School Science Lessons
Appendix F
Please send comments to: Alkaloids by name

Aconine, C25H41NO9,
Aconine, jesaconine, amorphous 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, in Aconitum species,
See diagram:

Aconitine, C34H47NO11, Diterpenoid Alkaloid
Aconitine, Acetylbenzoylaconitine, Lycoctonine type, C19 alkaloid, very poisonous and can be absorbed by skin, slows heart and lowers
blood pressure, neurotoxin, blocks neurotransmitters release, blocks norepinephrine (noradrenaline) uptake, causes ventricular tachycardia,
too dangerous to use internally, in Monkshood dried roots, Chinese herbal medicine, See diagram: Aconitine.

Acronidine, C18H17NO4 Quinoline Alkaloid
Acronidine, organic heterotetracyclic compound, (derived from a quinoline), plant metabolite, aromatic ether, in Acronychia,
See diagram: Acronidine.

Affinine, C21H24N2O2, Indole Alkaloid
Affinine, 17-Hydroxyvobasan-3-one, psychoactive, in Tabernaemontana catharinensis, (Pecschiera affinis), also Affinisine C20H24N2O2,
See diagram: Affinine.

Agroclavine, C16H18N2, Indole Alkaloid
Agroclavine, (8,9-Didehydro-6,8-dimethylergoline), tetracyclic indole alkaloid, ergot alkaloid, ( based on ergoline), in fungus Claviceps
purpurea, in Cuscuta, in Ipomoea, in Rivea, used for ergot-based drug synthesis, 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, in Dephinium species, See diagram: Ajaconine.

Ajmalicine, C21H24N2O2, Indole Alkaloid
Ajmalicine, Raubasine, delta-Yohimbine, Ajmalicin, monoterpenoid indole alkaloid and 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, in Rauwolfia sepentina, Catharanthus roseus, in Vinca,
in Mitragyna speciosa, antimicrobial activity, used to study effects as antagonist of adrenergic and nicotinic receptors, See diagram: Ajmalicine.

Alpinine, C23H29NO6, Isoquinoline Alkaloid
Alpinine, rhoeadine alkaloid, methylalpinigenine, in Papaver species, (also Alpinigenine), 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, in Amaranthus caudatus leaves, in Amaranthus tricolor inflorescences, in Celosia cristata,
in Atriplex hortense leaves, in Chenopodium amaranticolor, See diagram: Amaranthin.

Ambelline, C18H21NO5, Amaryllidaceae Alkaloid
Ambelline, isoquinoline derivative, amaryllis alkaloid, in Amaryllis, Boophane, Crinum, Hippeastrum, analgesic but too toxic,
See diagram: Ambelline.

Amurensine, C19H19NO4, Isoquinoline Alkaloid
Amurensine, pavine alkaloid, xanthopetaline, in Papaver species, pain relief, expectorant, tranquilliser, See diagram: Amuresine.

Amurine, C19H19NO4, Isoquinoline Alkaloid
Amurine, morphinan alkaloid, in Papaver, auranticum, Papaver nudicaule, relief, expectorant, tranquilliser, See diagram: Amurine.

Anabasine, C10H14N2, Pyrrolidine and Piperidine Alkaloid
Anabasine, Neonicotine, pyridine derivative, (polycyclic noncondensing pyridine derivative), plant metabolite, teratogenic agent, nicotine
analog so chemically similar to nicotine, skeletal muscle relaxant, formerly used as industrial piperidine botanical insecticide, trace in tobacco
smoke so used as test of smoking, in tree tobacco (Nicotiana glauca), in Nicotiana acuminata, in Anabasis aphylla.
See diagram: Anabasine.

Anagyrine, C15H20N2O, Quinolzidine Alkaloid
Anagyrine, Monolupine, Rhombinine, Anagyrine, highly toxic, teratogenic, cause "crooked calf's disease, cardiotonic, in Anagyris foetida,
in Ulex, in Thermopsis, in Cytisus, in Genista, in Lupinus, in Sophora, in Ammodendron, 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, in Nicotiana roots, 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, in Anisodus tanguticus, in Datura, See diagram: Anisodamine.

Anisodine, C17H21NO5, Tropane Alkaloid
Anisodine, Daturamine, alpha-Hydoxyscolopamine, antispasmodic, anticholinergic, used to treat circulatory shock, See diagram: Anisodine.

Annolobine, C17H15NO3, Isoquinoline Alkaloid
Annolobine, Anolobine, Anolobin, aporphine alkaloid, an alkaloid antibiotic, in Asimina triloba, See diagram: Annolobine.

Annonaine, C17H15NO2, Isoquinoline Alkaloid
Annonaine, Anonaine, Anonain, aporphine alkaloid, oxacycle, organic heteropentacyclic compound, insecticidal,
antimicrobial, anticancer, trypanocidal, antiplasmodial, in Annona reticulata, in Nelumbo nucifera, See diagram: Annonaine.

Apodine, C21H22N2O4, Indole Alkaloid
Apodine, hexacyclic indole alkaloid, methyl ester, in Tabernae montaina, See diagram: Apodine.

Apohyoscine, C17H19NO3, Tropane Alkaloid
Apohyoscine, Aposcopolamine, Aposcopolamin, epoxyatropyloxytropane, monocarboxylic acid, in Hyoscyamus, in Datura, in Duboisea
See diagram: Apohyoscine.

Apparicine, C18H20N2, Indole Alkaloid
Apparicine, Gomezine, Pericalline, Tabernoschizine, monoterpenoid indole alkaloid, antimicrobial, stimulates central nervous system,
active against polio virus, analgesic, in Aspidosperma, in Tabernae montaina, 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, cause
sweating, folk medicine, in Betel nut palm, 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 in Pacific Islands
in Betel nut palm, used in various salts to stimulate the parasympathetic nervous system and as a veterinary vermifuge, See diagram: Arecoline

Argentine, C23H26N4O3, Quinolzidine Alkaloid
Argentine, Carbonylbiscytisine, in Ammodendron, in Sophora, in Thermopsis, See diagram: Argentine.

Armepavine, C190H23NO3, Isoquinoline Alkaloid
Armepavine, benzylisoquinoline alkaloid, convulsions, irritation, irregular cardiac action, in Papaver, in Euonymus, in Rhamnus, in Nelumbo.
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, in Deadly nightshade | Jimson weed | Angel's trumpet.
Atropine sulfate used in anticholinergic medicines, to treat cardiac arrest, dilate pupils for eye examination, relax muscles, inhibit
secretions, See diagram: Atropine.

Baptifoline, C15H20N2O2, Quinolzidine Alkaloid
Baptifoline, Hydroxyanagyrene, Argentamin, in Baptisia, in Sophora, in Caulophyllum, in coffee and coffee products, in Caulophyllum
thalictroides blue cohosh, See diagram: Baptifoline.

Belladine, C19H25NO3, Amaryllidaceae Alkaloid
Belladine, N-Benzylphenethylamine, acetylcholinesterase and cholinesterase inhibitor, plant metabolite, in Amaryllis belladonna, bulbs,
in Crinum powellii bulbs, See diagram: Belladine

Berberine, C20H18NO4, +, Isoquinoline Alkaloid
Berberine, Berberin, Umbellatine, isoquinoline derivative, protoberberine alkaloid, bitter, yellow, used to treat bacillary dysentery,
in Barberry in Coelocline, in Coptis, in Evodia, in Mahonia, in Nandina, in Thalictrum, in Toddalia.
Berberine chloride, C20H18ClNO4, in Chinese herbs, antifungal, antiviral, anticancer
Berberine hemisulfate, C20H18NO4.1/2SO4, in Goldenseal anti-inflammatory, fluoresces under UV light
Berberine chloride hydrate, C20H18NO4.H2O, Natural Yellow 18 hydrate, intestinal infections, See diagram: Berberine.

Betalamic acid, C9H9NO5, Betalain Alkaloid
Betalamic acid, dicarboxylic acid, betalain, in Beta vulgaris pigment, in Celosia argentea, See diagram:
Betalamic acid.

Betanidin, C18H16N2O8, Betalain Alkaloid
Betanidin, purple pigment, (aglycone of betanin), in Mesembryanthemum flowers, in Portulaca, See diagram:

Betanin, C24H26N2O13, Betalain Alkaloid
Betanin, Betacyanin, Betanidin 5-O-beta-glucoside, a red-violet betacyanin, purple pigment, used in food industry, in Carpobrotus
flowers, in Drosanthemum, in Mesembryanthemum, in Opuntia, in Beta fruit red beet extract, in Phytolacca, in Portulaca
Beetroot Red, from beet, E number E162, See diagram:

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

Boldine, C19H21NO4, Isoquinoline Alkaloid
Boldine, Uniboldina, Boldin, aporphine alkaloid, 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, See diagram: Boldine.

Bracteoline, C19H21NO4, Isoquinoline Alkaloid
Bracteoline, aporphine alkaloid, in Papaver bracteatum, 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, in Strychnos.
See diagram: Brucine.

Bulleyaconitine A, C35H43NO9, Alkaloid
Bulleyaconitine, Bulleyanum, analgesic, anti-inflammatory, in Aconitum bulleyanum, has been used for the treatment of chronic pain
and rheumatoid arthritis, See diagram:

Calebassine, C40H48N4O4+2, Indole Alkaloid
Calebassine, Toxiferine IV, C-Alkaloid A, (18,18'-Dihydroxy-C-calebassine), highly toxic, neuromuscular blocker, arrow poison,
in "calabash curare" formerly packed into hollow gourds, 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, in Calystegia, in Atropa
Calystegin B2, Tetrahydroxynorpropane, C7H13NO4, in Convolvulus, in Solanum species, See diagram: Calystegin.

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

Candimine, C18H19NO6, Amaryllidaceae Alkaloid
Candimine, Maltotoxin, plant metabolite, in Hippeastrum, toxic, See diagram: Candimine
Capsaicin, C18H27NO3, Protoalkaloid
See diagram: Capsaicin.

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, in Camptotheca acuminata
stem wood of "happy tree", See diagram: Camptothecin.

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, in Amaryllis belladonna bulbs, in Clivia, See diagram: Caranine

Carboxystrictosidine, C28H34N2O4, Gluco Indole Alkaloid
5-Carboxystrictosidine, (5α-Carboxy-3-isovincoside), anti-inflammatory, in Uncaria tomentosa, cat's claw, See diagram: Carboxystrictosidine.

Carnegine, C13H19NO2, Isoquinoline Alkaloid
Carnegine, carnegin, Pectenin, simple isoquinoline, in Carnegiea, in Cereus, See diagram: Carnegine.

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

Cassine, C18H35NO2, Pyrrolidine and Piperidine Alkaloid
Cassine, in Cassia leaves, in Prosopis, See diagram: Cassine.

Cassythicine, C19H19NO4, Isoquinoline Alkaloid
Cassythicine, aporphine alkaloid, methylacinodaphnine, antimicrobial, cytotoxic, in Cassytha, in Annona, See diagram: Cassythicine.

Castanospermine, C8H15NO4, Pyrrolidine and Piperidine Alkaloid
Castanospermine, tetrahydroxyindolizidine alkaloid, inhibits glucosidases, causes severe gastrointestinal irrtation and perhaps death to
animals, may be useful in HIV/AIDS prevention research, in Castanospermum australe, black bean seeds.
Castanospermine derivative "celgosivir" possible antiviral drug to treat hepatitis C virus, See diagram: Castanospermine.

Caulophylline, C12H16N2O, Quinolzidine Alkaloid
Caulophylline, N-Methylcytisine, Caulophyllin, 12-Methylcytisine, irritant, in Cytisus, in Spartium, See diagram: Caulophylline.

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

Cephaeline, C28H33N2O4, Isoquinoline Alkaloid
Cephaeline, emetine alkaloid, cephaelic acid (ipecacuanhic acid), pyridoisoquinoline, (derives from a hydride of emetan C25H32N2,
in Carapichea ipecacuanha, in Ipecacuanha (Carapichea ipecacuanha), See diagram: Cephaeline.

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,
in Stephania cepharantha tubers, See diagram: Cepharanthine.

Cevadine, C32H49NO9, mixture of alkaloids
Cevadine, Veratrine, poisonous, irritates skin and mucous membranes, highly toxic to insects, less toxic to mammals,
in Schoenocaulon officinale, a mixture of alkaloids including veratridine, cevadillene, sabadine and cevadine, voltage-gated
sodium channel activator, See diagram: Cevadine.

Chelerythrine, C21H18NO4+, Benzophenanthridine alkaloid
Chelerythrine, Toddalin, Cheleritrine, Broussonpapyrine, benzophenanthridine alkaloid, organic cation, enzyme inhibitor,
antibacterial, antineoplastic, in Zanthoxylum simulans root, in Chelidonium majus (greater celandine), See diagram: Chelerythrine.

Cinchonidine, C19H22N2O, Cinchona Akaloid
Cinchonidine, Cinchovatine, (derived from a hydride of Cinchonan), diasteroisomer of cinchonine, in Cinchona bark,
See diagram: Cinchonidine.

Cinegalline, C23H30N2O6, Quinolzidine Alkaloid
Cinegalline, in Genista, See diagram: Cinegalline.

Clivorine, C21H27NO7, Pyrrolizidine Alkaloid
Clivorine, Senecionanium, heptacarcinogenic, in Anchusa, in Ligularia, 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, in Papaver somniferum
Codeine, heroin, methadone, abuse: 11.11.14, See diagram: Codeine.

Codonopsine, C14H21NO4, Pyrrolidine and Piperidine Alkaloid
Codonopsine, may decrease blood pressure, in Codonopsis clematidea, See diagram: Codonopsine.

Coniceine, C8H15N, Pyrrolidine and Piperidine Alkaloid
Coniceine, beta-Coniceine, [2-((E)-Prop-1-enyl)piperidine], beta-Coniceine, piperidine derivative, tetrahydro-6-propylpyridine,
extremley toxic, mouse-like odour, can be reduced to dl-coniine, causes abnormal embryos, with Coniine in Hemlock,
Conium maculatum seeds, in Aloe, See diagram: Coniceine.

Coniine, C8H17N, Pyrrolidine and Piperidine Alkaloid
Coniine, piperidine derivative, 2-propyl-piperidine, volatile, oily, extremley toxic, paralyses nerve endings, neurotoxic toxic principle,
used to paralyse insect prey, mouse smell, in Hemlock, Conium maculatum (caused death of Socrates), in Sarracenia flava pitcher
plant, in black elderberry, in Amorphophalus rivieri (devil's tongue), See diagram: Coniine.

Convolvine C16H21NO4, Tropane Alkaloid
Convolvine, O-Veratroylnortropine, (8-Azabicyclo[3.2.1]oct-3-yl 3,4-dimethoxybenzoate), a methoxybenzoic acid, acute yoxic, irritant,
in Convolvulus, in Datura, in Physalis, in Salpichroa, in Bruguiera (mangrove), See diagram: Convolvine.

Coptisine, C19H14NO4+, Alkaloid
Coptisine, Coptisin, cytotoxic alkaloid, related to Berberine, in opium, bitter taste, Chinese medicine for digestive disorders caused by
bacteria, plant metabolite, cytotoxic agent in heptoma and leukemic cells, in Chinese goldthread (Coptis chinensis), in Greater celandine
(Chelidonium majus), See diagram: Coptisine.

Corynoline, C21H21NO5, Benzophenanthridine Alkaloid
Corynoline, acetylcholinase inhibitor, hepatoproactive, in Chinese goldthread, in Corydalis, See diagram: Corynoline.

Cucurbitine, C5H10N2O2, Pyrrolidine and Piperidine Alkaloid
Cucurbitine, [3-amino-beta-proline], used to treat Schistosoma japonica infection, in Cucurbita moschata seeds,
Cularidine, C19H21NO4, Isoquinoline Alkaloid
Cularidine, Demethylcularine, cularine alkaloid, in Corydalis claviculata, in Dicentra cucullaria, cytotoxic, See diagram: Cularidine.

Cularimine, C19H21NO4, Isoquinoline Alkaloid
Cularimine, cularine alkaloid, alkaloid F30, kills malignant cells, 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, in Corydalis claviculata, in Dicentra cucullaria, in Berberis, See diagram: Cularine.

Cuscohygrine, C13H24N2O, Pyrrolidine and Piperidine Alkaloid
Cuscohygrine, Cuskhygrine, Hellaridine, folk medicines, used as sedatives or narcotics, in Hyoscyamus niger, in Atropa belladonna roots,
in Datura, in Scopolia, in Ethroxylum, in Convolvulus, See diagram: Cuscohygrine.

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, in Laburnum, Cytisus laborinum
Golden rain, See diagram: Cytisine.

Darlingine, C13H17NO2, Tropane Alkaloid
Darlingine, oxacycle, in Darlingea leaves, See diagram: Darlingine.

Delcosine, C24H39NO7, Diterpenoid Alkaloid
Delcosine, Delphamine, Lucaconine, Delcosin, Iliensine, poisonous, insecticidal, 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,
disordered heart rhythms, in Stavesacre, 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), in Delphinium, 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, in Meadow saffron,
Colchicum autumnale, See diagram: Demecolcine.

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

Denudadatine, C22H33NO2, Diterpenoid Alkaloid
Denudadatine, Denudatine, acute toxic, effects on action potential of ventricular fibers, inhibits arrhythmogenic action of aconitine,
in denudatum, roots used in Indian folk medicine for many ailments, 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, in Rauwolfia canescens, See diagram: Deserpidine.

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

Dioscorine, C13H19NO2, Pyrrolidine and Piperidine Alkaloid
Dioscorine, opalescent (yellow-red to blue), molecule, contains a non-aromatic pyran ring, neurotoxin, convulsant, arrow poison, in Yam
Dioscorea hispid.
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, in Coca leaves (Erythroxylum coca), See diagram: Ecgonine.

Echimidine, C20H31NO7, Pyrrolizidine Alkaloid
Echimidine, pyrrolizine, angelyl-9-echimidinylretronecine, Echimidine, toxic, heptatonic, in Echium, plantagineum, Patterson's curse,
in Symphytum officinale, See diagram: Echimidine.

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, in 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, in Ipecacuanda,
Carapichea ipecacuanha, Ipecac, See diagram: Emetine.

Ergine, C16H17N3O, Indole Alkaloid
Ergine, Lysergic acid amide, Lysergamide, (LSA), ergoline alkaloid, (derived from a hydride of an ergoline), South American folk
medicine, hallucinogen, in fungi, in Rivea corymbosa seeds, in Turbina, corymbosa (ololiuhqui), in Argyreia nervosa (Hawaiian baby
wood rose), in Ipomoea tricolor (morning glory), See diagram: Ergine.
Ergocristine, C35H39N5O5, Indole Alkaloid
Ergocristine, acute toxic, natural ergot alkaloid, (derived from a hydride of an ergotaman), prevents implantation and lactation,
in Claviceps purpurea (ergot), See diagram: Ergocristine.

Ergometrine, C19H23N3O2, Indole Alkaloid
Ergometrine, Ergonovine, Ergobasine, Ergotocine, Ergometrin, ergot alkaloid, monocarboxylic acid amide, (derived from lysergamide),
primary alcohol, tertiary amino compound, organic heterotetracyclic compound, secondary amino compound. causes contraction of uterine
and vascular smooth muscles, used to cause contractions of uterus if vaginal bleeding after childbirth, made from rye ergot fungus or lysergic
acid, can be used to make lysergic acid diethylamide (LSD) so it is a regulated substance, See diagram: Ergometrine.

Ergotamine, C33H35N5O5, Indole Alkaloid
Ergotamine, Gynergen, Ergomar, Ergotaminum, Ergonsvine, Ergopeptine, indole derivative, semiterpenoid indole alkaloid, ergot alkaloid,
vasoconstrictor, analgesic, serotonin agonist, used as oxytocic agent and in treatment of migraine disorders, activates serotonin receptors
on intracranial blood vessels causing vasoconstriction and reducing blood flow in cerebral arteries, binds to alpha-adrenergic receptors to
stimulate vascular smooth muscle and cause vasoconstriction in both arteries and veins, inhibits pro-inflammatory neuropeptide release,
used to treat bleeding after childbirth, 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, organic heterotetracyclic compound, tertiary amino compound, neuromuscular blocker, hypnotic, respiratory depressant,
muscle relaxant, plant metabolite, organic heterotetracyclic indole alkaloid, differs from the alpha isomer in location of the double bond
of the dihydropyranone ring, in Erythrina seeds (coral tree).
Dihydro-Beta-Erythroidine, (DHbetaE), C16H21NO3, organic heterotetracyclic compound, dihydro analog of beta-erythroidine, alkaloid
like curare, nicotinic antagonist, delta-lactone, tertiary amino compound, (derived from beta-erythroidine), in Erythrina seeds,
See diagram: Dihydro-Beta-Erythroidine.

Evodiamine, C19H17N3O, Indole Alkaloid
Evodiamine, anti-inflammatory, interferes with metastasis formation of new blood vessels, in Tetradium ruticarpum, See diagram: Evodiamine

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

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 gallamined triethiodide and tubocuarine, in Galanthus, in Crinum, in Hippeastrum,
in Hymenocallis leucojum, in Lycoris squamigera resurrection lily, naked lady, magic lily, in Narcissus, in Pancratium, in Ungernia,
in Galanthus woronowii Caucasian snowdrops, insecticidal, See diagram: Galanthamine

Gelsemicine, C20H26N2O4, Indole Alkaloid
Gelsemicine, very toxic, stimulates central nervous system, may cause respiratory paralysis, in Gelsemium supervirens folk medicine
used to treat pain and respiratory ailments, in Mostuea brunonis, See diagram: Gelsemicine

Glaucine, C21H25NO4, Isoquinoline Alkaloid
Glaucine, iquinoline derivative, aporphine alkaloid, bronchiodilator, anti-inflammatory, antitussive, in Galucium flavum, (yellow horn
poppy, horned poppy, sea poppy), See diagram: Glaucine.

Glaziovine, C18H19NO3, Isoquinoline Alkaloid
Glaziovine, isoquinoline derivative, proaporphine alkaloid, antidepressant, in Octea glaziovii, 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, in Betel nut palm, with methyl ester Guvacoline, See diagram: Guvacine.

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

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, in Sickingia rubra bark, in Symplocus racemosa,
in Passiflora incarnata passionflower may pop, in Peganum harmala, in Banisteriopsis caapi, in Tribulus terrestris, in tobacco smoke,
in Cichorium intybus common chicory, See diagram: Harman.

Harmine, C13H12N2O, Indole Harmine, Aribine, Loturine, Methyl carboline, Passiflorine, derivative of beta-carboline
β-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, See diagram: Harmine.

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

Heliosupine, C20H31NO7, Pyrrolizidine Alkaloid
Heliosupine, Cynoglossophine, heptatoxic, in Cynoglossum officinale hound's tongue, in Echium vulgare, in Heliotropium, in Symphytum,
See diagram: Heliosupine.

Heliotridine, C8H13NO2, Pyrrolizidine Alkaloid
Heliotridine, pyrolizidine derivative, non-ester, heptatoxic, in Heliotropium, See diagram: Heliotridine.

Heliotrine, C16H27NO5, Pyrrolizidine Alkaloid
Heliotrine, 9-Heliotrylheliotridine, Pyrrolizine, heptatoxic, mutagenic, in Heliotropium, See diagram: Heliotrine.

Humilixanthin, C14H18N2O7, Betalain Alkaloid
Humilixanthin, yellow pigment, alpha amino acid in Rivina humilis, in Phytolacca acinosa fruits, in Delosperma luteum petals,
in Lampranthus aurantiacus, in Portulaca grandiflora, in Beta vulgaris yellow-coloured root, See diagram: Humilixanthin.

Hydrastine, C21H21NO6, Isoquinoline Alkaloid
Hydrastine, isoquinoline derivative, phthalideisoquinoline alkaloid, astringent, alkaloid hydrastinine, C11H13NO3,
haemostatic drugs, in Hydrastis canadensis golden seal, See diagram: Hydrastine.

Hydroxylupanine, C15H24N2O2, Quinolzidine Alkaloid
Hydroxylupanine, 3-Hydroxylupanine, Jamaidine, Luparine, Oxylupanine, Octalupine, anti-arrhythmic, hypotensive, in Cyrtisus,
in Genista, in Thermopsis, in Cadia, in Lupinus, See diagram: Hydroxylupanine.

Hydroxystachydrine, C7H13NO3, Pyrrolidine and Piperidine Alkaloid
Hydroxystachydrine, 4-Hydroxystachydrine, urine biomarker citrus consumption, 3-Hydroxystachydrine, in Boscia, in Capparis,
in Steriphoma, See diagram: Hydroxystachydrine.

Hygrine, C8H15NO, Pyrrolidine and Piperidine Alkaloid
Hygrine, pyrrolidine derivative, pungent taste, pungent odour, yellow liquid, in Coca, Erythroxylum coca leaves,
in plants containing 16.3.30 Tropane alkaloids, 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, in Hyoscyamus niger (black henbane,
stinking nightshade, henpin), traditional medicine, for sleep and nervous disorders, toothache.
Hyoscine less toxic than hyoscyamine, See diagram: Hyoscyamine.

Hypaconitine, C33H45NO10, Diterpenoid Alkaloid
Hypaconitine, causes neuromuscular blocking action of aconite root, in Aconitum carmichaelii, See diagram: Hypaconitine.

Imizazole, C3H4N2, Imidazole Alkaloid
Imidazole, C, heterocyclic aromatic organic compound, classified as an alkaloid.
Imidazoles are a class of heterocycles with similar ring structure but varying substituents.
Glyoxaline is the parent compound of Imidazole alkaloids, "true alkaloids", e.g. Histamine, C5H9N3, and Histidine, C6H9N3O2,
See diagram: Imidazole parent compound C3H4N2

Indicaxanthin, C14H16N2O6 Betalain Alkaloid
Indicaxanthin, Betaxanthin, yellow-orange pigments, in Mirabilis jalapa flowers, in Bougainvillea, in Chenopodium,
in Mesembryanthemum, in Opuntia ficus-indica fruit, See diagram: Indicaxanthin.

Isobetanin, C24H26N2O13 Betalain Alkaloid
Isobetanin, Betacyanin, (Glucopyranosylisobetanidin), red-violet pigments, in Opuntia ficus-indica fruits, in Phyllocactus leaves,
in Mesembryanthemum flowers, See diagram: Isobetanin.

Isocorydine, C20H23NO4, Isoquinoline Alkaloid
Isocorydine, Artabotrine, Luteanine, Aporphine alkaloid, anti-adrenergic, animal sedative, in Corydalis, in Arbabotrys,
in Papaver species, in Phoebe, in Cherimoya, in Peumus boldus (boldo),See diagram: Isocorydine.

Juliflorine, C40H75N3O2, Pyrrolidine and Piperidine Alkaloid
Juliflorine, Juliprosopine, antibacterial, antifungal, in Prosopis juliflora, See diagram: Juliflorine.

Laudanidine, C20H25NO4, Isoquinoline Alkaloid
Laudanidine, benzylisoquinoline alkaloid, benzyltetrahydroisoquinoline, phenol, aromatic ether, laudanine, tritopine, toxic like strychnine,
in Papaver, in Machilus, in Thalictrum, in Xylopia, See diagram: Laudanidine.

Lasiocarpine, C21H33NO7, Pyrrolizidine Alkaloid
Lassiocarpine, hepatotoxic, in Heliotropium, in Symphytum, See diagram: Lasiocarpine.

Laudanosine, C21H27NO4, Isoquinoline Alkaloid
Laudanosine, laudanine methyl ether, benzylisoquinoline alkaloid, acute toxic, tetanic poison, depress blood pressure, cause convulsions,
in Papaver, See diagram: Laudanosine.

Leurosine, C46H56N4O9, Indole Alkaloid
Leurosine, Vinleurosine, VLR, amotin, antimitotic, antineoplastic, in Madagascar periwinkle, Vinca rosea, in Catharanthus, See diagram: Leurosinee.

Lilaline, C20H17NO7, Alkaloid
Lilaline, Tetrahydroxyflavone (derived from a flavone), Pyrrolidin-2-one, 7-Hydroxyflavonol, plant metabolite, in Lilium candidum
aerial parts, See diagram: Lilaline.

Littorine, C17H23NO3, Tropane Alkaloid
Littorine, in Anthocercis, in Atropa, in Datura, See diagram: Littorine.

Lobelanidine, C22H29NO2, Pyrrolidine and Piperidine Alkaloid
Lobelanidine, 8, 10-Diphenyllobelidiol, Citraconoyl group, from Lobeline, poison, in Lobelia, in Laurentia, in Sedum acre, See diagram: Lobelanidine.

Lobelanine, C22H25NO2, Pyrrolidine and Piperidine Alkaloid
Lobelanine, Diphenyllobelidone, precursor in the biosynthesis of lobeline, in Lobelia inflata, See diagram: Lobelanine.

Lobeline, C22H27NO2, Pyrrolidine and Piperidine Alkaloid
Lobeline, piperidine derivative, optically active piperidine alkaloid, tertiary amine, aromatic ketone, effects .similar to nicotine, smoking
deterrent, central nervous system stimulant, respiratory stimulant, in Indian tobacco dried stem and leaves, in Lobelia inflata,
in Campanula, See diagram: Lobeline.
Lobeline hydrochloride, C22H27NO2.HCl
Lobeline sulfate, C44H56N2O8S
Loline, 1-aminopyrrolizidine (loline), in Lolium temulentum.

Lunarine, C25H31N3O4 Polyamine Alkaloid
Lunarine, Spermidine derivative, in Lunaria biennis, in Lunaria annua (Honesty), See diagram: Lunarine.

Lupanine, C15H24N2O, Quinolizidine Alkaloid
Lupanine, quinolizidine derivative, sparteine group, D-lupanine, 2-Oxosparteine, lupanin, L-lysine-derived alkaloid, in Lupinus angustifolius
seeds have greatest concentration, hypoglycemic, strong bitter taste, may be toxic in high doses, mild sedative effect on the CNS, See diagram: Lupanine.

Lupinine, C10H41NO, Quinolizidine Alkaloid
Lupinine, quinolizidine derivative, lupinine group, L-lysine-derived alkaloid, bitter tasting crystalline, in Lupinus species (lupins)
but not in "sweet" varieties of lupins, mild sedative effect on the CNS, See diagram: Lupinine.

Lycoctonine, C2517NO7, Diterpenoid Alkaloid
Lycoctonine, Lycoctonum, in Aconin Aconitum in Delphinium, exceedingly poisonous, See diagram: Lycoctonine.

Lycopsamine, C15H25NO5, Pyrrolizidine Alkaloid
Lycopsamine, Viridiflorilretronecine, acutely toxic, hepatotoxic, in Amsinckia, in Borago, in Eupatorium, in Messerschmidia, in Parsonia,
in Symphytum, See diagram: Lycopsamine.

Lycorine, C1617NO4, Amaryllidaceae Alkaloid
Lycorine, Amarylline, Galanthidine, Narcissine, Licorine, indolizidine alkaloid, isoquinoline derivative, amaryllis alkaloid, (derives from a
hydride of a galanthan), acute toxic, antiviral, antimalarial, protein synthesis inhibitor, plant metabolite, in Licoris radiate, in Crinum asiaticum,
See diagram: Lycorine

Macarpine, C22H18NO6+, Isoquinoline Alkaloid
Macarpine, benzophenanthradine alkaloid, organic cation, (Sanguinarine + 2 methoxy substituents), in Macleaya, in Eschscholtzia,
in Stylophorum, See diagram: Macarpine.

Magnoflorine, C20H24NO4, Isoquinoline Alkaloid
Magnoflorine, aporphine alkaloid, escholin, in Papaver species, in Coptidis rhizoma, in Sinomenium acutum rhizome, in Pachygone ovata, See diagram: Magnoflorine.

Matrine, C15H24N2O, Quinolizidine Alkaloid
Matrine, quinolizidine derivative, Sparteine group, sophocarpidine, matridin-15-one, in herbal medicine and traditional Chinese medicine.
Sophora flavescens, kuhseng, necklace pod, oxymatrine, matrine alkaloid, See diagram: Matrine.

Mecambrine, C18H17NO3, Isoquinoline Alkaloid
Mecambrine, proaporphine alkaloid, fugapavine, toxic, causes convulsions, increases blood pressure, anti-inflammatory, in Papaver,
in Meconopsis, See diagram: Mecambrine.

Mecambroline, C18H17NO3, Isoquinoline Alkaloid
Mecambroline, aporphine alkaloid, isofugapavine, animal hypotensive, in Papaver, in Meconopsis, in Phoebe, See diagram: Mecambroline.

Mesaconitine, C33H35NO11, Diterpenoid Alkaloid
Mesaconitine, alpha-Hydroxyhypaconitine, in napellus (extracted commercially), pharmacological characteristics similar to aconitine,
See diagram: Mesaconitine.

Mesembrine, C17H23NO3, Indole Alkaloid
Mesembrine, Mesembrin, Mesembranone, bicyclic pyrrolidine, in Sceletium tortuosum, leaves fermented for folk medicine narcotic "channa", See diagram: Mesembrine.

Mesembrenone, C17H21NO3, Indole Alkaloid
Mesembrenone, bicyclic pyrrolidine, in kanna Sceletium tortuosum, See diagram: Mesembrenone.

Meteloidine, C13H21NO4, Tropane Alkaloid
Meteloidine, in Datura, in Anthocercis, in Erythroxylum, See diagram: Meteloidine.

Methyllycaconitine, C37H50N2O10, Diterpenoid Alkaloid
Methyllycaconitine, Delartine, Delsemidine, in Delphinium elatum, neuromuscular poison, See diagram: Methyllycaconitine.

Miraxanthin-I, C14H18N2O7S, Betalain Alkaloid
Miraxanthin, Betaxanthin, all miraxanthins are yellow pigments and in Mirabilis jalapa flowers.
Miraxanthin-I, C14H18N2O7S, Miraxanthin-II, C13H14N2O8, See diagram: Miraxanthin.
Miraxanthin-III, C17H17N2O5, Miraxanthin -V, C17H18N2O6, in red beetroot

Monocrotaline, C16H23NO6, Pyrrolizidine Alkaloid
Monocrotaline, Crotaline, hepatocarcinogenic, mutagenic, damage respiratory tissues, alkaloid contamination in bread from contaminated grains,
pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature, in Crotalaria, in Lindelofia, See diagram: Monocrotaline.

Morphine, C17H19NO3, Isoquinoline Alkaloid
Morphine, isoquinoline derivative, morphinan alkaloid, opioid alkaloid, analgesic, in Papaver somniferum,
activates receptors associated with different brain functions, causes analgesia, euphoria, sedation, respiratory depression, smooth muscle
contraction of gastro-intestinal system, See diagram: Morphine.

Musca-aurin-I, C14H13N3O8, Betalain Alkaloid
Musca-aurin-I, in red fly agaric Amanita muscaria, See diagram: Musca-aurin-I.

Napelline, C22H33NO3, Diterpenoid Alkaloid
Napelline, in Aconitum napellus, folk medicine for heart, respiratory problems, blood pressure, affects cats, See diagram: Napelline.

Narceine, C23H27NO8, Isoquinoline Alkaloid
Narceine, ring-opened isoquinoline alkaloid, narcein, a stilbene, narcotic, analgesic, occurs in dried latex of opium poppy,
in Papaver somniferum, See diagram: Narceine.

Narcotoline, C21H21NO7, Isoquinoline Alkaloid
Narcotoline, Desmethylnarcotine, phthalideisoquinoline alkaloid, spasmotic, respiratory stimulant, in Papaver, See diagram: Narcotoline.

Neopine, C18H21NO3, Isoquinoline Alkaloid
Neopine, morphinan alkaloid, neopin, beta-codeine, uses similar to Codeine, in Papaver, See diagram: Neopine.

Nicotine, C10H14N2, Pyrrolidine and Piperidine Alkaloid
Neopine, pyridine derivative, polycyclic noncondensingpyridine derivative, cholinergic nicotinic agonist, acute toxic, addictive, tranquillising,
insecticide, environment hazard, in Nicotiana, in Asclepias,
in Lycopodium, in Equisetum, in Sedum acre, See diagram: Nicotine.
See: Nicotine

Nicotyrine, C10H10N2, Pyrrolidine and Piperidine Alkaloid
Nicotyrine, beta-Nicotyrine, pyridine, [(1-Methyl-1H-pyrrol-2-yl)pyridine], alkaloid metabolite of nicotine, product of its pyrolysis, in cured tobacco
In theory, electronic cigarette (e-cig) users (vapers) achieve measurable serum nicotine levels when nicotyrine reversibly inhibits nicotine metabolism
in airways, See diagram: Nicotyrine.

Norharmane, C11H8N2, Indole Alkaloid
Norhame, β-carboline, 2, 9-diazofluorine, organic amine, in Peganum harmala, See diagram: Norharmane.

Nornicotine, C9H12N2, Pyrrolidine and Piperidine Alkaloid
Nornicotine, pyridine derivative, polycyclic noncondensingpyridine derivative, [3-(pyrrolidin-2-yl)pyridine], extracted from tobacco, related to nicotine
but lower toxicity, used as agricultural and horticultural
insecticide, in Nicotiana, in Duboisia, See diagram: Nornicotine.

Noscapine, C22H23NO7, Isoquinoline Alkaloid
Noscapine, Anarcotine, Capval, Coscopin, Methoxyhydrastine, Narcosine, Nectodon, Nospen, Opianine, Opiane, Terbenol, tusscapine,
isoquinoline derivative, phthalideisoquinoline alkaloid, alpha-narcotine, benzylisoquinoline alkaloid, phthalide benzylisoquinoline,
non-narcotic opium alkaloid, used to suppress coughs and muscle spasms, mild analgesic, antineoplastic, inhibits mitosis so causes
tumour cell death, in Opium poppy, contaminant in illegal heroin so used to identify drug addict use, See diagram: Narceine.

Nudicauline, C38H50N2O4, Diterpenoid Alkaloid
Nudicauline, andersoline, in Delphinium species, livestock poisoning if grazed, See diagram: Nudicauline.

Obaberine, C38H22N2O6, Isoquinoline Alkaloid
Obaberine, bisbenzylisoquinoline alkaloid, o-methyloxyacanthine, used against Leishmania, in Berberis, in Thalictrum, See diagram: Obaberine.

Oxyacanthine, C37H40N2O6, Isoquinoline Alkaloid
Oxyacanthine, vinetine, bisbenzylisoquinoline alkaloid, adrenaline antagonist, vasodilator, antimicrobial, in Berberis, in Mahonia, See diagram: Oxyacanthine.

Oxymatrine, C15H24N2O2, Quinolizidine Alkaloid
Oxymatrine, quinolizidine derivative, matrine group, in Sophora flavescens, Chinese medicine, antiviral, anticancer, See diagram: Oxymatrine.

Pachycarpine, C15H26N2, Quinolizidine Alkaloid
Pachycarpine. lupinidine, oxytocic agent, and anti-arrhythmic agent but not approved,
In Cytisus scoparius, Scotch broom, main alkaloid in Lupinus mutabilis, in Spartium, See diagram: Pachycarpine.

Paclitaxel, C45H51NO14
Paclitaxel, taxol A, abraxane, taxuyunnanine, anticancer chemotherapy drug, toxic, cyclodecane from Taxus brevifolia, Pacific yew tree bark
Inhibits mitosis, stabilizes microtubules leading to cell death, antileukaemia and antitumour medicine, See diagram: Paclitaxel.

Palmatine, C21H22NO4+, Isoquinoline Alkaloid
Palmatine, Berbericinine, Benzophenanthridine alkaloid, protoberberine alkaloid, antipyretic, detoxicant, protoberberine extract to treat
liver diseases, used to treat arrhythmia, analgesic in Coptis, in Corydalis, in Enantia, in Columba root Jateorrhiza, in Berberis, in Mahonia
Palmatine chloride hydrate, C21H22ClNO4.xH2O, palmatine, phytotoxin, in Phellodendron chinensis, huang bai, See diagram: Palmatine.

Papaverine, C20H21NO4, Isoquinoline Alkaloid
Papaverine, isoquinoline derivative, (derivatives of 1-and 2-benzyl-izoquinolines), benzylisoquinoline alkaloid, opium alkaloid,
antispasmodic, smooth muscle relaxant, in Papaver somniferum (opium poppy, common poppy), See diagram: Papaverine.

Peimine, C27H45NO3, alkaloid
Peimine, Verticine, Wanpeinine A, Zhebeinine, traditional Chinese medicine, antitussive, expectorant, anti-inflammatory
Peimine is a known MAPK inhibitor, as well as an inhibitor of p38, ERK and JNK phosphorylation, and NFB activation, See diagram: Peimine.

Pelletierine, C8H15NO, Pyrrolidine and Piperidine Alkaloid
Pelletierine, isopelletierine, dl-Pelletierine, citraconoyl group, used as anti-helminthic drug, e.g. tapeworm, in Punica granatrum,
in Duboisia, in Sedum, in Lupinus, See diagram: Pelletierine.

Phyllalbine, C16H21NO4, Tropane Alkaloid
Phyllalbine, Fillalbin, Methoxybenzoic acid, Vanilloyloxytropane, in Phyllanthus, in Convolvulus roots, See diagram: Phyllalbine.

Physostigmine, C15H21N3O2, Indole Alkaloid
Physostigmine, Eserine, indole derivative, pyrrolo-indole alkaloid, parasympathomimetic alkaloid, tertiary amine, cholinesterase
inhibitor, in Physostigma venenosum, poison bean but used in pharmacy for depression, antidote for belladonna poisoning, used to
treat glaucoma, anticholinergic delerium, See diagram: Physostigmine.

Piperine, C17H19NO3, Pyrrolidine and Piperidine Alkaloid
Piperine, piperidine derivative, piperinoyl piperidine, gives hot taste to black pepper Piper nigrum, in Curcumin, antimicrobial,
antiproliferative, used to give pungent taste to brandy, See diagram: Piperine.

Piplartine, C17H19NO5, Pyrrolidine and Piperidine Alkaloid
Piplartine, Piperinoylpiperidine, Piperlongumine, Cinnamamide, Dicarboximide, used to treat asthma and bronchitis, in Piper longum
roots. See diagram: Piplartine.

Portolacaxanthin, Betalain Alkaloid
Portulacaxanthin I, C14H16N2O7, non-proteinogenic alpha-amino acid, Portulacaxanthin II, C18H18N2O7, both are yellow pigments,
in Portulaca grandiflora, See diagram: Portolacaxanthin.

Prebetanin, C24H26N2O16S, Betalain Alkaloid
Prebetanin, Betanin sulfate glycoside, purple pigment, in Beta, in Phytolacca, in Rivina, See diagram: Prebetanin.

Pronuciferine, C19H21NO3, Isoquinoline Alkaloid
Pronuciferine, isoquinoline derivative, proaporphine alkaloid, plant metabolite, aromatic ether, cyclic ketone, organic heterotetracyclic
compound, mild anaesthetic, in Berberis, in Papaver species, in Croton, in Stephania, in Nelumbo, See diagram: Pronuciferine.

Prosopinne, C16H33NO3, Pyrrolidine and Piperidine Alkaloid
Prosopinine, piperidine alkaloid, hydroxypiperidine, metabolite, in Prosopis, See diagram: Prosopinine.

Protopine, C20H19NO5, Isoquinoline Alkaloid
Protopine, isoquinoline derivative, protopine alkaloid, benzylisoquinoline alkaloid, dibenzazecine alkaloid, fumarine, macleyine,
cordydalis C, corydinine, biflorine, acute toxic, irritant, analgesic, relax smooth muscles, antibacterial, in Papaver,
in Corydalis tubers, in Fumaria, Protopine hydrochloride, C20H20ClNO5, See diagram: Protopine.

Quinidine, C20H24N2O2, Quinoline Alkaloid
Quinidine, Chinidin, Pitayine, Cin-quin, optical isomer of quinine, in Chinchona tree bark, antimalarial, anti-arrhythmic in the heart,
dampens the excitability of cardiac and skeletal muscles, decreases conduction velocity of nerve impulses, See diagram: Quinidine.
See diagram: Quinidine.
Quinine, C20H25N2O2, Quinoline Alkaloid

Quinoline, C9H7N, Quinoline Alkaloid
Quinoline, heterocyclic aromatic organic compound, colourless hygroscopic liquid, strong odour, if exposed to light yellow then brown,
slightly soluble in cold water, flavouring ingredient in Mentha species, cocoa, black tea and scotch whisky.
Quinoline yellow, C18H11NO2, mixture of dyes based on quinoline, quinophthalone, solvent yellow, erio chinoline yellow 4G, E104,
azo dye based on quinoline, bright yellow colour, possible health risk is dermatitis, in lipsticks, See diagram: See diagram:

Rescinnamine, C35H42N2O9, vinca alkaloid
Rescinnamine, anti-hypertensive, tranquillizer, in Rauwolfia sepentina, See diagram: Rescinnamine.

Reserpine, C33H40N2O9, Indole Alkaloid
Reserpine, indole derivative alkaloid, monoterpenoid indole alkaloid, corynanthe type alkaloid, anti-hypertensive, antipsychotic,
control high blood pressure, tranquillizer, nowadays rarely used, in Rauwolfia sepentina, See diagram: Reserpine

Retamine, C15H26N2O, Quinolzidine Alkaloid
Retamine, Hydroxysparteine, hypotensive, diuretic, in Genista, See diagram: Retamine.

Reticuline, C190H23NO4, Isoquinoline Alkaloid
Reticuline, benzylisoquinoline alkaloid, coclanoline, alkaloid precursor, (precursor of morphine), in Papaver,
in Cryptocarpa, in Romneya, See diagram: Reticuline.

Retronecine, C8H13NO2, Pyrolizidine Alkaloid
Retronecine, Senecifolinene, pyrolizidine derivative, non-ester, may cause liver damage from excessive consumption, in Borago
officinalis, in Senecio vulgaris, in Tussilago farfara, borage leaf, comfrey, coltsfoot
in weeds in grain crops, e.g. Heliotropium, europaeum, Echium plantagineum, Crotalaria retusa, See diagram: Retronecine.

Rhoeadine, C21H21NO6, Isoquinoline Alkaloid
Rhoeadine, Rheadine, rhoeadan alkaloid, possibly antitumour, in Papaver species, (Papaver rhoeas, folk medicine,
expectorant, sedative), See diagram: Rhoeadine.

Rhombifoline, C15H20N2O, Quinolzidine Alkaloid
Rhombifoline, Butenylcytisine, in Genista, in Ammodendron, in Thermopsis, See diagram: Rhombifoline.

Ricinine, C8H8N2O2, Pyrrolidine and Piperidine Alkaloid
Ricinine, Ricidine, Ritsinin, pyridine derivative, simple derivative of pyridine, pyridine alkaloid, pyridone, nitrile, alkyl aryl ether R-O-R'
(where R is an alkyl group and R' is an aryl group), in Castor oil bush, castor,
seeds and leaves, bitter white crystals, may cause toxic burning feeling in mouth and throat, nausea, vomiting, severe pain in stomach,
diarrhoea, reactions, hepatic and renal damage, death, used as alkaloid marker for poisonous lectin ricin, e.g. in urine, toxic alkaloid,
in castor plant, insecticidal, See diagram:
Castor oil, ricinoleic acid:

Riddelline, C18H23NO6, Pyrrolizidine Alkaloid
Riddelline, diester of retronecine C8H13NO2, possible carcinogen
In Senecio riddelli, Senecio vulgaris, Jacobaea vulgaris, Crotalaria, Amsinckia, See diagram: Riddelline.

Salutaridine, C19H21NO4, Isoquinoline Alkaloid
Salutaridine, morphinan alkaloid, floripavine, in Papaver, in Croton, See diagram: Salutaridine.

Sanguinarine, C20H14NO4, Isoquinoline Alkaloid
Sanguinarine, isoquinoline derivative, benzophenanthridine alkaloid, toxic, bitter, antibacterial, cytotoxic, dental plaque inhibitor, used
to treat bronchial disorders, inhibits enzymes, in Sanguinaria canadensis dried rhizome and root, in Papaver, in Chelidonium, in Fumaria,
in Zantholem, in Pteridophyllum
Sanguinarine chloride hydrate, C20H14ClNO4.H2O, in Papaveraceae, See diagram: Sanguinarine.

Scopolamine, C17H21NO4, Tropane Alkaloid
Scopolamine, hyoscine, syrup, narcotic ("truth drug"), sedative, in Datura species (e.g. Jimson weed), nightshade family, and Scopolia,
in Hyoscyamus niger, in Atropa belladonna, See diagram: Scopolamine.
(-)-Scopolamine hydrobromide trihydrate, C17H21NO4.HBr.3H2O, hyoscine hypobromide
Scopolamine less toxic than Hyoscyamine, used for anaesthetic premedication, treat urinary incontinence, motion sickness,
antispasmodic, anticholinergic, anti-emetic and antivertigo properties, control the secretion of saliva and gastric acid, to slow gut motility,
and prevent vomiting.

Sedamine, C14H21NO, Pyrrolidine and Piperidine Alkaloid
Sedamine, Phenyllobellol, piperidine derivative, citraconoyl group, poison, in Sedum acre, See diagram: Sedamine.

Senecionine, C18H25NO5, Pyrolizidine Alkaloid
Senecionine, Aureine, Senecionin, plant metabolite, lactone, tertiary alcohol, from a senecionan, hepatotoxic, pneumotoxic, mutagenic,
used to study liver injury, in Castilleja, in Senecio species, See diagram: Senecionine.

Sinomenine, C19H23NO4, Isoquinoline Alkaloid
Sinomenine, isoquinoline derivative, morphinan alkaloid, morphinan derivative, cucoline, anti-rheumatic, suppresses coughs, weakly
analgesic, abortifacient, in Sinomenium, See diagram: Sinomenine.

Slaframine, C10H18N2O2, Pyrrolidine and Piperidine Alkaloid
Slaframine, alkaloidal mycotoxin, causes animal salivation, in Rhizoctonia leguminicola, pathogen of red clover Trifolium pratense
red clover, See diagram: Slaframine.

Sparteine, C15H26N2, Quinolizidine Alkaloid
Sparteine, lupinidine, quinolizidine derivative, sparteine group, (L-lysine derived alkaloid), toxic to livestock, oily, oxytocic,
anti-arrhythmic, formerly used to treat heart disorders, in Lupinus angustifolius, in Cytisus scoparius (scotch broom), Spatium junceum
(broom), lupin seed.
Lupinidine, oxytocic and anti-arrhythmic agent, indicator of CYP2D6 genotype, in Lupinus, in Spartium, in Cytisus, See diagram: Sparteine.

Stachydrine, C7H13NO2, Pyrrolidine and Piperidine Alkaloid
Stachydrine, pyrrolidine derivative, Proline betaine, L-proline betaine, amino acid betaine, food component, plant metabolite, human
blood serum metabolite, in urine, possible osmoprotective role for the kidney, in Capparis (used to treat rheumatism), in Stachys, in Achillea,
in Desmodium, in Asphodelus, in many citrus foods, biomarker for consumption of Citrus, See diagram: Stachydrine.

Strychnine, C21H22N2O2, Indole Alkaloid
Strychnine, indole derivative alkaloid, monoterpenoid indole alkaloid, corynanthe type alkaloid, CNS stimulant, colourless, bitter, crystalline,
used as rodenticide, highly toxic convulsant causing death by asphyxia, has been used as folk medicine in very small doses but not
recommended, Strychnos nux-vomica, (poison nut tree), See diagram:Strychnine

Supinidine, C8H13NO, Pyrolizidine Alkaloid
Supinidine, in Heliotropium, See diagram: Supinidine.

Swainsonine, C8H15NO3, Pyrrolidine and Piperidine Alkaloid
Swainsonine, indolizidine derivative, inhibits enzymes, antimetastatic, antiproliferative, immunomodulatory, in Swainsona canescens,
locoweed, stagger weed, from Astragalus, used to treat AIDs, See diagram: Swainsonine.

Symphytine, C20H31NO6, Pyrolizidine Alkaloid
Symphytine, hepatotoxic, in Myosotis, in Symphytum, See diagram: Symphytine.

Synephrine, C9H13NO2, Phenethylamine Alkaloid
Synephrine, Oxedrine, p-Synephrine, Parasympatol, long-acting adrenergic effects, vasoconstrictor, used to treat circulatory failure,
asthma, nasal congestion, glaucoma Chinese medicine, in Citrus x aurantium, whole dried oranges See diagram: Synephrine.

Tabersonine, C21H24N2O2, Indole Alkaloid
Tabersonine, terpene indole alkaloid, antitumour, hypoglycaemic, diuretic, in Apocynaceae, Amsonia elliptica
used to make other alkaloids,See diagram: Tabersonine.

Tetrahydropalmatine, C21H25NO4, alkaloid
Tetrahydropalmatine, Rotundine, l-Tetrahydropalmatineanalgesic, (berberine alkaloid by adding two molecules of hydrogen to pyridine
ring of palmatine), organic heterotetracyclic compoun, sedative, tranquillizer, in Corydalis ambigua, experimental treatment
of Schizophrenia with L-tetrahydropalmatine, Dopamine Antagonist, anti-inflammatory, antiprotozoal, See diagram: Tetrahydropalmatine.

Tetrandrine, C38H42N2O6, benzylisoquinoline alkaloid
Tetrandrine, anti-hypertensive, immunosuppressive, antiproliferative, free radical scavenger, lowers plasma glucose,
In Stephania tetrandra, in Radix stephania root, See diagram: Tetrandrine.

Thebaine, C19H21NO3, Isoquinoline Alkaloid
Thebaine, isoquinoline derivative, morphinan alkaloid, opiate alkaloid, paramorphine, organic heteropentacyclic compound, weak
narcotic, analgesic, may cause strychnine-like convulsions, acutely toxic, main alkaloid from Iranian poppy, Papaver bracteum,
usually produced from poppy straw, controlled opiate substance, habit forming, See diagram: Thebaine.

Tigloidine, C13H21NO2, Tropane Alkaloid
Tigloidine, Tigloyloxytropane, Tiglylpseudotropane, Tigloidin, Tropigline, depresses central nervous system, anticholinergic, used
to treat muscle rigidity and Parkinson's disease, in Duboisea, in Datura, See diagram: Tigloidine.

Tinctorine, C15H20N2O, Quinolzidine Alkaloid
Tinctorine, Alteramine, in Baptisia, in Genista, in Thermopsis, See diagram: Tinctorine.

Tomatidine, C27H45NO2, Steroidal Alkaloid
Tomatidine, glycoalkaloid, supposed to be anabolic and increase muscle, in green tomato, See diagram: Tomatidine.

Topotecan, C23H23N3O5, quinoline-based alkaloid
Topotecan, Hycamptamine, (derivative of camptothecin), antitumour, anticancer agent, antineoplastic,
used to treat ovarian cancer, inhibits topoisomerase, in Camptotheca acuminata, Asian "happy tree", See diagram: Topotecan.

Trichostachine, C16H17NO3, Pyrrolidine and Piperidine Alkaloid
Trichostachine, Piperyline, Trichostachin, Pyrroperine, in Piper nigrim, in Piper guineense, See diagram: Trichostachine.

Tubocurarine, C37H41CN2O6+, Isoquinoline Alkaloid
Tubocurarine, bisbenzylisoquinoline alkaloid, toxic, skeletal muscle relaxant, arrow poison, induce neuromuscular paralysis, active
ingredient in curare, in Chondodendron tomentosum (curare vine), curare, on poison-tipped arrows, blocks the action of acetylcholine,
See diagram: Tubocurarine.
Tubocurarine hydrochloride, C37H41ClN2O6.HCl.5H2O.

Valepotriate, C22H30O8, Iridoid Alkaloid
Valapotriate, baldrisedon, iridoid monoterpenoid, sedative, in Valerian, Kentranthus sp. (valtratum), See diagram: Valepotriate.

Valeroidine, C13H23NO3, Tropane Alkaloid
Valeroidine, Isovaleroxyhydroxypropane, in Datura, in Duboisia, See diagram: Valeroidine.

Vasicine, C11H12N2O, Quinoline Alkaloid, quinazoline derivative,
Vasicine, Vazicine, Peganine, quinoline derivative, pyrrolidine and piperidine quinazoline derivative, expectorant, bronchiodilator, oxytocic
properties, abortifacient, in Lesser periwinkle, Adhatoda vasica, Acanthaceae, Peganum harmala, seeds
In Vinca minor, (periwinkle), See diagram: Vasicine.

Veratridine, C35H51NO11, Steroidal Alkaloid
Veratridine, Benzoate-cevane, Dimethoxybenzoate, (derivative of veracevine alkaloid), C27H43NO8, neurotoxin,
activates sodium chanels to remain open longer, sodium channel modulator, in lily family, Veratrum
used to treat nervous disorders, pain, in Schoenocaulon officinale, Sabadilla seeds, Veratrum album, rhizome, See diagram: Veratridine.

Verbenalin, C17H24O10, Iridoid Glycoside Alkaoid
Verbenalin, Cornin, very bitter, hepato-protective, sleep inducing, used to treat menstrual cramping, in Verbena officinalis, In Crampbark
(Viburnum opulus), and related species, e.g. black haw (Viburnum prunifolium), See diagram: Verbenalin, Cornin, See diagram: Verbenalin.

Vinblastine, C46H58N4O9, Indole Alkaloid
Vinblastine, vinca alkaloid, antitumour, antileukemic agent, antimicrotubule agent, in Madagascar periwinkle, Vinca rosea, See diagram: Vinblastine.

Vincamine, C21H26N2O3, Indole Alkaloid
Vincamine, indole derivative alkaloid, monoterpenoid indole alkaloid, aspidosperma-type alkaloid, vinca alkaloid, minorine, anti-aging, peripheral
vasodilator, increases blood flow to the brain, anti-hypertensive, used to treat cerebrovascular disorders, in Lesser periwinkle, See diagram: Vincamine.

Vincristine, C46H56N4O10, Indole Alkaloid
Vincristine, vinca alkaloid, oncovine, antitumuor, antimicrotubule agent, used to treat acute leukaemia, malignant lymphoma, Hodkin's disease,
In Madagascar periwinkle, (Vinca rosea), See diagram: Vincristine.

Vindoline, C25H32N2O6, Indole Alkaloid
Vindoline, used to synthesise anticancer antibiotics vinblastine and vinchristine, antimitotic activity, in Madagascar periwinkle,
tabersonine, See diagram: Vindoline.
(C21H24N2O2) --> vindoline --> vinblastine (C40H58N4O9).

Vinorelbine, C45H54N4O8, vinca alkaloid
Vinorelbine, antitumour, antimicrotubule agent, in Madagascar periwinkle, See diagram: Vinorelbine.

Vinpocetine, C22H26N2O2, Vinpocetine, synthetic derivative of vinca alkaloid vincamine
ethyl apovincaminate, anti-inflammatory, See diagram: Vinpocetine.

Vulgaxanthin, C14H17N3O7, Betalain Alkaloid
Vulgaxanthin, betaxanthins, Vulgaxanthin I and Vulgaxanthin II, yellow pigments, in Mirabilis jalapa flowers, in Beta, See diagram: Vulgaxanthin.

Yohimbine, C21H26N2O3, Indole Alkaloid
Yohimbine, indole derivative alkaloid, monoterpenoid indole alkaloid, corynanthe type alkaloid, herbal medicine, aphrodisiac, used to
treat erectile disfunction, cause pupil of eye to dilate, reverse veterinary sedation, in Pausinystalia yohimbe bark, See diagram: Yohimbine.
Yohimbine hydrochloride.