HARMANE Chemical Properties

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

pka

7.37, 14.6(at 25℃)

form 

Solid

color 

White to Dark Brown

Water Solubility 

1523g/L(20 ºC)

Merck 

13,4630

BRN 

143898

LogP

3.100

CAS DataBase Reference

486-84-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21-36/37/38

Safety Statements 

22-24/25-36-26

RIDADR 

1544

WGK Germany 

3

RTECS 

UV0280000

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 i.p. in mice: 50 mg/kg (Sigg)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

HARMANE Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

• Harmane was used in trace level determination of harmane by planar chromatography coupled with (tandem) mass spectrometry.
• It was used to study interactions of norharman and harman with DNA.
• It may be used as matrix for analysis of cyclodextrins and for sulfated oligosaccharides in combination with DHB as co-matrix.

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

HARMANE(486-84-0)Related Product Information

• HARMINE HYDROCHLORIDE
• SERPENTINE HYDROGEN TARTRATE
• HARMOL HYDROCHLORIDE
• HARMANE
• HARMANE HYDROCHLORIDE,harmane hcl
• BANISTERINE MONOHYDRATE
• HARMOL HYDROCHLORIDE DIHYDRATE
• Pyridine
• Indole
• Vasicine
• 9H-PYRIDO[3,4-B]INDOLE
• HARMANE-1,2,3,4-TETRAHYDRO-3-CARBOXYLIC ACID
• HARMANE FREE BASE
• HARMANE(SECONDARY STANDARD)
• ZERENEX E/6026463
• HARMINE METHYL IODIDE
• BROMOHARMINE HBR
• HARMANE METHYL IODIDE