopis species, Senna spectabilis, and in Elaeodendron matabelicum.
See diagram: Cassine

Cassythicine, (C19H19NO4), Isoquinoline Alkaloid
Cassythicine, aporphine alkaloid, methylacinodaphnine, antimicrobial, cytotoxic.
It occurs in Cassytha filiformis, Annona glabra, and in Neolitsea sericea.
See diagram: Cassythicine

Castanospermine, (C8H15NO4), Pyrrolidine and Piperidine Alkaloid
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 grandiflora, and in Alexa wachenheimii.
See diagram: Castanospermine

Catharine, (C46H54N4O10), alkaloid, a natural product found in Catharanthus lanceus and Catharanthus roseus.
See diagram: Catharine

Caulophylline, (C12H16N2O), Quinolzidine Alkaloid
Caulophylline, Methylcytisine, (12-Methylcytisine), toxic, repels snails.
It occurs in Caulophyllum thalictroides, Cytisus laburnum, Spartium junceum, Thermopsis lanceolata, and in Sophora chrysophyll.
See diagram: Caulophylline

Celosianin, (C40H42N2O2), Betalain Alkaloid
Celosianin, Betacyanin, Celosianin II, monoferulylamaranthin, glycoside, (derives from betanidin), purple pigment.
It occurs in Chenopodium rubrum.
See diagram: Celosianin

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

Cepharanthine, (C37H38N2O6), Isoquinoline Alkaloid
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.
See diagram: Cepharanthine
.

Cevadine, (C32H49NO9), mixture of alkaloids.
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.
See diagram: Cevadine

Chaconine, (C45H73NO14), Steroidal Alkaloid
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.
See diagram: Chaconine

Chelerythrine, (C21H18NO4) + , Benzophenanthridine alkaloid.
Chelerythrine, Toddalin, Cheleritrine, Broussonpapyrine, benzophenanthridine alkaloid, organic cation, enzyme inhibitor, antibacterial, antineoplastic.
It occurs in Zanthoxylum simulans root, and in Chelidonium majus, (greater celandine).
See diagram: Chelerythrine
Chelerythrine chloride, (C21H18ClNO4), benzophenanthridine alkaloid, irritant, is a salt of an unstable naturally fluorescent material.
It is anti-inflammatory, and anti-tumour.
It occurs in Chelidonium majus.

Cinchonidine, (C19H22N2O), Cinchona Alkaloid
Cinchonidine, Cinchovatine, (derived from a hydride of Cinchonan), diasteroisomer of cinchonine, antimalarial.
It occurs in Cinchona officinalis, and in Cinchona calisaya.
See diagram: Cinchonidine

Cinchonine, (C19H22N2O), Cinchona Alkaloid
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
Cinegalline is a quinolizidine alkaloid.
It occurs in Genista species.
See diagram: Cinegalline

Clivorine, (C21H27NO7), Pyrrolizidine Alkaloid
Clivorine, Senecionanium, heptacarcinogenic.
It occurs in Anchusa species, and in Ligularia species.
See diagram: Clivorine

Codeine, (C18H21NO3), Isoquinoline Alkaloid
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 species.
Codeine, heroin, methadone, abuse: 5.5.14
See diagram: Codeine

Codonopsine, (C14H21NO4), Pyrrolidine and Piperidine Alkaloid
Codonopsine, may decrease blood pressure.
It occurs in Codonopsis clematidea, and in Averrhoa bilimbi.
See diagram: Codonopsine

Colchicine, (C22H25NO6), Unclassified Alkaloid
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, not associated with liver injury except overdoses.
It occurs in Colchicum autumnale, (meadow saffron).
Protoalkaloid
See diagram: Colchicine

Coniceine, (C8H15N), Pyrrolidine and Piperidine Alkaloid
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 species.
See diagram: Coniceine

Coniine, (C8H17N), Pyrrolidine and Piperidine Alkaloid
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 Amorphophalus rivieri, (black elderberry).
Conium maculatum was used to cause the death of Socrates.
See diagram: Coniine

Convolvine (C16H21NO4), Tropane Alkaloid
Convolvine, O-Veratroylnortropine, (8-Azabicyclo[3.2.1]oct-3-yl 3,4-dimethoxybenzoate), a methoxybenzoic acid, acutely toxic, irritant.
It occurs in Convolvulus species, Datura species, Physalis species, Salpichroa species, and in Bruguiera species.
See diagram: Convolvine

Coptisine, (C19H14NO4) + , Alkaloid
Coptisine, Coptisin, cytotoxic alkaloid, related to Berberine.
It occurs in opium, bitter taste, Chinese medicine for digestive disorders caused by bacteria, cytotoxic agent occurs in heptoma and leukemic cells.
It occurs in Coptis chinensis, Chelidonium majus> and in Fumaria species.
See diagram: Coptisine

Corynoline, (C21H21NO5), Benzophenanthridine Alkaloid
Corynoline, acetylcholinase inhibitor, hepatoproactive.
It occurs in Coptis species, (Chinese goldthread, and in Corydalis incisa.
See diagram: Corynoline

Crassicauline A, (C35H49NO10), Diterpenoid Alkaloid
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 species.
See diagram: Crassicauline A

Cryptopleurine, (C24H27NO3), Unclassified Alkaloid
Cryptopleurine, organic heteropentacyclic compound, aromatic ether, alkaloid antibiotic, protein synthesis inhibitor, antineoplastic, antiviral against herpes
It occurs in Cryptocarya species, Boehmeria species, and in Cissus species.
See diagram: Cryptopleurine

Cucurbitine, (C5H10N2O2), Pyrrolidine and Piperidine Alkaloid
Cucurbitine is a non-proteinogenic alpha-amino acid.
Cucurbitine, [3-amino-beta-proline], used to treat Schistosoma japonica infection.
It occurs in Cucurbita moschata.
See diagram: Cularidine

Cularidine, (C19H21NO4), Isoquinoline Alkaloid
Cularidine, Demethylcularine, cularine alkaloid, cytotoxic.
It occurs in Corydalis claviculata, Dicentra cucullaria, Sarcocapnos baetica, and in Sarcocapnos saetabensis.
See diagram: Cularidine

Cularimine, (C19H21NO4), Isoquinoline Alkaloid
Cularimine, cularine alkaloid, alkaloid F30, kills malignant cells.
It occurs in Dicentra eximia.
See diagram: Cularimine

Cularine, (C20H23NO4), Isoquinoline Alkaloid
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 species, and in Sarcocapnos saetabensis.
See diagram: Cularine

Curarine, (C38H44N2O6), Indole Alkaloid
zzz 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 species.
See diagram: Curarine, Tubocurarine.
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.
Tubocurarine chloride, chloride salt form of tubocurarine, muscle relaxant, (inhibits action of acetylcholine) naturally occurring curare alkaloid.
It occurs in Chondodendron tomentosum bark and stem.

Cuscohygrine, (C13H24N2O), Pyrrolidine and Piperidine Alkaloid
Cuscohygrine, Cuskhygrine, Hellaridine, folk medicines, used as sedatives or narcotics.
It occurs in Hyoscyamus niger, Atropa belladonna roots, Datura species, Scopolia species, Convolvulus species, Erythroxylum argentinum, and in Physalis peruviana.
See diagram: Cuscohygrine

Cyclovirobuxine, (C26H46N2O).
Steroidal Alkaloid
Cyclovirobuxine, Bebuxine, Cyclovirobuxin D, acutely toxic, anti-arrhythmic, purgative It occurs in Buxus species.
See diagram: Cyclovirobuxine

Cytisine, (C11H14N2O), Quinolzidine Alkaloid
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 species, and in Cytisus laborinum, (golden rain).
See diagram: Cytisine

Darlingine, (C13H17NO2), Tropane Alkaloid
Darlingine, oxacycle.
It occurs in Darlingea ferruginea.
See diagram: Darlingine

Delcosine, (C24H39NO7), Diterpenoid Alkaloid
Delcosine, Delphamine, Lucaconine, Delcosin, Iliensine, poisonous, insecticidal.
It occurs in Aconitum species and in Delphinium consolida.
See diagram: Delcosine

Delphinine, (C33H45NO9), Diterpenoid Alkaloid
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 species, and in Staphisagria macrosperma.
See diagram: Delphinine

Deltaline, (C27H41NO8), Diterpenoid Alkaloid
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.
See diagram: Deltaline

Demecolcine, (C21H25NO5), Colchicine Alkaloid
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, bisbenzylisoquinoline alkaloid, cardiac stimulant, "Higenamine", in coffee and coffee products.
It occurs in Aconitum species, Nelumbo nucifera, Delphinium caeruleum, and in Berberis bealei.
See diagram: Demethylcoclaurine

Dendrobine, (C16H25NO2), Monoterpenoid and Sesquiterpenoid Alkaloid
Dendrobine, antiviral, antitumour, lowers blood pressure, may cause death by convulsions.
It occurs in Dendrobium species.
See diagram: Dendrobine

Denudatine, (C22H33NO2), Diterpenoid Alkaloid
Denudatine, acute toxic, effects on action potential of ventricular fibres, inhibits arrhythmogenic action of aconitine.
It occurs in Delphinium species.
See diagram: Denudatine

Deserpidine, (C32H38N2O8), Indole Alkaloid
Deserpidine, Raunormine, Recanescin, alkaloid ester, methyl ester, benzoate ester, yohimban alkaloid, anti-hypertensive, causes decrease in blood pressure.
It hasbeen used for the control of high blood pressure and for the relief of psychotic behavior, as a tranquillizer.
It occurs in Rauvolfia canescens, Apocynaceae.
See diagram: Deserpidine

Diethanolamine, Secondary Amine.
Diethanolamine, [HN(CH2CH2OH)2], DEA, secondary amineweak base, oily colourless liquid or white crystals, fish smell, denser than water
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, (CH3-CH2-NH-CH2-CH3), diethyl amine, toxic, irritant and corrosive to eyes and skin, strongly alkaline, flammable, volatile
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, Dihydroavicine, benzophenanthridine alkaloid, dihydroavicine, benzophenanthrodine
It is an antifungal agent, antiseptic, and anti-inflammatory.
It occurs in Fumaria species, Corydalis species, Eschscholzia species, Pteridophyllum species, Sarcocapnos baetica, and in Sarcocapnos saetabensis.
See diagram: Dihydrosanguinarine

Dimethylamine, (C2H7N), Secondary Amine.
Dimethylamine, [C2H7N(CH3)2NH], DMA, [NH = imino group], colourless, flammable gas, fish odour
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, 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 Dioscorea bulbifera, (yams).
See diagram: Dioscorine

Ecgonine, (C9H15NO3), Tropane Alkaloid
Ecgonine, tropaine derivative, cocaine group, 2-hydroxy monocarboxylic acid
It is a precursor to cocaine, and a controlled substance.
It occurs in Erythroxylum coca leaves, cocaine.
See diagram: Ecgonine

Echimidine, (C20H31NO7), Pyrrolizidine Alkaloid
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.
See diagram: Echimidine compound.

Echinopsine, (C10H9NO), Quinoline lkaloid
Echinopsine, (1-Methyl-4-quinolone), simple quinoline structure.
It occurs in Echinops niveus, Echinops ritro, and Echinops echinatus.
See diagram: Echinopsine

Elaeocarpine, (C16H19NO2), Unclassified Alkaloid
Elaeocarpine, Isoelaeocarpine, indolizidine alkaloid.
It occurs in Elaeocarpus polydactylus leaves.
See diagram: Elaeocarpine

Elatine, (C38H50N2O10), Diterpenoid Alkaloid
Elatine, Elatin, dicarboximide, pyrrolidinone, benzoate ester, folk medicine used for neurological disorders.
It occurs in Delphinium shawurense.
See diagram: Elatine

Emetine, (C29H40N2O4), Isoquinoline Alkaloid
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.
(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, vomiting.
It occurs in Carapichea ipecacuanha, (ipecac), Hedera helix, and in Alangium longiflorum.Emetine

Ephedrine, (C10H15NO), Protoalkaloid.
Ephedrine, alkaloid with nitrogen in the side chain (protoalkaloid), beta-phenylethylamine derivative alkaloid, hydroxylated form of phenethylamine, sympathomimetic, bronchodilatory and anti-hypertensive, activates post-synaptic noradrenergic receptors, alpha-adrenergic agonist, and beta-adrenergic agonist.
May increase release of norepinephrine (noradrenaline), used to treat asthma, heart failure, rhinitis, and urinary incontinence, and depression.
Has been less used with use of more selective agonists.
It occurs in Ephedra sinica.
9.8.21
Protoalkaloid
See diagram: Ephedrine
Pseudoephredine is an isomer of ephedrine.
.

Ergine, (C16H17N3O), Indole Alkaloid
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 Rivea corymbosa seeds, Turbina corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose), and in Ipomoea ricolo.
See diagram: Ergine

Ergocristine, (C35H39N5O5), Indole Alkaloid
Ergocristine, acute toxic, natural ergot alkaloid, (derived from a hydride of an ergotaman), prevents implantation and lactation.
It occurs in Claviceps purpurea (ergot), Scolochloa festucacea, and in Calamagrostis arundinacea.
See diagram: Ergocristine

Ergometrine, (C19H23N3O2), Indole Alkaloid
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 species.
See diagram: Ergometrine

Ergotamine, (C33H35N5O5), Indole Alkaloid
Ergotamine, C33H35N5O5, gynergen, ergomar, ergotaminum, ergonsvine, ergopeptine, semiterpenoid indole alkaloid, ergot alkaloid, vasoconstrictor, analgesic.
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 Claviceps purpurea, ergot fungus of Central Europe.
See diagram: Ergotamine

Erythroidine, (C16H19NO3), Isoquinoline Alkaloid
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 Erythrina species, (coral trees).
Dihydro-Beta-Erythroidine, (DHbetaE), (C16H21NO3), organic heterotetracyclic compound, alkaloid like curare, nicotinic antagonist.
Dihydro-Beta-Erythroidine occurs in Erythrina seeds.
See diagram: Dihydro-Beta-Erythroidine

Ethanolamine, (NH2CH2CH2OH), Primary Amine + Primary Alcohol.
Ethanolamine, (NH2CH2CH2OH) (usually called monoethanolamine, MEA) (2-aminoethanol).
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).
serine --> monoethanolamine + carbon dioxide.

Evodiamine, (C19H17N3O), Indole Alkaloid
Evodiamine, anti-inflammatory, interferes with metastasis formation of new blood vessels.
It occurs in Tetradium ruticarpum, Vepris soyauxii, and in Cryptocarya species.
See diagram: Evodiamine

Febrifugine, (C16H19N3O3), Quinoline Alkaloid
Febrifugine, quinazoline derivative, (3,4-Dihydro-4-quinazolone derivative), antimalarial.
It occurs in Dicrroa febrifuga, Hydrangea febrifuga, and in Hydrangea macrophylla.
See diagram: Febrifugine

Ficine, (C20H19NO4), Unclassified Alkaloid
Ficine, dihydroxyflavone, N-alkylpyrrolidine.
It occurs in Ficus pantoniana, (wild fig).
See diagram: Ficine

Frangulanine, (C28H44N4O4), Peptide and Cyclopeptide Alkaloid
Frangulanine, Ceanothamine A, Peptide alkaloids with a 14-membered cycle, Frangulanine type, frangula bark used as a purgative, weak antibiotic.
It occurs in Ramnus species, Waltheria species, Ceanothus americanus root bark (New Jersey tea), Hovenia dulcis, (raisin tree), and in Zizyphus jujuba.
See diagram: Frangulanine

Galanthamine, (C17H21NO3), Amaryllidaceae Alkaloid
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.
It occurs in Galanthus species, Amaryllis belladonna, Hymenocallis leucojum, Lycoris squamigera, Narcissus species, Pancratium species, Ungernia species, Galanthus woronowii, and in Galanthus nivalis.
See diagram: Galanthamine

Gelsemicine, (C20H26N2O4), Indole Alkaloid
Gelsemicine, very toxic, stimulates central nervous system, may cause respiratory paralysis.
It occurs in Gelsemium supervirens, Gelsemium elegans, and in Mostuea brunonis.
See diagram: Gelsemicine

Gentianadine, (C8H7NO2), Monoterpenoid and Sesquiterpenoid Alkaloid
Gentianadine, [3,4-dihydropyrano[3,4-c]pyridin-1-one], a pyranopyridine, mildly toxic, anti-inflammatory, hypothermic, hypotensive muscle relaxant.
It occurs in Gentiana species aerial parts.
See diagram: Gentianadine

Gentianaine, (C6H7NO3), Monoterpenoid and Sesquiterpenoid Alkaloid
Gentianaine, Gentiocrucine, low inflammatory activity.
It occurs in Gentiana species, Causasa species, and in Enicostemma species.
See diagram: Gentianaine

Gentianine, (C10H9NO2), Monoterpenoid and Sesquiterpenoid Alkaloid
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 Trigonella species, (fenugreek), Gentiana macrophylla, large leaf gentian.
See diagram: Gentianine

Gentioflavine, (C10H11NO3), Monoterpenoid and Sesquiterpenoid Alkaloid
Gentioflavine.
It occurs in some Gentiana species, Erythrea species, and in Swertia species.
See diagram: Gentioflavine

Glaucine, (C21H25NO4), Isoquinoline Alkaloid
Glaucine, iquinoline derivative, aporphine alkaloid, bronchiodilator, anti-inflammatory, antitussive.
It occurs in Galucium flavum, Sarcocapnos baetica, and in Sarcocapnos saetabensis.
See diagram: Glaucine

Glaziovine, (C18H19NO3), Isoquinoline Alkaloid
Glaziovine, isoquinoline derivative, proaporphine alkaloid, antidepressant.
It occurs in Octea glaziovii, Hypserpa nitida, Litsea cubeba, and in Annona cherimola.
See diagram: Glaziovine

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 species.
See diagram: Guvacine

Harmaline, (C13H14N2O), Indole Alkaloid
Harmaline, Dihydroharmine, Harmalol methyl ether, beta-carboline alkaloid, fluorescent
It is a psychoactive, central nervous system stimulant, and acetylcholinesterase inhibitor.
It occurs in Peganum harmala (Syrian rue), 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.
See diagram: Harmaline
Tetrahydroharmine, C13H16N2O, UNII-AF812R7053, AF812R7053, C09243, a harmala alkaloid.

Harman, (C12H10N2), Indole Alkaloid
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, Cichorium intybus, Tribulus terrestris, Ophiopogon species, and in Strychnos johnsonii.
It also occurs in tobacco smoke.
See diagram: Harman

Harmine, (C13H12N2O), Indole Alkaloid
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.
It occurs in Thalictrum foetidum, and in Acraea andromacha.
See diagram: Harmine

Harzianopyridone, (C14H19NO5), Pyrrolidine and Piperidine Alkaloid
Harzianopyridone, phytotoxin, blocks electron transfer in oxidative phosphorylation, potential and antibacterial uses.
It occurs in Trichoderma harzianum, and in Zea mays, (maize).
See diagram: Harzianopyridone

Heliosupine, Cynoglossophine, heptatoxic.
It occurs in Cynoglossum officinale, Echium species, Heliotrope species, and in Symphytum officinale.
See diagram: Heliosupine

Heliotridine, (C8H13NO2), Pyrrolizidine Alkaloid
Heliotridine, pyrolizidine derivative, non-ester, heptatoxic.
It occurs in Heliotropium species, and in Cynoglossum species.
See diagram: Heliotridine

Heliotrine, (C16H27NO5), Pyrrolizidine Alkaloid
Heliotrine, 9-Heliotrylheliotridine, Pyrrolizine, heptatoxic, mutagenic.
It occurs in Heliotropium arborescense.
See diagram: Heliotrine

Humilixanthin, (C14H18N2O7), Betalain Alkaloid
Humilixanthin, a betaxanthin, yellow pigment, alpha amino acid.
It occurs in Phytolacca species, Delosperma species, Lampranthus species, Portulaca species, and in Beta vulgaris subsp. vulgaris, (beetroot).
See diagram: Humilixanthin

Huperzine B, (C16H20N2O), Lycopodium Alkaloid
Huperzine, Fordine, Selagine, anticholinesterase, in Lycopodium, Chinese medicine, neuroprotective, possibly used to treat Alzheimer’s disease.
It occurs in Huperezia species, (the water tassel-fern).
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.
See diagram: Huperzine

Hydrastine, (C21H21NO6), Isoquinoline Alkaloid
Hydrastine, isoquinoline derivative, phthalideisoquinoline alkaloid, astringent, alkaloid hydrastinine, (C11H13NO3), haemostatic drugs.
It occurs in Hydrastis species, (goldenseal), and in Fumaria species.
See diagram: Hydrastine

Hydroxylupanine, (C15H24N2O2), Quinolzidine Alkaloid
Hydroxylupanine, 3-Hydroxylupanine, Jamaidine, Luparine, Oxylupanine, Octalupine, anti-arrhythmic, hypotensive.
It occurs in Cyrtisus species, Genista species, Thermopsisspecies, and in Lupinus species.
See diagram: Hydroxylupanine

Hydroxystachydrine, (C7H13NO3), Pyrrolidine and Piperidine Alkaloid
Hydroxystachydrine, 4-Hydroxystachydrine, urine biomarker citrus consumption, 3-Hydroxystachydrine.
It occurs in Boscia augustifolia, and in Capparis species.
See diagram: Hydroxystachydrine

Hygrine, (C8H15NO), Pyrrolidine and Piperidine Alkaloid
Hygrine, pyrrolidine derivative, pungent taste, pungent odour, yellow liquid.
It occurs in Picea breweriana, and in Erythroxylum argentinums.
See diagram: Hygrine

Hyoscyamine, (C17H23NO3), Tropane Alkaloid
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.
See diagram: Hyoscyamine
Hyoscine, (Scopolamine), less toxic than hyoscyamine.

Hypaconitine, (C33H45NO10), Diterpenoid Alkaloid
Hypaconitine, causes neuromuscular blocking action of aconite root.
It occurs in Aconitum species.
See diagram: Hypaconitine