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Lysergol

HCID 14987
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Basic information

CAS
1413-67-8
Standard SMILES
CN1C[C@H](CO)C=C2c3cccc4[nH]cc(c34)C[C@H]21
InChIKey
BIXJFIJYBLJTMK-MEBBXXQBSA-N
Molecular formula
C16H18N2O
Average molar mass
254.33 g/mol
Monoisotopic mass
254.1419132

Overview

Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi and in the morning glory family of plants. Its structure is that of ergoline with a methyl group at N-6 and a beta-hydroxymethyl substituent at C-8.

Names & identifiers

Preferred name
Lysergol
IUPAC
[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol

Names & synonyms

lysergol602-85-7NTR684Z1AZ[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol9,10-Didehydro-6-methyl-8-hydroxymethylergoline(6-methyl-9,10-didehydroergolin-8beta-yl)methanol9,10-didehydro-6-methylergoline-8b-methanolCHEBI:60528(7-Methyl-4,6,6a,7,8,9-hexahydro-indolo(4,3-fg)quinolin-9-yl)-methanolMethanol, 1-((8beta)-9,10-didehydro-6-methylergolin-8-yl)-(7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol((6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-yl)methanol
Show more names
DTXSID40975627((6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinolin-9-yl)methanol[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]methanolRefChem:154751DTXCID10220393(6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),2,9,12,14-pentaen-4-yl)methanol210-024-5Prestwick_308

Database identifiers

CAS
1413-67-8、602-85-7
PubChem CID
14987
ChEMBL
CHEMBL39947

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
39.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
19
Formal charge
0
Complexity
394

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H300 (97.6%): Fatal if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 2 (97.6%)

Toxicology

Treatment · 1 item

Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921)

Health EffectsIngestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. (A2914, A2915, A2916)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Uses & manufacturing

Uses · 1 item

Lysergol, is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi (most within Claviceps), and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea. Lysergol can be utilized as an intermediate in the manufacture of some ergoloid medicines. (L1928)

Related reactions

10 records
New reaction record
HRID 547956 reaction equation
HRID 547956As reactantuspto-grants-2011_05
HRID 547957 reaction equation
HRID 547957As reactantuspto-grants-2011_05
HRID 1089871 reaction equation
HRID 1089871As reactantuspto-grants-1992_01
HRID 1195070 reaction equation
HRID 1195070As reactantuspto-grants-1989_03
HRID 1195071 reaction equation
HRID 1195071As reactantuspto-grants-1989_03
HRID 1195072 reaction equation
HRID 1195072As reactantuspto-grants-1989_03
HRID 1723027 reaction equation
HRID 1723027As reactantuspto-grants-1989_08
HRID 1905369 reaction equation
HRID 1905369As reactantuspto-grants-1989_06
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Compound notes

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ChEBI
CHEBI:60528
UNII
NTR684Z1AZ
EC Number
210-024-5
Nikkaji
J14.234D
Signs and Symptoms · 1 item

Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).