Pimprinine

Base Information

• Chemical Name: Pimprinine
• CAS No.: 13640-26-1
• Molecular Formula: C12H10 N2 O
• Molecular Weight: 198.224
• Hs Code.: 29349990
• NSC Number: 80793
• UNII: CRW4NIT4W1
• DSSTox Substance ID: DTXSID80159782
• Nikkaji Number: J14.303K
• Wikidata: Q77375798
• Metabolomics Workbench ID: 113182
• Mol file: 13640-26-1.mol

Synonyms:5,3'-indolyl-2-methyloxazole;pimprinine

Chemical Property of Pimprinine

Chemical Property:

• Vapor Pressure: 1.74E-06mmHg at 25°C
• Melting Point: 213.5 °C (polymorph)
• Boiling Point: 407.8°Cat760mmHg
• PKA: 15.78±0.30(Predicted)
• Flash Point: 210°C
• PSA: 41.82000
• Density: 1.243g/cm³
• LogP: 3.13130
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 198.079312947
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

98%min ^*data from raw suppliers

Pimprinine ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(O1)C2=CNC3=CC=CC=C32
• Uses: Pimprinine is an indole alkaloid produced by many species of Streptomyces. Pimprinine is a potent inhibitor of monoamine oxidase. More recently, pimprinine showed promising anticonvulsant activity in electric seizure threshold tests in mice, comparable to phenylhydantoin. Pimprinine also inhibits tremorine-induced tremors and analgesia in mice.

Technology Process of Pimprinine

There total 30 articles about Pimprinine 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: 100.0%

34N (73053-91-5) → pimprinine (13640-26-1)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; acetonitrile; at 100 ℃; for 1h; Microwave irradiation;

DOI:10.1016/j.tetlet.2019.04.024

Reference yield: 100.0%

5-(1-benzenesulfonylindol-3-yl)-2-methyloxazole → pimprinine (13640-26-1)

Guidance literature:

With water; sodium hydroxide; In methanol; at 55 ℃; for 4h;

DOI:10.1021/ol1019597

Reference yield: 99.0%

5-(1-methoxyindol-3-yl)-2-methyloxazole (98258-84-5) → pimprinine (13640-26-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1.5h; under 760.051 Torr;

DOI:10.3987/COM-19-14031

upstream raw materials:

34N

1-acetyl-3-(2-methyl-oxazol-5-yl)-indole

N-Acetyltryptamine

2,3-dicyano-5,6-dichloro-p-benzoquinone

Refernces

• 1、 Xiang, Jiachen,Wang, Jungang,Wang, Miao,Meng, Xianggao,Wu, Anxin. "One-pot total synthesis: The first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners from amino acids". . p. 7470 - 7475. Retrieved 2014.
• 2、 Szabó, Tímea,Dancsó, András,ábrányi-Balogh, Péter,Volk, Balázs,Milen, Mátyás. "First reported propylphosphonic anhydride (T3P) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles". . p. 1353 - 1356. Retrieved 2019.
• 3、 Joshi,B.S. et al.. "-". . p. 1437 - 1440. Retrieved 1963.
• 4、 -. "Indole heterocyclic compound, preparation method thereof and application of indole heterocyclic compound in prevention and treatment of plant diseases". . . Retrieved 2020/07/15.