487-93-4

Basic information

• Product Name: BUFOTENINE
• Synonyms: BUFOTENINE;1H-Indol-5-ol, 3-[2-(dimethylamino)ethyl]-;3-(2-(dimethylamino)ethyl)-indol-5-o;3-(2-dimethylaminoethyl)-5-indolol;3-(beta-dimethylaminoethyl)-5-hydroxyindole;3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol;3-[2-(Dimethylamino)ethyl]-5-indolol;3-[2-(Dimethylamino)ethyl]indol-5-ol
• CAS NO: 487-93-4
• Molecular Formula: C₁₂H₁₆N₂O
• Molecular Weight: 204.27
• EINECS: 207-667-9
• Product Categories: Amines;Aromatics;Heterocycles
• Mol File: 487-93-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 62-64°C
• Boiling Point: bp0.1 320°
• Flash Point: 2℃
• Appearance: /
• Density: 1.0565 (rough estimate)
• Vapor Pressure: 9.89E-07mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Bufotenine is soluble in dilute acids and alkalis.
• PKA: 10.11±0.40(Predicted)
• CAS DataBase Reference: BUFOTENINE(CAS DataBase Reference)
• NIST Chemistry Reference: BUFOTENINE(487-93-4)
• EPA Substance Registry System: BUFOTENINE(487-93-4)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37
• RIDADR: 1544
• WGK Germany: 2
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 487-93-4(Hazardous Substances Data)

Usage

Chemical Properties

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.

History

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.

Uses

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.

Definition

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.

InChI:InChI=1/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

Upstream product

• 855245-09-9 [2-(5-ethoxy-indol-3-yl)-ethyl]-dimethyl-amine 
• 1019-45-0 N,N-dimethyl-5-methoxytryptamine 
• 7647-01-0 hydrogenchloride 
• 15992-84-4 6-hydroxy-5,5-dimethyl-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinolinium; chloride 
• 61-50-7 N,N-dimethyltryptamine 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 18086-24-3 2-(2,5-dimethoxyphenyl)acetonitrile 
• 5594-91-2 1H-indol-5-yl acetate 
• 1215-59-4 5-benzyloxy-1H-indole 
• 50-00-0 formaldehyd 
• 153-98-0 serotonin hydrochloride 
• 64656-15-1 N,N-dimethylserotonin 5-O-β-glucoside 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 231289-63-7 2-(2,5-dimethoxy-phenyl)-4-dimethylamino-butyronitrile 

Downstream Products

• 487-91-2 bufotenidine 
• 185259-85-2 GR 46611 
• 102250-02-2 {2-[5-Methoxy-1-(2-nitro-phenylsulfanyl)-1H-indol-3-yl]-ethyl}-dimethyl-amine 
• 102250-03-3 {2-[5-Methoxy-2-(2-nitro-phenylsulfanyl)-1H-indol-3-yl]-ethyl}-dimethyl-amine 
• 102250-05-5 3-(2-Dimethylamino-ethyl)-2-(2-nitro-phenylsulfanyl)-1H-indol-5-ol 
• 5787-02-0 5-hydroxy-N,N-dimethyltryptamine iodomethylate 

Relevant articles and documents

Structure Elucidation and Spectroscopic Analysis of Chromophores Produced by Oxidative Psilocin Dimerization

Psilocin (1) is the dephosphorylated and psychotropic metabolite of the mushroom natural product psilocybin. Oxidation of the phenolic hydroxy group at the C-4 position of 1 results in formation of oligomeric indoloquinoid chromophores responsible for the

Benzocarbazoles heterocyclic compound and its preparation and use (by machine translation)

The present invention provides a class of non-nucleoside anti-viral inhibitors, in particular to such as shown in formula I benzo heterocyclic compound or its pharmaceutically acceptable salt or hydrate, the invention also provides the compound or its pharmaceutically acceptable salt or hydrate of the preparation method. Pharmacological test indicates that the compound or its pharmaceutically acceptable salt or hydrate can effectively inhibit hepatitis b virus DNA replication and hepatitis c virus RNA replication, therefore, the invention also provides the compounds in the preparation of preventing and/or the treatment of viral infections, particularly hepatitis b virus (HBV) infection, hepatitis c virus (HCV) infection of use of the medicament. (by machine translation)

Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus

A series of tryptamine derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. The preliminary SAR was discussed. Compounds 2e and 4a showed potent antiviral activity (IC50 = 0.4 and 50 = 40.6 and >25 μM, respectively).