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3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol

Bufotenine

HCID 10257
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Grundinformationen

CAS
487-93-4
Standard-SMILES
CN(C)CCc1c[nH]c2ccc(O)cc12
InChIKey
VTTONGPRPXSUTJ-UHFFFAOYSA-N
Summenformel
C12H16N2O
Durchschnittliche Molmasse
204,27 g/mol
Monoisotopische Masse
204,12626314

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Bufotenine
IUPAC
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
Lokaler Name
3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol
Englischer Name
Bufotenine
Summenformel
C12H16N2O
Molmasse
204.27

Namen und Synonyme

BufotenineBufotenin487-93-4N,N-DimethylserotoninMappineN,N-Dimethyl-5-hydroxytryptamineMappinDimethylserotoninCohoba5-Hydroxy-N,N-dimethyltryptamineDM5-HT3-(2-Dimethylaminoethyl)-5-indolol
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,2
Polarare Oberfläche (TPSA)
39,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
15
Formalladung
0
Komplexität
208

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

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

Physikochemische Eigenschaften

Schmelzpunkt
62 · 62-64°C
Siedepunkt
0.1 · bp0.1 320°
Dichte
1.0565 · 1.0565 (rough estimate)
Brechungsindex
1.6 · 1.6000 (estimate)
Flammpunkt
2 ℃ · 2℃
storage temp.
Refrigerator, Under Inert Atmosphere

Sicherheit und Regulatorisches

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GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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

Toxikologische Informationen

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

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)

Chemie und Industrie

Pharmakologische Informationen

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

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 Einträge

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.

Verwendung und Herstellung

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

HistoryBufotenin 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.

VerwendenControlled 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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Löslichkeit
Bufotenine is soluble in dilute acids and alkalis.
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
InChIKey
VTTONGPRPXSUTJ-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(O)C=C2)C(CCN(C)C)=C1
EPA chemische Informationen
1 H-Indol-5-ol, · 1H-Indol-5-ol, 3-[2-(dimethylamino)ethyl]- (487-93-4)
Signs and Symptoms
Bufotenin exposure produces local irritation and causes hallucinations. It may also cause circulation problems peripheral nervous system effects such as flushing and hyperventilation. (L1081)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

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

Anbieter32 Anbieter

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.