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
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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL214 |
2.3 nM [Ki] | ||
1.6 nM [EC50] | |||
6.6 nM [EC50] | |||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22982401 |
199.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24410373
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.
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NTR684Z1AZ
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1413-67-8
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LYSERGOL
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14987
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SUBSTANCE RECORD