180001-34-7

Basic information

• Product Name: 1400W
• Synonyms: 1400W;1400W DIHYDROCHLORIDE;N-[[3-(AMINOMETHYL)PHENYL]METHYL]-ETHANIMIDAMIDE DIHYDROCHLORIDE;N-(3-(AMINOMETHYL)BENZYL)ACETAMIDINE;N-(3-(AMINOMETHYL)BENZYL)ACETAMIDINE 2HCL;N-(3-(AMINOMETHYL)BENZYL)ACETAMIDINE, DIHYDROCHLORIDE
• CAS NO: 180001-34-7
• Molecular Formula: C₁₀H₁₅N₃
• Molecular Weight: 250.17
• Product Categories: Nitric Oxide Reagents;Nitric Oxide;Aromatic Building Blocks;Signalling
• Mol File: 180001-34-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 208-220 °C
• Boiling Point: 329 °C at 760 mmHg
• Flash Point: 152.7 °C
• Appearance: /solid
• Density: 1.09 g/cm³
• Vapor Pressure: 0.000183mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: DMSO, Methanol, Water
• PKA: 11.33±0.50(Predicted)
• CAS DataBase Reference: 1400W(CAS DataBase Reference)
• NIST Chemistry Reference: 1400W(180001-34-7)
• EPA Substance Registry System: 1400W(180001-34-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 180001-34-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 180001-34-7 differently. You can refer to the following data:
1. A selective inducible nitric oxide synthase (iNOS) inhibitor. A long-acting human iNOS inhibitor possessing an IC50 value of 2.0uM
2. 1400W selectively inhibits inducible nitric oxide synthase. W 1400 has been implicated to prevent Doxorubicin and Trastuzumab induced cardiotoxicity.

Biological Activity

Slow, tight binding, potent and highly selective inhibitor of inducible nitric oxide synthase (K d = 7 nM). Selective over nNOS and eNOS (K i values are 2 and 50 μ M respectively). Cell-permeable and active in vivo .

InChI:InChI=1/C10H15N3.2ClH/c1-8(12)13-7-10-4-2-3-9(5-10)6-11;;/h2-5H,6-7,11H2,1H3,(H2,12,13);2*1H

Upstream product

• 108467-99-8 1-(N-Boc-aminomethyl)-3-(aminomethyl)benzene 
• 180001-98-3 N-(3-(N-Boc-aminomethyl)benzyl)acetimidine hydrochloride 

Relevant articles and documents

Screening of NOS activity and selectivity of newly synthesized acetamidines using RP-HPLC

Nitric Oxide Synthase (NOS) inhibitors could play a powerful role in inflammatory and neurodegenerative diseases. In this work, novel acetamidine derivatives of NOS were synthesized and the inhibitor activity was evalued. To screen the activity and selectivity, the l-citrulline residue, after the enzymatic NOS assay, was derivatized with o-phthaldialdehyde/N-acetyl cysteine (OPA/NAC) and then evaluated by RP-HPLC method with fluorescence detection.All compounds did not affect the activity of endothelial and neuronal isoforms, while nine of them possessed a percentage of iNOS activity at 10 μM lower than 50%, and were selected for IC50 evaluation. Among them, a compound emerged as a very potent (IC50 of 53 nM) and selective iNOS inhibitor.

Acetamidine derivatives and their use as inhibitors for the nitric oxide synthase

A class of acetamidine derivatives of general formula (I) STR1 wherein R1 is hydrogen, C1-6 hydrocarbyl group optionally substituted by halo, halo, nitro, cyano or a group XR3 wherein X is oxygen, C(O)m wherein m is 1 or 2, S(O)n wherein n is 0, 1 or 2, or a group NR4 wherein R4 is hydrogen or C1-6 alkyl; and R3 is hydrogen, C1-6 alkyl, or a group NR5 R6 wherein R5 and R6 are independently hydrogen or C1-6 alkyl, provided that R3 is not NR5 R6 when X is oxygen or S(O)n; R1a and R1b are independently selected from hydrogen and halo; R2 is a C1-14 hydrocarbyl group which may optionally contain one or two heteroatoms, the group R2 being optionally substituted by one or more groups independently selected from halo; N3 ; nitro; CF3 ; ZR7 wherein Z is oxygen, C(O)m' wherein m' is 1 or 2, S(O)n' wherein n' is 0, 1 or 2, or a group NR8 wherein R8 is hydrogen or C1-6 alkyl and R7 is hydrogen, C1-6 alkyl or a group NR9 R10 wherein R9 and R10 are independently hydrogen or C1-6 alkyl; or R2 is substituted by a group (a) STR2 wherein R11 has a definition the same as for R1 ; with the proviso that when R1 is a C1-6 alkyl group and R2 is a C1-14 hydrocarbyl substituted by two groups ZR7 wherein one group ZR7 is CO2 H, the other group ZR7 is not NH2; and salts thereof, methods for the manufacture thereof, and therapies, particularly inhibtion of nitric oxide synthase, is disclosed.