N,N-Dimethyltryptamine

Base Information

• Chemical Name: N,N-Dimethyltryptamine
• CAS No.: 61-50-7
• Deprecated CAS: 68677-25-8
• Molecular Formula: C12H16N2
• Molecular Weight: 188.272
• European Community (EC) Number: 200-508-4
• NSC Number: 63795
• UNII: WUB601BHAA
• DSSTox Substance ID: DTXSID60110053
• Nikkaji Number: J10.685B
• Wikipedia: N,N-Dimethyltryptamine
• Wikidata: Q407217
• Pharos Ligand ID: TLVAMAXP48DT
• Metabolomics Workbench ID: 38791
• ChEMBL ID: CHEMBL12420
• Mol file: 61-50-7.mol

Synonyms:Dimethyltryptamine;N,N Dimethyltryptamine;N,N-Dimethyltryptamine

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Chemical Property of N,N-Dimethyltryptamine

Chemical Property:

• Appearance/Colour: tan solid
• Vapor Pressure: 0.000149mmHg at 25°C
• Melting Point: 42-44 °C
• Refractive Index: 1.615
• Boiling Point: 332.1 °C at 760 mmHg
• PKA: 8.68 (ethanol-water)
• Flash Point: 154.7 °C
• PSA: 19.03000
• Density: 1.076 g/cm³
• LogP: 2.27200
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: soluble15mg/mL, clear
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 188.131348519
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC1=CNC2=CC=CC=C21
• Recent ClinicalTrials: Mindfulness and Psychedelics
• Uses: It is an endogenous Sigma-1 receptor regulator. A labelled endogenous Sigma-1 receptor regulator.

Technology Process of N,N-Dimethyltryptamine

There total 47 articles about N,N-Dimethyltryptamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → N,N-dimethyltryptamine (61-50-7,68677-25-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 18h;

DOI:10.1021/jo01296a019

Reference yield: 100.0%

5,6-Dibromo-N,N-dimethyltryptamine (72853-80-6) → N,N-dimethyltryptamine (61-50-7,68677-25-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 18h;

DOI:10.1021/jo01296a019

Reference yield: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + tryptamine (61-54-1) → N,N-dimethyltryptamine (61-50-7,68677-25-8)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2011.04.004

upstream raw materials:

3-(2-bromoethyl)-1H-indole

dimethyl amine

2-(1H-indol-3-yl)-N,N-dimethylacetamide

2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

Downstream raw materials:

N,N-dimethyl-1-(2'-bromobenzoyl)tryptamine

rizatriptan benzoate

dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine

rizatriptan

Refernces

• 1、 Ghosal,Mazumder. "-". . p. 2840. Retrieved 1971.
• 2、 Moura, Sidnei,Carvalho, Felipe Garcia,de Oliveira, Carolina Dizioli Rodrigues,Pinto, Ernani,Yonamine, Mauricio. "qNMR: An applicable method for the determination of dimethyltryptamine in ayahuasca, a psychoactive plant preparation". . p. 79 - 83. Retrieved 2010.
• 3、 Biswas, Nandita,Sharma, Rahul,Srimani, Dipankar. "Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols". supporting information. p. 2902 - 2910. Retrieved 2020/06/03.
• 4、 Lator, Alexis,Gaillard, Sylvain,Poater, Albert,Renaud, Jean-Luc. "Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol". supporting information. p. 5985 - 5990. Retrieved 2018/10/02.