lysergol

General Material Information

Preferred name	lysergol
Trivial Name	Lysergol
Short Description	ergoline-8-methanol, 9,10-didehydro-6-methyl-, (8beta)- (9CI)
Formula	C16 H18 N2 O
CAS Number	602-85-7
ECHA Number	210-024-5
FDA UNII	Search
Nikkaji Number	J2.673.613G
Beilstein Number	0088476
MDL	MFCD00010029
NMR Predictor	External link
Applications	natural substances and extractives
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 Ergoline-8-methanol, 9,10-didehydro-6-methyl-, (8β)- Ergoline-8β-methanol, 9,10-didehydro-6-methyl- Indolo[4,3-fg]quinoline, ergoline-8-methanol deriv. (8β)-9,10-Didehydro-6-methylergoline-8-methanol NSC 196867 (+)-Lysergol

Potential Uses

US / EU / FDA / JECFA / FEMA / Scholar / Patents

Google Scholar	Start search
Google Books	Start search
Google Patents	Start search
Perfumer & Flavorists	Start search
EU Patents	Start search
PubMeb	Start search
NCBI	Start search

Literature & References

	[(6aS,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]methanol
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	99212
Pubchem (sid):	135057547

Publications by PubMed
Identification of legal highs--ergot alkaloid patterns in two Argyreia nervosa products.
Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax.
Application of quantitative structure-activity relationship models of 5-HT1A receptor binding to virtual screening identifies novel and potent 5-HT1A ligands.
Antibacterial and synergy of clavine alkaloid lysergol and its derivatives against nalidixic acid-resistant Escherichia coli.
High-throughput screening with a miniaturized radioligand competition assay identifies new modulators of human α2-adrenoceptors.
Lysergol monohydrate.
Simultaneous quantification of berberine and lysergol by HPLC-UV: evidence that lysergol enhances the oral bioavailability of berberine in rats.
Quantitative determination of bioactive alkaloids lysergol and chanoclavine in Ipomoea muricata by reversed-phase high-performance liquid chromatography.
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.
Enantioselective total synthesis of (+)-lysergic acid, (+)-lysergol, and (+)-isolysergol by palladium-catalyzed domino cyclization of allenes bearing amino and bromoindolyl groups.
Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.
Large-scale separation of clavine alkaloids from Ipomoea muricata by pH-zone-refining centrifugal partition chromatography.
Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.
Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography.
Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds.
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.
Ergot alkaloid transport across ruminant gastric tissues.
[Potential role of serotonin-sensitive structures in amplification of duodenal motor activity due to irritation of sympathetic trunk].
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.
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.
Vaccination against ergot alkaloids and the effect of endophyte-infected fescue seed-based diets on rabbits.
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.
Naturally occurring clavines: antagonism/partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels.
Ergot alkaloid glycosides with immunomodulatory activities.
Antibody binding of circulating ergot alkaloids in cattle grazing tall fescue.
Cell-specific coupling of the cloned human 5-HT1F receptor to multiple signal transduction pathways.
5-Hydroxytryptamine (5-HT) contracts the guinea-pig isolated iliac artery via 5-HT1-like and 5-HT2 receptors.
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.
Confirmation of LSD intoxication by analysis of serum and urine.
Effect of ergot alkaloids from fungal endophyte-infected grasses on fall armyworm (Spodoptera frugiperda).
Substituted ergolines: potential antipsychotics with unique profile. I. Psychopharmacological characterization.
Substituted ergolines: potential antipsychotics with unique profile. II. Neurochemical characterization.
Regulation of the immune response by ergot alkaloids.
Synthesis of 10alpha-methoxy-delta8,9-lysergaldehyde from elymoclavine.

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
CHEMBL:	View
HMDB (The Human Metabolome Database):	Search
Export Tariff Code:	2939.60.0000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Suppliers

BOC Sciences	Carbosynth
Santa Cruz Biotechnology	Sigma-Aldrich: Aldrich

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	254.33265686035
Flash Point TCC Value	235.5 °C TCC
logP (o/w)	1.76 est
Solubility
water, 722.8 mg/L @ 25 °C (est)	Yes

Safety Information

Safety information

Preferred SDS: View

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:
intravenous-rabbit LD50 320 ug/kg "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 97, 1972.
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

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.

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 :99212

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

[(6aS,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]methanol

Chemidplus:0000602857

RTECS:KE6330000 for cas# 602-85-7