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뷰포테닌

Bufotenine

HCID 10257
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
487-93-4
표준 SMILES
CN(C)CCc1c[nH]c2ccc(O)cc12
InChIKey
VTTONGPRPXSUTJ-UHFFFAOYSA-N
분자식
C12H16N2O
평균 분자량
204.27 g/mol
단동위원소 질량
204.12626314

개요

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.

이름 및 식별자

우선 이름
Bufotenine
IUPAC
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
현지명
뷰포테닌
영어명
Bufotenine
분자식
C12H16N2O
분자량
204.27

이름 및 동의어

BufotenineBufotenin487-93-4N,N-DimethylserotoninMappineN,N-Dimethyl-5-hydroxytryptamineMappinDimethylserotoninCohoba5-Hydroxy-N,N-dimethyltryptamineDM5-HT3-(2-Dimethylaminoethyl)-5-indolol
이름 더 보기
뷰포테닌MapineNSC 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

데이터베이스 식별자

CAS
487-93-4
PubChem CID
10257
DTXSID
DTXSID0048894
ChEMBL
CHEMBL416526
ChEBI
CHEBI:3210
UNII
0A31347TZK
EC Number
207-667-9
Nikkaji
J6.027E

물성

구조 계산 물성

XLogP
1.2
극성 표면적
39.3 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
15
형식 전하
0
복잡도
208

실험 및 물리화학적 성질

Drugs · 3건

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

물리화학적 성질

녹는점
62 · 62-64°C
끓는 점
0.1 · bp0.1 320°
밀도
1.0565 · 1.0565 (rough estimate)
굴절률
1.6 · 1.6000 (estimate)
인화점
2 ℃ · 2℃
저장 조건
Refrigerator, Under Inert Atmosphere
용해도
부포테닌은 묽은 산과 알칼리에 용해됩니다.
산도 계수 (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

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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

독성 정보

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

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)

화학 및 산업

약리 정보

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

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 · 2건

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.

용도 및 제조

UsesBufotenin is a toxin found in some toads (genus Bufo) and mushrooms (genus Amanita). (L1081)
Use ClassificationPharmaceuticals
응용 분야 · 2건

역사Bufotenin 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.

용도Controlled 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.

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
InChIKey
VTTONGPRPXSUTJ-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(O)C=C2)C(CCN(C)C)=C1
EPA
1 H-Indol-5-ol, · 1H-Indol-5-ol, 3-[2-(dimethylamino)ethyl]- (487-93-4)
화학적 성질 · 1건

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.

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

안전 데이터

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

공급사32 곳

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추가 설명 · 1건

정의ChEBI: 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.