21463-31-0

Basic information

• Product Name: AMT HYDROCHLORIDE
• Synonyms: 5,6-DIHYDRO-6-METHYL-4H-1,3-THIAZIN-2-AMINE, HYDROCHLORIDE;AMT HYDROCHLORIDE;AMT HCL;2-AMINO-5,6-DIHYDRO-6-METHYL-4H-1,3-THIAZINE HYDROCHLORIDE;2-AMINO-5,6-DIHYDRO-6-METHYL-4H-1,3-THIAZINE HCL
• CAS NO: 21463-31-0
• Molecular Formula: C5H11ClN2S
• Molecular Weight: 166.67
• Mol File: 21463-31-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 146-150°C
• Boiling Point: 236.1 °C at 760 mmHg
• Flash Point: 96.6 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 0.0482mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: 0-6°C
• CAS DataBase Reference: AMT HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: AMT HYDROCHLORIDE(21463-31-0)
• EPA Substance Registry System: AMT HYDROCHLORIDE(21463-31-0)

Safety Data

• Hazardous Substances Data: 21463-31-0(Hazardous Substances Data)

Usage

Description

AMT HYDROCHLORIDE, also known as Aminoguanidine hydrochloride, is a potent and relatively selective inhibitor of inducible nitric oxide synthase (iNOS) with a Ki of 4.2 nM in mouse macrophages. It is a white to off-white powder in its chemical form. AMT HYDROCHLORIDE inhibits other isoforms of NOS, but at higher concentrations, making it a promising candidate for therapeutic applications in various medical fields.

Uses

Used in Pharmaceutical Industry:
AMT HYDROCHLORIDE is used as an inhibitor for iNOS, which plays a significant role in the treatment of inflammatory and autoimmune diseases. By selectively inhibiting iNOS, it can help regulate the production of nitric oxide, reducing inflammation and alleviating the symptoms associated with these conditions.
Used in Research Applications:
AMT HYDROCHLORIDE is also used as a research tool to study the role of nitric oxide in various biological processes. Its potency and selectivity make it an ideal compound for investigating the functions of iNOS and other NOS isoforms in cellular and molecular biology.

Biological Activity

Potent, selective and reversible inhibitor of iNOS (IC 50 = 3.6 nM; approximately 30 and 40 times selective over nNOS and eNOS respectively).

InChI:InChI=1/C5H10N2S/c1-4-2-3-7-5(6)8-4/h4H,2-3H2,1H3,(H2,6,7)/t4-/m1/s1

Synthetic route

Boc-D-Phe-ψL[(E)-C(CH3)=CH]-Ala-Val-OMe (914955-66-1) + (+/-)-2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine hydrochloride (21463-31-0) → Boc-D-Phe-ψL[(E)-C(CH3)=CH]-Ala-Val-AMT (1205539-92-9)

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 36h;	96%

(2S,5S,E)-2-benzyl-5-((tert-butoxycarbonyl)amino)-7-methyloct-3-enoic acid (109065-09-0) + (+/-)-2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine hydrochloride (21463-31-0) → Boc-Leu-ψ[(E)-CH=CH]-D-Phe-AMT (927908-75-6)

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃;	63%

Boc-Leu-D-Phe-Pro-Val-Orn(Cbz)-OH + (+/-)-2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine hydrochloride (21463-31-0) → Boc-Leu-ψ[(E)-CH=CH]-D-Phe-Pro-Val-Orn(Cbz)-AMT (1205536-62-4)

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 20h;

Boc-Leu-D-Phe-Pro-Val-Orn(Z)-OH (153886-90-9) + (+/-)-2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine hydrochloride (21463-31-0) → Boc-Leu-D-Phe-Pro-Val-Orn(Cbz)-AMT (1205536-66-8)

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 24h;

(S)-2-((S)-2-{[(S)-1-((E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-butyrylamino)-5-benzyloxycarbonylamino-pentanoic acid + (+/-)-2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine hydrochloride (21463-31-0) → Boc-Leu-ψ[(E)-C(CH3)=CH]-D-Phe-Pro-Val-Orn(Cbz)-AMT (1205536-64-6)

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 48h;

(S)-2-{(S)-5-Benzyloxycarbonylamino-2-[(S)-2-((E)-(2R,5R)-5-tert-butoxycarbonylamino-2,4-dimethyl-6-phenyl-hex-3-enoylamino)-3-methyl-butyrylamino]-pentanoylamino}-4-methyl-pentanoic acid + (+/-)-2-amino-5,6-dihydro-6-methyl-4H-1,3-thiazine hydrochloride (21463-31-0) → Boc-D-Phe-ψ[(E)-C(CH3)=CH]-Ala-Val-Orn(Cbz)-Leu-AMT (1205539-90-7)

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 36h;

Downstream Products

• 927908-75-6 Boc-Leu-ψ[(E)-CH=CH]-D-Phe-AMT 
• 1205536-62-4 Boc-Leu-ψ[(E)-CH=CH]-D-Phe-Pro-Val-Orn(Cbz)-AMT 
• 1205536-66-8 Boc-Leu-D-Phe-Pro-Val-Orn(Cbz)-AMT 
• 1205536-64-6 Boc-Leu-ψ[(E)-C(CH3)=CH]-D-Phe-Pro-Val-Orn(Cbz)-AMT 
• 1205539-90-7 Boc-D-Phe-ψ[(E)-C(CH3)=CH]-Ala-Val-Orn(Cbz)-Leu-AMT 
• 1205539-92-9 Boc-D-Phe-ψL[(E)-C(CH3)=CH]-Ala-Val-AMT