CAS 486-84-0|Harmane
| Common Name | Harmane | ||
|---|---|---|---|
| CAS Number | 486-84-0 | Molecular Weight | 182.221 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 386.9±22.0 °C at 760 mmHg |
| Molecular Formula | C12H10N2 | Melting Point | 235-238 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 176.2±13.6 °C |
Names
| Name | harman |
|---|---|
| Synonym | More Synonyms |
Harmane BiologicalActivity
| Description | Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4]. |
|---|---|
| Related Catalog | Signaling Pathways >>Neuronal Signaling >>Imidazoline ReceptorResearch Areas >>CancerSignaling Pathways >>GPCR/G Protein >>Imidazoline ReceptorSignaling Pathways >>Neuronal Signaling >>Monoamine OxidaseSignaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorResearch Areas >>Neurological Disease |
| Target | hMAO-A:0.5 μM (IC50) MAO-B:5 μM (IC50) α2-adrenergic receptor:18 μM (IC50) I1-Imidazoline receptor:30 nM (IC50) |
| References | [1]. Louis ED, et, al. Blood harmane concentrations and dietary protein consumption in essential tremor. Neurology. 2005 Aug 9;65(3):391-6. [2]. Musgrave IF, et, al. Harmane produces hypotension following microinjection into the RVLM: possible role of I(1)-imidazoline receptors. Br J Pharmacol. 2000 Mar;129(6):1057-9. [3]. Glover V, et, al. β-Carbolines as selective monoamine oxidase inhibitors:In vivo implications [4]. Umezawa K, et, al. Comutagenic effect of norharman and harman with 2-acetylaminofluorene derivatives. Proc Natl Acad Sci U S A. 1978 Feb;75(2):928-30. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 386.9±22.0 °C at 760 mmHg |
| Melting Point | 235-238 °C(lit.) |
| Molecular Formula | C12H10N2 |
| Molecular Weight | 182.221 |
| Flash Point | 176.2±13.6 °C |
| Exact Mass | 182.084396 |
| PSA | 28.68000 |
| LogP | 3.26 |
| Vapour Pressure | 0.0±0.8 mmHg at 25°C |
| Index of Refraction | 1.750 |
| InChIKey | PSFDQSOCUJVVGF-UHFFFAOYSA-N |
| SMILES | Cc1nccc2c1[nH]c1ccccc12 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 50 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 200 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- DNA adduct
MUTATION DATA - TYPE OF TEST :
- Mutation in mammalian somatic cells
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 100 mg/L
- REFERENCE :
- CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 17,249,1983
- TYPE OF TEST :
- Mutation in mammalian somatic cells
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 100 mg/L
- REFERENCE :
- CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 17,249,1983
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Hazard Codes | Xn: Harmful; |
| Risk Phrases | 20/21 |
| Safety Phrases | S22-S24/25 |
| RIDADR | 1544 |
| WGK Germany | 3 |
| RTECS | UV0280000 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles47
More Articles| Chemical genetics reveals a complex functional ground state of neural stem cells. Nat. Chem. Biol. 3(5) , 268-273, (2007) The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc... | |
| Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Nat. Chem. Biol. 5 , 765-71, (2009) Studies of gene function and molecular mechanisms in Plasmodium falciparum are hampered by difficulties in characterizing and measuring phenotypic differences between individual parasites. We screened... | |
| The use of natural product scaffolds as leads in the search for trypanothione reductase inhibitors Bioorg. Med. Chem. 16 , 6689, (2008) Twenty-three heterocyclic compounds were evaluated for their potential as trypanothione reductase inhibitors. As a result, the harmaline, 10-thiaisoalloxazine, and aspidospermine frameworks were ident... |
Synonyms
| 1-Methyl-9H-β-carboline |
| 2-Methyl-b-carboline |
| Harmane |
| Aribine |
| MFCD00004957 |
| Harman |
| 1-Methyl-β-carboline |
| 1-methylbetacarboline |
| Aribin |
| 1-Methyl-9H-pyrid[3,4-b]indole |
| EINECS 207-642-2 |
| 9H-Pyrido[3,4-b]indole, 1-methyl- |
| Passiflorin |
| Loturine |
| 1-methyl-9H-pyrido[3,4-b]indole |
| 1-Me-carboline |
| Locuturine |
| Locuturin |
| Phorbol 12,13-dibutyrate |
