| Identification | More | [Name]
HARMANE | [CAS]
486-84-0 | [Synonyms]
1-METHYL-9H-PYRIDO[3,4-B]INDOLE
1-METHYL-9H-PYRIDOL[3,4-B]INDOLE
2-METHYL-B-CARBOLINE
2-METHYL-BETA-CARBOLINE
ARIBINE
HARMAN
HARMANE
METHYL-4-CARBOLINE
METHYLCARBOLINE
TIMTEC-BB SBB003735
1-Methyl-9H-beta-carboline
1-Methyl-9H-pyrid(3,4-b)indole
1-Methyl-9H-β-carboline
1-Methyl-beta-carboline
1-Methylnorharman
3-Methyl-4-carboline
4-b)indole,1-methyl-9h-pyrido(
Aribin
Locuturin
Locuturine | [EINECS(EC#)]
207-642-2 | [Molecular Formula]
C12H10N2 | [MDL Number]
MFCD00004957 | [Molecular Weight]
182.22 | [MOL File]
486-84-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
235-238 °C(lit.)
| [Boiling point ]
305.62°C (rough estimate) | [density ]
1.1485 (rough estimate) | [refractive index ]
1.6266 (estimate) | [storage temp. ]
Store at RT | [solubility ]
methanol: soluble50mg/ml | [form ]
Solid | [pka]
7.37, 14.6(at 25℃) | [color ]
White to Dark Brown | [Water Solubility ]
1523g/L(20 ºC) | [Usage]
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.
| [Merck ]
13,4630 | [BRN ]
143898 | [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 | [SMILES]
N1C2=C(C=CC=C2)C2C=CN=C(C)C1=2 | [LogP]
3.100 | [CAS DataBase Reference]
486-84-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21:Harmful by inhalation and in contact with skin .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
1544 | [WGK Germany ]
3
| [RTECS ]
UV0280000
| [HazardClass ]
1.049 g/mL at 25 °C(lit.) | [PackingGroup ]
117-118 °C(lit.) | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Skin Irrit. 2 | [Toxicity]
LD50 i.p. in mice: 50 mg/kg (Sigg) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
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.
| [Definition]
ChEBI: An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, P
ssiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 37, p. 1429, 1972 DOI: 10.1021/jo00974a030
Tetrahedron, 49, p. 3325, 1993 DOI: 10.1016/S0040-4020(01)90161-9 | [General Description]
- Harmane is a potent tremor-producing β-carboline alkaloid and neurotoxin.
- It is major representative of heterocyclic aromatic amines, a group of mutagenic and carcinogenic substances which are formed in meat from the precursors creatine, creatinine, amino acids and sugars during the heating at high temperatures.
- Blood harmane concentration is elevated in essential tremor, late-life neurological disease.
| [Biological Activity]
Proposed as the endogenous ligand for imidazoline binding sites. Binds to I 1 -sites in rat kidney with an IC 50 of 31 nM, and I 2 -sites with a K i of 49 nM. In vivo, produces a dose-dependent hypotension that is reversed by efaroxan (2-(2-Ethyl-2,3-dihydro-2-benzofuranyl)-4,5-dihydro-1H-imidazole hydrochloride ). Also a potent inhibitor of monoamine oxidases A and B (I 50 values are 0.5 and 5 μ M respectively). | [Biochem/physiol Actions]
I1 imidazoline binding site agonist. | [storage]
Room temperature |
|
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