lycopsamine

butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3S)-

CAS: 10285-07-1 C15 H25 N O5 MW: 299.36725000

Identification

Namelycopsamine
CAS Number10285-07-1
FDA UNIIUER4ET3OHI
Molecular FormulaC15 H25 N O5
Molecular Weight299.36725000
Nikkaji NumberJ15.603E

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 2.092e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for lycopsamine usage levels up tonot for fragrance use.
Recommendation for lycopsamine flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

None Found

Natural Occurrence

borage leaf borage shoot

Synonyms

butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3S)- [(7R,8R)-7- hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate (1R-(1alpha,7(2S*,3S*),7abeta))-(2,3,5,7a- tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl 2,3-dihydroxy-2-(1-methylethyl)butanoate PubMed: Toxic pyrrolizidine alkaloids provide a warning sign to overuse of the ethnomedicine Arnebia benthamii. PubMed: Development and validation of a QuEChERS method coupled to liquid chromatography and high resolution mass spectrometry to determine pyrrolizidine and tropane alkaloids in honey. PubMed: Penetration of lycopsamine from a comfrey ointment through human epidermis. PubMed: Survey of pyrrolizidine alkaloids in seven varieties of Lappula squarrosa: An alternative source of heart-healthy vegetable oil. PubMed: Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation. PubMed: A Validated, Rapid HPLC-ESI-MS/MS Method for the Determination of Lycopsamine. PubMed: Pyrrolizidine alkaloids in food and feed on the Belgian market. PubMed: The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus). PubMed: Pro-toxic dehydropyrrolizidine alkaloids in the traditional Andean herbal medicine "asmachilca". PubMed: Characterization and screening of pyrrolizidine alkaloids and N-oxides from botanicals and dietary supplements using UHPLC-high resolution mass spectrometry. PubMed: An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. PubMed: Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae). PubMed: TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound. PubMed: Development of a fast isocratic LC-MS/MS method for the high-throughput analysis of pyrrolizidine alkaloids in Australian honey. PubMed: Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine. PubMed: Profiling of dehydropyrrolizidine alkaloids and their N-oxides in herbarium-preserved specimens of amsinckia species using HPLC-esi(+)MS. PubMed: Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed. PubMed: Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity. PubMed: Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper's bugloss (Echium spp.). PubMed: Dehydropyrrolizidine alkaloids in two Cryptantha species: including two new open chain diesters one of which is amphoteric. PubMed: Improved method for isolation of lycopsamine from roots of comfrey (Symphytum officinale). PubMed: Comparison of metabolism-mediated effects of pyrrolizidine alkaloids in a HepG2/C3A cell-S9 co-incubation system and quantification of their glutathione conjugates. PubMed: Detection of high levels of pyrrolizidine-N-oxides in the endangered plant Cryptantha crassipes (Terlingua Creek cat's-eye) using HPLC-ESI-MS. PubMed: Metabolism, genotoxicity, and carcinogenicity of comfrey. PubMed: Pyrrolizidine alkaloids in honey: comparison of analytical methods. PubMed: Chiral stationary phases for separation of intermedine and lycopsamine enantiomers from Symphytum uplandicum. PubMed: Determination of pyrrolizidine alkaloids in comfrey by liquid chromatography-electrospray ionization mass spectrometry. PubMed: Lycopsamine and cumambrin B from Eupatorium maculatum. PubMed: Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species. PubMed: Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids. PubMed: Major components in the hairpencil secretion of a butterfly, Euploea mulciber (Lepidoptera, Danaidae): their origins and male behavioral responses to pyrrolizidine alkaloids. PubMed: Differential utilization of pyrrolizidine alkaloids by males of a danaid butterfly, Parantica sita, for the production of danaidone in the alar scent organ. PubMed: Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura. PubMed: Solid-phase extraction and HPLC-MS profiling of pyrrolizidine alkaloids and their N-oxides: a case study of Echium plantagineum. PubMed: On-line structure characterization of pyrrolizidine alkaloids in Onosma stellulatum and Emilia coccinea by liquid chromatography-ion-trap mass spectrometry. PubMed: Sequestration and metabolism of protoxic pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults. PubMed: Pyrrolizidine alkaloids from Lithospermum canescens Lehm. PubMed: Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. PubMed: Toxic pyrrolyzidine alkaloids from three mongolian plants. a possible risk for cattle poisoning. PubMed: Pyrrolizidine alkaloids in Pulmonaria obscura. PubMed: Dual chemical sequestration: a key mechanism in transitions among ecological specialization. PubMed: Sequestration, metabolism and partial synthesis of tertiary pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. PubMed: Pyrrolizidine alkaloids from Ageratum houstonianum Mill. PubMed: Pyrrolizidine alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae). PubMed: Pyrrolizidine alkaloids from Heliotropium megalanthum. PubMed: Preparative separation of pyrrolizidine alkaloids by high-speed counter-current chromatography. PubMed: Stereochemical inversion of pyrrolizidine alkaloids byMechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance. PubMed: Pyrrolizidine alkaloids in the arctiid mothHyalurga syma. PubMed: Investigation into the Presence of Pyrrolizidine Alkaloids in Eupatorium cannabinum by Means of Positive and Negative Ion Chemical Ionization GC-MS. PubMed: Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents. PubMed: Pyrrolizidine alkaloids from Symphytum officinale L. and their percutaneous absorption in rats. PubMed: [II1: TLC and HPLC-Analysis of Pyrrolizidine-N-oxid Alkaloids of Symphyti Radix].