487-93-4

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 
• 46880-50-6 2-(2,5-dimethoxy-phenyl)-N⁴,N⁴-dimethyl-butanediyldiamine 
• 25390-67-4 5-Benzyloxy DMT 
• 15992-84-4 6-hydroxy-5,5-dimethyl-1,3,4,5-tetrahydro-pyrrolo[4,3,2-de]quinolinium; chloride 
• 1019-45-0 N,N-dimethyl-5-methoxytryptamine 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 161202-91-1 1-hydroxy-N,N-dimethyltryptamine 
• 38662-17-8 2-(dihydroindol-3-yl)-N,N-dimethylethylamine 
• 3471-31-6 5-methoxy-1H-indole-3-acetic acid 
• 23304-48-5 (5-methoxy-1H-indol-3-yl)acetic acid methyl ester 
• 858000-71-2 2-(5-ethoxy-indol-3-yl)-ethanol 
• 2436-16-0 (5-ethoxy-indol-3-yl)-acetonitrile 
• 857809-50-8 5-ethoxy-3-indoleacetic acid 

Downstream Products

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

Relevant academic research and scientific papers

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

Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: Synthesis of psilocin, bufotenin, and serotonin

Observations concerning the synthesis of substituted tryptamine derivatives starting from indoles and 1,n-amino alcohols via the borrowing hydrogen process are discussed. This catalytic, single-step, and modular approach to tryptamines and homotryptamines allows the synthesis of branched and nonbranched tryptamines as well as tryptamine-based natural products such as psilocin, bufotenin, and serotonin.

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)

NOVEL COMPOSITIONS AND METHODS FOR TREATING CANCER

Provided herein are methods and compositions inter alia for treating diseases, including hyperproliferative diseases, migraine headaches, and depression.

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).

Isolation of N,N-dimethyl and N-methylserotonin 5-0-ss-glucosides from immature zanthoxylum piperitum seeds

Two serotonin derivatives, N,N-dimethylserotonin 5-O-ss-glucoside (la) and N-methylserotonin 5-O-ss-glucoside (lb) were isolated from immature seeds of Zanthoxylum piperitum. Their structures were determined by multi-step conversion reactions and spectro-scopic analyses. Immature seeds of Z. piperitum contained extremely high levels of compounds la and lb of approximately 0.29% and 0.15% (w/w), respectively.

Aromatization of 1,6,7,7a-tetrahydro-2H-indol-2-ones by a novel process. Preparation of key-intermediate methyl 1-benzyl-5-methoxy-1H-indole-3-acetate and the syntheses of serotonin, melatonin, and bufotenin

Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry

Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.

Syntheses of Serotonin, N-Methylserotonin, Bufotenine, and Melatonin, and the First Total Synthesis of N-(Indol-3-yl)methyl-N-methyl-5-methoxytryptamine from Tryptamine through a Common Intermediate, 1-Hydroxytryptamine

Simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), and melatonin (2), and the first total synthesis of N-(indol-3-yl)methyl-N-methyl-5-methoxytryptamine (3) from tryptamine (4a) are reported through acid catalyzed nucleophilic substitution reaction of 1-hydroxytryptamines.

Synthesis of 131I derivatives of indolealkylamines for brain mapping

The synthesis and spectral properties of new radioiodinated indolealkylamines like 2-[131 I]-iodo-N,N-dimethyltryptamine, 2-[131 I]-iodo-N-methyltryptamine, 2-[131 I]-iodo-5-methoxy-N,N-dimethyltryptamine, 2-[131 I]-iodo-5-hydroxy-N,N-dimethyltryptamine (2-[131 I]-iodo-bufotenine), and 2-[131I]-iodo-tryptamine and the known 2-[131I]-iodo-N-acetyl-5-methoxy-tryptamine (2-[131I]-iodo-melatonine) are described herein. These were synthesized by a high-yield novel method, and their spectral properties are fully described. These compounds are of biological importance and can be used for brain mapping with SPECT technology.