343-94-2

Basic information

• Product Name: TRYPTAMINE HYDROCHLORIDE
• Synonyms: TRYPTAMINE HCL;TRYPTAMINE HYDROCHLORIDE;TIMTEC-BB SBB000359;3-(2-AMINOETHYL)INDOLE HCL;3-(2-AMINOETHYL)INDOLE HYDROCHLORIDE;2-(3-INDOLYL)ETHYLAMINE HYDROCHLORIDE;1h-indole-3-ethanamine,monohydrochloride;2-(1H-indol-3-yl)ethanamine hydrochloride
• CAS NO: 343-94-2
• Molecular Formula: C₁₀H₁₃N₂*Cl
• Molecular Weight: 196.68
• EINECS: 206-446-4
• Product Categories: Indole;Heterocyclic Compounds;Indoles;Tryptamines
• Mol File: 343-94-2.mol

Chemical Properties

• Melting Point: 253-255 °C(lit.)
• Boiling Point: 378.8°Cat760mmHg
• Flash Point: 187.7°C
• Appearance: Beige to light orange/Powder
• Density: 1.157g/cm³
• Vapor Pressure: 6.14E-06mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: water: soluble0.1g/10 mL, clear to slightly hazy, colorless to y
• Sensitive: Light Sensitive
• Merck: 14,9796
• BRN: 3568419
• CAS DataBase Reference: TRYPTAMINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRYPTAMINE HYDROCHLORIDE(343-94-2)
• EPA Substance Registry System: TRYPTAMINE HYDROCHLORIDE(343-94-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-41-37/38-22
• Safety Statements: 22-24/25-36/37/39-36-26
• WGK Germany: 3
• RTECS: NL4375000
• F: 3-8-10
• TSCA: Yes
• Hazardous Substances Data: 343-94-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tryptamine hydrochloride is used as a reactant for the preparation of various pharmaceutical compounds, including:
1. Tryptamine derivatives as inhibitors against hepatitis B virus: These derivatives help in the development of treatments for hepatitis B by inhibiting the virus's replication and spread.
2. Carbamoyl epipodophyllotoxins as potential antitumor agents: These compounds have shown potential in treating various types of cancer due to their ability to inhibit cell division and proliferation in cancer cells.
3. Anthranilic acid derivatives as CCK receptor antagonists: These derivatives are used in the development of drugs targeting cholecystokinin (CCK) receptors, which play a role in various physiological processes, including digestion and pain transmission.
4. Brassinin derivatives as indoleamine 2,3-dioxygenase inhibitors: These compounds inhibit the enzyme indoleamine 2,3-dioxygenase, which is involved in the breakdown of tryptophan. Inhibition of this enzyme has potential therapeutic applications in various diseases, including neurodegenerative disorders and cancer.
5. Antispasmodic agents: Tryptamine hydrochloride and its derivatives can be used in the development of antispasmodic drugs, which help in relieving muscle spasms and pain.
6. β-carbolinium cations as new antimalarial agents: These cations, derived from tryptamine hydrochloride, have shown potential as new antimalarial agents, offering an alternative to traditional treatments for malaria.

Purification Methods

Crystallise the salt from EtOH/water or EtOH/Et2O. See previous entry for UV. [Beilstein 22 II 347, 22 III/IV 4319, 22/10 V 46.]

InChI:InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2/p+1

Upstream product

• 3156-51-2 3-[(E)-2-nitroeth-1-enyl]-1H-indole 
• 54-12-6 Trp 
• 1016-47-3 N-Acetyltryptamine 
• 107-21-1 ethylene glycol 
• 120-72-9 indole 
• 27520-72-5 N-formyl-L-tryptophan 
• 61-54-1 tryptamine 
• 153-94-6 D-tryptophan 
• 3389-21-7 3-(2-bromoethyl)-1H-indole 
• 54322-20-2 4-chloro-1-hydroxy-1-butanesulfonate sodium 
• 59-88-1 phenylhydrazine hydrochloride 
• 487-89-8 Indole-3-carboxaldehyde 
• 57073-81-1 3-(Phenylhydrazone) of 2,3-piperidinedione 
• 17952-82-8 1,2,3,4-tetrahydronorharman-1-one 

Downstream Products

• 26759-28-4 1-(4-methoxy-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 69225-88-3 (1RS)-1,2,3,4-Tetrahydro-1-(2-oxopropyl)-β-carbolin 
• 73554-61-7 1-(3,4,5-trimethoxy-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 562810-25-7 1-cyclohex-1-enylmethyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 114926-78-2 (+/-)-1-(3-methoxybenzyl)-1,2,3,4-tetrahydro-β-carboline 
• 113222-73-4 2-methoxy-4-(2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-phenol 
• 53629-44-0 1-(3,4-dimethoxy-benzyl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 102181-71-5 2,6-dimethoxy-4-(2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl)-phenol 
• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 
• 3851-30-7 1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 4753-09-7 N-benzoyltryptamine 
• 6543-83-5 1-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-carboxylic acid 
• 93742-16-6 2-(1H-indol-3-yl)-N-(1H-indol-3-ylmethyl)ethanamine 
• 124-40-3 dimethyl amine 

Relevant articles and documents

Kinetics and mechanism of the condensation of pyridoxal hydrochloride with L-tryptophan and D-tryptophan, and the chemical transformation of their products

The kinetics and mechanism of interaction between pyridoxal and L-tryptophan, D-tryptophan, and their derivatives are studied. It is found that condensation reactions proceed via three kinetically distinguishable stages: (1) the rapid intraplanar addition of the NH2 groups of the amino acids to pyridoxal with the formation of amino alcohols; (2) the rotational isomerism of amino alcohol fragments with their subsequent dehydration and the formation of a Schiff base with a specific configuration; (3) the abstraction of α-hydrogen in the product of condensation of pyridoxal with L-tryptophan, or the abstraction of СО2 in the product of condensation of pyridoxal with D-tryptophan with the formation of quinoid structures, hydrolysis of which results in the preparation of pyridoxamine and keto acid or pyridoxal and tryptamine, respectively. Schiff bases resistant to further chemical transformations are formed in the reaction with tryptophan methyl ester.

Catalytic Staudinger Reduction at Room Temperature

We report an efficient catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides over other common functionalities, including nitriles, alkenes, alkynes, esters, and ketones.

Sustainable organophosphorus-catalysed Staudinger reduction

A highly efficient and sustainable catalytic Staudinger reduction for the conversion of organic azides to amines in excellent yields has been developed. The reaction displays excellent functional group tolerance to functionalities that are otherwise prone to reduction, such as sulfones, esters, amides, ketones, nitriles, alkenes, and benzyl ethers. The green nature of the reaction is exemplified by the use of PMHS, CPME, and a lack of column chromatography.

Indolamide compound capable of selectively inhibiting gastric cancer cells

The invention discloses an indolamide compound capable of selectively inhibiting gastric cancer cells. The compound is capable of inhibiting the gastric cancer cells, particularly MGC-803 (human gastric cancer cells) cell strains, therefore the compound can be used as medicines for the selectively treatment of gastric cancer and has better developing prospect.

Cyclometalated beta-carboline ruthenium complex and preparation method and application thereof

The invention relates to the technical field of antitumor drugs and concretely discloses a cyclometalated beta-carboline ruthenium complex and a preparation method and application thereof. The ruthenium complex takes 1-phenyl-9H-pyrido[3,4-b] indole as a main ligand, and takes 2,2-bipyridyl or 4,4-dimethyl-2,2 bipyridyl as an ancillary ligand. The ruthenium complex has a very excellent anti-tumor effect and has more excellent activity against liver cancer, breast cancer, lung cancer and cervical cancer cell lines than cis-platinum and similar polypyridine carboline ruthenium complexes.

Rapid Conventional and Microwave-Assisted Decarboxylation of L-Histidine and Other Amino Acids via Organocatalysis with R-Carvone under Superheated Conditions

This article reports a new methodology taking advantage of superheated chemistry via either microwave or conventional heating for the facile decarboxylation of alpha amino acids using the recoverable organocatalyst, R-carvone. The decarboxylation of amino acids is an important synthetic route to biologically active amines, and traditional methods of amino acid decarboxylation are time consuming (taking up to several days in the case of L-histidine), are narrow in scope, and make use of toxic catalysts. Decarboxylations of amino acids including L-histidine occur in just minutes while replacing toxic catalysts with green catalyst, spearmint oil. Yields are comparable to or exceed previous methods and purification of product ammonium chloride salts is aided by an isomerization reaction of residual catalyst to phenolic carvacrol. The method has been shown to be effective for the decarboxylations of a range of natural, synthetic, and protected amino acids.

METHOD FOR DECARBOXYLATION OF AMINO ACIDS VIA IMINE FORMATION

The present application provides methods for decarboxylation of amino acids via imine formation with a catalyst under superheated conditions in either a microwave or oil bath.

Low-temperature deacylation of N-monosubstituted amides

(Chemical Equation Presented) The (PhO)3P-Cl2 reagent, prepared in situ by titrating a solution of triphenyl phosphite with chlorine, is used to convert N-monosubstituted amides into their corresponding amines. The reaction, if compared to other traditional methods, shows the advantage of very mild conditions and low temperature (-30°C→rt).

Versatile Reagent for Reduction of Azides to Amines

Triphenylphosphine (TPP) in refluxing methanol effectively reduces a variety of azides 1a-k to amines 2a-k in very good yields.

N6-Substituted Adenosine Receptor Agonists. Synthesis and Pharmacological Activity as Potent Antinociceptive Agents

Novel N6-(indol-3-yl)alkyl derivatives of adenosine were synthesized.The adenosine receptor affinity and the antinociceptive activity of these compounds were assessed in binding studies and the phenylbenzoquinone-induced writhing test.Most of these analogues exhibited a potent analgesic activity without side effects.Among them, compound 3c (UP 202-32) bound to A1 (Ki = 110 nM) and A2 (Ki = 350 nM) adenosine receptors in a specific manner since it did not interact with many other receptors, especially opioid binding sites.The antinociceptive activity in the phenylbenzoquinone assay (ED50 = 3.3 mg/kg po) was antagonized by 8-cyclopentyltheophylline, suggesting that an adenosinergic mechanism underlies the analgesic activity observed with this compound.The data obtained with these new N6-substituted adenosine receptor agonists emphasize the interest of such compounds in the treatment of pain.