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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18N2O
Molecular Weight 254.3269
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYSERGOL

SMILES

[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@@H](CO)CN2C

InChI

InChIKey=BIXJFIJYBLJTMK-MEBBXXQBSA-N
InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15-/m1/s1

HIDE SMILES / InChI
Lysergol {LYZ; (7-methyl- 4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol} has shown potential to enhance BA of berberine (poorly water soluble herbal anticancer agent). It is obtained from the seeds of Ipomoea muricata, I. turbinate and Calonyction muricata belonging to the family Convolvulaceae. Seeds are commonly known as ‘Kaladana’ in trade and are being used as a purgative in India and Pakistan. LYZ is an indole alkaloid present in the microfungi of Claviceps purpurea as well. It is one of the minor constituents of the ancient Mexican hallucinogenic drug Ololiuqui, which is obtained from Rivea corymbosa seeds. LYZ has been used by the 17th century midwives to induce labour and stop postpartum bleeding because of its ability to induce uterine contractions. It may also cause ergot poisoning, diarrhea, hallucinations, delirium, seizures, burning sensations, and gangrene in the limbs. However, it is not being used presently in the clinic.

CNS Activity

Curator's Comment: Lysergol has only a weak central stimulating activity at 20 mg/kg dose in mice.

Approval Year

PubMed

PubMed

TitleDatePubMed
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
1992 Apr 15
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.
1996 Nov
Ergot alkaloid transport across ruminant gastric tissues.
2001 Feb
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.
2004 Nov
Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds.
2005 Nov
Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography.
2006 Jul
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.
2007
Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.
2008 Nov 20
Large-scale separation of clavine alkaloids from Ipomoea muricata by pH-zone-refining centrifugal partition chromatography.
2009 Jun 15
Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.
2010 Jun 4
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

The PK study of CUR in male Sprague Dawley rats at 100 mg/kg was performed with and without coadministration of Lysergol (LYZ) (20 mg/kg) and the results revealed that the animals tolerated the treatment as no peculiarities in their behavior were observed.
Route of Administration: Oral
Lysergol yielded 98.20% binding inhibition against 5-HT1A receptor at 10 uM and its Ki value was found to be 2.3 nM afterward.
Name Type Language
LYSERGOL
Common Name English
(7-METHYL-4,6,6A,7,8,9-HEXAHYDRO-INDOLO(4,3-FG)QUINOLIN-9-YL)-METHANOL
Common Name English
Code System Code Type Description
FDA UNII
NTR684Z1AZ
Created by admin on Fri Dec 15 14:57:45 GMT 2023 , Edited by admin on Fri Dec 15 14:57:45 GMT 2023
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CAS
1413-67-8
Created by admin on Fri Dec 15 14:57:45 GMT 2023 , Edited by admin on Fri Dec 15 14:57:45 GMT 2023
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WIKIPEDIA
LYSERGOL
Created by admin on Fri Dec 15 14:57:45 GMT 2023 , Edited by admin on Fri Dec 15 14:57:45 GMT 2023
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PUBCHEM
14987
Created by admin on Fri Dec 15 14:57:45 GMT 2023 , Edited by admin on Fri Dec 15 14:57:45 GMT 2023
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