101-25-7

Usage

General Description

Flammable explosive solid.

Reactivity Profile

Self-reactive. N,N'-DINITROSOPENTAMETHYLENETETRAMINE is a blowing agent with an exothermic decomposition slightly above its melting point of 203°C, Ellern, 161(1968). N,N'-DINITROSOPENTAMETHYLENETETRAMINE is shock sensitive.

Safety Profile

Poison by intravenous, intraperitoneal, and subcutaneous routes. Moderately toxic by ingestion. Questionable carcinogen. Mutation data reported. Can ignite when handled and burns very rapidly. Many N-nitroso compounds are carcinogens. A blowing agent. When heated to decomposition it emits toxic fumes of NO,. See also N-NITROSO COMPOUNDS.

InChI:InChI=1/C6H11N5O2/c12-6-10-2-8-1-9(3-10)5-11(4-8)7-13/h6H,1-5H2

Upstream product

• 50-00-0 formaldehyd 
• 100-97-0 hexamethylenetetramine 

Relevant academic research and scientific papers

New NO donors with antithrombotic and vasodilating activities, part 22: Nitrosation products of hexamethylenetetramine

Two nitrosation products of hexamethylenetetramine, namely 1,3,5- trinitrosohexahydro-1,3,5-triazine (1) and 3,7-dinitroso-1,3,5,7- tetrazabicyclo[3.3.1]nonane (2), were synthesized. It is shown that both compounds in vitro a 37 °C (1 h, pH 7.4) form nitric oxide at a rate of 3.1% (1) or 1.3% (2), respectively. In rats (60 mg/kg p.o.) both compound inhibit thrombus formation in arterioles (1: 20%; 2: 16%) and venules (1. 18%; 2. 9%). Compound 2 does not influence the blood pressure in spontaneously hypertensive rats.

Identifying urotropine derivatives as co-donors of formaldehyde and nitric oxide for improving antitumor therapy

A pharmacophore integration strategy was utilized to develop the first co-donor of formaldehyde and nitric oxide (FANO), composed of urotropine derived nitramine/nitrosamine. FANO simultaneously generated formaldehyde and nitric oxide on-demand, resulting in synergistic anticancer effects. Importantly, liposomal formulation of FANO effectively inhibited tumor growth with minimal side-effects, providing a potent combined nitric oxide therapy for malignancy.