lysergol
ergoline-8-methanol, 9,10-didehydro-6-methyl-, (8beta)- (9CI)
Identification
| Name | lysergol |
| CAS Number | 602-85-7 |
| EINECS | 210-024-5 |
| FDA UNII | Search |
| Molecular Formula | C16 H18 N2 O |
| Molecular Weight | 254.33266000 |
| MDL Number | MFCD00010029 |
| Nikkaji Number | J2.673.613G |
| Beilstein | 0088476 |
| XlogP3 | 2.20 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 465.80 °C. @ 760.00 mm Hg (est) |
| Flash Point | 456.00 °F. TCC ( 235.50 °C. ) (est) |
| logP (o/w) | 1.760 (est) |
| Soluble in | water, 722.8 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intravenous-rabbit LD50 320 ug/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for lysergol usage levels up to | not for fragrance use. |
| Recommendation for lysergol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
9,10-
didehydro-6-methyl-8-hydroxymethylergoline
9,10-
didehydro-6-methylergoline-8beta-methanol
ergoline-8-methanol, 9,10-didehydro-6-methyl-, (8-beta)- (9CI)
ergoline-8-methanol, 9,10-didehydro-6-methyl-, (8beta)- (9CI)
ergoline-8beta-methanol, 9,10-didehydro-6-methyl- (8CI)
ergoline, 9,10-didehydro-8-hydroxymethyl-6-methyl-
lysergole
[(6aS,9S)-7-
methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]methanol
PubMed:
Identification of legal highs--ergot alkaloid patterns in two Argyreia nervosa products.
PubMed:
Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax.
PubMed:
Application of quantitative structure-activity relationship models of 5-HT1A receptor binding to virtual screening identifies novel and potent 5-HT1A ligands.
PubMed:
Antibacterial and synergy of clavine alkaloid lysergol and its derivatives against nalidixic acid-resistant Escherichia coli.
PubMed:
High-throughput screening with a miniaturized radioligand competition assay identifies new modulators of human α2-adrenoceptors.
PubMed:
Lysergol monohydrate.
PubMed:
Simultaneous quantification of berberine and lysergol by HPLC-UV: evidence that lysergol enhances the oral bioavailability of berberine in rats.
PubMed:
Quantitative determination of bioactive alkaloids lysergol and chanoclavine in Ipomoea muricata by reversed-phase high-performance liquid chromatography.
PubMed:
Changes in concentrations of lysergol in urine and prolactin in plasma, rectal temperature and respiration rate in sheep selected for resistance or susceptibility to ryegrass staggers and fed ergovaline.
PubMed:
Enantioselective total synthesis of (+)-lysergic acid, (+)-lysergol, and (+)-isolysergol by palladium-catalyzed domino cyclization of allenes bearing amino and bromoindolyl groups.
PubMed:
Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.
PubMed:
Large-scale separation of clavine alkaloids from Ipomoea muricata by pH-zone-refining centrifugal partition chromatography.
PubMed:
Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.
PubMed:
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.
PubMed:
Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography.
PubMed:
Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds.
PubMed:
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.
PubMed:
Ergot alkaloid transport across ruminant gastric tissues.
PubMed:
[Potential role of serotonin-sensitive structures in amplification of duodenal motor activity due to irritation of sympathetic trunk].
PubMed:
Simple O-acylated derivatives of lysergol and dihydrolysergol-I: synthesis and interaction with 5-HT2A, 5-HT2C and 5-HT1B receptors, and alpha1 adrenergic receptors.
PubMed:
Cycloalkanecarboxylic esters derived from lysergol, dihydrolysergol-I, and elymoclavine as partial agonists and antagonists at rat 5-HT2A receptors: pharmacological evidence that the indolo[4,3-fg]quinoline system of the ergolines is responsible for high 5-HT2A receptor affinity.
PubMed:
Vaccination against ergot alkaloids and the effect of endophyte-infected fescue seed-based diets on rabbits.
PubMed:
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
PubMed:
Naturally occurring clavines: antagonism/partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels.
PubMed:
Ergot alkaloid glycosides with immunomodulatory activities.
PubMed:
Antibody binding of circulating ergot alkaloids in cattle grazing tall fescue.
PubMed:
Cell-specific coupling of the cloned human 5-HT1F receptor to multiple signal transduction pathways.
PubMed:
5-Hydroxytryptamine (5-HT) contracts the guinea-pig isolated iliac artery via 5-HT1-like and 5-HT2 receptors.
PubMed:
O-acylated lysergol and dihydrolysergol-I derivatives as competitive antagonists of 5-HT at 5-HT2 receptors of rat tail artery. Allosteric modulation instead of pseudoirreversible inhibition.
PubMed:
Confirmation of LSD intoxication by analysis of serum and urine.
PubMed:
Effect of ergot alkaloids from fungal endophyte-infected grasses on fall armyworm (Spodoptera frugiperda).
PubMed:
Substituted ergolines: potential antipsychotics with unique profile. I. Psychopharmacological characterization.
PubMed:
Substituted ergolines: potential antipsychotics with unique profile. II. Neurochemical characterization.
PubMed:
Regulation of the immune response by ergot alkaloids.
PubMed:
Synthesis of 10alpha-methoxy-delta8,9-lysergaldehyde from elymoclavine.