61-52-9

Basic information

• Product Name: N,N-DIPROPYLTRYPTAMINE
• Synonyms: N,N-DIPROPYLTRYPTAMINE;DPT;3-[2-(Dipropylamino)ethyl]-1H-indole;N,N-Dipropyl-1H-indole-3-ethanamine;2-(1H-indol-3-yl)ethyl-dipropyl-amine;N-[2-(1H-indol-3-yl)ethyl]-N-propyl-propan-1-amine;N-[2-(1H-indol-3-yl)ethyl]-N-propylpropan-1-amine;1H-Indole-3-ethanaMine,N,N-dipropyl-
• CAS NO: 61-52-9
• Molecular Formula: C₁₆H₂₄N₂
• Molecular Weight: 244.38
• Product Categories: Indoline & Oxindole
• Mol File: 61-52-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 174-178 °C
• Boiling Point: 387.4 °C at 760 mmHg
• Flash Point: 188.1 °C
• Appearance: /
• Density: 1.014 g/cm³
• Vapor Pressure: 3.3E-06mmHg at 25°C
• Refractive Index: 1.574
• PKA: 17.30±0.30(Predicted)
• CAS DataBase Reference: N,N-DIPROPYLTRYPTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIPROPYLTRYPTAMINE(61-52-9)
• EPA Substance Registry System: N,N-DIPROPYLTRYPTAMINE(61-52-9)

Safety Data

• Hazardous Substances Data: 61-52-9(Hazardous Substances Data)

Usage

Uses

N,N-Dipropyl-1H-indole-3-ethanamine is a tryptamine designer drug used in toxicology studies which was one of the findings in an analysis of street drugs in seized material without primary reference standards.

InChI:InChI=1/C16H24N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h5-8,13,17H,3-4,9-12H2,1-2H3

Synthetic route

tryptamine (61-54-1) + propionaldehyde (123-38-6) → Dipropyltryptamine (61-52-9)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 0 - 20℃; Inert atmosphere;	94%

tryptamine (61-54-1) + 1-iodo-propane (107-08-4) + N-ethyl-N,N-diisopropylamine (7087-68-5) → Dipropyltryptamine (61-52-9)

Conditions	Yield
In diethyl ether at 20℃; for 16h;	46%

3-(2-bromoethyl)-1H-indole (3389-21-7) + di-n-propylamine (142-84-7) → Dipropyltryptamine (61-52-9)

indol-3-yl-glyoxylic acid dipropylamide → Dipropyltryptamine (61-52-9)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

Dipropyltryptamine (61-52-9) → C16H24N2O (1310826-96-0)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 0.166667h; Inert atmosphere;	85%

Upstream product

• 3389-21-7 3-(2-bromoethyl)-1H-indole 
• 142-84-7 di-n-propylamine 
• 61-54-1 tryptamine 
• 107-08-4 1-iodo-propane 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 123-38-6 propionaldehyde 

Relevant articles and documents

Binding properties of dipropyltryptamine at the human 5-HT1a receptor

Dipropyltryptamine (DPT) is a synthetic indolealkylamine first characterized in the 1960s. Largely forgotten since the discovery of multiple serotonin receptor subtypes, some of the properties of DPT at the cloned human 5-HT1a receptor are described here. When [3H]8-OH-DPAT is bound to the receptor, DPT inhibits the interaction with an IC50 of 0.1 μmol/l. This interaction is shown to be competitive when double-reciprocal plots of the DPT/agonist interaction are analyzed. DPT's effects in the signal transduction system are complex. While DPT alone (0.1-1,000 μmol/l) activates Gi when both cAMP and γ-S-GTP incorporation are measured, in the presence of 5-HT (0.1-10 μmol/l), DPT blocks the agonist effect. In combination, the findings suggest that DPT is a moderate affinity partial agonist at the human 5-HT1a receptor. These results provide evidence that DPT has potential as a versatile experimental tool at 5-HT1a receptors. Copyright

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).