HARMANE Property

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

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

HARMANE Chemical Properties,Usage,Production

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