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3-[2-(ジメチルアミノ)エチル]-5-ヒドロキシ-1H-インドール

Bufotenine

HCID 10257
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
487-93-4
標準SMILES
CN(C)CCc1c[nH]c2ccc(O)cc12
InChIKey
VTTONGPRPXSUTJ-UHFFFAOYSA-N
分子式
C12H16N2O
平均分子量
204.27 g/mol
単同位体質量
204.12626314

概要

Bufotenin is a tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5. It has a role as a hallucinogen and a coral metabolite. It is a tertiary amine and a tryptamine alkaloid. It is functionally related to a N,N-dimethyltryptamine.

名称と識別子

優先名称
Bufotenine
IUPAC
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
現地名
3-[2-(ジメチルアミノ)エチル]-5-ヒドロキシ-1H-インドール
英語名
Bufotenine
分子式
C12H16N2O
分子量
204.27

名称と別名

BufotenineBufotenin487-93-4N,N-DimethylserotoninMappineN,N-Dimethyl-5-hydroxytryptamineMappinDimethylserotoninCohoba5-Hydroxy-N,N-dimethyltryptamineDM5-HT3-(2-Dimethylaminoethyl)-5-indolol
名称をさらに表示
N,N-ジメチル-5-ヒドロキシ-1H-インドール-3-(エタンアミン)マッピン5-ヒドロキシ-N,N-ジメチルトリプタミン3-[2-(ジメチルアミノ)エチル]-5-ヒドロキシ-1H-インドール3-[2-(ジメチルアミノ)エチル]-1H-インドール-5-オール5-ヒドロキシ-N,N-ジメチル-1H-インドール-3-エタンアミンブホテニンN,N-ジメチル-5-ヒドロキシトリプタミンブフォテニン3-(2-(ジメチルアミノ)エチル)-1H-インドール-5-オールMapineNSC 89Bafotenine
3-[2-(Dimethylamino)ethyl]-1H-indol-5-olN,N-Dimethyl-5-HT5-OH-DMT3-(beta-Dimethylaminoethyl)-5-hydroxyindole1H-Indol-5-ol, 3-(2-(dimethylamino)ethyl)-DTXSID00488943-[2-(Dimethylamino)ethyl]-5-indolol3-[2-(Dimethylamino)ethyl]indol-5-ol

データベース識別子

CAS
487-93-4

物性

構造計算による物性

XLogP
1.2
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
3
重原子数
15
形式電荷
0
複雑度
208

実験および物理化学的性質

Drugs · 3 件

DEA Schedule I Controlled Substance -> Hallucinogenic substances

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesCrystal structure
Human DrugsPharmaceuticals
Melting Point146.5 °C
Physical DescriptionSolid

物理化学的性質

融点
62 · 62-64°C
沸点
0.1 · bp0.1 320°
比重(密度)
1.0565 · 1.0565 (rough estimate)
屈折率
1.6 · 1.6000 (estimate)
闪点
2 ℃ · 2℃
貯蔵温度
Refrigerator, Under Inert Atmosphere
溶解性
ブフォテニンは、希酸および希アルカリに可溶です。
酸解離定数(Pka)
10.11 · 10.11±0.40(Predicted)
InChI
InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

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

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, 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)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationDEA schedule I controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Health EffectsBufotenin is neurotoxic and can cause hallucinations. (L1081)
Exposure RoutesIngestion (L1815)
Toxicity Summary · 3 件

Bufotenin is present in the skin of some common species of frogs, and its ingestion (such as from licking or kissing a frog) can result in vivid hallucinations.

Bufotenin (5-hydroxy-N,N-dimetyltryptamine) is a tryptamine alkaloid widely present in frogs as a component of their chemical defense system. It is a potent hallucinogen, with activity similar activity to LSD from interacting with the 5HT2 human receptor.

Bufotenin is a neurotoxin similar to the mushroom toxin psilocin. Thus it likely acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is likely also a 5-HT1A and 5-HT2A/2C agonist. (L1081, L1673)

Signs and SymptomsBufotenin exposure produces local irritation and causes hallucinations. It may also cause circulation problems peripheral nervous system effects such as flushing and hyperventilation. (L1081)

化学と産業

薬理情報

PharmacodynamicsBufotenin is a tryptamine related to the neurotransmitter serotonin.
Metabolism/Metabolites · 2 件

Upon oral administration, bufotenine is extensively metabolized by monoamine oxidase enzymes.

Bufotenine is a known human metabolite of n,n-dimethyl-5-methoxytryptamine.

MeSH Pharmacological Classification · 2 件

Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise.

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.

Absorption, Distribution and ExcretionRapidly absorbed following intravenous administration.

用途と製造

UsesBufotenin is a toxin found in some toads (genus Bufo) and mushrooms (genus Amanita). (L1081)
Use ClassificationPharmaceuticals
応用分野 · 3 件

解説ブホテニン.ヒキガエルBufo vulgaris Laurentiの皮腺分泌物(漢薬名センソ),毒キノコ,あるいは南米のマメ科植物などから単離されている.また,2,5-ジメトキシベンズアルデヒドから数工程で合成されている.無色の結晶.融点146~147 ℃,沸点320 ℃(0.1 kPa).エタノールに易溶,エーテル,アセトン,希酸およびアルカリに可溶,水に不溶.セロトニンのN,N-ジメチル誘導体である.幻覚剤であるが,発がん性や精神錯乱作用も認められている.

来歴Bufotenin was isolated from toad skin, and named by the Austrian chemist Handovsky at the University of Prague during World War I.The structure of bufotenine was confirmed in 1934 by Heinrich Wieland's laboratory in Munich, and the first reported synthesis of bufotenine was by Toshio Hoshino and Kenya Shimodaira in 1935.

関連反応

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化合物ノート

読み込み中…

このページの内容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
PubChem CID
10257
DTXSID
DTXSID0048894
ChEMBL
CHEMBL416526
ChEBI
CHEBI:3210
UNII
0A31347TZK
EC Number
207-667-9
Nikkaji
J6.027E
InChIKey
VTTONGPRPXSUTJ-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(O)C=C2)C(CCN(C)C)=C1
EPAの化学物質情報
1 H-Indol-5-ol, · 1H-Indol-5-ol, 3-[2-(dimethylamino)ethyl]- (487-93-4)
化学的性質 · 2 件

化学的特性Bufotenine is an indole alkaloid obtained from the seeds and leaves of Piptadenia peregrine and P. macrocarpa. It has also been isolated from the skin glands of toads (Bufo species). The base is typically seen as white crystalline powder and the oxalate hydrate as a lavender to brown powder. The oxalate hydrate is slightly soluble in chloroform and can be separated from chloroform insoluble material for analysis.

化学性质ブフォテニンは複雑な有機分子であり分子式はC31H48O9と表されますこの分子は光に対して高い感受性を示し紫外線を吸収して可視光を放出する能力がありますこの特性は蛍光性物質としての使用を可能にします

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

安全データ

wgk
2
ridadr
1544
risk_code
11-20/21/22-36
hazard_code
F,Xn
safety_code
16-36/37
hazard_class
6.1(b)
packing_group
III
DEA Controlled Substances
CSCN: 7433CSA SCH: Schedule INARC: No

使用Controlled substance (hallucinogen).Bufotenine is a hallucinogenic serotonin analog found in frog and toad skins, mushrooms, plants and some mammals (especially in the brains, plasma, and urine of schizophrenics). It is a potent hallucinogen used in its natural state by several shaman sects and in some drug abuse situations in the United States and Australia. It causes schizophrenia and other psychotic symptoms.

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補足説明 · 1 件

定義ChEBI: Bufotenine is a tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5. It has a role as a hallucinogen and a coral metabolite. It is a tryptamine alkaloid and a tertiary amine. It derives from a N,N-dimethyltryptamine.