2506-09-4

Basic information

• Product Name: Harman 2-oxide
• Synonyms: 1-Methyl-9H-pyrido[3,4-b]indole 2-oxide;1-Methyl-β-carboline 2-oxide;Harman 2-oxide;Harmanine
• CAS NO: 2506-09-4
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.22
• Mol File: 2506-09-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Harman 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Harman 2-oxide(2506-09-4)
• EPA Substance Registry System: Harman 2-oxide(2506-09-4)

Safety Data

• Hazardous Substances Data: 2506-09-4(Hazardous Substances Data)

Usage

Description

This alkaloid from Calligonium minimum has the structure of harman N-oxide.

References

Sadykov, Abduralamov, Dokl. Akad. Nauk. Uzbek SSR, 12,25 (1960) Sadykov, Abduralamov, Uzbek Khim. Zh., 6, 47 (1961) Abduralamov, Sadykov, ibid, 4, 79 (1962)

Upstream product

• 486-84-0 harmane 

Downstream Products

• 486-84-0 harmane 

Relevant articles and documents

Unexpected ipso-Substitutions at the β-Carboline Nucleus

Minisci-type radical carbamoylation of 1-bromo-β-carboline (1) gives the 3-substituted product in low yield, whereas 1-acetyl-β-carboline (3a) reacts under ipso-substitution of the acetyl group. Cyanations of the N-oxides of 1 and 3a occur under clean ipso-substitution of the groups in 1-position. 1-Methyl derivatives show no tendency to react under ipso-substitution.

Microbial metabolites of harman alkaloids

Several microorganisms showed the ability to transform the harman alkaloids, harmaline (1), harmalol (2) and harman (5). Harmaline (1) and harmalol (2) were converted by Rhodotorula rubra ATCC 20129 into the tryptamines, 2-acetyl-3-(2-acetamidoethyl)-7-methoxyindole (3) and 2-acetyl-3-(2-acetamidoethyl)-7-hydroxyindole (4), respectively. Harman (5) was biotransformed by Cunninghamella echinulata NRRL 3655 into 6-hydroxyharman (6) and harman-2-oxide (7).