Learn about alkaloids, amines and agar in the diet.

School Science Lessons
2024-06-16

appendix A, Amines, Alkaloids
(appendixA)
Contents
Amines
16.1.0 Amines
16.2.0 Plant amines by trivial names
16.3.0 Catecholamines, adrenaline, noradrenaline, dopamine
Alkaloids
16.1.0 Alkaloids, introduction
16.2.0 Alkaloid classifications
16.3.0 Alkaloid diagrams
16.5.0 Principle classes of alkaloids
16.8.0 Alkaloids by trivial names

16.1.0 Amines
Amines, (C2H5NH2), are produced by the decay of organic matter, ammonia-derivative organic compounds of nitrogen.
In amine molecules one or more hydrogen atoms has been replaced by a hydrocarbon radical, an alkyl or aryl group.
Amines are organic derivative of ammonia, where one, two or three hydrogen atoms are replaced by alkyl groups as a primary, secondary or tertiary amine.
For example: Trimethylamine, (C3H9N).
Amines usually act as weak bases that form ammonium salts that are more soluble in water than the original amine, Cough medicines may contain cough suppressant dextramethorphan hydrobromide or decongestant and 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.
Amines
Aliphatic amines (RNH2^-, R = alkyl group)
19.2.1 Amine intolerance
16.2.4.3.01 Amines, methylamine ionization reaction
16.2.4.3.0 Amines
18.7.23.0 Chloramines in swimming pools
List of amines
16.2.1 Primary amines
16.2.2 Secondary amines
16.2.3 Tertiary amines
16.2.4 Aromatic amines

16.3.0 Catecholamines
The catecholamines, epinephrine, norepinephrine and dopamine are synthesized in the central nervous system, and central part of the adrenal gland.
Catecholamines 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, e.g. the 1,2-dihydroxybenzenes.
Catecholamines are derived from the amino acid tyrosine.
Conversions activated by enzymes:
Phenylalanine --> L-Tyrosine---> L-DOPA ------> Dopamine-----> Norepinephrine --> Epinephrine
C9H11NO2 ----> C9H11NO3 --> C9H11NO4 --> C8H11NO2 --> C8H11NO3-------> C9H13NO3
Epinephrine, (C9H13NO3)
Norepinephrine, (C8H11NO3)
Dopamine, (C8H11NO2)

16.4.0 Alkaloids, introduction
The classification systems in this document is 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 are not essential to the organism, usually occurring in only a few species of vascular plants and some fungi.
Alkaloids are 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 have the properties of amines and are natural bitter, alkaline, nitrogenous compounds.
The names of alkaloids usually end in "ine".
The function of alkaloids 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 usually contain at least one nitrogen atom in a heterocyclic ring structure, phenolic or indole rings.
The term "alkaloid" was first used to describe chemical bases from plants used in medicines, but now there is no exact definition of alkaloids.

16.5.0 Alkaloid classifications
Alkaloid classifications are usually based on structure or origin.
16.3.1 True alkaloids are derived from amino acids, have nitrogen in a heterocyclic ring, e.g. atropine.
16.3.2 Protoalkaloids are derived from amino acids, no nitrogen in a heterocyclic ring, e.g. Adrenaline, Ephedrine and Mescaline.
16.3.3 Pseudoalkaloids are not derived from amino acids, but have nitrogen in a heterocyclic ring, e.g. Caffeine.

16.6.0 Alkaloid diagrams
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

16.7.0 Principle classes of alkaloids
16.6.1 Amaryllidaceae alkaloids
16.6.2 Betalain alkaloids
16.6.3 Diterpene alkaloids
16.6.4 Indole alkaloids, Indolizidine group
16.6.5 Isoquinoline alkaloids
16.6.6 Lycopodium alkaloids
16.6.7 Monoterpenoid and sesquiterpenoid alkaloids
16.6.8 Peptide alkaloids
16.6.9 Piperidine and pyridine alkaloids
16.6.10 Purines and pyrimidines alkaloids
16.6.11 Pyrrolidine and piperidine alkaloids
16.6.12 Pyrrolizidine alkaloids
16.6.13 Quinoline, quinazoline alkaloids
16.6.14 Quinolizidine alkaloids
16.6.15 Steroidal alkaloids, pseudoalkaloids
16.6.16 Tropane alkaloids
16.6.17 Unclassified alkaloids

16.8.0 Alkaloids by trivial names
appendixF16.4.0, Aconine to Hypaconitine
appendixH16.5.0, Ibogaine to Zizyphine
appendixH16.6.0, Phenethylamine group of alkaloids

16.2.1 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).

16.2.2 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,[HN(CH2CH2OH)2]
Diethylamine, (C4H11N)
Dimethylamine, (CH3)2NH, (C2H7N)
Cyclic secondary amines:
Pyrrolines, cyclic amines

16.2.3 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).

16.2.4 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 simple aromatic rings fused together by sharing two carbon atoms, e.g. Benzene, Toluene, Ortho-xylene, Para-xylene.
Most 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 200^oC, the primary and secondary amine salts dehydrate to form corresponding amides.
Aromatic amines include:
Dopamine (C8H11NO2)
Noradrenaline (C8H11NO3)
Phenethylamine (C8H11N)
|

Cadaverine, [C5H14N2, NH2(CH2)5NH2], Plant Amine
Cadaverine, Pentane-1,5-diamine, 1,5-Diaminopentane, colourless syrupy liquid produced in decaying flesh, foul odour, urine odour, bacterial vaginosis disease.
It is formed by bacterial decarboxylation of lysine.
See diagram: Cadaverine.

Candicine, (C11H18NO), Plant Amine, hypertension, occurs in Trichocereus root, in Fagara, in Philodendron, in Magnolia, in Lysichitum.
See diagram: Candicine.

Cathine, (C9H13NO), Plant Amine
Cathine, Pseudonorephedrine, (+)-Norpseudoephedrine, Katine, D-Cathine, 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.
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 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, occurs in Catha edulis, Khat chewing in Arabian peninsula.
See diagram: Catha edulis.
See diagram: Cathinone.

Dimethyltryptamine, (C12H16N2), Plant Amine
Dimethyltryptamine, (DMT), N,N-dimethyltryptamine, [3-(2-Dimethylaminoethyl)indole], [2-(3-Indolyl)ethyldimethylamine], non-isoprene indole alkaloid, tryptamine alkaloid, methylated indoleamine derivative, (from tryptamine), protect from air and light in a freezer, pure white DMT crystals explosive, psychotropic drug, acts as agonist or antagonist of certain serotonin receptors, used in South American shamanic practices, in yopo snuff and ayahuasca drink, serotonergic hallucinogen, powerfully psychoactive, substance causing hallucinacions and anxiety, autonomic hypetension, papillary dilation, illegal in many countries, prohibited in Australia and United States Schedule I drug, broken down by digestive enzyme monoamine oxidase so inactive if taken orally unless combined with a monoamine oxidase inhibitor (MAOI), occurs in Prestonia amazonica leaves, (trace amounts in mammalian brain, blood, and urine), in Psychotria viridis leaves, in Arundo donax flowers, in Piptadenia peregrina seeds and leaves, in cowhage Mucuna pruriens, in Diplopterys cabrerana, in Reed canary grass (Phalaris arundinacea), in Harding grass (Phalaris aquatica).
See diagram: Dimethyltryptamine.

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
May increase release of norepinephrine (noradrenaline), used to treat asthma, heart failure, rhinitis, and urinary incontinence, and depression
Has been less used with use of more selective agonists, occurs in Ephedra sinica.
Ephedra
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.

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

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

Histamine, (C5H9N3), Plant Amine
See diagram 14.05: Histamine, major tranquillizers, tricyclic anti-depressants
Histamine, biogenic amine, many physiological functions, immune responses, stimulant of gastric secretion, constrictor of bronchial smooth muscle, centrally acting neurotransmitter, inflammatory response, itch, (from 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, occurs 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.

Mescaline, (C11H17NO3), Plant Amine
Mescaline, mescalin, (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, occurs in Lophophora williamsii flowering heads (peyote, mescal buttons).
See diagram: Mescaline.

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, delirium, muscular spasms, no medical use, occurs in Amarita (mushroom).
See diagram: Muscimol.

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

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, occurs 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.

Trimethylamine, (CH3-NCH3-CH3), Plant Amine
(TMA), smell of hawthorn flower, cotoneaster, ammoniacal fishy smell, flammable
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
Tests for trimethylamine fish smell: 16.6.1
See diagram: Trimethylamine.

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, occurs 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.

Methyl bufotanine, Plant amine
Methyl bufotanine, O-Methylbufotanine, MeO-DMT, 5-MeO-DMT, (5-methoxy-N,N-dimethyltryptamine), methoxybufotenine, (C13H18N2O), hallucinogen, irritant, aromatic ether, tertiary amino compound, (from a bufotenin), psychedelic of the tryptamine class, close relative of DMT and bufotenin (5-HO-DMT), causes delusions and delirium, used for shamanic practices in South America, psychoactive ingredient of Anadenanthera peregrina seeds used to prepare Yopo snuff, 5-MeO-DMT on parsley used as a sacrament of the Church of the Tree of Life, toxic, causes Phalaris staggers, occurs in Phalaris pasture grasses, in Desmodium

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

Aniline, (C6H5NH2), 16.2.4 Aromatic amines
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 oil, C6H5NH2, 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
Experiments
Prepare aniline hydrochloride solution: 3.4
Prepare aniline sulfate solution: 3.5
Tests for wood: 9.144
Vortex, vortices: 13.5.0 (See 3.)
Aniline, (C6H5NH2), 16.2.4 Aromatic amines
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 -6^oC, boiling point 184.1^oC, flash point about 70^oC, 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).

Dopamine, (C8H11NO2)
Dopamine, (3-hydroxytyramine), (oxytyramine), plant amine, alkaloid with nitrogen in the side chain (protoalkaloid), phenylethylamine derivative, (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.
Dopamine is catechol in which the hydrogen at position 4 is substituted by a 2-aminoethyl group.
It has a role as a cardiotonic drug, a beta-adrenergic agonist, a dopaminergic agent, a sympathomimetic agent.
One of the catecholamine neurotransmitters in the brain.
It is derived from tyrosine and is the precursor to norepinephrine and epinephrine.
Dopamine is important in regulating movement.

Norepinephrine, (C8H11NO3)
Norepinephrine, noradrenaline, L-Noradrenaline, levarterenolalkaloid with nitrogen in the side chain (protoalkaloid), plant amine, catecholamine, active by injection sympathomimetic neurohormone, used for vasoconstriction, pupil dilatation, treat cardiac infarction, occurs in Albizia, in Musa (banana), in Passiflora, in Pisum, in Phaseolus, in Portulaca, in Samanea.
See diagram: Norepinephrine.
Norepinephrine is both a catecholamine and a phenethylamine.
It has a role as a vasoconstrictor agent, an alpha-adrenergic agonist, a sympathomimetic agent, and a neurotransmitter.
It is the precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter.
It is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus.
It occurs in plants and is used pharmacologically as a sympathomimetic.

Epinephrine, (C9H13NO3)
Epinephrine, Adrenaline, l-Adrenaline, L-epinephrine, with nitrogen in the side chain, plant amine, 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: See diagram 14.03 : Amphetamine, Adrenaline (Epinephrine)
Amine intolerance, 19.2.2 (for food)
Epinephrine appears as white to nearly-white microcrystalline powder or granules, odourless, MP 211-212 °C, slightly alkaline aqueous solutions, slightly bitter numbing taste
It is a hormone secreted by the adrenal glands resulting in the 'fight-or-flight' response. It has a role as a hormone, an adrenergic agonist, a vasodilator agent, an alpha-adrenergic agonist, a bronchodilator agent, a vasoconstrictor agent, a beta-adrenergic agonist, a sympathomimetic agent, a mydriatic agent and a mouse metabolite. It is a hormone and neurotransmitter produced by the adrenal glands that can also be used as a drug due to its various important functions. Though it has long been used in the treatment of hypersensitivity reactions, epinephrine in the auto-injector form (EpiPen) has been available since 1987 in the USA. Many new products/biosimilars and dosage routes have been approved under various names over the last several decades,,. On August 16, 2018, Teva Pharmaceuticals USA gained approval to market its generic epinephrine auto-injector in 0.3 mg and 0.15 mg strengths. Dosage delivery routes for epinephrine include intravenous, inhalation, nebulization, intramuscular injection, and subcutaneous injection. In general, the most common uses of parenteral epinephrine are to relieve respiratory distress due to bronchospasm, to provide rapid relief of hypersensitivity (anaphylactic or anaphylactoid) reactions to drugs, animal serums and other allergens, and to prolong the action of infiltration anesthetics. In addition to the above functions, epinephrine is the primary drug administered during cardiopulmonary resuscitation

Diethanolamine, Secondary Amine
Diethanolamine, [HN(CH2CH2OH)2], DEA, secondary amine (also "dialcohol", because two OH groups), weak base, oily colourless liquid or white crystals, fish smell, denser than water, used to make soaps, surfactants, dishwashing detergents, anticorrosion agent.
Diethanolamine (photography developer), Irritates skin and eyes.
Diethanolamine, Solution < 10%, Not hazardous
Diethanolamine bisulfite (photography developer), Irritates skin and eyes.

Diethylamine, (C4H11N), Secondary Amine
Diethylamine, [C4H11N(C2H5)2NH], (CH3-CH2-NH-CH2-CH3), diethyl amine, Toxic by all routes, Irritant to eyes, corrosive to eyes and skin, strongly alkaline, flammable, volatile, mixes with water and ethanol, colourless liquid (if pure), strong unpleasant odour, combustion forms dangerous nitrogen gases.
Diethylamine, Solution <2%, Not hazardous.

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.

Methylamine, (CH3NH2), Methyl Amine
Methylamine, Monomethylamine, Methanamine, Aminomethane, Monomethylamine, anhydrous colourless 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.
It is NOT permitted in schools.
DEA list of chemicals: 3.9.5
Fish smell, trimethylamine: Trimethylamine
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: Trimethylamine
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.3.5
CH3OH + NH3 --> CH3NH2 + H20.

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

Phenethylamine, (C8H11N), 16.2.4 Aromatic amines
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, (precursor to the neurotransmitter phenylethanolamine), acute toxic, skin irritant, sensitiser, in chocolate, in bitter almonds, in banana, in Rhodophyceae algae, in dietary supplements, in human urine, prepared by fermentation of sugar cane molasses, used as bronchodilator, nasal decongestants, in human body excitatory action on skeletal muscles.
See diagram: Phenethylamine.

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, occurs in Piper nigrum, 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, occurs in grapes and vegetables, colourless liquid, strong ammonia-like odour, highly flammable, explosive in air, harmful if swallowed, burns skin.
See diagram: Propylamine.

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, occurs in carrot and tobacco leaves, Propylamine.

16.6.1 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 |.
Ambelline and Lycorine occur in Crinum latifolium.
Belladine occurs in Nerium species and Apis cerana
Candimine occurs in Hippeastrum morelianum and Apis cerana
Caranine occurs in Clivia miniata and Orang River lily Crinum bulbispermum.
Galanthamine (Galantamine) occurs in Galanthus species

16.6.3 Diterpene 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 | Denudatine | Elatine | Lycoctonine | Mesaconitine
| Methyllycaconitine | Napelline | Nudicauline | Yunaconitine

16.6.6 Lycopodium alkaloids
The Lycopodium alkaloids have an unique ring system and were first studied as the alkaloids of the club moss Lycopodium serratum var. serratum, the serratezomines.
Huperzine A, isolated from the club moss Huperzia serrata, has been used in the treatment of Alzheimer's disease.
Huperzine A is a potent inhibitor of acetylcholinesterase (AChE), the key brain enzyme responsible for the rapid degradation of the neurotransmitter acetylcholine.
Huperzine A is also used as a dietary supplement for the correction of memory impairment.
| Annotine | Huperzine | Inundatine | Lycopodine | Selagine |.

16.6.8 Peptide alkaloids
| Frangulanine | Zizyphine |.

16.6.9 Piperidine and pyridine alkaloids
1. Alkaloids chemically derived from piperidine.
Coniine occurs in Conium maculatum, Sarracenia flava, Aethusa cynapium.
Lobeline occurs in Lobelia sessilifolia, Lobelia inflata
Pelletierine occurs in Sedum alpestre, Sedum annuum
Piperine occurs in Piper boehmeriifolium, Macropiper spp.
Sedamine occurs in Sedum acre, Phedimus aizoon.
2. Alkaloids chemically derived from pyridine.
Anabasine occurs in Nicotiana species.
Lobeline occurs in Lobelia inflata.
Nicotine occurs in Nicotiana tabacum.
Nicotine molecule contains both pyridine (left) and pyrrolidine rings (right).
Piperine occurs in Piper longum.
Ricinine occurs in Ricinus communis.
Trigonelline occurs in Trigonella foenum-graecum, Hypoestes phyllostachya.

16.6.10 Purines and pyrimidines alkaloids
(Purine-like compounds not from amino acids, so called "pseudoalkaloids".) (Purine derivatives)
Methylated purines: | Caffeine | Theobromine | Theophylline |.
Purine alkaloids occur in plants
Caffeine occurs in Camellia sinensis, Coffea arabica, Cola nitida, Paullinia cupana, Ilex paraguaensis
Theobromine occurs in Theobroma cacao Theophylline occurs in Camellia sinensis, Coffea arabica, Cola nitida, Paullinia cupana, Ilex paraguaensis

16.6.12 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.
| Betonicine | Clivorine | Echimidine | Glycyrrhizin | Heliosupine | Heliotridine | Heliotrine | Lasiocarpine | Lycopsamine | Monocrotaline | Retronecine
| Riddelline | Senecionine | Supinidine |. Symphytine |.
Pyrrolizidine alkaloids occur in plants
Glycyrrhizin occurs in Glycyrrhiza uralensis, Glycyrrhiza glabra, Senecio symphytine, Symphytum officinale, Tussilago farfara, Borago officinalis