1-methyl-9H-pyrido[3,4-b]indole

• ChemBase ID: 37475
• Molecular Formular: C12H10N2
• Molecular Mass: 182.2212
• Monoisotopic Mass: 182.08439833
• SMILES: c1ccc2c(c1)c1c([nH]2)c(ncc1)C
• Canonical SMILES: Cc1nccc2c1[nH]c1c2cccc1
• InChI: InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
• InChIKey: PSFDQSOCUJVVGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-9H-pyrido[3,4-b]indole
• IUPAC Traditional name: harmane; 1-methyl-9H-pyrido[3,4-b]indole
• Synonyms: 1-Methyl-9H-beta-carboline; ARIBINE; 3-Methyl-4-carboline; Loturine; Passiflorin; Harman; Harman; 1-Methyl-9H-pyrido[3,4-b]indole; 2-Methyl-β-carboline; Aribine; Harmane; 1-甲基-9H-吡啶并[3,4-b]吲哚; 2-甲基-β-咔啉; 阿锐碱; 哈尔满碱; More...

Database IDs

• CAS Number: 486-84-0
• EC Number: 207-642-2
• MDL Number: MFCD00004957
• Beilstein Number: 143898
• PubChem SID: 161000782; 24873706; 24846602
• PubChem CID: 5281404

CALCULATED PROPERTIES

• Acid pKa: 13.718027
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.4493957
• LogD (pH = 7.4): 1.9892261
• Log P: 2.0045834
• Molar Refractivity: 55.9068 cm^3
• Polarizability: 24.108831 Å^3
• Polar Surface Area: 28.68 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dilute Aqueous Acid
• Apperance: Off-White to Pale Brown Solid; Powder
• Melting Point: 229-230°C; 235-238 °C(lit.); 236-238 °C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• RTECS: UV0280000
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: stupéfiant

Pharmacology Properties

• Gene Information: human ... CYP2D6(1565)rat ... Gabra2(29706); rat ... Gabra2(29706)
• Mechanism of Action: GABA-ergic effects; Inhibitor of serotonergic dorsal raphe neurons

Product Information

• Purity: ≥98.0% (NT); 98%
• Grade: purum
• Biological Source: Alkaloid from Arariba rubra (Rubiaceae), Passiflora incarnata (Passifloraceae) and many other Passiflora spp., and a wide range of spp. in several families. Also present in tobacco smoke. Prod. by Nocardia sp. and Streptomyces sp.
• Application(s): Cytotoxic intercalating agent; Hallucinogen; Sedative
• Empirical Formula (Hill Notation): C12H10N2

DETAILS

MP Biomedicals - 05201596

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 103276

Application
Used as matrix for analysis of cyclodextrins and for sulfated oligosaccharides in combination with DHB as co-matrix.
Biochem/physiol Actions
I1 imidazoline binding site agonist.
Packaging
1 g in glass bottle
Protocols & Applications
Methods of glycosylated protein analysis by Mass Spectrometry

Sigma Aldrich - 51370

Biochem/physiol Actions
I1 imidazoline binding site agonist.

Toronto Research Chemicals - H105000

Harman alkaloid like harmane, harmine, harmalol, harmaline obtained from Banisteriopsis caapi L. showed cytotoxicity, antimicrobial activity against Staphylococcus aureus, Escherichia coli, Proteus vulgaris and Candida albicans.

REFERENCES

• Sigg, E.B., et al.: Arch. Int. Pharmacodyn., 149, 164 (1964)
• Saano, V., et al.: Acta Pharmacol. Toxicol., 51, 300 (1964)
• Tse, S., et al.: Biochem. Pharmacol., 42, 459 (1964)
• Rommelspacher, H., et al.: Eur. J. Pharmacol., 252, 51 (1964)
• Louis, E., et a