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 is a potent, relatively selective inhibitor of iNOS with a Ki of 4.2 nM in mouse macrophages. It inhibits other isoforms of NOS, but at higher concentrations; the IC50 values for rat nNOS and bovine eNOS are 34 and 150 nM, respectively.

Chemical Properties

white to off-white powder

Uses

AMT Hydrochloride is a potent and selective inhibitors of inducible nitric oxide synthase, which may lead to therapeutic applications in the treatment of inflammatory and autoimmune diseases.

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

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