CHEBI:3210 - bufotenin

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ChEBI Name bufotenin
ChEBI ID CHEBI:3210
Definition A tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H16N2O
Net Charge 0
Average Mass 204.26820
Monoisotopic Mass 204.126
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 CN(C)CCc1c[nH]c2ccc(O)cc12
Metabolite of Species Details
Paramuricea clavata (NCBI:317549) CH2Cl2:MeOH(1:1) extract of lyophilized material See: PubMed
Roles Classification
Biological Role(s): coral metabolite
Any animal metabolite produced during a metabolic reaction in corals (marine invertebrates).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): hallucinogen
Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
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ChEBI Ontology
Outgoing bufotenin (CHEBI:3210) has functional parent N,N-dimethyltryptamine (CHEBI:28969)
bufotenin (CHEBI:3210) has role coral metabolite (CHEBI:76498)
bufotenin (CHEBI:3210) has role hallucinogen (CHEBI:35499)
bufotenin (CHEBI:3210) is a tertiary amine (CHEBI:32876)
bufotenin (CHEBI:3210) is a tryptamine alkaloid (CHEBI:48274)
Incoming 5-methoxy-N,N-dimethyltryptamine (CHEBI:2086) has functional parent bufotenin (CHEBI:3210)
IUPAC Name
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
Synonyms Sources
3-[2-(dimethylamino)ethyl]-5-indolol NIST Chemistry WebBook
3-[2-(dimethylamino)ethyl]indol-5-ol NIST Chemistry WebBook
3-[β-(dimethylamino)ethyl]-5-hydroxyindole NIST Chemistry WebBook
5-hydroxy-N,N-dimethyltryptamine ChemIDplus
Bufotenin KEGG COMPOUND
Bufotenine KEGG COMPOUND
DM5-HT NIST Chemistry WebBook
N,N-dimethylserotonin ChemIDplus
N,N-Dimethylserotonin KEGG COMPOUND
Database Links Databases
Bufotenin Wikipedia
C00001402 KNApSAcK
C08299 KEGG COMPOUND
DB01445 DrugBank
View more database links
Registry Numbers Types Sources
160628 Reaxys Registry Number Reaxys
160628 Beilstein Registry Number Beilstein
487-93-4 CAS Registry Number KEGG COMPOUND
487-93-4 CAS Registry Number ChemIDplus
487-93-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11718320 PubMed citation Europe PMC
16095048 PubMed citation Europe PMC
19303230 PubMed citation Europe PMC
20150873 PubMed citation Europe PMC
20206139 PubMed citation Europe PMC
20942780 PubMed citation Europe PMC
21624387 PubMed citation Europe PMC
4091027 PubMed citation Europe PMC
658125 PubMed citation Europe PMC
8532147 PubMed citation Europe PMC
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8895112 PubMed citation Europe PMC
Last Modified
26 May 2015