School Science Lessons
Appendix A
2019-08-15
Please send comments to: J.Elfick@uq.edu.au

16.3.0.0 Alkaloids
Table of contents
16.3.0.1 Alkaloids
16.3.0.2 Amines
16.3.0.4 Alkaloids by trivial names
16.3.0.5 Plant Amines by trivial names
16.3.0.6 Principle classes of alkaloids
16.3.0.7 Phenethylamine group of alkaloids
16.3.0.1 Alkaloids
The classification system and examples of plants in this document are based on
"Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants", Second Edition
by Herbert Baxter, J.B. Harborne, Gerald P. Moss, December 16, 1998, CRC Press, Taylor and Francis Group,
Reference - 992 Pages
ISBN 9780748406203 - CAT# TF2051
Alkaloids are secondary metabolites, so not essential to the organism, usually occurring in only a few species of plants as complex
organic bases of vegetable origin,
Alkaloids are basic organic nitrogen compounds in plants with powerful action on animals, e.g. nicotine, morphine, quinine, strychnine.
Alkaloids usually contain at least one nitrogen atom in a heterocyclic ring.
Alkaloids occur mainly in vascular plants and some fungi.
Alkaloids have the properties of amines and are natural bitter, alkaline, nitrogenous compounds, nitrogenous organic bases in plants.
They usually contain one or more N and a heterocyclic ring structure.
The names of alkaloids usually end in "ine".
Their function is probably to defend against grazing animals or being eaten by insects.
Many alkaloids are plant metabolic by-products derived from amino acids.
More than 10 000 different alkaloids may exist in more than 300 plant families.
Alkaloids often contain one or more phenolic or indole rings, usually with a nitrogen atom in the ring.
The term alkaloid was first used to describe chemical bases from plants used in medicines, but now there is no exact definition of
alkaloid.
Some classifications of alkaloids are based on structure and some on origin.
Alkaloids are secondary metabolites, so not essential to the organism, usually occurring in only a few species of plants.
"True alkaloids" are derived from amino acids and have nitrogen in a heterocyclic ring, e.g. atropine.
"Protoalkaloids" are derived from amino acids and do not have nitrogen in a heterocyclic ring, e.g. ephedrine.
"Pseudoalkaloids" are not derived from amino acids, but have nitrogen in a heterocyclic ring, e.g. caffeine.

Diagrams of Alkaloid
See diagram 16.20.0 Caffeine, cocaine, coniine, heroin, LSD, morphine, nicotine, quinine, strychnine, theobromine, theophylline
See diagram 16.20.1 Codeine, heroin, methadone, morphine, nicotine, pethidine
See diagram 16.21.7 Mescaline, dopamine, ergine, LSD, tropane

16.3.0.2 Amines
Amines, C2H5NH2
Amines are produced by the decay of organic matter, ammonia-derivative organic compounds of nitrogen where one or more
hydrogen atoms has been replaced by a hydrocarbon radical, an alkyl or aryl group.
Amines are organic derivative of ammonia, NH3, where one, two or three hydrogen atoms are replaced by alkyl groups as a primary
amine, secondary amine or tertiary amine, e.g. Trimethylamine , C3H9N
Amines usually act as weak bases that form ammonium salts that are more soluble in water than the original amine, e.g. cough medicine
may contain the cough suppressants dextramethorphan hydrobromide or the decongestant, expectorant, pseudoephidrine
hydrochloride and ephedrine.
Ethane is an important product of microbial metabolism.
Amines, RNH2 (amino, -NH2), amine, e.g. methylamine CH3NH2
Plant amines occur in most plant cells, formed by decarboxylation of amino acids or by transamination of aldehydes. There is no sharp distinction between plant amines and alkaloids.
16.4.3.1 Amine topics
Aliphatic amines (RNH2-, R = alkyl group)
19.2.2 Amine intolerance
16.2.4.3.0 Amines, methylamine ionization reaction
18.7.23 Chloramines in swimming pools
Lists of amines
16.4.3.2 Primary Amines
16.4.3.3 Secondary Amines
16.4.3.4 Tertiary Amines
16.4.3.5 Aromatic Amines
16.3.0.5 Plant Amines by trivial names

16.4.3.2, Primary Amines
In primary amines, one of three hydrogen atoms in ammonia is replaced by organic substituents.
Formula for primary amines: RNH2, where R = alkyl group
Methylamine , CH3NH2, monomethylamine
Ethanolamine , NH2CH2CH2OH
Aniline , C6H5NH2, phenylamine
Propylamine , C3H9N.

16.4.3.3, Secondary amines
In secondary amines, two organic substituents bound to N together with one H, RR'NH
Formula for secondary amines: R2NH, where R = alkyl group
Diethanolamine , C4H11NO2
Diethylamine , C4H11N
Dimethylamine , C2H7N
Cyclic secondary amines
Pyrrolines, cyclic amines
Acetyl pyrroline , C6H9NO.

16.4.3.4, Tertiary amines
In tertiary amines, all three hydrogen atoms are replaced by organic substituents. RR'R''N
Formula for secondary amines: R3N, where R = alkyl group
Hordenine Trimethylamine , C3H9N
Cyclic tertiary amines
Piperidine , C5H11N.

16.4.3.5, Aromatic amines
Aromatic amines have the nitrogen atom connected to an aromatic ring, as in aniline. Aniline , C6H5NH2
Heterocyclic aromatics have one or more of the atoms in the aromatic ring + an element other than carbon.
Sometimes aromatic amines are classified as alkaloids.
Polycyclic aromatic hydrocarbons (PAH) have two or more simple aromatic rings fused together by sharing two carbon atoms:
Benzene, toluene, ortho-xylene and para-xylene.
In general, amines act as bases and are reasonably strong.
Because amines are basic, they neutralize carboxylic acids to form corresponding ammonium carboxylate salts.
Upon heating to 200oC, the primary and secondary amine salts dehydrate to form corresponding amides.

16.3.34 Catecholamines
| Adrenaline | Norepinephrine | Dopamine |.
[catechol, C6H4(OH)2 + side chain amine], function as psychoactive compounds, hormones or neurotransmitters
Catecholamines are monoamines, which contain catechol ( benzene with two OH side groups at carbons 1 and 2) and a side-chain amine.
Catechol may be a free molecule or part of a larger molecule as the 1, 2-dihydroxybenzene group.
Catecholamines are derived from the amino acid tyrosine.

16.3.0.5 Plant Amines by trivial names
| Bufotenine
| Cadaverine | Capsaicin | Candicine | Cathine | Cathinone
| Diethanolamine | Diethylamine | Dimethylamine | Dimethyltryptamine | Dopamine
| Ephedrine | Ethanolamine
| Galegine | Gramine
| Histamine | Hordenine
| Indole | Indoleacetic acid
| Mescaline | Methylamine | Muscarine | Muscimol
| Noradrenaline
| Octopamine
| Phenethylamine | Piperidine | Propylamine | Pseudoephedrine | Psilocin | Psilocybin | Putrescine | Pyrrolidine |
| Serotonin
| Trimethylamine | Tryptamine | Tyramine |.

16.3.0.4 Alkaloids by trivial names
| Acanthicifoline | Aconine | Aconitine | Acronidine | Actinidine | Adrenaline | Affinine | Agroclavine | Ajaconine | Ajmalicine
| Alpinine | Amaranthin | Ambelline | Amurensine | Amurine | Anabasine | Anagyrine | Anatabine | Aniline | Anisodamine | Anisodine | Annolobine
| Annonaine | Annotine | Apodine | Apohyoscine | Apparicine | Arecaidine | Arecoline | Arenaine | Argentine | Armepavine | Atropine
| Baptifoline | Belladine | Berberine | Betalamic acid | Betanidin | Betanin | Bocconine | Boldine | Boschniakine | Bracteoline | Brucine | Bulleyaconitine
| Caffeine | Calebassine | Calystegin | Camptothecin | Cancentrine | Candimine | Cannabisativine | Cantleyine
| Caranine | Carboxystrictosidine | Carnegine | Carpaine | Cassine | Cassythicine | Castanospermine | Caulophylline | Celosianin | Cephaeline | Cepharanthine | Cevadine
| Chaconine | Chelerythrine | Cinchonidine | Cinegalline | Clivorine | Cocaine | Codeine | Codonopsine | Colchicine | Coniceine
| Coniine | Convolvine | Coptisine | Corynoline | Crassicauline A | Cryptopleurine | Cucurbitine | Curarine | Cularidine | Cularimine | Cularine
| Cuscohygrine | Cyclovirobuxine | Cytisine
| Darlingine | Delcosine | Delphinine | Deltaline | Demecolcine | Demethylcoclaurine | Dendrobine | Denudadatine | Deserpidine
| Dihydrosanguinarine | Dioscorine
| Ecgonine | Echimidine | Elaeocarpine | Elatine | Emetine | Ergine | Ergocristine | Ergometrine | Ergotamine | Erythroidine | Evodiamine
| Febrifugine | Ficine | Frangulanine
| Galanthamine | Gelsemicine | Gentianadine | Gentianaine | Gentianine | Gentioflavine | Glaucine | Glaziovine | Guvacine
| Harmaline | Harman | Harmine | Harzianopyridone | Heliosupine | Heliotridine | Heliotrine | Hordenine | Humilixanthin
| Huperzine | Hydrastine | Hydroxylupanine | Hydroxystachydrine | Hygrine | Hyoscyamine | Hypaconitine
| Ibotenic acid | Imidazole | Indicaxanthin | Inundatine | Irinotecan | Isobetanin | Isocorydine
| Jasminine | Jervine | Juliflorine
| Lannaconitine
| Lasiocarpine | Laudanidine | Laudanosine | Leurosine | Lilaline | Littorine | Lobelanidine | Lobelanine | Lobeline | LSD | Lunarine | Lupanine | Lupinine | Lycoctonine
| Lycopodine | Lycopsamine | Lycorine |
| Macarpine | Magnoflorine | Matrine | Mecambrine | Mecambroline | Mesaconitine
| Mesembrine | Mesembrenone | Meteloidine | Methyllycaconitine | Miraxanthin | Monocrotaline | Morphine | Musca-aurin-I | Myosmine
| Napelline | Narceine | Narcotoline | Neopine | Nicotine | Nicotyrine | Norharmane | Nornicotine | Noscapine | Nudicauline
| Obaberine | Oxyacanthine | Oxymatrine
| Pachycarpine | Palmatine | Papaverine | Peganine | Peimine | Pelletierine | Phyllalbine | Physostigmine | Pilocarpine | Piperine | Pipernonaline | Piplartine | Portolacaxanthin | Prebetanin
| Pronuciferine | Prosopinine | Protopine | Protostephanine | Protoveratrine
| Quinine | Quinidine
| Rescinnamine | Reserpine | Retamine | Reticuline | Retronecine | Rhoeadine | Rhombifoline | Ricinine | Riddelline | Rotundine | Rutaecarpine
| Salutaridine | Sanguinarine | Scopalamine | Securinine | Sedamine | Selagine | Senecionine | Sinomenine | Sirodesmin | Slaframine | Solamargine | Solanidine | Solanine
| Solasodine | Solasonine | Sparteine | Stachydrine | Strychnine | Supinidine | Swainsonine | Symphytine | Synephrine
| Tabersonine | Taxine | Taxol | Tetrahydropalmatine | Tetrandrine | Thebaine | Theobromine | Theophylline | Tigloidine | Tinctorine | Tomatidine | Tomatine | Topotecan | Trichostachine | Tubocurarine
| Valepotriate | Valerianine | Valeroidine | Veracevine | Veratramine | Verruculotoxin | Verticine | Vinblastine | Vincamine | Vincristine | Vindoline | Vinorelbine | Vinpocetine | Vulgaxanthin
| Yohimbine | Yunaconitine | Zizyphine

16.3.0.6 Principle classes of alkaloids
16.3.17 Amaryllidaceae Alkaloids
16.3.18 Betalain Alkaloids
16.3.19 Diterpenoid Alkaloids
16.3.20 Indole Alkaloids
16.3.21 Isoquinoline Alkaloids
16.3.22 Lycopodium Alkaloids
16.3.23 Monoterpenoid and Sesquiterpenoid Alkaloids
16.3.24 Peptide Alkaloids
16.3.33 Purines and Pyrimidines
16.3.25 Pyrrolidine and Piperidine Alkaloids
16.3.26 Pyrrolizidine Alkaloids
16.3.27 Quinoline Alkaloids
16.3.28 Quinolizidine Alkaloids
16.3.29 Steroidal Alkaloids
16.3.30 Tropane Alkaloids
16.3.31 Unclassified Alkaloids

16.3.17 Amaryllidaceae Alkaloids
Occur only in this daffodil family, usually in the bulbs, but sometimes in the aerials, probably based on Belladine.
Many are toxic if the bulbs are mistaken for onions.
The first alkaloid was the isolation of lycorine from Narcissus pseudonarcissus in 1877.
| Ambelline | Belladine | Candimine | Caranine | Galanthamine | Lycorine |.

16.3.18 Betalain Alkaloids
Coloured alkaloids occurring in plant vacuoles of nine plant families, divided into betacyanins and betaxanthins.
Occur in all Cactaceae, Beta vulgaris, Mirabilis, Portulaca
| Amaranthin | Betalamic acid | Betanidin | Betanin | Celosianin | Humilixanthin | Indicaxanthin | Isobetanin | Miraxanthin |
| Musca-aurin-I | Portolacaxanthin | Prebetanin | Vulgaxanthin |.

16.3.19 Diterpenoid Alkaloids
Similar structure to terpene and including the toxins: aconitine, barbitine, lycoctinine, delphine, heteratisine.
(Terpenoid alkaloids), pseudoalkaloids, C19-diterpenooid alkaloids, cryptoalkaloids, mainly in Ranunculaceae, Aconitum and Delphinium
Also in Garrya, Icacina, Inula, Spiraea, Anopterus, Erythrophleum bark (Leguminosae)
Types of diterpenoid alkaloids: aconitine-type, lycoctonine-type, pyro-type, lactone-type, 17-seco-type, rearranged-type
| Aconitine | Ajaconine | Crassicauline A | Delcosine | Delphinine | Deltaline | Denudadatine | Elatine | Lycoctonine | Mesaconitine | Methyllycaconitine |
| Napelline | Nudicauline | Yunaconitine

16.3.20 Indole Alkaloids
Alkaloids with nitrogen heterocycles from amino acids + peptide fragments, so they can be called "true alkaloids", from the protein amino
acid tryptophan C11H12N2O2
1. Non-isoprene indole alkaloids, 2. Semiterpenoid indole Alkaloid
| Agroclavine | Ajmalicine | Apodine | Apparicine | Brucine | Calebassine | Carbostrictosidine | Curarine | Dimethyltryptamine | Ergine
| Ergocristine | Ergometrine | Gelsemicine | Harman | Harmine | LSD | Physostigmine | Psilocybin | Reserpine | Strychnine | Vinblastine
| Vincristine | Yohimbine |.

16.3.21 Isoquinoline Alkaloids
Alkaloids with nitrogen heterocycles from amino acids, so they can be called "true alkaloids".
| Alpinine | Amurensine | Amurine | Annolobine | Annonaine | Berberine | Boldine | Bracteoline | Cancentrine | Carnegine | Cassythicine |
| Cephaeline | Codeine | Cularidine | Cularimine | Cularine | Cepharanthine | Demethylcoclaurine | | Dihydrosanguinarine | Emetine |
| Erythroidine | Glaucine | Glaziovine | Hydrastine | Isocorydine | Laudanidine | Laudanosine | Macarpine | Magnoflorine | Mecambrine |
| Morphine | Narceine | Narcotoline | Neopine | Noscapine | Obaberine | Oxyacanthine | Papaverine | Pronuciferine | Protopine | Reticuline |
| Salutaridine | Sanguinarine | Sinomenine | Thebaine | Tubocurarine |.

16.3.22 Lycopodium Alkaloids
Related to quinolizidines, in club mosses
| Annotine | Huperzine | Inundatine | Lycopodine | Selagine |.

16.3.23 Monoterpenoid and Sesquiterpenoid Alkaloids
| Acanthicifoline | Actinidine | Arenaine | Boschniakine | Cantleyine | Dendrobine | Gentianadine | Gentianaine | Gentianine | Gentioflavine
| Jasminine | Valerianine |.

16.3.24 Peptide Alkaloids
| Frangulanine | Zizyphine |.

16.3.33 Purines and Pyrimidines
(Purine-like compounds not from amino acids, so called "pseudoalkaloids".) (Purine derivatives)
Methylated purines: | Caffeine | Theobromine | Theophylline |.

16.3.25 Pyrrolidine and Piperidine Alkaloids
(Alkaloids with nitrogen heterocycles from amino acids, so they can be called "true alkaloids").
| Anabasine | Anatabine | Arecaidine | Arecoline | Carpaine | Cassine | Codonopsine | Coniceine | Coniine | Cucurbitine | Cuscohygrine
| Dioscorine | Guvacine | Harzianopyridone | Hygrine | Isonitramine | Juliflorine | Lobelanidine | Lobelanine | Lobeline | Myosmine
| Nicotine | Nicotyrine | Nornicotine | Pelletierine | Piperine | Piplartine | Prosopinine | Ricinine | Sedamine | Slaframine | Stachydrine
| Swainsonine | Trichostachine |
.
16.3.26 Pyrrolizidine Alkaloids
( PAs) (Alkaloids with nitrogen heterocycles from amino acids, so they can be called "true alkaloids".)
Pyrrolizidine alkaloids (PAs) are a class of naturally-occurring plant toxins.
"Senecio alkaloids", most poisonous group of alkaloids for humans and farm animals, have fused five-member ring system with nitrogen
bridge, most are esters of amino alcohols, e.g. diester Echimidine, ragwort Senecio jacobaea, Borago, Crotalaria, comfrey Symphytum,
toxic to liver, hepatic cirrhosis
| Clivorine | Echimidine | Heliosupine | Heliotridine | Heliotrine | Lasiocarpine | Lycopsamine | Monocrotaline | Retronecine | Riddelline
| Senecionine | Supinidine |. Symphytine |.

16.3.27 Quinoline alkaloids
Quinazolene derivatives, derived from 2-aminobenzoic acid, bicyclic molecules - benzene ring + pyridine ring, common in Rutaceae
Ruta graveolens contains about 30 quinoline alkaloids.
| Acronidine | Acronycine | Camptothecin | Cinchonidine | Echinopsine | Febrifugine | Peganine | Quinine |.

16.3.28 Quinolizidine alkaloids
(Alkaloids with nitrogen heterocycles from amino acids, so they can be called "true alkaloids".) (Quinolizidine derivative)
All from lysine --> cadaverine -->
| Anagyrine | Argentine | Baptifoline | Caulophylline | Cinegalline | Cytisine | Hydroxylupanine | Lupanine | Lupinine | Matrine | Retamine
| Rhombifoline | Sparteine | Tinctorine |.

16.3.29 Steroidal Alkaloids, Pseudoalkaloids
| Chaconine | Cyclovirobuxine | Jervine | Protoveratrine | Solamargine | Solanidine | Solasodine | Solanine | Solasodine | Tomatine
| Tomatidine | Veracevine | Veratramine | Veratridine | Verticine |.

16.3.30 Tropane Alkaloids
(Alkaloids with nitrogen heterocycles from amino acids, so they can be called "true alkaloids".)
| Anisodamine | Anisodine Apohyoscine | Calystegin | Convolvine | Darlingine | Littorine | Meteloidine | Phyllalbine | Tigloidine | Valeroidine |
| Atropine | Bellendine | Hyoscyamine | Scopalamine (Hyoscine) |
Cocaine group:
| Cocaine | Ecgonine |.

16.3.31 Unclassified Alkaloids
| Candicine | Cannabisativine | Colchicine | Cryptopleurine | Elaeocarpine | Ficine | Ibotenic acid | Lilaline | Pilocarpine | Securinine |
| Sirodesmin | Taxine C | Taxol C | Verruculotoxin |.

16.3.32 Alkaloids by trivial names

Aniline, C6H5NH2, Aromatic Amine
Aniline, Phenylamine, Aminobenzene, Not permitted in schools
Aniline blue, stain Highly toxic if ingested, 3.5.1 (Collagen)
Aniline dyes: blue (water soluble) CI 42780 (CI acid blue 22)
Aniline hydrochloride, Highly toxic if ingested
Aniline hydrochloride, Solution < 3%, Not hazardous
Aniline-formaldehyde, thermoset plastics: 3.8.6
Aniline hydrochloride, microscopy stain: 3.4
Aniline oil, oily, poisonous, liquid amine, used to make dyes, plastics, medicines, Not permitted in schools
Aniline sulfate, Highly toxic chemical if ingested, give water, induce vomiting
Aniline sulfate, Solution < 3%, Not hazardous
Aniline sulfate, anilinium sulfate, microscopy stain: 3.5
Aniline sulfate, Tests for wood: 9.144
Aniline sulfate, Vortex, vortices: 13.5.0 (See 3.)

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), in Acanthus ilicifolius,
contains secondary metabolites, traditional use in India and China to treat dyspepsia, paralysis, asthma, headache, rheumatism, diseases.
See diagram: Acanthicifoline.

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 Actinidia polygama,
in Valerian, in Tecoma stans leaves, See diagram: Actinidine.

Adrenaline, C9H13NO3, Aromatic Amine
Adrenaline, l-Adrenaline, Epinephrine, L-epinephrine, with nitrogen in the side chain (protoalkaloid), plant amine, catecholamine, acute
toxic, active sympathomimetic hormone from the adrenal medulla, stimulates alpha- and beta- adrenergic autonomic nervous system, causes
vasoconstriction, gastrointestinal relaxation, stimulates heart, dilates bronchi and cerebral vessels, used to treat asthma, cardiac failure, delay
absorption of local anaesthetics,
See diagram: Epinephrine.

Aniline, C6H5NH2, Aromatic Amine
Aniline, Benzenamine, Phenylamine, 2-Phenylamine, Aminobenzene (phenylammonium ion, anilinium ion, C6H5NH3+), phenyl
group attached to an amino group, aniline oil, clear, oily, liquid, colourless but the colour darkens to brown red, distinct rotten fish
odour and taste, poisonous vapour, acute toxicity and tumour formation, inflammable, melting point -6oC, boiling point 184.1oC, flash
point about 70oC, store in dark secure bottles.
With alkyl iodides forms secondary and tertiary amines.
Precursor to many industrial chemicals, e.g. polyurethane.
Phenylamine can be used in lava lamps because it has the same density as water and is NOT soluble in water, so it rises when heated by the
incandescent bulb below and falls when cooled by air at the surface.
Salicylanilide, a compound of salicylic acid and aniline derivatives, is as an antiseptic in soap.
Prepare phenylamine
1. Benzene + concentrated nitric acid + concentrated sulfuric acid --> nitrobenzene, C6H5NO2
2. Nitrobenzene + tin catalyst Sn + reducing agent hydrochloric acid --> phenylamine + water
C6H5NO2 + 6 H+ --> C6H5NH2 + 2H2O
in Indigofera suffruticosa
2-Phenylethylamine hydrochloride, C6H5CH2CH2NH2.HCl.

Annotine, C16H21NO3, Lycopodium Alkaloid
Annotine, azaspiro compound, in Lycopodium annotinum (Icelandic club moss), Chinese herbal medicine, treat skin disorders, See diagram: Annotine.

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,
in Plantago arenaria (sand plantain seeds), some narcotine in fruits, See diagram: Arenaine.

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

Bufotenine, C12H16N2O, Plant Amine
Indole derivative alkaloid, Non-isoprene indole alkaloid, Simple indole derivative, Bufotenin, N,N-Dimethylserotonin, Mappin,
N,N-Dimethyl-5-hydroxytryptamine, tryptamine alkaloid, dimethyl serotonin, in skin of toads, in psychedelic compounds,
illegal in USA, in Anadenanthera colubrina, in reed Arundo, in Piptadenia.
See diagram: Bufotenine.

Cadaverine, NH2(CH2)5NH2, Plant Amine
Cadaverine, NH2(CH2)5NH2, produced in decaying flesh, foul odour, urine odour, bacterial vaginosis disease, See diagram: Cadaverine.

Caffeine, C8H10N4O2, Purines and Pyrimidines Alkaloid
Caffeine, Guaranine, (1,3,7-Trimethylxanthine), (3-Methyltheobromine), Thein, purine derivative alkaloid, methylxanthine alkaloid,
methylated purine, odourless white powder or white glistening needles, usually melted together, bitter taste, solutions neutral to litmus,
odourless, from xanthosine, weak stimulant, diuretic, CNS stimulant, causes wakefulness and increased mental activity, diuretic, cardiac
and respiratory stimulant, may block absorption of calcium, fatal dose about 10 mg but not from tea, coffee, or other beverages), included
in proprietary analgesics in Camellia, in Coffea, in Cola, in Ilex, in Paullinias,.
See diagram: Caffeine Theobromine, Theophylline.
Caffeine: 19.2.9.0
Isolation of caffeine in cola (kola), soft drink: 16.8.3.1
Separate aspirin, caffeine and paracetamol by thin layer plate chromatography: 10.2.2.6
Toxic effect of drugs on water fleas: 16.7.29.

Candicine, C11H18NO, Plant Amine
Candicine, Candicin, primary amine, 4-Hydroxy-N, N, N-trimethylbenzeneethanaminium, action like nicotine, hypertension,
in Trichocereus root, in Fagara, in Philodendron, in Magnolia, in Lysichitum, See diagram: Candicine.

Cannabisativine, C21H39N3O3, Unclassified Alkaloid
Cannabisativine, azamacrocycle, lactam, 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, in Cantleya corniculata (tree bark), in Dipsacus, in Strychnos nux-vomica, See diagram: Cantleyine.

Cathine, C9H13NO, Plant Amine
Cathine, Norephedrine, Mydriatin, l-Phenylpropanolamine, an amphetamine, sympathomimetic, monoamine alkaloid, psychoactive drug,
euphoriant, stimulant, used for khat chewing in Arabian peninsula, anorexic, causes release of norepinephrine, used as nasal
vasoconstrictor and appetite suppressant, not recommended in USA, controlled substance in Australia, in Catha edulis, See diagram: Cathine.
See diagram: Catha edulis

Cathinone, C9H11NO, Plant Amine
Cathinone, Benzoylethanamine, beta-keto-Amphetamine, Norephedrone, d-Cathinone, l-Cathinone, Cathinonum, monoamine alkaloid,
alkaloid with nitrogen in the side chain (protoalkaloid), beta-phenylethylamine derivative alkaloid, (has ketone functional group),
controlled substance, causes mild stimulant euphoria effect (WHO drug of abuse), central nervous system stimulant similar to Cathine,
active ingredient in khat, in Catha edulis, khat chewing in Arabian peninsula, See diagram: Catha edulis,
See diagram: Cathinone.

Chaconine, C45H73NO14, Steroidal Alkaloid
Chaconine, glycoalkaloid, poison, in green potato skins, in Solanum tuberosum, bitter taste, 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

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),
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, in Meadow saffron, in Flame lily, See diagram: Colchicine.

Cryptopleurine, C24H27NO3, Unclassified Alkaloid
Cryptopleurine, organic heteropentacyclic compound, aromatic ether, alkaloid antibiotic, protein synthesis inhibitor, antineoplastic, antiviral
against herpes but not antitumour, in Cryptocarya, in Boehmeria, in Cissus, See diagram: Cryptopleurine.

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, 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, in Chondodendron tomentosum bark and stem.

Cyclovirobuxine, C26H46N2O, Steroidal Alkaloid
Cyclovirobuxine, Bebuxine, Cyclovirobuxin D, acutely toxic, anti-arrhythmic, purgative, in Buxus, See diagram: Cyclovirobuxine.
Cyclovirobuxine C, C27H48N2O

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

Diethanolamine, C4H11NO2, Secondary Amine
Diethanolamine, C4H11NO2 (CH2CH2OH)2NH, 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.

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.

Dimethyltryptamine, C12H16N2, Plant Amine
Dimethyltryptamine, N,N-dimethyltryptamine, [3-(2-Dimethylaminoethyl)indole], [2-(3-Indolyl)ethyldimethylamine], non-isoprene
indole alkaloid, tryptamine alkaloid, simple indole derivative, derivative of tryptamine with two additional methyl groups at the amine
nitrogen atom, N-methylated indoleamine derivative, psychotropic drug, acts as agonist or antagonist of certain serotonin receptors,
ritual use in native cultures, serotonergic hallucinogen, illegal in many countries, prohibited in Australia, in many plants and animals,
in Prestonia amazonica leaves, in Psychotria veridis, in Piptadenia, in Mucuna, trace amounts in mammalian brain, blood, and urine,
See diagram: Dimethyltryptamine.

Dopamine, C8H11NO2, Aromatic Amine
Dopamine, [4-(2-Aminoethyl)benzene-1,2-diol], [3-Hydroxy tyramine], Oxytyramine, plant amine, naturally occurring catecholamine,
alkaloid with nitrogen in the side chain (protoalkaloid), phenylethylamine derivative, (derived from Tyrosine), (precursor to Norepinephrine
and Epinephrine), catecholamine neurotransmitter in the brain for regulating movement, increases heart rate and cardiac output, stimulates
smooth muscle leading to vasoconstriction, increased renal blood flow, sodium excretion, urine output, Parkinson's disease occurs as a
result of the death of dopamine-producing neurones in the substantia nigra of the midbrain leading to tremor of limbs and facial rigidity.
See diagram: Dopamine.

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,
in Elaeocarpus polydactylus leaves, See diagram: Elaeocarpine.

Ephedrine, C10H15NO, Plant Amine
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, and may also increase release of norepinephrine (noradrenaline), used to treat asthma, heart failure,
rhinitis, and urinary incontinence, and depression, but has been less used with use of more selective agonists, in Ephedra sinica,
See diagram: Ephedrine.
Pseudoephredine is an isomer of ephedrine.

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

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

Galegine, C6H13N3, Plant Amine
Galegine, Galegin, Isopentenyl guanidine, (N-3,3-Dimethylallylguanidine), a guanidine, toxic, affects mitachondria, in Galega, in Verbesina,
See diagram: Galegine.

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, in Gentiana aerial parts, See diagram: Gentianadine.

Gentianaine, C6H7NO3, Monoterpenoid and Sesquiterpenoid Alkaloid
Gentianaine, Gentiocrucine, low inflammatory activity, in Gentiana 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, in 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, in Gentiana, in Erythrea, in Swertia, See diagram: Gentioflavine.

Gramine, C11H14N2, Plant Amine
Gramine, 3-(Dimethylaminomethyl)indole, Donaxine, aminoalkylindole, toxic, in Arundo, Acer, Hordeum, Phalaris, cabbage,
See diagram: Gramine.

Histamine, C5H9N3, Plant Amine
Histamine, biogenic amine, many physiological functions, immune responses, stimulant of gastric secretion, constrictor
of bronchial smooth muscle, centrally acting neurotransmitter, inflammatory response, itch, (derived from decarboxylation of the
amino acid histidine).
Many plants and herbs contain natural anti-histamine compounds, e.g. Basil, Chamomile, Jewel weed, papaya, stinging nettle.
See diagram: Histamine.

Hordenine, C10H15NO, Plant Amine
Hordenine, tertiary amine, N, N-dimethyltyramine, phenylethylamine alkaloid, antibacterial, antibiotic, in Lophophora
williamsii, in Selenicereus grandiflorus, prepared by barley germination, no advantage if taken in nutritional supplement, from beer in diet
Hordenine interfere with tests for opioid drugs, See diagram: Hordenine.

Huperzine B, C16H20N2O, Lycopodium Alkaloid
Huperzine, Fordine, Selagine, anticholinesterase, in Lycopodium, Chinese medicine, neuroprotective, possibly used to treat Alheimer's
disease, in Huperezia.
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.

Ibotenic acid, C5H6N2O4, Unclassified Alkaloid
Ibotenic acid, Ibotenate, isoxazole derivative, non-proteinogenic alpha-amino acid, (Ibotenic acid decarboxylation---> muscimol, pantherine,
agarine; 3(2H)-isoxazolone), neurotoxic, used for experimental treatment of epilepsy and Parkinson's disease, formerly used as sedative
and anti-emetic, causes motor depression, ataxia, changes in mood, excitatory amino acid agonist, in Amanita mushrooms,
See diagram: Ibotenic acid.

Inundatine, C15H18N2O, Lycopodium Alkaloid
See diagram: Inundatine.

Jasminine, C11H12N2O3, Monoterpenoid and Sesquiterpenoid Alkaloid
Jasminine, naphthyridine derivative, in Jasmium, in Ligustrum, in Olea, in Syringea, See diagram: Jasminine.

Jervine, C27H39NO3, Steroidal Alkaloid
Jervine, Jervanin-11-one, 11-Ketocyclopamine, Iervin, acutely toxic, teratogenic to pregnant ewes, in Veratrum rhizomes,
See diagram: Jervine.

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

Lycopodine, C16H25NO, Lycopodium Alkaloid
Lycopodine, moss alkaloid, from a hydride of a lycopodane, toxic, herbal medicine, skin disorders, in Lycopodium clavatum,
See diagram: Lycopodine.

Mescaline, C11H17NO3, Plant Amine
Mescaline, mescalin, tmpea, (3, 4, 5-Trimethoxyphenethylamine), may be classified as a beta-phenylethylamine alkaloid with
nitrogen in the side chain (protoalkaloid), but Mescaline is not usually classified as an alkaloid, hallucinogen, no accepted
therapeutic uses, in Lophophora williamsii flowering heads (peyote, mescal buttons), See diagram: Mescaline.

Methylamine, CH3NH2, Methyl Amine
Methylamine, Monomethylamine, Methanamine, Aminomethane, Monomethylamine, anhydrous colorless gas or a liquid, fishy odour
like ammonia, easily ignited, heated the containers may rupture violently, used to make pharmaceuticals, insecticides, paint removers,
surfactants, rubber chemicals. Not permitted in schools
DEA list of chemicals: 3.9.5
Fish smell, trimethylamine: 16.7.21.0
Ionization reaction of methylamine, cyanic acid, melamine: 16.2.4.2.1
Methanotrophs (methane to methanol): 4.12.7
Methylamines, ionization reaction: 16.2.4.3.01
Trimethylamine, C3H9N
Simplest primary amine, poisonous, noxious inflammable gas, fish-like odour, can be explosive so sold as white deliquescent crystals
of methylamine hydrochloride or as aqueous solution
Methylamine is used in the illegal manufacture of the drug MDMA (ecstasy) and methamphetamine.
Usually prepared by reaction of ammonia with methanol with zeolites as catalyst.
CH3OH + NH3 --> CH3NH2 + H20.

Muscarine, C9H20NO2, Plant Amine
Muscarine, alkaloid with nitrogen in the side chain, (protoalkaloid), Muscarine alkaloid, in Amanita muscaria (fly agaric), Inocybe and
Clitocybe mushrooms, also in rotten fish, binds to acetylcholine receptors to affect parasympathetic nervous system and cause convulsions
and death if no atropine treatment, See diagram: Muscarine.

Muscimol, C4H6N2O2, Plant Amine
Muscimol, Agarin, Pantherine, (5-Aminomethyl-3-hydroxyisoxazole), isoaxole, hallucinogenic, delerium, muscular spasms, no medical
use, in Amarita (mushroom), See diagram: Muscimol.

Noradrenaline, C8H11NO3, Aromatic Amine
L-Noradrenaline, (NA), L-Norepinephrine, alkaloid with nitrogen in the side chain (protoalkaloid), plant amine, catecholamine,
active by injection sympathomimetic neurohormone, used for vasoconstriction, pupil dilatation, treat cardiac infarction, in Albizia, in Musa
(banana), in Passiflora, in Pisum, in Phaseolus, in Portulaca, in Samanea, See diagram: Norepinephrine.

Norephedrine, C8H13NO, Amine
Norephedrine, Mydriatin, l-Phenylpropanolamine, an amphetamine, sympathomimetic, causes release of norepinephrine, used as nasal
vasoconstrictor and appetite depressant.

Octopamine, C8H11NO2, Plant Amine
Octopamine, Norsympathol, Norsympatol, Norden, Norsynephrine, (Hydroxyphenylethanolamine), alpha-adrenergic sympathomimetic
amine, (derived from tyramine in the CNS and platelets) used to treat hypotension, cardiotonic, biogenic phenylethanolamine,
neurotransmitter, phenylethanolamine, tyraminesin Coryphantha, in Capsicum frutescens, in Citrus species, in Cyperus,
See diagram: Octopamine.
Octopamine hydrochloride, C8H12ClNO2, in weight loss supplements but possibly not effective

Phenethylamine, C8H11N, Aromatic Amine
Phenethylamine (PEA), beta-Phenethylamine, 2-Phenethylamine, monamine alkaloid, primary aromatic amine, colourless, liquid at
room temperature, fishy odour, strongly basic, (Soluble in water, ethanol, and ether.), (End product of phenylalanine in the putrefaction
of tissue.), psychoactive substance, high concentration is corrosive, can cause burns, cause allergic skin reaction if ingested,
aralkylamine, neurotransmitter, (derived from L-phenylalanine), (precursor to the neurotransmitter phenylethanolamine), acute toxic,
skin irritant, sensitiser, in chocolate, in bitter almonds, in banana, in Rhodophyceae algae, in dietary supplements, human metabolite,
in human urine, prepared by fermentation of sugar cane molasses, used as bronchodilator, nasal degcongestant, in human body excitatory
action on skeletal muscles. See diagram: Phenethylamine.

Pilocarpine, C11H16N2O2, Unclassified Alkaloid
Pilocarpine, parasympathomimetic cholinergic alkaloid, no nicotinic effects, mitotic, cholinergic receptor agonist, in Pilocarpus jaborandi
(Indian hemp), in Pilocarpus microphyllus, See diagram: Pilocarpine.
Pilocarpine hydrochloride is used to stimulate parasympathetic nerve system, like physostigmine and arecoline, antagonist of atropine,
promotes secretion of sweat, saliva, tears, causes myosis, used to treat dry mouth and glaucoma.

Piperidine, C5H11N, Secondary Amine
Piperidine, C5H11N, CH2(CH2)4NH, heterocyclic secondary amine, colourless fuming liquid, pepper-like odour, less dense than
water so floats on water, miscible with water, used as a solvent and to make pharmaceuticals and rubber, antibiotic, anti-hypertensive,
flavouring agent, may be toxic by ingestion and inhalation, irritates skin and eyes, in:
| Black pepper
| Barley, See diagram: Piperidine.

Propylamine, C3H9N, Amine
Propylamine, Propan-1-amine, (1-Aminopropane), (n-propylamine), alkylamine, corrosive, toxic. colourless liquid, soluble in water, less
dense than water, in grapes and vegetables, colourless liquid, strong ammonia-like odour, highly flammable, explosive in air, harmful if
swallowed, burns skin, See diagram: Propylamine.

Protoveratrine , Steroidal Alkaloid
Protoveratrine is a mixture of alkaloids:
Protoveratrine A, C41H63NO14, Protalba
Protoveratrine B, C41H63NO15, Neoprotoveratrine, Veratetrine
in Veratrum album, formerly used to treat hypertension, causes nausea,
See diagram: Protoveratrine.

Pseudoephedrine, C10H15NO, Plant Amine
Pseudoephedrine, L-Ephedrine, beta-phenylethylamine alkaloid with nitrogen in the side chain (protoalkaloid), T isomer of ephedrine,
sympathomimetic, used to treat asthma, heart failure, rhinitis, urinary disorders, depression, improves release of norepinephrine,
in Ephedra sinaca, See diagram: Pseudoephedrine, (See: Ephedrine)

Putrescine, NH2(CH2)4NH2, Plant Amine
Putrescine, produced in decaying flesh, toxic in excess, odour of semen, See diagram: Putrescine.

Pyrrolidine, C4H9N, Cyclic Secondary Amine
Pyrrolidine, C4H9N (CH2)4NH, 1-pyrrolidine, tetrahydropyrrole, tetramethyleneimine, cyclic secondary amine, saturated nitrogen
heterocycle 5-membered cyclic amine, in volatile amine fractions of brewing, odour like semen, colourless liquid, miscible with water,
in carrot and tobacco leaves, Propylamine.

Securinine, C13H15NO2, Unclassified Alkaloid
Securinine, Securinin, in Securinega, in Phyllanthus, indolizine alkaloid, See diagram: Securinine.

Selagine, C15H18N2O, Lycopodium Alkaloid
Selagine, Huperzine A, sesquiterpene alkaloid, neuroprotective activity, an acetylcholinesterase inhibitor, plant metabolite, sesquiterpene
alkaloid, pyridone, primary amino compound and an organic heterotricyclic compound, treatment of swelling, fever and blood disorders,
possibly Alzheimer's disease, in club moss Huperzia serrata, in Lycopodium, See diagram: Selagine.

Serotonin, C10H12N2O, Plant Amine
Serotonin, 5-HT, (5-Hydroxytryptamine), [3-(2-Aminoethyl)-1H-indol-5-ol], Enteramine, acute toxic, human metabolite, primary amino
compound, a phenol, neurotransmitter, biochemical messenger and regulator, in CNS, in gastrointestinal tract, in blood platelets, (drived
from essential amino acid 5-hydroxytryptophan), in Musa (banana fruit), in Lycopersicon (tomato), in Urtica (nettle stinging hairs),
in Mucuna (cowhage), See diagram: Serotonin.

Sirodesmin, C19H23NO4, Unclassified Alkaloid
Sirodesmin, Sirodesmin H, Sirodesmin A, Dethiosirodesmin A, [(5'R,7S)-14-Dethiosirodesmin A], organic molecule, antibiotic, in Phoma ligan
(black leg fungus), attacks Brassica species, See diagram: Sirodesmin.

Solamargine, C45H73NO15, Steroidal Alkaloid
Solamargine, beta-Solamarine, Solamargin, azaspiro compound (steroid + oxaspiro compound), (derivative of solasodine), glycoalkaloid,
poisonous, unsuccessful anticancer drug, used to treat pre-cancerous skin thickening (Actinic Keratosis), in Solanumnigrum (leaves and
fruit), See diagram: Solamargine.

Solanidine, C27H43NO, Steroidal Alkaloid
Solanidine, Purapuradine, pseudoalkaloid, poisonous, in Solanum nigrum, from hydrolysis of solanine,
toxic concentration in potato sprouts, inhibits serum cholinesterases, used to synthesise steroidal drugs, See diagram: Solanidine.

Solanine, C45H73NO15, Steroidal Alkaloid
Solanine, alpha-Solanine, steroidal alkaloid, glycoalkaloid, bitter taste, inhibits serum cholinesterases, apotosis inducer, i.e. contributes
to the normal death of cells by opening the mitochondrial membrane permeability, oral ingestion about 3 mg/kg toxic to humans, induces
programmed cell death so is possibly anticancerous, in Solanum tuberosum, poison, in Lycopersicon esculentum (tomato), See diagram: Solanine.
Solanine hydrochloride used as agricultural pesticide.

Solasodine, C27H43NO2, Steroidal Alkaloid
Solasodine, Spirosol-5-en-3-ol, Purapuridine, Solancarpidine, pseudoalkaloid, poison, used to produce steroids, in Chilli Project,
in Solanum nigrum, See diagram: Solasodine.

Solasonine, C45H73NO16, Steroidal Alkaloid
Solasonine, glycoalkaloid, derivative of solasodine, poisonous, unsuccessful anticancer drug, in Solanum linnaeanum, See diagram: Solasonine.

Taxine, C35H47NO10, Unclassified Alkaloid
Taxine, Taxine A and Taxine B, toxic cardiotoxins, no medical uses, in Taxus baccata, in Taxus cuspidata, yew leaves cattle poisoning,
See diagram: Taxine.

Taxol, C47H51NO14, Unclassified Alkaloid
Taxol, Paclitaxel, Taxol A, Abraxane, cyclodecane, antineoplastic, antileukaemic, antitumour, (inhibits cellular mitosis of ovarian, breast,
and lung cancer), in Taxus brevifolia, in Taxus cuspidata, See diagram: Taxol.

Theobromine, C7H8N4O2, Purines and Pyrimidines Alkaloid
Theobromine, (3,7-Dimethyl xanthine), purine derivative, (from xanthosine, 3, 7-dimethylxanthine), methylated purine, odourless, white,
crystalline powder, bitter taste, main alkaloid in cacao bean, bronchodilator, vasodilator, less diuretic and less smooth muscle stimulant
than theophylline, less CNS stimulant than caffeine, formerly used as diuretic and used to treat hypertension, in Theobroma cacao (cocoa),
Cola acuminata (cola, kola nut), in Paullinia cupana, See diagram: Caffeine Theobromine, Theophylline.
(Theobromine does not contain bromine!).

Theophylline, C7H8N4O2, Purines and Pyrimidines Alkaloid
Theophylline, 1,3-Dimethylxanthine, theocin, purine derivative, (xanthine derivative alkaloid, from xanthosine), anhydrous, methylxanthine,
(1, 3-dimethylxanthine), diuretic, methylxanthine derivative from tea, odourless, white crystalline powder, bitter taste, smooth muscle relaxant,
by presence of other drugs, e.g. erythromycin, in Theobroma Cacao (crillo cocoa beans), much less in Camellia sinensis, tea,
See diagram: Caffeine Theobromine, Theophylline.

Tomatine, C50H83NO21, Steroidal Alkaloid
Tomatine, Lycopersicin, alpha-Tomatine, Tomatin, (derived from Tomatidine), antibiotic, glycoside, anti-histamine activity, insecticide,
in extract of leaves of wild tomato plants, phytotoxin, antifungal, antibacterial, precipitating agent for steroids, in Solanum lycopersicon,
See diagram: Tomatine.

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

Trimethylamine, CH3-NCH3-CH3, Plant Amine
Trimethylamine, CH3-NCH3-CH3 (CH3)3N, (TMA), smell of hawthorn flower, cotoneaster, ammoniacal fishy smell, flammable
Amines, C2H5NH2: 16.4.3.0
Trimethylamine, Amines, aliphatic amines (RNH2-), R = alkyl group,
Trimethylamine solution, 50%, Harmful if ingested, highly irritant vapour, skin irritant, highly flammable
Trimethylamine solution, 25%
Trimethylamine solution, < 20% Not hazardous
Fish smell, trimethylamine: 16.7.21.0.
See diagram: Trimethylamine.

Tryptamine, C10H12N2, Plant Amine
Tryptamine, Monamine 2-(3-Indolyl)ethylamine, monoamine alkaloid, heterocyclic monamine, produced from amino acid
tryptophan and precursor molecule to many hormones and neurotransmitters called tryptamines, e.g. serotonin and melatonin
derivative, vasoactive, neuromodular, hallucinogenic drug, in many plants, e.g. Acacia species, See diagram: Tryptamine.
Tryptamine hydrochloride, C10H12N2, HCl, antimalarial, See diagram 16.21.8 Tryptamine
THC, Tetrahydrocannabinol, marijuana, precursor of indoleacetic acid

Tyramine, C8H11NO, Plant Amine
Oxazole alkaloid, 4-(2-aminoethyl)phenol, monamine, from tyrosine, C9H11NO3, in fermented or spoilt meat, chocolate, cheese, excess
causes hypertension
Occurs in plants and animals, in the body to help support blood pressure
Hallucinogen, so large dietary intake or while taking MAO inhibitors can cause high blood pressure, and headaches.
High content in aged, smoked, fermented foods, aged cheeses, e.g. Stilton cheese, have the highest levels of tyramine.
Bacterial enzymes in some foods may convert amino acid tyrosine to tyramine.
People who eat aged cheeses, e.g. Stilton, might get nightmares from the excess of tyramine in such cheeses, e.g. Ebenezer Scrooge
in "A Christmas carol" by Charles Dickens.
12.3.1 Monoamine oxidase inhibitors (MAOI), tyramine, C8H11NO.
See diagram: Tyramine.

Valerianine, C11H15NO, Monoterpenoid and Sesquiterpenoid Alkaloid
Valerianine, in Valeriana officinalis roots, See diagram: Valerianine.

Veracevine, C27H43NO8, Steroidal Alkaloid
Veracevine, Veratridine, Protocevine, cyclic hemiketal (derived from a hydride of cevane), heptol, tertiary amino compound, tertiary alcohol,
secondary alcohol, insecticide, used as a source of veratridine or cevine, See diagram: Veracevine.

Veratramine, C27H39NO2, Steroidal Alkaloid
Veratramine, in Veratrum species rhizomes, extracts of Veratrum viride used a veterinary medicine, See diagram: Veratramine.

Veratridine, C35H51NO11, Steroidal Alkaloid
Veratridine, Benzoate-cevane, Dimethoxybenzoate, (derivative of veracevine alkaloid, protocevine, 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.

Verruculotoxin, C15H20N2O, Unclassified Alkaloid
Verruculotoxin, organonitrogen heterocyclic compound, organic heterobicyclic compound, toxic metabolite, mycotoxin in Penicillium
veraculosum, hypogoea, cause ataxia and loss of muscle control in day-old chicks, in Arachis (green peanuts), See diagram: Verruculotoxin.

Verticine, C27H45NO3, Steroidal Alkaloid
Verticine, Peimine, used to treat chest disorders, in Fritillaria, See diagram: Verticine.

Zizyphine, C33H49N5O6, Peptide and Cyclopeptide Alkaloid
Zizyphine type alkaloid, Zizyphine, herbal medicine, aphrodisiac, used to treat erectile disfunction
Zizyphine A, C33H49N5O6, cyclic peptide, in Ramnus frangula, alder buckthorn, See diagram: Zizyphine.
Zizyphine F, C32H47N5O6, in Ziziphus, in Ceanothus americanus

16.3.0.7 Phenethylamine group of alkaloids
Phenethylamine Plant Amine
3.10.0 , Poisons and First Aid ( See: adrenalin) ( Table)
See diagram 14.03 : Amphetamine, Adrenaline (Epinephrine)
Adrenaline (Epinephrine), C9H13NO3, [(HO)2.C6H3.CHOH.CH2, NHCH3], 3, 4-trihydroxy-N-methylphenethylamine, compound not usually
classified as alkaloid, it is a "protoalkaloid" with nitrogen in the side chain, a catecholamine, active sympathomimetic hormone from the
adrenal medulla, adrenergics mimic the effects of epinephrine, it is an alpha-adrenergic agonist so stimulates alpha-adrenoreceptors and
it is a beta-adrenergic agonist so stimulates beta-adrenoreceptors, causes vasoconstriction, increase in blood pressure, gastrointestinal
relaxation, stimulates the heart, dilates bronchi smooth muscle, and used to treat asthma by bronchidilation.
The "fight or fright hormone"
When we have a fright or have to fight or run, extra adrenaline is released into the blood, which makes the heart beat faster, gets more
air into our lungs and increases the blood supply to the muscles, so epinephrine helps to cop with emergencies and causes palpitations
when we are frightened.
Heart disorders
Epinephrine and Norepinephrine secreted by the adrenal medulla, causes systemic vasoconstriction and
gastrointestinal relaxation, stimulates the heart, dilates bronchi and cerebral vessels, and helps to regulate functions such as heart rate,
blood pressure and breathing.
Adrenaline injections are used to treat some emergency situations which can occur in the heart and lungs.
Adrenaline 1:10, 000 is used in people whose hearts have suddenly stopped (cardiac arrest).
The adrenaline can help to restart the heart and stimulates it to beat strongly.
It can be given cautiously to people who are elderly, have high blood pressure, thyroid problems and high pressure in the eye.
However, care must also be taken if giving adrenaline to diabetics, people with heart disease and people allergic to adrenaline.
Common side effects include: palpitations, tremor, restlessness, anxiety, weakness, dizziness, headache, shortness of breath, cold
hands and feet.

The class of phenethylamines include the following:
1. Fight or fright hormones
Dopamine , C8H11NO2, (3-hydroxy tyramine) ( 3, 4-dihydroxy-phenylethylamine)
Adrenaline , C9H13NO3, Epinephrine
Norepinephrine , C8H11NO3, noradrenaline.
2. Stimulant activity, monamine releasing agent
Amphetamine , C9H13N, Amphetamines: 11.4.0
Methamphetamine , C10H15N.
3. Stimulant / decongestant activity
Ephedrine , C10H15NO, / Pseudoephedrine, C10H15NO
Ephedra sinica contains ephedrine.
4. Psychedelic activity:
Mescaline |.
Designer hallucinogens (2C- series), e.g. 2C-B, C10H14BrNO2
Bupropion, C13H18ClNO, commonly prescribed antidepressant.
5. Plant compounds
L-DOPA, C9H11NO4, levodopa ( L-3-4-dihydroxyphenylalanine), precursor of the psychoactive compounds called catecholamines,
i.e. dopamine, norepinephrine (noradrenaline), and epinephrine ( adrenaline)
[CH4(OH)2= catechol ring],
MDMA , C11H15NO2, 3, 4-methylenedioxy-methamphetamine, psychoactive drug, "ecstasy"
Substituted amphetamines, e.g. catecholamine ether, guaiacol ( HOC6H4OCH3, 2-hydroxyphenol, 1, 2-hydroxybenzene).