222733-86-0

Basic information

• Product Name: 5-TERT-BUTYLTRYPTAMINE
• Synonyms: 5-TERT-BUTYLTRYPTAMINE;2-(5-tert-Butyl-1H-indol-3-yl)-ethylamine
• CAS NO: 222733-86-0
• Molecular Formula: C₁₄H₂₀N₂
• Molecular Weight: 216.32
• Mol File: 222733-86-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 375.2 °C at 760 mmHg
• Flash Point: 208.6 °C
• Appearance: /
• Density: 1.054 g/cm³
• Vapor Pressure: 7.9E-06mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: 5-TERT-BUTYLTRYPTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-TERT-BUTYLTRYPTAMINE(222733-86-0)
• EPA Substance Registry System: 5-TERT-BUTYLTRYPTAMINE(222733-86-0)

Safety Data

• Hazardous Substances Data: 222733-86-0(Hazardous Substances Data)

Usage

General Description

5-TERT-BUTYLTRYPTAMINE is a synthetic chemical compound that belongs to the family of tryptamines, which are known for their psychoactive and hallucinogenic effects. This particular compound is a derivative of tryptamine and has a tert-butyl group attached to the nitrogen atom. It is also known by the street name 5-TBTT and has been used recreationally for its psychedelic effects, including visual distortions and alterations in perception. Research on the effects and potential medicinal uses of 5-TERT-BUTYLTRYPTAMINE is limited, but it is known to interact with serotonin receptors in the brain, leading to its psychoactive properties. Its use is not approved for medical or recreational purposes, and its legality varies by country.

InChI:InChI=1/C14H20N2/c1-14(2,3)11-4-5-13-12(8-11)10(6-7-15)9-16-13/h4-5,8-9,16H,6-7,15H2,1-3H3

Upstream product

• 769-92-6 4-tert-Butylaniline 
• 222733-84-8 2-[2-(5-tert-butyl-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione 
• 36600-66-5 4-tert-butylphenylhydrazine hydrochloride 

Downstream Products

• 1014700-19-6 C₂₂H₂₃F₃N₂O₂ 

Relevant articles and documents

New synthetic technologies for the construction of heterocycles and tryptamines

New synthetic methods for the construction of novel heterocycles and tryptamines are described. Thus, N-Boc anilines (I) are sequentially converted to heterocycles II ((3-(2-aminophenyl)pyrrolidin-3-ol) derivatives),III (substituted 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrol idines), and VI (2-(4,5-dihydro-1H-pyrrol-3-yl)aniline) derivatives through a route involving t-BuLi induced ortho-metalation/ LaCl3 2LiCl metalexchange, reaction with N-Boc pyrrolidin-3-one (5), and subsequent deca rboxylative fragmentation. Labile intermediates VI are effectively converted to tryptamines Xa and Xb under controlled proticacidconditions.Inadditiontoprovidingexpedientaccesstothe2-oxo- 1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrolidines (III), the method is applicable to the synthesis of the corresponding 2-oxo-1,2-dihydrospirobenzo[d] [1,3]oxazine-4,3'-piperidine series of spirocycles (e.g., 42) and their precursors (3-(2-aminophenyl)piperidin-3-ol derivatives, e.g., 43) by using N-Boc-protected piperidin-3-one (40). Applications of the developed synthetic technologies to the synthesis of regioisomeric spirocycles 87 and 90, tryptamines 88 and 91, Corey's aspidophytine tryptamine (97), and efavirenz (1) are also described.

N-methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT(1D) receptor agonist

It has been observed that reported 5-HT(1D) receptor agonists have at least one heteroatom (N, O, or S) on the 5-substituent of the indole. This has led to the hypothesis that a 5-substituent capable of participating in hydrogen bonding is critical for conveying high affinity. This article describes the synthesis and biological evaluation of a new series of 5- alkyltryptamine analogues, which does not have a heteroatom in the 5- substituent group. In contrast to the hypothesis, 5-alkyltryptamines all exhibit high binding affinities for the human 5-HT(1D) receptor. The size of the lipophilic alkyl group at the 5-position of the indole has significant impact on the 5-HT(1D) binding affinity. Compounds with a tert-butyl group at the 5-position such as 9d, 10, and 11 were identified. These analogues display high binding affinity (K(i) 1 nM) and moderate receptor selectivity in comparison with known antimigraine agents such as sumatriptan, naratriptan, rizatriptan, and VML-251.