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Alkaloids of indole group
A- Calabar beans alkaloids B- Ergot alkaloids C- Nux vomica alkaloids A- Calabar beans alkaloids; Physostigmine (Eserine); from Physostigma venenosum Fam. Leguminosae
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Chemical test for identity:
1- Physostigmine + Strong NH4OH + heat yellowish red colour (w.b./ evaporate) blue residue. 2- Physostigmine + K-ferricynide + FeCl3 blue colour. 3- Physostigmine + KOH + heat deep yellow colour. Uses: In eye treatment (Glaucoma) as myotic agent
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B- Ergot alkaloids; Clavicepes purpurea Fam
B- Ergot alkaloids; Clavicepes purpurea Fam. Hypocreaceae, arising in the ovary of rye, Secale cereale Fam. Graminae. The Ergot alkaloids: are substituted amide derivative of lysergic acid and its isomer iso- lysergic acid (differ in C-8 configuration).
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Ergot alkaloids Lysergic acid derivatives Iso lysergic acid deriv.
End up with suffix (-ine). Ergometrine, Ergotamine Ergocryptine, Ergosine Optically active, levorotatory (l) Pharmacologically active Iso lysergic acid deriv. End up with suffix (-inine). Ergometrinine, Ergotaminine Ergocryptinine, Ergosinine Optically active, dextrorotatory (d) Pharmacologically less active Only Ergometrine and Ergometrinine are Water soluble
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A series of condensation of several amino acid and pyruvic with the amine salts of lysergic and iso lysergic acid to produce series of ergot alkaloid. There are 12 different alkaloids divided into 6 pairs according to their peptide moieties e.g. (some contain one peptide moiety as ergometrine and some contain polypeptide moieties as ergotamine. These alkaloids: are grouped to 4 major groups according to their hydrolytic products. Group A are water soluble alkaloids, while groups B, C and D are water insoluble. A. Ergometrine group B. Ergotamine group C. Ergotoxine group D. Ergocristine group hydrolysis 2-amino propanol group Pyruvic acid. Dimethyl pyruvic. L-phenyl alanine
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Used as oxytocic agent. 2-amino propanol group + lysergic acid
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- Used as analgesic for treatment of migraine.
- Vaso-constrictor for cerebral vessels.
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Lysergic acid diethylamide (LSD) Detection of Ergot alkaloids
LSD not naturally occurring in ergot, produces transient psychosis (euphoria) which lead to Schizophrenia. Detection of Ergot alkaloids Van Urk Test: (P-dimethylamino benzaldehyde); Reagent + alkaloid deep blue colour (Quantitative determination).
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C- Nux Vomica alkaloids
Strychnos Nux vomica and Strychnos ignatii, Family Loganaceae
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Tests for identity Uses
- Strychnine + HNO3 yellow. - Brucine + HNO3 intense orange red color. Uses 1- Strychnine is used as circulatory stimulant in cases if surgical shock; but now is limited due to its toxicity. 2- Rodenticide. 3- Sexual tonic. 4- Brucine is less toxic so used as CNS stimulant.
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Separation of a mixture of strychnine and brucine
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Alkaloids of carboline group
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A- Yohimba alkaloids Yohimbine Uses: Aphrodisiac
Yohimbine occur in the bark of Corynanthe yohimba; Family Rubiaceae. Uses: Aphrodisiac
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Quantitative evaluation of Rauwolfia alkaloids:
Tests for identity Quantitative evaluation of Rauwolfia alkaloids: 1- Reserpine by non-aqueous titration. 2- Reserpine by flourimetric determination (fluoresce with sodium nitrite and H2SO4). Reserpine is used in hypertension
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B- Rauwolfia alkaloids
Reserpine; Occurs in Rauwolfia species root, Family Apocyanaceae. Reserpine
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Occur as a major alkaloid in Vinca minor, Family Apocyanaceae.
C- Vinca alkaloids 1- Vincamine Occur as a major alkaloid in Vinca minor, Family Apocyanaceae. Uses Vincamine used as vasodilator (Oxybral).
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2- Vinblastine and Vincristine
Occur in Catharanthus roseus, Family Apocyanacae Uses Treatment of Hodgkin’s disease, potent anticancer as in treatment of infantile leukaemia and carcinoma. Hodgkin's disease (HD) is a type of lymphoma, which is a blood cancer that starts in the lymphatic system. Leukemia is cancer of the body's blood-forming tissues, including the bone marrow
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