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Lysergol

HCID 14987
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
1413-67-8
標準SMILES
CN1C[C@H](CO)C=C2c3cccc4[nH]cc(c34)C[C@H]21
InChIKey
BIXJFIJYBLJTMK-MEBBXXQBSA-N
分子式
C16H18N2O
平均分子量
254.33 g/mol
単同位体質量
254.1419132

概要

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.

名称と識別子

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

名称と別名

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
名称をさらに表示
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

データベース識別子

CAS
1413-67-8、602-85-7
PubChem CID
14987
ChEMBL
CHEMBL39947
ChEBI
CHEBI:60528
UNII
NTR684Z1AZ
EC Number
210-024-5
Nikkaji
J14.234D

物性

構造計算による物性

XLogP
2.2
極性表面積
39.3 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
1
重原子数
19
形式電荷
0
複雑度
394

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 2 (97.6%)

毒性情報

Treatment · 1 件

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 件

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)

Signs and Symptoms · 1 件

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).

化学と産業

薬理情報

MeSH Pharmacological Classification · 1 件

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.

用途と製造

Uses · 1 件

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)

関連反応

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