Pyrrolizidine Alkaloids
Pyrrolizidine alkaloids were found mainly in Asteraceae and Boraginaceae families (only)
Asteraceae: Doronicum, Eupatorium, Petasites, Senecio, Tussilago genus Boraginaceae: Alkanna, Anchusa, Cynoglossum, Echium, Heliotropium, Symphytum genus
Drogs containing these alkaloids, Senecio and Symphytum species are prominent.
These species are toxic plants, several species have no therapeutic value other than the cytotoxic (in vitro) effect.
Although pyrolizidine alkaloids are not medically important, they are important, because they contain toxic hepatotoxic compounds, such as Senecio (Compositae) species (Sometimes animals can eat them)
This is due to the contamination of cereals by plants carrying these alkaloids (pyrrole toxicity). Pyrrolizidine alkaloids
Alkaloids are often present as esters.
The hepatotoxic effect of senesionin are formed by the destruction of alkaloids in the liver to strongly alkylated pyrrole esters.
2 • The quinoleine is one of the isomers of benzopyridine. It carries nitrogen atom in alfa position. The isomer one, bearing N atom in beta position, is called as isokinolein.
β
3 Herba Ephedra
•Ephedra “Ma Huang” •E. sinica ve E. equisetina growing in China •E. gerardiana , E. intermedia ve E. major growing in India and Pakistan, which are used to obtain ephedrine ve pseudoefedrine
4 Ephedrine HCl
•Ephedrine is obtained either by extraction from Ephedra species or by chemical synthesis. •Ephedrine; white, needle crystals. Soluble in water, alcohol, chloroform, ether and petroleum ether. •Ephedrine; relaxes bronchial smooth muscles when used orally or parenterally (-adrenergic receptor stimulation) •It makes vasoconstriction in skin and mucous membranes.
5
Catha edulis Khat veya Abyssinian Tea
Catha edulis (Celastraceae) Tropical East African plant from Ethiopia and Yemen.
The major ingredient in fresh and young leaves is cathinon.
Cathinone turns into norpseudoepherdin and norephedrine in dry drog and old leaves.
6 The cathinone; pharmacologically similar effects to D-amphetamine. It causes loss of appetite, increase in body temperature, respiratory stimulant, mydriasis, arrhythmia and hypertension.
7 Sanguinaria canadensis-Bloodroot
Papaveraceae fam.
A perennial, the plant produce red latex It grows widely in North America.
Usually alkaloids are found in rhizom as 4-7%. A red resin and starch are also present.
Main components: Sangunarin –benzophenanthridine alkaloid (50%) causes mating on chromosomes, just like colchicine.
8 The Alkaloids Derived from Phenylalanin, Tyrozin ve Dihydro phenylalanin
9 There are many alkaloids from isoquinoline group
This section includes protoalkaloids such as mescaline and ephedrine. Apart from phenylethylamines, there are 5 main alkaloid groups according to the shape of the final structure formed by the reaction of precursors with amino belongings.
10 OPIUM (TF)-AFYON
Opium is obtained from capsule-type fruits latex (milk) of Papaver somniferum (Papaveraceae) known as Turkish Poppy/ Haşhaş.
It is a spherical capsule with flattened fruits. Capsule mesocarp has secretory channels. There is a latex in these channels.
11 Poppy is one of the important crops of our country.
Both alkaloids found in capsules, as well as oil is used.
Alkaloids such as papaverine, thebaine and codeine, especially morphine, are important pharmaceutical raw materials found in the capsule shell.
12 Since the Hittites in Anatolia has been cultivated poppy.
For the first time in 1933, the agriculture of the plant was taken under state control and production continued until 1971 with the laws and regulations issued from time to time.
13 Production was allowed again in 1974, but capsule drawing was forbidden.
A factory was established in 1976 in Bolvadin district of Afyon to obtain alkaloids from dry capsules.
The factory started production in 1981 and partial production in 1983.
14 • There are two subspecies of Papaver somniferum. • P. somniferum subsp. spontaneum (Open Poppy in Anatolia)
• P. somniferum subsp. anatolicum (Blind poppy in Anatolia) (Capsules do not open at maturity)
15 The plant is cultivated in Turkey, Australia, France, Spain, India, Pakistan, Iran ve Mecsico.
16 If we draw a line between Ankara and Mersin;
Eskişehir, Bilecik, Kütahya, Usak, Afyon, Isparta, Burdur, Denizli (Drogist Region-one knife to the west of the line)
Amasya, Tokat, Çorum, Malatya (Soft zone-east of the line-4-5 knife blade)
Obtaining opium starts early in the morning by drawing capsules that are just beginning to mature.
The depth of the line should be sufficient to reach the mesocarp, but the capsule should not be torn. The latex, which flows out when the capsule is drawn and collects as droplets outside the capsule, is initially flowing and light colored, darkens towards the evening and becomes darker in color.
Raw opium is a mass of yellow, brown and black color, with special odor, fresh, elastic and hardening when dry
17 The ratio of alkaloids in Opium is between 10-25%. About 25 alkaloids from this drug are used in pharmacy: morphine, codeine, thebaine, papaverine, laudanine, narcotin (noscapine), and narceine etc.
18 Determintion, Morphine, powdered drugs, soaked with ammonia, extracted with chloroform, chloroform is evaporated, concentrated, sulfuric acid is treated and the red color is observed.
Codeine, added concentrated sulphuric acid. and dark blue color if dissolved in acid, and added ferric chloride.
Papaverine, added potassium ferri cyanure, sulfuric acid-formol is added and green-blue color is observed.
19 Opium (TF)-Afyon Poppy: Papaver somniferum-Haşhaş
• Papaveraceae Opium in small amounts is a respiratory accelerator, but in high doses it will be stopped breathing, small amounts of painkillers. It is used in severe pain.
20 Opium Alkaloids
• Several alkaloids were isolated from opium latex (about 50) • Morphine and codeine are the most important. • Morphine affects the central nervous system. • Makes sleepy and depresses breathing.
21 Eroin Heroin; is a semi-synthetic morphine derivative, it is a diacetyl morphine
22 • Poppy capsules produced in controlled manner are processed in Alkaloid Factory in Afyon Bolvadin.
Morphine is strong analgesic and narcotic.
Codeine effect weak, cough suppressant .. Increases the effect of other analgesics.
Papaverine relaxed muscle spasm.
Narcotine, noscapine, effect like papaverine.
Narceine is analgesic, as morphine.
23 Fructus papaveris immaturi-haşhaş kellesi:
Poppy heads that are not yet ripe and scraped.
Drog, 0.2-0.8% alkaloids. In the past, it was given to children with toothache and as a sleeping pill. This drug is used in the production of alkaloids in the industry.
24 Codeine Less hypnotic and analgesic than morphine.
25 Noscapine Minor alkaloids are also obtained from Bolvadin Factory. Calming cough and excite breathing
26 Dionine cough suppressant
Apomorphine Vomiting as-HCl salt by desitration of morphine
Heroin analgesic and hypnotic
Nalorphine Allyl group instead of nitrogen-bound methyl in Morphine-respiratory depression, morphine antagonist
Naloxone The oxidized product of morphine is a strong morphine antagonist than nalorphine Paracodine Codeine dihydro derivative in cough
Dikodid cough sedative
Pholcodine Cough
Cotarnine It is formed from the molecule Narcotin, by the oxidation of narcotine by the separation of the benzyl group.
27 As the usage of these, habit-forming opiates Papaver bracteatum Papaver orientale, some of them.
Papaver bracteatum Tebain is the major constituent of this species, and is cultivated in many countries.
Papaver orientale This species is generally cultivated as ornamental plant. Generally, the alkaloid, oripavine, formed by demethylation of the aromatic ring of thebaine, stands out as the major compound.
28