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Alkaloids

Alkaloid is a kind of nitrogen-containing natural compound of physiological function with the majority of them containing complicated heterocyclic structures and a few of them being non-nitrogen heterocyclic organic amine. They generally have similar properties of the alkaline. Some kinds of natural derived vitamins, amino acids and peptides, although also belonging to nitrogen-containing compound, but generally are not classified into the range of alkaloids. In fact the word “alkaloid” still has not yet strict and precise definition to now.

Alkaloid is widely distributed in nature, especially in the plant kingdom. There are also some kinds found in animal kingdom such as the bufotenine found in toad, the hypoxanthine found in the earthworm. According to statistics, it has been found of alkaloids from at least 140 species of plants, especially in poppy, Menispermaceae, Solanaceae, Leguminosae, oleander, Ranunculaceae and barberry Branch. In general, alkaloids are mostly distributed in dicots with less being contained in monocots. There are rarely kinds of alkaloids found in gymnosperms and ferns or even lower plants. Alkaloid-containing plants often contain a variety of alkaloids of similar chemical structure. Plants have close family & genus relationship often contains alkaloids of similar structure while some being the same.

There are several ways of classifications of alkaloids, plant sources, the chemical structure or physiological effect can all be taken as classification references with the later one being more reasonable. Common types include pyrroles, pyridines, quinolines, isoquinolines, indoles, imidazoles, purines, tropane, terpenes, steroids and organic amines. Some people have divided alkaloids into 59 kinds, illustrating the complexity of their structure.

Alkaloids, except for a very few kinds which are liquid at room temperature, mostly appears as crystalline solid. They are generally colorless with bitterness, optically active and mostly left-handed. They exhibit alkalinity with the strength of the alkalinity exhibiting a significant relationship with the molecular structure especially the binding state of the nitrogen atoms. Quaternary ammonium alkaloids exhibit strong alkalinity with tertiary amines and secondary amines alkaloids being moderate or weak alkaline. Some kinds of alkaloids molecules contain phenol groups or carboxyl groups, thus having amphoteric property. The plants alkaloids can mostly bind with organic acid into salt or have condensation reaction with sugar to become glycosides. A few kinds of alkaloids having weak alkalinity exist in their free states. Alkaloid salts, after alkalization or alkaloid glycosides, after hydrolysis can obtain free alkaloid. Most kinds of alkaloids are insoluble or poorly soluble in water, soluble in organic solvents such as benzene, chloroform, ether, acetone, ethanol, and forming salt after being dissolved in dilute acid. Alkaloid salts are more soluble in water and alcohol, insoluble or poorly soluble in organic solvents. Alkaloids can react with some kinds of reagents, such as potassium iodide, bismuth, mercury, potassium iodide, iodine-potassium iodide to form precipitates of different colors. This precipitation reaction is often applied to identify specific alkaloids.

There are many ways for extracting alkaloid. Generally, we can first use water, acid water or alcohol to extract the crushed samples; the extract was concentrated; use organic solvent to extract out the total alkaloids after alkalization. Or first send the crushed sample to alkalization; further apply organic solvent to extract the total alkaloids. The total alkaloids can be further separated through various methods such as chromatography, preparative derivatives. There are few sublimated or volatile alkaloids which can be purified through water steam distillation or sublimation purification.

Though the alkaloid content is very small inside plants, they have intimate relationship with humans. Mankind has long been recognized that some alkaloid-containing plants or crude extracts can be used for treatment of disease or being used as poisoning drugs. Since 1806 when Serturner had isolated morphine from the opium poppy, there have been over 6000 kinds of alkaloids extracted from plants and animals. Among them, nearly 100 kinds have been used or tested in clinical application. Many kinds of alkaloids are effective medicine, such as the berberine contained in Ranunculaceae rhizome has anti-bacterial as well as anti-inflammatory effect; the reserpine in Rauwolfia can lower blood pressure; the galantamine of Lycoris has efficacy in treating post-polio syndrome. The morphine contained in the poppy peel is a kind of famous analgesics; quinine alkaline is a valuable antipyretic drug; Cephalotaxine and vinblastine are effective cancer medicine; colchicine (alkaline) mutagenesis can produce polyploid. Some kinds of alkaloids can be used to make pesticides of agricultural purpose. It has been also isolated in vertebrates and invertebrates of alkaloids, among which, the alkaloids contained in some animals are related to their intake of plant. The alkaloids found in toads, newts and some kinds of fishes are real animal metabolites.

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Structure Chemical Name CAS MF
Tryptophol Tryptophol 526-55-6 C10H11NO
(+)-Pilocarpine hydrochloride (+)-Pilocarpine hydrochloride 54-71-7 C11H17ClN2O2
8-Chlorotheophylline 8-Chlorotheophylline 85-18-7 C7H7ClN4O2
Tropine Tropine 120-29-6 C8H15NO
CYTOCHALASIN D CYTOCHALASIN D 22144-77-0 C30H37NO6
SANGUINARINE SANGUINARINE 2447-54-3 C20H14NO4
2,2,6,6-Tetramethyl-4-piperidone hydrochloride 2,2,6,6-Tetramethyl-4-piperidone hydrochloride 33973-59-0 C9H18ClNO
Indole-3-carboxylic acid Indole-3-carboxylic acid 771-50-6 C9H7NO2
3-(2-Pyrrolidinyl)pyridine 3-(2-Pyrrolidinyl)pyridine 5746-86-1 C9H12N2
Triacetonamine Triacetonamine 826-36-8 C9H17NO
9-Aminocamptothecin 9-Aminocamptothecin 91421-43-1 C20H17N3O4
Oxindole Oxindole 59-48-3 C8H7NO
BANISTERINE MONOHYDRATE BANISTERINE MONOHYDRATE 442-51-3 C13H12N2O
3-Methyl-7-propylxanthine 3-Methyl-7-propylxanthine 55242-64-3 C9H12N4O2
Gramine Gramine 87-52-5 C11H14N2
Vindoline Vindoline 2182-14-1 C25H32N2O6
Trigonelline hydrochloride Trigonelline hydrochloride 6138-41-6 C7H8ClNO2
Methyl indole-3-carboxylate Methyl indole-3-carboxylate 942-24-5 C10H9NO2
CACOTHELINE CACOTHELINE 561-20-6 C21H21N3O7
(+)-MAGNOFLORINE IODIDE (+)-MAGNOFLORINE IODIDE 2141-09-5 C20H24INO4
CORYNANTHINE CORYNANTHINE 483-10-3 C21H26N2O3
SWAINSONINE SWAINSONINE 72741-87-8 C8H15NO3
DAURICINE DAURICINE 524-17-4 C38H44N2O6
VERATRIDINE VERATRIDINE 71-62-5 C36H51NO11
L-MIMOSINE L-MIMOSINE 500-44-7 C8H10N2O4
TOMATINE TOMATINE 17406-45-0 C50H83NO21
Ryanodine Ryanodine 15662-33-6 C25H35NO9
Boldine Boldine 476-70-0 C19H21NO4
1-(3-CHLOROPROPYL)THEOBROMINE 1-(3-CHLOROPROPYL)THEOBROMINE 74409-52-2 C10H13ClN4O2
LUMICHROME LUMICHROME 1086-80-2 C12H10N4O2
SCOPOLAMINE METHYL NITRATE SCOPOLAMINE METHYL NITRATE 6106-46-3 C18H24N2O7
HARRINGTONINE HARRINGTONINE 26833-85-2 C28H37NO9
ALPHA-AMANITIN ALPHA-AMANITIN 23109-05-9 C39H54N10O14S
STRYCHNINE STRYCHNINE 60-41-3 C21H22N2O2.1/2H2O4S
SOLASONINE SOLASONINE 19121-58-5 C45H73NO16
NICOTINE BI-L-(+)-TARTRATE NICOTINE BI-L-(+)-TARTRATE 2624-48-8 C18H26N2O12
(-)-ANABASINE (-)-ANABASINE 13078-04-1 C10H14N2
SANGUINARINE CHLORIDE SANGUINARINE CHLORIDE 5578-73-4 C20H14ClNO4
GELSEMINE GELSEMINE 509-15-9 C20H22N2O2
(-)-LUPININE (-)-LUPININE 486-70-4 C10H19NO
2-Propylpiperidine 2-Propylpiperidine 3238-60-6 C8H17N
(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE (+)-TUBOCURARINE CHLORIDE PENTAHYDRATE 6989-98-6 C37H44Cl2N2O7
D-Tetrahydropalmatine D-Tetrahydropalmatine 3520-14-7 C21H25NO4
HYOSCYAMINE HYDROBROMIDE HYOSCYAMINE HYDROBROMIDE 306-03-6 C17H24BrNO3
ISOTETRANDRINE ISOTETRANDRINE 477-57-6 C38H42N2O6
ELLIPTICINE ELLIPTICINE 519-23-3 C17H14N2
HORDENINE SULFATE HORDENINE SULFATE 622-64-0 C20H32N2O6S
NICOTINE SULFATE NICOTINE SULFATE 65-30-5 C20H30N4O4S
LOBELINE SULFATE LOBELINE SULFATE 134-64-5 C44H56N2O8S
(-)-EBURNAMONINE (-)-EBURNAMONINE 4880-88-0 C19H22N2O
HYOSCYAMINE SULFATE HYOSCYAMINE SULFATE 620-61-1 C34H48N2O10S
MYOSMINE MYOSMINE 532-12-7 C9H10N2
CASTANOSPERMINE CASTANOSPERMINE 79831-76-8 C8H15NO4
HARMALINE HARMALINE 304-21-2 C13H14N2O
Seneciphylline Seneciphylline 480-81-9 C18H23NO5
(+)-B-HYDRASTINE HCL (+)-B-HYDRASTINE HCL 5936-28-7 C21H22ClNO6
CYCLO(-GLY-PRO) CYCLO(-GLY-PRO) 3705-27-9 C7H10N2O2
Moringa extract Moringa extract
CALYCANTHINE CALYCANTHINE 595-05-1 C22H26N4
Solamargine Solamargine 20311-51-7 C45H73NO15
ISOMITRAPHYLLINE ISOMITRAPHYLLINE 4963-01-3 C21H24N2O4
Dicentrin Dicentrin 517-66-8 C20H21NO4
piperlonguminine piperlonguminine 5950-12-9 C16H19NO3
BETONICINE BETONICINE 515-25-3 C7H13NO3
BULBOCAPNINE HYDROCHLORIDE BULBOCAPNINE HYDROCHLORIDE 632-47-3 C19H20ClNO4
HARMALOL HCL HARMALOL HCL 6028-07-5 C12H13ClN2O
ISORHYNCHOPHYLLINE ISORHYNCHOPHYLLINE 6859-01-4 C22H28N2O4
HOMATROPINE HYDROCHLORIDE HOMATROPINE HYDROCHLORIDE 637-21-8 C16H22ClNO3
6-METHOXY-2-BENZOXAZOLINONE 6-METHOXY-2-BENZOXAZOLINONE 532-91-2 C8H7NO3
4-AMINO-4-METHYL-2-PENTANONE HYDROGENOXALATE 4-AMINO-4-METHYL-2-PENTANONE HYDROGENOXALATE 625-04-7 C6H13NO
TETRAHYDROALSTONINE TETRAHYDROALSTONINE 6474-90-4 C21H24N2O3
3,4-DIMETHOXYBENZAMIDE 3,4-DIMETHOXYBENZAMIDE 1521-41-1 C9H11NO3
SYROSINGOPINE SYROSINGOPINE 84-36-6 C35H42N2O11
SCOPOLAMINE N-OXIDE HYDROBROMIDE SCOPOLAMINE N-OXIDE HYDROBROMIDE 6106-81-6 C17H22BrNO5
RHOEADINE RHOEADINE 2718-25-4 C21H21NO6
DIHYDROERGOTAMINE TARTRATE CRYSTALLINE DIHYDROERGOTAMINE TARTRATE CRYSTALLINE 5989-77-5 2C33H37N5O5.C4H6O6
yuanamide yuanamide 102421-42-1 C22H23NO5
α-Chaconine α-Chaconine 20562-03-2 C45H73NO14
daurisoline daurisoline 70553-76-3 C37H42N2O6
INDACONITINE INDACONITINE 4491-19-4 C34H47NO10
1-METHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE 1-METHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE 525-40-6 C12H14N2
(+/-)-EvodiaMine (+/-)-EvodiaMine 518-18-3 C19H17N3O
INDOLE-3-GLYOXYLAMIDE INDOLE-3-GLYOXYLAMIDE 5548-10-7 C10H8N2O2
SENECIONINE SENECIONINE 130-01-8 C18H25NO5
2-Piperidinoethanol 2-Piperidinoethanol 3040-44-6 C7H15NO
2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one 526-43-2 C19H17N3O2
PIPERLONGUMINE PIPERLONGUMINE 20069-09-4 C17H19NO5
2-(3-(4-hydroxyphenyl)propanamido)benzoic acid 2-(3-(4-hydroxyphenyl)propanamido)benzoic acid 697235-49-7 C16H15NO4
TABERSONINE TABERSONINE 4429-63-4 C21H24N2O2
Tropolone Tropolone 533-75-5 C7H6O2
ATROPINE METHYL NITRATE ATROPINE METHYL NITRATE 52-88-0 C18H26N2O6
Notoginseng triterpenes Notoginseng triterpenes 88105-29-7 C47H80O17
Sophocarpine Sophocarpine 6483-15-4 C15H22N2O
songorine songorine 509-24-0 C22H31NO3
2α,5α-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester 2α,5α-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester 4684-32-6 C20H22N2O3
SERPENTINE HYDROGEN TARTRATE SERPENTINE HYDROGEN TARTRATE 18786-24-8 C25H26N2O9
Mesaconine Mesaconine 6792-09-2 C24H39NO9
HYOSCYAMINE HYDROCHLORIDE HYOSCYAMINE HYDROCHLORIDE 5934-50-9 C17H24ClNO3
BRUCINE SULFATE HEPTAHYDRATE BRUCINE SULFATE HEPTAHYDRATE 60583-39-3 C46H68N4O19S
BOLDINE DIMETHYL ETHER BOLDINE DIMETHYL ETHER 475-81-0 C21H25NO4
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