(R)-alpha-Methylhistamine

Base Information

• Chemical Name: (R)-alpha-Methylhistamine
• CAS No.: 75614-87-8
• Molecular Formula: C6H11 N3
• Molecular Weight: 125.173
• Hs Code.: 29332900
• DSSTox Substance ID: DTXSID00873372
• Nikkaji Number: J139.260C
• Wikidata: Q72491200
• Pharos Ligand ID: G3Y8FBPK34HD
• Metabolomics Workbench ID: 66370
• ChEMBL ID: CHEMBL268229
• Mol file: 75614-87-8.mol

Synonyms:(R)-alpha-Methylhistamine;75614-87-8;(2R)-1-(1H-imidazol-5-yl)propan-2-amine;CHEBI:73337;r-alpha-methylhistamine;(R)alpha-Me-histamine;[3H]-R-alpha-Methylhistamine;CHEMBL268229;(R)-[3H]alpha-methylhistamine;[3H](R)-alpha-methylhistamine;(2R)-1-(1H-imidazol-4-yl)propan-2-amine;(R)-(-)-alpha-methylhistamine;R(-)-alpha-Methylhistamine.2HBr;1H-Imidazole-4-ethanamine, alpha-methyl-, (alphaR)-;(R)-(-)-4-(2-aminopropyl)imidazole;(R)-1-(1H-Imidazol-5-yl)propan-2-amine;(2R)-1-(3H-imidazol-4-yl)propan-2-amine;Alpha-Methylhistamine-R;C6H11N3;Alpha Methylhistamine;(R)-alpha-MeHA;RAMH;Alpha-Methylhistane-R;Tocris-0569;R(-)-|A-Methyl Histamine Dihydrochloride;r(-)alpha methylhistamine;D03SAM;D04HEZ;R-2-(1H-Imidazol-4-yl)-1-methyl-ethylamine;Lopac0_000618;SCHEMBL73663;GTPL1236;GTPL1237;SCHEMBL4155130;BDBM22904;DTXSID00873372;alpha-methylhistamine, (R)-isomer;BDBM50215536;PDSP1_000535;PDSP1_000541;PDSP1_000542;PDSP2_000507;PDSP2_000533;PDSP2_000539;AKOS006343508;CCG-204707;SDCCGSBI-0050600.P002;NCGC00024656-01;NCGC00024656-02;NCGC00024656-03;NCGC00024656-04;NCGC00024656-08;LS-177199;LS-191796;alpha-methylhistamine-dihydrobromide-(R)-(-);(R)-2-(3H-Imidazol-4-yl)-1-methyl-ethylamine;EN300-1817458

Chemical Property of (R)-alpha-Methylhistamine

Chemical Property:

• Vapor Pressure: 0.000315mmHg at 25°C
• Refractive Index: 1.55
• Boiling Point: 320.6 °C at 760 mmHg
• Flash Point: 173.7 °C
• PSA: 54.70000
• Density: 1.094 g/cm³
• LogP: 2.60370
• Storage Temp.: Desiccate at RT
• Solubility.: H2O: soluble
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 125.095297364
• Heavy Atom Count: 9
• Complexity: 84.4

Purity/Quality:

99% ^*data from raw suppliers

(R)-(-)-alpha-Methylhistaminedihydrobromide ≥99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC1=CN=CN1)N
• Isomeric SMILES: C[C@H](CC1=CN=CN1)N
• Uses: R(-)-alpha-Methylhistamine is a potent agonist of the histamine H3-receptor.

Technology Process of (R)-alpha-Methylhistamine

There total 14 articles about (R)-alpha-Methylhistamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(S)-(+)-4-(2-amino-3-chloropropyl)-imidazole dihydrochloride (75614-85-6,75614-86-7) → (R)-2-(1H-Imidazol-4-yl)-1-methyl-ethylamine (75614-87-8)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In acetic acid; for 72h; under 18751.5 Torr;

DOI:10.1002/ardp.19803130810

Reference yield:

(S)-histidinol (4836-52-6) → (R)-2-(1H-Imidazol-4-yl)-1-methyl-ethylamine (75614-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / SOCl₂ / tetrahydrothiophene 1,1-dioxide / 7 h / 55 °C

2: 90 percent / H₂, CH₃COONa / 10percent Pd-C / aq. acetic acid / 72 h / 18751.5 Torr

With thionyl chloride; hydrogen; sodium acetate; palladium on activated charcoal; In sulfolane; acetic acid;

DOI:10.1002/ardp.19803130810

Reference yield:

L-histidine monohydrochloride (645-35-2) → (R)-2-(1H-Imidazol-4-yl)-1-methyl-ethylamine (75614-87-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / HCl / 3 h / Heating

2: LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 90 percent / SOCl₂ / tetrahydrothiophene 1,1-dioxide / 7 h / 55 °C

4: 90 percent / H₂, CH₃COONa / 10percent Pd-C / aq. acetic acid / 72 h / 18751.5 Torr

With hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; hydrogen; sodium acetate; palladium on activated charcoal; In tetrahydrofuran; sulfolane; acetic acid;

DOI:10.1002/ardp.19803130810

upstream raw materials:

S-(+)-α-Chloromethylhistamine

(S)-(+)-4-(2-amino-3-chloropropyl)-imidazole dihydrochloride

L-histidine monohydrochloride

(S)-histidinol

Refernces

• 1、 Krause, Michael,Rouleau, Agnes,Stark, Holger,Luger, Peter,Garbarg, Monique,Schwartz, Jean-Charles,Schunack, Walter. "New potent azomethine prodrugs of the histamine H3-receptor agonist (R)-α-methylhistamine1 containing a heteroarylphenyl partial structure". . p. 209 - 215. Retrieved 2007/10/03.
• 2、 Elz, Sigurd,Gerhard, Guenter,Schunack, Walter. "Histamine analogues. 32nd communication: synthesis and pharmacology of sopromidine, a potent and stereoselective isomer of the achiral H2-agonist impromidine". . p. 259 - 262. Retrieved 2007/10/02.