Learn about alkaloids, amines and agar in the diet.

School Science Lessons
(appendixF)
2024-09-07

Acanthicifoline, (C10H12N2O2), Monoterpenoid and Sesquiterpenoid Alkaloid
Acanthicifoline, (5-methoxy-1-methyl-1,4-dihydro-2,7-naphthyridin-3(2H)-one), [derivative of (2,7-naphthyridine), occurs in Acanthus ilicifolius, contains secondary metabolites, traditional use in India and China to treat dyspepsia, paralysis, asthma, headache, rheumatism, diseases.
See diagram: Acanthicifoline.

Aconine, (C25H41NO9)
Aconine, jesaconine, main constituent of aconitine, amorphous alkaloid with a polycyclic molecule, polyether, tertiary amino compound, pentol, secondary alcohol and tertiary alcohol, plant metabolite, human urinary metabolite, from hydrolysis of aconitine, limited physiological activity.
Aconines: group of compounds closely related to aconine, for research only, not for human or veterinary use, active metabolite of aconitine, inhibits osteoclast differentiation and bone resorption, induces flaccid paralysis, toxic to rats and mice.
It occurs in Aconitum species.
See diagram: Aconine.

Aconitine, (C34H47NO11), Diterpenoid Alkaloid
Aconitine, Acetylbenzoylaconitine, (C34H47NO11), Lycoctonine type, C19 norditerpenoid alkaloid, very poisonous and can be absorbed by skin, slows heart and lowers blood pressure, acute toxic, neurotoxin, anti-inflammatory, antineuralgic, blocks neurotransmitters release, blocks norepinephrine (noradrenaline) uptake, causes ventricular tachycardia, too dangerous to use internally.
It occurs in Aconitum species.
See diagram: Aconitine.

Acronidine, (C18H17NO4), Quinoline Alkaloid
Acronidine, organic heterotetracyclic compound, (derived from a quinoline), plant metabolite, 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 specie.
See diagram: Acronycine.

Actinidine, (C10H13N), Monoterpenoid and Sesquiterpenoid Alkaloid
Actinidine, [5H-Cyclopenta[c]pyridine, 6,7-dihydro-4,7-dimethyl-, (7S)-], pyridine derivative, cyclopentapyridine, pyridine alkaloid, (derived from pyridine), plant metabolite, insect pheromone, attracts cats, in Actinidiaceae, Actinidia polygama, in Valerian, 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, (8,9-Didehydro-6,8-dimethylergoline), tetracyclic indole alkaloid, ergot alkaloid, (based on ergoline), used for ergot-based drug synthesis.
It occurs in fungus Claviceps purpurea, in Rivea bernoulliana, in Jacquemontia tamnifolia
See diagram: Agroclavine.

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

Ajmalicine, (C21H24N2O2), Indole Alkaloid
Ajmalicine, Raubasine, delta-Yohimbine, Ajmalicin, monoterpenoid indole alkaloid, a methyl ester indole derivative alkaloid, corynanthe type alkaloid, pentacyclic indole alkaloid, biosynthesis metabolite, (delta-yohimbine, py-tetrahydroserpentine, raubasine), anti-hypertensive and sedative, used to treat circulatory disorders, antimicrobial activity, used to study effects as antagonist of adrenergic and nicotinic receptors.
It occurs in Rauwolfia sepentina, 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, plant metabolite, biological pigment, tetrahydropyridine, indole.
It occurs in Atriplex hortensis, in Amaranthus species, in Celosia cristata, in Chenopodium album.
See diagram: Amaranthin.

Ambelline, (C18H21NO5), Amaryllidaceae Alkaloid
Ambelline, isoquinoline derivative, amaryllis alkaloid, analgesic but too toxic.
It occurs in Amaryllis, in Crinum × powellii, 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, 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, in Ulex europaeus, Thermopsis species, in Cystisus scoparius, in Genista species, in Lupinus species, in Sophora species, in Ammodendron species, in Ormosia cocconia, 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, Hyoscamine, 6-Hydroxyhyoscamine, (atropine derivative), monocarboxylic acid, anticholinergic, Chinese medicine, used to treat circulatory shock, possible treatment of intestinal diseases.
It occurs in Anisodus tanguticus, in Datura species, in Duboisia species, in Hyoscyamus species
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, in Goniothalamus amuyon
See diagram: Annolobine.

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

Annotine, (C16H21NO3),
Annotine, azaspiro compound, occurs in Lycopodium annotinum (Icelandic club moss), Chinese herbal medicine, treat skin disorders.
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, in Datura species, in Duboisia hopwoodii.
See diagram: Apohyoscine.

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

Arecaidine, (C7H11NO2), Pyrrolidine and Piperidine Alkaloid
Arecaidine, Methylguvacine, (1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid), 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, simple derivative of pyridine, stimulates muscarinic and nicotinic receptors, toxic may cause convulsions and paralysis, seeds used medically for parasympathetic stimulant action, used as euphoriant, used in various salts to stimulate the parasympathetic nervous system and as a veterinary vermifuge.
It occurs in Areca catechu
See diagram: Arecoline.

Arenaine, (C11H17N3O), Monoterpenoid and Sesquiterpenoid Alkaloid
Arenaine, [7-ethenyl-1-imino-4,7-dimethyl-octahydropyrrolo(1,2-c)pyrimidin-3-one], aliphatic heteropolycyclic compound, a pyrimidine, occurs in seeds of sand plantain, (Plantago arenaria), some narcotine in fruits.
See diagram: Arenaine.

Argentine, (C23H26N4O3), Quinolzidine Alkaloid
Argentine, Carbonylbiscytisine.
It occurs in Sophora species, Thermopsis species, 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, in Rhamnus species, Nelumbo species, in Berberis integerrima.
See diagram: Armepavine.

Atropine, (C17H23NO3), Tropane Alkaloid
Atropine, dl-Hyoscyamine, Tropine tropate, Atropin, Atropen, tropane derivative, atropine group, poisonous, highly toxic, lethal dose for humans 100 mg, blocks the action of acetylcholine, like curare on poison-tipped arrows, anticholinergic activity, causing blurred vision, suppressed salivation, vasodilation, delirium.
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, in Datura species, in Cyphanthera tasmanica, in Anthocercis ilicifolia.
See diagram: Atropine.

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

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

Bellendine, (C12H15NO2), Tropane Alkaloid
Bellendine, (10-methylpyranotropane), oxacycle.
It occurs in Bellendena montana, 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 Barberry, in Coptis (Coptis chinensis), in Evodia rutaecarpa, in Mahonia, in Nandina, in Thalictrum, in Toddalia, in goldenseal, in Oregon grape
Berberine chloride, (C20H18ClNO4).
It occurs in Chinese herbs, antifungal, antiviral, anticancer
Berberine hemisulfate, (C20H18NO4.1/2SO4), anti-inflammatory, fluoresces under UV light
It occurs in Hydrastis species
Berberine chloride hydrate, (C20H18NO4.H2O), Natural Yellow 18 hydrate, used for intestinal infections.
See diagram: Berberine.
Betalamic acid, (C9H9NO5), Betalain Alkaloid
Betalamic acid, dicarboxylic acid, betalain.
It occurs in Beta vulgaris pigment, in Beetroot, Beta vulgaris, in Celosia cristata, in Cistanthe species, 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, in Portulaca species, in Ullucus tuberosus
See diagram: Betanidin.

Betanin, (C24H26N2O13), Betalain Alkaloid
Betanin, Betanine, Betacyanin, Betanidin 5-O-beta-glucoside, a red-violet betacyanin, purple pigment, glucopyranosylbetanidin, a phytolaccanin, a cyanogenic glycoside (betacyanin), purple pigment, E162 Beetroot Red, from beet, Food additive, colorant 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), and so cause distress in people who think they are suffering haematuria, (blood in the urine).
Betalains: indole-derived glycoside pigments, contain nitrogen.
Betanin aglycone is betanidin, (C18H16N2O8).
Betanin occurs in Beta vulgaris, in Carpobrotus species, in Drosera species, in Mesembryanthemum species, in Opuntia species, in Phytolacca species, in Portulaca species
. See diagram: Betanin.

Betonicine, (C7H13NO13), Pyrrolidine and Piperidine Alkaloid
Betonicine, Achillein, (trans-4-hydroxy-L-proline betaine), plant metabolite, amino-acid betaine, secondary alcohol, (derived from a trans-4-hydroxy-L-proline zwitterion).
It occurs in herbs and spices, in Achillea millefolium (yarrow).
in Achillea millefolium, in Achillea sibirica

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

Boldine, (C19H21NO4), Isoquinoline Alkaloid
Boldine, Uniboldina, Boldin, aporphine alkaloid.
It occurs in Boldo, in Lindera root, antioxidant, hepatoprotective, cytoprotective, antipyretic, anti-inflammatory, used in laxatives, used to increase bile secretion and treat gallstones, in Boldea fragrans, in Peumus, in Monimia, in Litsea, in Sassafras, in Desmos, in Liriodendron, in Retanilla, in aurelia.
in Lindera umbellata, in Damburneya salicifolia
See diagram: Boldine.

Boschniakine, (C10H11NO), Monoterpenoid and Sesquiterpenoid Alkaloid
Boschniakine, Indicaine, [(R)-6,7-Dihydro-7-methyl-5H-2-pyrindinecarboxaldehyde], occurs in Boschniakia rossica, in Tecoma, in Plantago, in Pedicularis,
See diagram: Boschniakine.

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

Brucine, (C23H16N2O4), Indole Alkaloid
Brucine, Brucinum, (10,11-Dimethoxystrychnine), l-Brucine, indole derivative alkaloid, monoterpenoid indole alkaloid, corynanthe type alkaloid, acute toxic, white crystalline solid, combustible but hard to ignite, toxic vapour or dust by inhalation and ingestion.
It occurs in Strychnos axillaris, in Strychnos ignatii
See diagram: Brucine.

Bufotenine, (C12H16N2O), Tryptamine alkaloid and tertiary amine
Indole derivative alkaloid, Non-isoprene indole alkaloid, Simple indole derivative, Bufotenin, N,N-Dimethylserotonin, Mappin, N,N-Dimethyl-5-hydroxytryptamine, dimethyl serotonin, occurs in skin of toads, in psychedelic compounds, illegal in USA, in Anadenanthera colubrina, in reed Arundo, in Piptadenia.
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), thein, 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, Coffea, Cola, Ilex, Paullinias, Yerba mate (Ilex paraguariensis).
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, (18,18'-Dihydroxy-C-calebassine), highly toxic, neuromuscular blocker, arrow poison.
It occurs in "calabash curare" formerly packed into hollow gourds It occurs in Strychnos.
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, in alcoholic beverages.
It occurs in Calystegia species, in Convolvulus species, in Solanum species
See diagram: Calystegin.

Camptothecin, (C20H16N2O4), Quinoline Alkaloid
Camptothecin, Camptothecine, pyranoindolizinoquinoline, tertiary alcohol, delta-lactone, antitumour activity, inhibits nuclear enzyme topoisomerase, used 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, occurs in Trichocereus root, in Fagara, in Philodendron, in Magnolia, in Lysichitum.
See diagram: Candicine.

Candimine, (C18H19NO6), Amaryllidaceae Alkaloid
Candimine, Maltotoxin, plant metabolite, 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, occurs in Cannabis sativa, roots and leaves.
See diagram: Cannabisativine.

Cantleyine, (C11H13NO3), Monoterpenoid and Sesquiterpenoid Alkaloid
Cantleyine, [methyl (6S,7R)-6-hydroxy-7-methyl-6,7-dihydro-5H-cyclopenta[c]pyridine-4-carboxylate], aromatic carboxylic acid, a pyridine, occurs in Cantleya corniculata (tree bark), in Dipsacus, in Strychnos nux-vomica.
See diagram: Cantleyine.

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

Caranine, (C16H17NO3), Amaryllidaceae Alkaloid
Caranine, (2-Deoxylycorine), indolizidine alkaloid, organic heteropentacyclic compound, secondary alcohol, (derived from a hydride of galanthan, (C15H19N), plant metabolite, toxic to animals.
It occurs in Amaryllis belladonna, in Clivia miniata, in Crinum bulbispermum,
See diagram: Caranine.

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

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

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

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

Cassythicine, (C19H19NO4), Isoquinoline Alkaloid
Cassythicine, aporphine alkaloid, methylacinodaphnine, antimicrobial, cytotoxic.
It occurs in Cassytha filiformis, in Annona glabra, 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, may be useful in HIV/AIDS prevention research.
Castanospermine derivative "celgosivir" possible antiviral drug to treat hepatitis C virus.
It occurs in Castanospermum australe, in Alexa grandiflora, 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, in Cytisus laburnum, in Spartium junceum, in Thermopsis lanceolata, in Sophora chrysophylla
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, bisbenzylisoquinoline alkaloid, (CEP), Japanese medicine, antitumour, anti-allergic, anti-inflammatory, immunimo-modulatory and antineoplastic alkaloid, inhibits efflux transporter multidrug-resistant protein in cancer cells by preventing the intracellular accumulation of certain antitumour drugs, inhibits the entry of HIV-1 by reducing plasma membrane fluidity, stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation
It occurs in Stephania cepharantha, 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, (a mixture of alkaloids including veratridine, cevadillene, sabadine and cevadine, voltage-gated sodium channel activator), 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, so 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, Greater celandine (Chelidonium majus).
See diagram: Chelerythrine.
Chelerythrine chloride, Chelerythrine hydrochloride, Toddaline chloride, (C21H18ClNO4), benzophenanthridine alkaloid, irritant, salt of an unstable naturally fluorescent material, a PKC inhibitor, anti-inflammatory, 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, in Cinchona calisaya.
See diagram: Cinchonidine.

Cinchonine, (C19H22N2O), Cinchona Alkaloid
Cinchonine, irritant, in the bark of most varieties of Cinchona shrubs, metabolite, (derived from a hydride of a cinchonan)
It occurs in Cinchona calisaya, 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, in Ligularia species.
See diagram: Clivorine.

Codeine, (C18H21NO3), Isoquinoline Alkaloid
Codeine, isoquinoline derivative, morphinan alkaloid, 3-methylmorphine, opioid analgesic related to morphine, but with less potent analgesic properties and mild sedative effects, 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, in Averrhoa bilimbi
See diagram: Codonopsine.

Colchicine, (C22H25NO6), Unclassified Alkaloid
Colchicine, Colchicin, Colchicina, Colchisol, alkaloid with nitrogen in the side chain, (protoalkaloid), yellow, irritant, carcinogen, extremely toxic by all routes, inhibits cell division, because is a mitosis spindle poison, used for laboratory investigation of mitosis it is a mitosis spindle poison at metaphase, used in plant breeding to induce polyploidy mutations, (Cytochrome P450 3A4 Inhibitor, P-Glycoprotein Interaction), 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, occurs in Meadow saffron, (Colchicum autumnale), Liliaceae
Protoalkaloid
See diagram: Colchicine.

Coniceine, (C8H15N), Pyrrolidine and Piperidine Alkaloid
Coniceine, beta-Coniceine, [2-((E)-Prop-1-enyl)piperidine], beta-Coniceine, piperidine derivative, tetrahydro-6-propylpyridine, extremely toxic, mouse-like odour, can be reduced to dl-coniine, causes abnormal embryos, with Coniine
It occurs in Conium maculatum, in Aloe.
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, used to paralyse insect prey, mouse smell.
It occurs in Conium maculatum, in Sarracenia flava, in black elderberry, in Amorphophalus rivieri.
Conium maculatum was used to cause 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, in Datura species, in Physalis, in Salpichroa, in Bruguiera.
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, plant metabolite, cytotoxic agent occurs in heptoma and leukemic cells
It occurs in Coptis (Coptis chinensis), in Chelidonium majus in Fumaria.
See diagram: Coptisine.

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

Crassicauline A, (C35H49NO10), Diterpenoid Alkaloid
Crassicauline A, plant metabolite, human urinary metabolite, xenobiotic, acetate ester, aromatic ether, benzoate ester, bridged compound, organic heteropolycyclic compound, polyether, tertiary amino compound tertiary alcohol, (derives from an aconitane hydride), analgesic drug 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, but not antitumour, occurs in Cryptocarya, in Boehmeria, in Cissus.
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, in Dicentra cucullaria, in Sarcocapnos baetica, 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, in Dicentra cucullaria, in Berberis species, in Sarcocapnos baetica, Sarcocapnos saetabensis.
See diagram: Cularine.

Curarine, (C38H44N2O6), Indole Alkaloid
Curarine, C-Curarine, Dimethylbebeerinium, very toxic neuromuscular blocking agent, arrow poison, in calabash curare, used as a muscle relaxant or paralysant in general anaesthesia called tubocurarine, (competes with acetylcholine where motor nerves stimulate muscle fibres), obtained from curare paralysing poison, occurs in Strychnos.
See diagram: Curarine, Tubocurarine.
Tubocurarine, toxic benzylisoquinoline alkaloid, chief active constituent of curare, used as an hydrated hydrochloride (C37H41ClN2O6.HCl.5H2O), 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, 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 in Hyoscyamus niger, in Atropa belladonna roots, in Datura species, in Scopolia, in Ethroxylum, in Convolvulus species, in Erythroxylum argentinum, in Physalis peruviana
See diagram: Cuscohygrine.

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

Cytisine, (C11H14N2O), Quinolzidine Alkaloid
Cytisine, Sophorine, Baptitoxine, quinolizidine, organic heterotricyclic compound, secondary amino compound, lactam, cytisine group, phytotoxin, plant metabolite, nicotinic acetylcholine agonist used to treat smokers to stop smoking.
It occurs in Laburnum, 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. in Delphinium consolida
See diagram: Delcosine.

Delphinine, (C33H45NO9), Diterpenoid Alkaloid
Delphinine, diterpene alkaloid, lycoctonine type, cardiovascular toxicity, dangerous herbal medicine, causes low blood pressure, used to treat disordered heart rhythms.
It occurs in Delphinium species, in Staphisagria macrosperma
See diagram: Delphinine.

Deltaline, (C27H41NO8), Diterpenoid Alkaloid
Deltaline, Delphelatine, eldeline, tertiary alcohol, tertiary amino compound, acetate ester, cyclic acetal, organic polycyclic compound, (derived from an aconitane hydride).
It occurs in Delphinium cheilanthum, 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, secondary amino compound where the N-acetyl group of (S)-colchicine is replaced by an N-methyl group, less toxic than colchicine, used to inhibit growth of malignant cells.
It occurs in Colchicum autumnal, Colchicum alpinum, Colchicum arenarium
Demecolcine.

Demethylcoclaurine, (C16H17NO3), Isoquinoline Alkaloid
Demethylcoclaurine, bisbenzylisoquinoline alkaloid, (norcochlorine, a conjugate base of a (RS)-norcoclaurinium), cardiac stimulant, "Higenamine", in coffee and coffee products
It occurs in Aconitum species, in Nelumbo nucifera, in Delphinium caeruleum, in Berberis bealei
See diagram: Demethylcoclaurine.

Dendrobine, (C16H25NO2), Monoterpenoid and Sesquiterpenoid Alkaloid
Dendrobine, occurs in Dendrobium species, antiviral, antitumour, lowers blood pressure, may cause death by convulsions.
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, Deserpidin, alkaloid ester, methyl ester, benzoate ester, yohimban alkaloid, anti-hypertensive, causes decrease in blood pressure, tranquillizer.
It occurs in Rauvolfia canescens.
See diagram: Deserpidine.

Diethanolamine, Secondary Amine
Diethanolamine, [HN(CH2CH2OH)2], DEA, secondary amine (also "dialcohol", because two OH groups), weak base, oily colourless liquid or white crystals, fish smell, denser than water, used to make soaps, surfactants, dishwashing detergents, 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(C2H5)2NH], (CH3-CH2-NH-CH2-CH3), diethyl amine, Toxic by all routes, Irritant to eyes, corrosive to eyes and skin, strongly alkaline, flammable, volatile, mixes with water and ethanol, colourless liquid (if pure), strong unpleasant odour, combustion forms dangerous nitrogen gases.
Diethylamine, Solution <2%, Not hazardous.

Dihydrosanguinarine, (C20H15NO4), Isoquinoline Alkaloid
Dihydrosanguinarine, Dihydroavicine, benzophenanthridine alkaloid, dihydroavicine, benzophenanthrodine, (derived from a hydride of a sanguinarine), metabolite, antifungal agent, antiseptic, anti-inflammatory.
It occurs in Fumaria, in Corydalis, in Eschscholzia, in Pteridophyllum, in Sarcocapnos baetica, in Sarcocapnos saetabensis
See diagram: Dihydrosanguinarine.

Dimethylamine, (C2H7N), Secondary Amine
Dimethylamine, [C2H7N(CH3)2NH], DMA, [NH = imino group], colourless, flammable gas, fish odour, increase in human urine after fish diet, used in tanning dyes, soaps, fungicides.

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 Yam Dioscorea hispids, in Dioscorea dregeana, in Dioscorea bulbifera
See diagram: Dioscorine.

Ecgonine, (C9H15NO3), Tropane Alkaloid
Ecgonine, tropaine derivative, cocaine group, 2-hydroxy monocarboxylic acid, metabolite of cocaine and precursor to cocaine, controlled substance.
It occurs in Cocaine leaves (Erythroxylum coca).
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, in Echium plantagineum, Echium pininanam, 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, Echinops echinatus
See diagram: Echinopsine.

Elaeocarpine, (C16H19NO2), Unclassified Alkaloid
Elaeocarpine, Isoelaeocarpine, [11-methyl-1,2,3,5,6,6a,12a,12b-octahydrochromeno[2,3-g]indolizin-12-one], indolizidine alkaloid, occurs in Elaeocarpus polydactylus leaves.
See diagram: Elaeocarpine.

Elatine, (C38H50N2O10), Diterpenoid Alkaloid
Elatine, Elatin, dicarboximide, pyrrolidinone, benzoate ester, (derived from a hydride of an aconitane), folk medicine for neurological disorders, similar effects to Methyllycaconitine.
It occurs in Delphinium shawurense.
See diagram: Elatine.

Emetine, (C29H40N2O4), Isoquinoline Alkaloid
Emetine, Emetin, Cephaeline methyl ether, Methyl cephaeline, isoquinoline derivative, ipecacuanha alkaloid, (derives from a cephaeline), principal alkaloid of ipecac, plant metabolite, used as amoebicide (antiprotozoal), emetic, inhibits protein synthesis by blocking ribosome movement along the mRNA, strand and may cause cardiac, hepatic, or renal damage, violent diarrhea, vomiting.
The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae.
It occurs in Ipecacuanda, Carapichea ipecacuanha, Ipecac, in Hedera helix, Alangium longiflorumEmetine.

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, 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.
Ergine occurs in fungi, in Rivea corymbosa seeds, in Turbina, corymbosa (ololiuhqui), in Argyreia nervosa (Hawaiian baby woodrose), 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
Ergocristine occurs in Claviceps purpurea (ergot), in Scolochloa festucacea, 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.
Ergometrine occurs in Jacquemontia tamnifolia, in Acremonium
See diagram: Ergometrine.

Ergotamine, (C33H35N5O5), Indole Alkaloid
Ergotamine, 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.
Ergotamine occurs in ergot 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, plant metabolite, organic heterotetracyclic indole alkaloid.
Erythroidine occurs in Erythrina species (coral tree).
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, in Vepris soyauxii, in Cryptocarya
See diagram: Evodiamine.

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

Ficine, (C20H19NO4), Unclassified Alkaloid
Ficine, dihydroxyflavone, N-alkylpyrrolidine, [5,7-dihydroxy-8-(1-methylpyrrolidin-2-yl)-2-phenylchromen-4-one], 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, occurs in Ramnus, in Waltheria, in Ceanothus americanus root bark (New Jersey tea), in Hovenia dulcis (raisin tree), in Zizyphus jujuba.
See diagram: Frangulanine.

Galanthamine, (C17H21NO3), Amaryllidaceae Alkaloid
Galanthamine, Galantamine, Lycoremin, Benzazepine, iIsoquinoline derivative, Amaryllis alkaloid, (derived from norbelladine), oral cholinesterase inhibitor, used to treat Alzheimer's disease, analgesic, inhibits cholinesterase activity, herbal medicine nervous diseases, used to reverse the muscular effects of gallamine triethiodide (Flaxedil) (C30H60N3O3) and tubocurarine (C37H41N2O6+).
It occurs in Galanthus, in Amaryllis belladonna, in Hymenocallis leucojum, in Lycoris squamigera, in Narcissus, in Pancratium, in Ungernia, in Galanthus woronowii, 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, in Gelsemium elegans, 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, occurs in Gentiana aerial parts.
See diagram: Gentianadine.

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

Gentianine, (C10H9NO2), Monoterpenoid and Sesquiterpenoid Alkaloid
Gentianine, Pyridine derivative, polycyclic condensed pyridine derivative, [4-(2-hydroxyethyl)-5-vinylnicotinate g-lactone], pyranopyridine, polycyclic aromatic compound, bitter tasting, occurs in Trigonellasp, Fenugreek, in Gentiana macrophylla, large leaf gentian, qin jiao, in Gentian roots, gentian liquor is a hypotensive medicine.
See diagram: Gentianine.

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

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

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

Guvacine, (C6H9NO2), Pyrrolidine and Piperidine Alkaloid
Guvacine, Tetrahydronicotinic acid, Hydrogenated nicotinic acid, Alpha, beta-unsaturated monocarboxylic acid, pyridine alkaloid, secondary amino compound, inhibits 4-aminobutanoic acid, no known uses.
It occurs in Areca species, with methyl ester uvacoline.
See diagram: Guvacine.

Harmaline, (C13H14N2O), Indole Alkaloid
Harmaline, Dihydroharmine, Harmidine, Armalin, Harmalol methyl ether, beta-carboline alkaloid, fluorescent, (partially hydrogenated form of harmine).
It occurs in Peganum harmala (Syrian rue), in the hallucinogenic beverage ayahuasca brewed from Banisteriopsis caapi, psychoactive, central nervous system stimulant, acetylcholinesterase inhibitor, in Passiflora pilosicorona, in Passiflora boenderi
See diagram: Harmaline.
Tetrahydroharmine, C13H16N2O, UNII-AF812R7053, AF812R7053, C09243, a harmala alkaloid.

Harman, (C12H10N2), Indole Alkaloid
Harman, indole derivative, Non-isoprene indole alkaloid, Simple derivatives of beta-carboline, (Indole alkaloid fundamental parent), harmala alkaloid, inhibits monoamine oxidase A, plant metabolite, anti-HIV agent.
It occurs in Sickingia rubra, in Symplocus racemosa, in Passiflora incarnata, in Peganum harmala, in Banisteriopsis caapi, in Tribulus terrestris, in tobacco smoke, in Cichorium intybus, in Tribulus terrestris, in Ophiopogon, in Strychnos johnsonii
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, 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, in Maize, Zea mays.
See diagram: Harzianopyridone.

Heliosupine, (C20H31NO7), Pyrrolizidine Alkaloid Heliosupine, Cynoglossophine, heptatoxic.
It occurs in Cynoglossum officinale. in Echium, in Heliotrope, in Symphytum officinale.
See diagram: Heliosupine.

Heliotridine, (C8H13NO2), Pyrrolizidine Alkaloid
Heliotridine, pyrolizidine derivative, non-ester, heptatoxic.
It occurs in Heliotropium, in Cynoglossum.
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, in Delosperma, in Lampranthus, in Portulaca species, in 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, occurs in Huperezia the water tassel-fern, Lycopodiaceae
Huperzine A sesquiterpene alkaloid, in Huperzia serrata, neuroprotective, acetylcholinesterase inhibitor, neuroprotective agent, plant metabolite, pyridone, primary amino compound, organic heterotricyclic compound.
Huperzine B, 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 Goldenseal, in Fumaria
See diagram: Hydrastine.

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

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

Hyoscyamine, (C17H23NO3), Tropane Alkaloid
Hyoscyamine, toxic, laevorotatory isomer, anticholinergic with both central and peripheral nervous system actions, used to treat motion sickness and pre-operative medication for sedation and to induce anaesthesia, weak poisoning causes rapid breathing, nervousness, frequent urination, fatal poisoning 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.