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protopine
bis(1,3)benzodioxolo(4,5-C:5',6'-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-

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CAS Number: 130-86-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:204-999-6
FDA UNII: UIW569HT35
Nikkaji Web:J40.085H
MDL:MFCD00022322
XlogP3-AA:2.80 (est)
Molecular Weight:353.37443000
Formula:C20 H19 N O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 208.00 °C. @ 760.00 mm Hg
Boiling Point: 547.50 °C. @ 760.00 mm Hg (est)
Flash Point: 545.00 °F. TCC ( 284.90 °C. ) (est)
logP (o/w): 3.760 (est)
Soluble in:
 water, 5.076 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Protopine 98%
BOC Sciences
For experimental / research use only.
Protopine 98%
Odor: characteristic
Use: Protopine isolated from the tubers of Corydalis yanhusuo W.T.Wang. It shows weak spasmolytic, smooth muscle stimulant activities. bactericidal; sedative; antihypertensive;
ExtraSynthese
For experimental / research use only.
Protopine (HPLC) ≥95%
Sigma-Aldrich
For experimental / research use only.
Protopine analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-guinea pig LD50 116 mg/kg
Therapie. Vol. 28, Pg. 767, 1973.

oral-guinea pig LD50 237 mg/kg
Therapie. Vol. 28, Pg. 767, 1973.

intraperitoneal-mouse LD50 482 mg/kg
Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 16(6), Pg. 7, 1981.

intravenous-mouse LD50 31 mg/kg
Pharmaceutical Chemistry Journal Vol. 11, Pg. 640, 1977.

intraperitoneal-rat LDLo 100 mg/kg
National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 24, 1953.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for protopine usage levels up to:
 not for fragrance use.
 
Recommendation for protopine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :4970
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0000130869
RTECS:VS2800000 for cas# 130-86-9
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):4970
Pubchem (sid):134973206
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C05189
HMDB (The Human Metabolome Database):HMDB03920
FooDB:FDB023249
Export Tariff Code:2939.90.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
bis(1,3)benzodioxolo(4,5-C:5',6'-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-
 corydinine
 fumarine
 macleyine
4,6,7,14-tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one
 

Articles:

PubMed:Simultaneous determination of the content of isoquinoline alkaloids in Dicranostigma leptopodum (Maxim) Fedde and the effective fractionation of the alkaloids by high-performance liquid chromatography with diode array detection.
PubMed:Direct analysis of quaternary alkaloids by in situ reactive desorption corona beam ionization MS.
PubMed:Influence of vinegar and wine processing on the alkaloid content and composition of the traditional Chinese medicine Corydalis Rhizoma (Yanhusuo).
PubMed:Antidiabetic effects of the Cimicifuga racemosa extract Ze 450 in vitro and in vivo in ob/ob mice.
PubMed:Natural products as potential human ether-a-go-go-related gene channel inhibitors - screening of plant-derived alkaloids.
PubMed:Cytotoxicity of Aporphine, Protoberberine, and Protopine Alkaloids from Dicranostigma leptopodum (Maxim.) Fedde.
PubMed:Simultaneous determination of paeoniflorin, albiflorin, ferulic acid, tetrahydropalmatine, protopine, typhaneoside, senkyunolide I in Beagle dogs plasma by UPLC-MS/MS and its application to a pharmacokinetic study after Oral Administration of Shaofu Zhuyu Decoction.
PubMed:Comparisons of pharmacokinetic and tissue distribution profile of four major bioactive components after oral administration of Xiang-Fu-Si-Wu Decoction effective fraction in normal and dysmenorrheal symptom rats.
PubMed:[Network pharmacology study on major active compounds of siwu decoction analogous formulae for treating primary dysmenorrhea of gynecology blood stasis syndrome].
PubMed:Improved sanguinarine production via biotic and abiotic elicitations and precursor feeding in cell suspensions of latex-less variety of Papaver somniferum with their gene expression studies and upscaling in bioreactor.
PubMed:Facile synthesis of tetrahydroprotoberberine and protoberberine alkaloids from protopines and study on their antibacterial activities.
PubMed:Identification and quantification of the main active anticancer alkaloids from the root of Glaucium flavum.
PubMed:A HPLC-MS/MS method for the simultaneous quantitation of six alkaloids of Rhizoma Corydalis Decumbentis in rat plasma and its application to a pharmacokinetic study.
PubMed:A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain.
PubMed:[In vitro transdermal delivery of the active fraction of xiangfusiwu decoction based on principal component analysis].
PubMed:Pharmaceutical applications of the benzylisoquinoline alkaloids from Argemone mexicana L.
PubMed:Identification of the absorbed constituents after oral administration of Yuanhu Zhitong prescription extract and its pharmacokinetic study by rapid resolution liquid chromatography/quadrupole time-of-flight.
PubMed:Dioxygenases catalyze O-demethylation and O,O-demethylenation with widespread roles in benzylisoquinoline alkaloid metabolism in opium poppy.
PubMed:Revealing the anti-tumoral effect of Algerian Glaucium flavum roots against human cancer cells.
PubMed:Comparative pharmacokinetics and bioavailability of four alkaloids in different formulations from Corydalis decumbens.
PubMed:Simultaneous quantification of 11 isoquinoline alkaloids in Corydalis impatiens (Pall.) Fisch by HPLC.
PubMed:A review on ethnobotany, phytochemistry and pharmacology of Fumaria indica (Fumitory).
PubMed:Capillary electrophoretic study of the synergistic biological effects of alkaloids from Chelidonium majus L. in normal and cancer cells.
PubMed:Integration of transcriptome, proteome and metabolism data reveals the alkaloids biosynthesis in Macleaya cordata and Macleaya microcarpa.
PubMed:Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis.
PubMed:A sensitive and selective liquid chromatography-tandem mass spectrometry method for simultaneous determination of five isoquinoline alkaloids from Chelidonium majus L. in rat plasma and its application to a pharmacokinetic study.
PubMed:Large-scale separation of alkaloids from Corydalis bungeana Turcz. by pH-zone-refining counter-current chromatography.
PubMed:Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics, tissue distribution and excretion studies of Dactylicapnos scandens in rats.
PubMed:Identification of pavinane alkaloids in the genera Argemone and Eschscholzia by GC-MS.
PubMed:Establishment of a search library about benzylisoquinoline alkaloids based on selective separation on the binaphthyl column and standard analysis on C18 column.
PubMed:[Study on absorption ingredients of yuanhuzhitong pill by everted intestinal sac method].
PubMed:Genetic and chemical components analysis of Papaver setigerum naturalized in Korea.
PubMed:Phytochemical and biological activity studies of the Bhutanese medicinal plant Corydalis crispa.
PubMed:Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia.
PubMed:[Chemical constituents from Corydalis yanhusuo].
PubMed:Fluorescence spectral analysis for the discrimination of complex, similar mixtures with the aid of chemometrics.
PubMed:Design and evaluation of self-emulsifying drug delivery systems of Rhizoma corydalis decumbentis extracts.
PubMed:Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells.
PubMed:Protopine reduces the inflammatory activity of lipopolysaccharide-stimulated murine macrophages.
PubMed:Effect of wine and vinegar processing of Rhizoma Corydalis on the tissue distribution of tetrahydropalmatine, protopine and dehydrocorydaline in rats.
PubMed:Alkaloids from Papaver coreanum.
PubMed:Induction of heme oxygenase-1 by Macleaya cordata extract and its constituent sanguinarine in RAW264.7 cells.
PubMed:[Determination of four alkaloids in Corydalis decumbens by HPLC].
PubMed:Preparative isolation of alkaloids from Dactylicapnos scandens using pH-zone-refining counter-current chromatography by changing the length of the separation column.
PubMed:Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines.
PubMed:Rapid discrimination and quantification of alkaloids in Corydalis Tuber by near-infrared spectroscopy.
PubMed:Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells.
PubMed:CYP2C19 progress curve analysis and mechanism-based inactivation by three methylenedioxyphenyl compounds.
PubMed:In vitro metabolic interactions between black cohosh (Cimicifuga racemosa) and tamoxifen via inhibition of cytochromes P450 2D6 and 3A4.
PubMed:Identification of a novel bacterial K(+) channel.
PubMed:Simultaneous quantification of 17 constituents from Yuanhu Zhitong tablet using rapid resolution liquid chromatography coupled with a triple quadrupole electrospray tandem mass spectrometry.
PubMed:Capillary electrophoresis with LED-induced native fluorescence detection for determination of isoquinoline alkaloids and their cytotoxicity in extracts of Chelidonium majus L.
PubMed:Alkaloids and flavonoids of Argemone mexicana.
PubMed:[Simultaneous determination of four alkaloids in Corydalis decumbens (Thunb.) Pers. by high performance liquid chromatography-tandem mass spectrometry].
PubMed:Chemical study and anti-inflammatory, analgesic and antioxidant activities of the leaves of Aristotelia chilensis (Mol.) Stuntz, Elaeocarpaceae.
PubMed:Seasonal variation of bioactive alkaloid contents in Macleaya microcarpa (Maxim.) Fedde.
PubMed:Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR.
PubMed:Preparative isolation of alkaloids from Corydalis bungeana Turcz. by high-speed counter-current chromatography using stepwise elution.
PubMed:Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae).
PubMed:[Determination of protopine in Corydalis racemose by HPLC].
PubMed:Phytochemical and antimicrobial characterization of Macleaya cordata herb.
PubMed:Optimization of microwave-assisted extraction of protopine and allocryptopine from stems of Macleaya cordata (Willd) R. Br. using response surface methodology.
PubMed:A study on separation and extraction of four main alkaloids in Macleaya cordata (Willd) R. Br. with strip dispersion hybrid liquid membrane.
PubMed:In vivo anthelmintic activity of five alkaloids from Macleaya microcarpa (Maxim) Fedde against Dactylogyrus intermedius in Carassius auratus.
PubMed:Validated liquid chromatography-tandem mass spectrometry method for quantitative determination of dauricine in human plasma and its application to pharmacokinetic study.
PubMed:Acetylcholinesterase inhibitors from Corydalis yanhusuo.
PubMed:BIAdb: a curated database of benzylisoquinoline alkaloids.
PubMed:Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection.
PubMed:Extractions of isoquinoline alkaloids with butanol and octanol.
PubMed:Screening of antinociceptive components in Corydalis yanhusuo W.T. Wang by comprehensive two-dimensional liquid chromatography/tandem mass spectrometry.
PubMed:Electron ionisation mass spectral study of 2-(2-carboxy-4, 5-dimethoxyphenyl)-6,7-dimethoxyisoquinolinium inner salt.
PubMed:Isoquinoline alkaloids from Macleaya cordata active against plant microbial pathogens.
PubMed:[Alkaloids from Dactylicapnos scandens Hutch].
PubMed:[Alkaloids from Macleaya cordata].
PubMed:Alkaloids from Mongolian species Hypecoum lactiflorum Kar. et Kir. Pazij.
PubMed:Antiplasmodial agents from the Bhutanese medicinal plant Corydalis calliantha.
PubMed:Simultaneous determination of tetrahydropalmatine, protopine, and palmatine in rat plasma by LC-ESI-MS and its application to a pharmacokinetic study.
PubMed:Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.
PubMed:Protective effects of protopine on hydrogen peroxide-induced oxidative injury of PC12 cells via Ca(2+) antagonism and antioxidant mechanisms.
PubMed:Rapid TLC/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts.
PubMed:Hepatoprotective potential of Fumaria indica Pugsley whole plant extracts, fractions and an isolated alkaloid protopine.
PubMed:On the synthesis of protopine alkaloids.
PubMed:Protective effect of protopine on the focal cerebral ischaemic injury in rats.
PubMed:Conventional sample enrichment strategies combined with high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance analysis allows analyte identification from a single minuscule Corydalis solida plant tuber.
PubMed:Antiviral and antimicrobial profiles of selected isoquinoline alkaloids from Fumaria and Corydalis species.
PubMed:Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy.
PubMed:New tetrahydroprotoberberine N-oxide alkaloids and cytotoxic constituents of Corydalis tashiroi.
PubMed:Rapid determination of protopine, allocryptopine, sanguinarine and chelerythrine in fruits of Macleaya cordata by microwave-assisted solvent extraction and HPLC-ESI/MS.
PubMed:Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding.
PubMed:Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism.
PubMed:Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro.
PubMed:Intestinal spasmolytic effects of STW 5 (Iberogast) and its components.
PubMed:Large-scale separation of alkaloids from Corydalis decumbens by pH-zone-refining counter-current chromatography.
PubMed:Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro.
PubMed:Protopine inhibits serotonin transporter and noradrenaline transporter and has the antidepressant-like effect in mice models.
PubMed:Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway.
PubMed:Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS.
PubMed:Regulation of glutamate level in rat brain through activation of glutamate dehydrogenase by Corydalis ternata.
PubMed:Theoretical and experimental NMR study of protopine hydrochloride isomers.
PubMed:Effects of protopine on intracellular calcium and the PKC activity of rat aorta smooth muscle.
PubMed:[Studies on the alkaloids from the herb of Corydalis adunca].
PubMed:[Determination of protopine and isocorydine in root of Dactylicapnos scandens by HPLC].
PubMed:Effect of binary combination of some plant-derived molluscicides with MGK-264 or piperonyl butoxide on the reproduction of the snail Lymnaea acuminata.
PubMed:Acetylcholinesterase inhibitors from the aerial parts of Corydalis speciosa.
PubMed:Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells.
PubMed:Protopine alkaloids in horse urine.
PubMed:1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae).
PubMed:How to treat tremor.
PubMed:Cytochrome P450 isoenzymes involved in rat liver microsomal metabolism of californine and protopine.
PubMed:Inhibition of mouse liver respiration by Chelidonium majus isoquinoline alkaloids.
PubMed:Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum.
PubMed:Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry.
PubMed:In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis.
PubMed:Cytotoxic activity and quality control determinations on Chelidonium majus.
PubMed:Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana.
PubMed:[RP-HPLC method for determination of protopine in plasma and pharmacokinetics in rats].
PubMed:[Concentration of four alkaloids in the aerial parts of Eomecon chionantha from different mounth in year].
PubMed:Direct determination of alkaloid contents in Fumaria species by GC-MS.
PubMed:Assay of nematocidal activity of isoquinoline alkaloids using third-stage larvae of Strongyloides ratti and S. venezuelensis.
PubMed:Elevational trends in defense chemistry, vegetation, and reproduction in Sanguinaria canadensis.
PubMed:A new tetrahydroprotoberberine N-oxide alkaloid and anti-platelet aggregation constituents of Corydalis tashiroi.
PubMed:Protopine hydrochloride.
PubMed:New protopine alkaloids from Aristolochia constricta reduce morphine withdrawal in vitro.
PubMed:Electrophysiological effects of protopine in cardiac myocytes: inhibition of multiple cation channel currents.
PubMed:Effect of protopine on cytosolic Ca2+ in rabbit platelets.
PubMed:Effect of molluscicidal components of Abrus precatorius, Argemone mexicana and Nerium indicum on certain biochemical parameters of Lymnaea acuminata.
PubMed:Protopine from Corydalis ternata has anticholinesterase and antiamnesic activities.
PubMed:Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum.
PubMed:An assessment of the potential of protopine to inhibit microsomal drug metabolising enzymes and prevent chemical-induced hepatotoxicity in rodents.
PubMed:New protopine and benzyltetrahydroprotoberberine alkaloids from Aristolochia constricta and their activity on isolated guinea-pig ileum.
PubMed:Isoquinoline alkaloids from Argemone mexicana reduce morphine withdrawal in guinea pig isolated ileum.
PubMed:Anti-thrombotic and anti-inflammatory activities of protopine.
PubMed:[Protective action of corynoline, acetylcorynoline and protopine against experimental liver injury in mice].
PubMed:Chelidonium majus L.: components with in vitro affinity for the GABAA receptor. Positive cooperation of alkaloids.
PubMed:[Effect of protopine on rabbit platelet function].
PubMed:Opioid, calcium, and adrenergic receptor involvement in protopine analgesia.
PubMed:[HPTLC separation and fluorodensitometric determination of isoquinoline alkaloids in Chelidonine majus L].
PubMed:Ca(2+)-channel blockade in rat thoracic aorta by protopine isolated from Corydalis tubers.
PubMed:Antihaemostatic and antithrombotic effect of some antiplatelet agents isolated from Chinese herbs.
PubMed:Chemical Study on the Alkaloids of Corydalis hsuchowensis.
PubMed:Effects of protopine on blood platelet aggregation. III. Effect of protopine on the metabolic system of arachidonic acid in platelets.
PubMed:[Isoquinoline alkaloids from Corydalis thyrsiflora prain].
PubMed:Characterization of Sanguinaria canadensis L. fluid extract by FAB mass spectrometry.
PubMed:[Relaxant effects of protopine on smooth muscles].
PubMed:Stepwise gradient in thin-layer chromatography of Chelidonium alkaloids.
PubMed:Effects of protopine on blood platelet aggregation. II. Effect on metabolic system of adenosine 3',5'-cyclic monophosphate in platelets.
PubMed:New hydroxylated benzo[c]phenanthridine alkaloids from Eschscholtzia californica cell suspension cultures.
PubMed:Antiplatelet effects of protopine isolated from Corydalis tubers.
PubMed:Cytotoxicity of isoquinoline alkaloids and their N-oxides.
PubMed:Effects of protopine on blood platelet aggregation; 1.
PubMed:In vitro study of the anticholinergic and antihistaminic activities of protopine and some derivatives.
PubMed:Chemical Study of Alkaloids from Corydalis bungeana.
PubMed:[Effects of alkaloids of Corydalis decumbens on cerebral and peripheral circulation in the dog].
PubMed:Enhancement of gamma-aminobutyric acid receptor binding by protopine-type alkaloids.
PubMed:Comparison of chemical and botanical studies of Turkish papaver belonging to the section pilosa.
PubMed:[Chemical study on a traditional Tibetan drug Hypecoum leptocarpum].
PubMed:Separation and Quantification of Some Alkaloids from Fumaria parviflora by Capillary Isotachophoresis1.
PubMed:[TLC separation and densitometric determination of six isoquinoline alkaloids in Corydalis bungeana].
PubMed:Isoquinoline alkaloids from cell suspension cultures of Fumaria capreolata.
PubMed:Alkaloids of Fumaria indica: Further Studies on Narceimine and Narlumidine.
PubMed:Beta-phenylethylamines and the isoquinoline alkaloids.
PubMed:Alkaloids of Fumaria densiflora*.
PubMed:The alkaloids of Corydalis meifolia.
PubMed:The alkaloids of Corydalis meifolia.
PubMed:Somatic embryogenesis of tissue cultures of Papaver somniferum and Papaver orientale and its relationship to alkaloid and lipid metabolism.
PubMed:Alkaloids of Turkish Glaucium species.
PubMed:Alkaloids from Fumaria parviflora and F. kralikii.
PubMed:Alkaloids of Corydalis slivenensis.
PubMed:Alkaloids from Corydalis bulbosa.
PubMed:[The antibacterial effects of some alkaloids isolated from Glaucium flavum Crantz].
PubMed:Alkaloids from Corydalis marschalliana.
PubMed:[Analgesic and antispastic effects of protopine (author's transl)].
PubMed:Alkaloids from Papaver armeniacum, P. fugax and P. tauricola.
PubMed:Variability of alkaloid spectrum in early stages of development of Glaucium flavum Crantz.
PubMed:High pressure liquid chromatographic determination of the five major alkaloids in Papaver somniferum L. and thebaine in Papaver bracteatum Lindl. capsular tissue.
PubMed:[Prevention of ventricular fibrillation with the aid of protopine in animal experiments].
PubMed:Alkaloids of papaver genus IX. Alkaloids of Glaucium vitellinum Boiss and Buhse, population Seerjan and Glaucium pulchrum Stapf, population Elika.
PubMed:Alkaloids of Glaucium flavum Grantz, populations Isfahan and Kazerun.
PubMed:Alkaloids of Glaucium oxylobum Boiss and Buhse, Population Ab-Ali.
PubMed:[Transformation of indole alkaloids. III. The partial synthesis of protopine type indole alkaloid "burnamicine" (author's transl)].
PubMed:Isolation and chemistry of alkaloids from plants of the family Papaveraceae LXVII: Corydalis cava (L.) Sch. et K. (C. tuberosa DC).
PubMed:Antimicrobial agents from higher plants. Additional alkaloids and antimicrobial agents from Thalictrum rugosum.
PubMed:[Extractive photometric determination of protopine].
PubMed:The structures of coulteropine and other protopine-type alkaloid acid salts.
PubMed:The nuclear resonance spectrum of protopine: rate of racemization and ring inversion.
PubMed:Alkaloids of the Papaveraceae. VI. Protopine and allocryptopine from Arctomecon alifornica.
PubMed:Phenol oxidation and biosynthesis. 8. Investigations on the biosynthesis of berberine and protopine.
PubMed:THE ANTITUMOR FACTORS PRESENT IN CHELIDONIUM MAJUS L. I. CHELIDONINE AND PROTOPINE.
PubMed:[Partition of chelidonine and protopine by means of countercurrent cascade extraction].
PubMed:Separation and determination of the dissociation constants of chelidonine and protopine by paper chromatography.
PubMed:Origin of the methylenedioxy groups of the alkaloid protopine.
 
Notes:
Protopine is a benzylisoquinoline alkaloid occurring in opium poppies and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic [HMDB]
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