1-Methyl-L-histidine supplier

Name
1-Methyl-L-histidine
EINECS 206-368-0
CAS No. 332-80-9
Article Data8
CAS DataBase
Density 1.37 g/cm³
Solubility
Melting Point ~240 °C (dec.)(lit.)
Formula C₇H₁₁N₃O₂
Boiling Point 415 °C at 760 mmHg
Molecular Weight 169.183
Flash Point 204.8 °C
Transport Information
Appearance
Safety 26-36-24/25-22
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Histidine,1-methyl-, L- (8CI);(S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid;1-Methylhistidine;1-N-Methyl-L-histidine;N1-Methyl-L-histidine;NSC 524367;
PSA 81.14000
LogP 0.07480

Synthetic route

: 69618-95-7
(S)-7-(methoxycarbonyl)-2-methyl-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c] pyrimidin-2-ium iodide

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With hydrogenchloride Heating;	99%

: 118891-68-2
Nα-Trityl-Nτ-methyl-L-histidin

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With acetic acid In water; ethyl acetate for 1h; Heating;	71%

: 71-00-1
L-histidine

: 74-88-4
methyl iodide

A: 368-16-1
3-methyl-L-histidine

B: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With ammonia; sodium

...Expand

: 83471-81-2
(S)-2-Amino-3-{5-[5-((S)-2-amino-2-carboxy-ethyl)-3-methyl-3H-imidazol-4-yldisulfanyl]-1-methyl-1H-imidazol-4-yl}-propionic acid

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With nickel In ethanol for 0.5h; Heating;

: 124017-72-7
1-methyl<2-(3)H>-L-histidine

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With methylmercuric nitrate In water at 85℃; Rate constant; Mechanism; effect of pH; variation of concentration of MeHgNO3;

: 79950-65-5
N-[(1,1-dimethylethoxy)carbonyl]-3-[(phenylmethoxy)methyl]-L-histidine

: 74-88-4
methyl iodide

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With hydrogenchloride 1.) (DMF), 24 h, room temp., 2.) reflux, 24 h; Multistep reaction;

: 90653-43-3
N(α)-benzyloxycarbonyl-N(ϖ)-t-butoxymethyl-L-histidine methyl ester

: 74-88-4
methyl iodide

A: 368-16-1
3-methyl-L-histidine

B: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With hydrogenchloride 1.) (DMF), 24 h, room temp., 2.) reflux, 24 h; Multistep reaction;

...Expand

: 99523-88-3
N(α)-benzyloxycarbonyl-N(ϖ)-(2-methoxyethoxy)methyl-L-histidine methyl ester

: 74-88-4
methyl iodide

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
Multistep reaction;

: 99523-90-7
N(α)-benzyloxycarbonyl-N(ϖ)-(2-trimethylsilylethoxy)methyl-L-histidine methyl ester

: 74-88-4
methyl iodide

A: 368-16-1
3-methyl-L-histidine

B: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With hydrogenchloride 1.) (DMF), 24 h, room temp., 2.) reflux, 24 h; Multistep reaction;

...Expand

: 99523-91-8
N(α)-benzyloxycarbonyl-N(τ)-(2-trimethylsilylethoxy)methyl-L-histidine methyl ester

: 74-88-4
methyl iodide

A: 368-16-1
3-methyl-L-histidine

B: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With hydrogenchloride 1.) (DMF), 24 h, room temp., 2.) reflux, 24 h; Multistep reaction;

...Expand

: N(α)-benzyloxycarbonyl-N(ϖ)-(2,4,6-trimethylbenzyloxy)methyl-L-histidine methyl ester

: 74-88-4
methyl iodide

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With hydrogenchloride 1.) (DMF), 24 h, room temp., 2.) reflux, 24 h; Multistep reaction;

: 1-Me-AcHis

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
With (2)H8O4Pd(2+); deuteroperchloric acid In water-d2 at 40℃; Rate constant;

: 90653-42-2
N(α)-benzyloxycarbonyl-N(τ)-tert-butyloxycarbonyl-L-histidine methyl ester

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temp., 3 h View Scheme

: 15545-10-5
Z-His-OMe

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 27 percent / triethylamine / ethyl acetate / 1.) 0 deg C, 1 h, 2.) room temp., 6 h. 2: 2.) 'constant boiling' hydrochloric acid / 1.) (DMF), 24 h, room temp., 2.) reflux, 24 h View Scheme

: 62982-24-5
L-5-sulfanyl-1-methylhistidine

: 332-80-9
His(1-CH3)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: air, iodide / H2O / 24 h 2: Raney Nickel / aq. ethanol / 0.5 h / Heating View Scheme

: 109-72-8, 29786-93-4
n-butyllithium

: 332-80-9
His(1-CH3)

: 57519-09-2
(S)-methyl 2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoate

Conditions

Conditions	Yield
With hydrogenchloride at 20℃;	95%

: 50-00-0
formaldehyd

: 332-80-9
His(1-CH3)

: (S)-3-methyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride In water at 0℃; Reflux;	80%

: 332-80-9
His(1-CH3)

: 83471-81-2
(S)-2-Amino-3-{5-[5-((S)-2-amino-2-carboxy-ethyl)-3-methyl-3H-imidazol-4-yldisulfanyl]-1-methyl-1H-imidazol-4-yl}-propionic acid

Conditions

Conditions	Yield
Stage #1: His(1-CH3) With hydrogenchloride; N-Bromosuccinimide In water at 1℃; for 0.05h; Stage #2: With tiolacetic acid In water at 0℃; for 0.5h; Stage #3: With 3-mercaptopropionic acid In water at 100℃; for 20h;	65%

: 332-80-9
His(1-CH3)

: 1205535-89-2
[αR-2H]-Nτ-methylhistamine

Conditions

Conditions	Yield
With histidine decarboxylase; pyridoxal 5'-phosphate; water-d2 at 37℃; for 192h; pH=4.7; aq. phosphate buffer; Enzymatic reaction;	58%

: 109-87-5
Dimethoxymethane

: 332-80-9
His(1-CH3)

: 114787-98-3
3-methylspinacine dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride 1) RT, overnight, 2) 3h, steam-bath;	45%

: 332-80-9
His(1-CH3)

: 1205535-90-5
[αR-3H]-Nτ-methylhistamine

Conditions

Conditions	Yield
With (1)H,(3)H-water; histidine decarboxylase; pyridoxal 5'-phosphate at 37℃; for 192h; pH=4.7; aq. phosphate buffer; Enzymatic reaction;	35%

: 75-77-4
chloro-trimethyl-silane

: 332-80-9
His(1-CH3)

: 118891-70-6
C10H19N3O2Si*ClH

Conditions

Conditions	Yield
In chloroform for 1h; Heating;

: 19804-21-8
peridoxal

: 332-80-9
His(1-CH3)

: 83984-06-9
N-pyridoxylidene-L-Nτmethylhistidine

Conditions

Conditions	Yield
In methanol

: 61507-75-3
bufotalin 3-hemisuberate p-nitrophenyl ester

: 332-80-9
His(1-CH3)

: 90038-13-4
bufotalin 3-suberoyl-L-3-methylhistidine ester

Conditions

Conditions	Yield
In pyridine; water for 12h; Ambient temperature;	11 mg

: 332-80-9
His(1-CH3)

: 124017-72-7
1-methyl<2-(3)H>-L-histidine

Conditions

Conditions	Yield
With tritium oxide at 85℃; for 408h;

: 67-56-1
methanol

: 332-80-9
His(1-CH3)

: L-Nτ-methylhistidine methyl ester dihydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 0℃; for 3h; Heating / reflux;

: 332-80-9
His(1-CH3)

: (S)-3-(1-Methyl-1H-imidazol-4-yl)-2-[((R)-3-oxo-cyclopentanecarbonyl)-amino]-propionic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / HCl gas / 20 °C 2: ethyl acetate / 24 h / 20 °C View Scheme

: 332-80-9
His(1-CH3)

: (S)-3-(1-Methyl-1H-imidazol-4-yl)-2-[((S)-3-oxo-cyclopentanecarbonyl)-amino]-propionic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / HCl gas / 20 °C 2: ethyl acetate / 24 h / 20 °C View Scheme

: 332-80-9
His(1-CH3)

: 406939-49-9
(S)-3-(1-Methyl-1H-imidazol-4-yl)-2-[((R)-3-oxo-cyclopentanecarbonyl)-amino]-propionic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / HCl gas / 20 °C 2: ethyl acetate / 24 h / 20 °C 3: 0.5N NaOH / methanol / 0.5 h / 20 °C View Scheme

: 332-80-9
His(1-CH3)

: 406939-48-8
(S)-3-(1-Methyl-1H-imidazol-4-yl)-2-[((S)-3-oxo-cyclopentanecarbonyl)-amino]-propionic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / HCl gas / 20 °C 2: ethyl acetate / 24 h / 20 °C 3: 0.5N NaOH / methanol / 0.5 h / 20 °C View Scheme

: 332-80-9
His(1-CH3)

: (S)-1-{(S)-3-(1-Methyl-1H-imidazol-4-yl)-2-[((R)-3-oxo-cyclopentanecarbonyl)-amino]-propionyl}-pyrrolidine-2-carboxylic acid amide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / HCl gas / 20 °C 2: ethyl acetate / 24 h / 20 °C 3: 0.5N NaOH / methanol / 0.5 h / 20 °C 4: 36 percent / HOBt; DCC / dimethylformamide / 0.8 h / 20 °C View Scheme

: 332-80-9
His(1-CH3)

: (S)-1-{(S)-3-(1-Methyl-1H-imidazol-4-yl)-2-[((S)-3-oxo-cyclopentanecarbonyl)-amino]-propionyl}-pyrrolidine-2-carboxylic acid amide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / HCl gas / 20 °C 2: ethyl acetate / 24 h / 20 °C 3: 0.5N NaOH / methanol / 0.5 h / 20 °C 4: 23 percent / HOBt; DCC / dimethylformamide / 0.8 h / 20 °C View Scheme

1-Methyl-L-histidine Specification

The L-Histidine, 1-methyl-, with the CAS registry number 332-80-9, is also known as 3-(1-Methylimidazol-4-yl)-L-alanine. It belongs to the product categories of Pharmaceutical Raw Materials; Histidine [His, H]; Amino Acids and Derivatives; Amino Acids Methyl; Ethyl; t-Butyl Series. Its EINECS registry number is 206-368-0. This chemical's molecular formula is C₇H₁₁N₃O₂ and molecular weight is 169.18. What's more, its IUPAC name is (2S)-2-Amino-3-(1-methylimidazol-4-yl)propanoic acid and systematic name is called 1-Methyl-L-histidine.

Physical properties about L-Histidine, 1-methyl- are:(1) ACD/LogP: -1.31; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): -4.37; (4) ACD/LogD (pH 7.4): -3.88; (5) ACD/BCF (pH 5.5): 1; (6) ACD/BCF (pH 7.4): 1; (7) ACD/KOC (pH 5.5): 1; (8) ACD/KOC (pH 7.4): 1; (9) #H bond acceptors: 5; (10) #H bond donors: 3; (11) #Freely Rotating Bonds: 4; (12) Polar Surface Area: 47.36 Å²; (13) Index of Refraction: 1.613; (14) Molar Refractivity: 42.69 cm³; (15) Molar Volume: 122.6 cm³; (16) Surface Tension: 55.4 dyne/cm; (17) Density: 1.37 g/cm³; (18) Flash Point: 204.8 °C; (19) Enthalpy of Vaporization: 70.43 kJ/mol; (20) Boiling Point: 415 °C at 760 mmHg; (21) Vapour Pressure: 1.25E-07 mmHg at 25 °C; (22) Melting Point: 240 °C.

When you are dealing with this chemical, you should be very careful. This chemical is irritating to eyes, respiratory system, skin and may cause inflammation to the skin or other mucous membranes. The gas of this chemical can not be breathed. Therefore, you should wear suitable protective clothing and avoid contacting with skin and eyes. And in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)[C@@H](N)Cc1ncn(c1)C
(2) InChI: InChI=1/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
(3) InChIKey: BRMWTNUJHUMWMS-LURJTMIEBU

Product Name

1-Methyl-L-histidine

Synthetic route

1-Methyl-L-histidine Specification

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