CAS 244-63-3|Norharmane
| Common Name | Norharmane | ||
|---|---|---|---|
| CAS Number | 244-63-3 | Molecular Weight | 168.195 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 391.3±15.0 °C at 760 mmHg |
| Molecular Formula | C11H8N2 | Melting Point | 219-221 ºC |
| MSDS | ChineseUSA | Flash Point | 182.1±11.7 °C |
Names
| Name | β-carboline |
|---|---|
| Synonym | More Synonyms |
Norharmane BiologicalActivity
| Description | Norharmane (Norharman), isolated from coffee, is a potent and selective monoamine oxidase A (MAO-A) inhibitor with a Ki of 3.34 μM[1]. |
|---|---|
| Related Catalog | Signaling Pathways >>Neuronal Signaling >>Monoamine OxidaseResearch Areas >>Neurological Disease |
| Target | MAO-A:3.34 μM (Ki) Human Endogenous Metabolite |
| References | [1]. Herraiz T, et al. Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. Life Sci. 2006 Jan 18;78(8):795-802. [2]. Lee HW, et al. Potent Selective Inhibition of Monoamine Oxidase A by Alternariol Monomethyl Ether Isolated from Alternaria brassicae. J Microbiol Biotechnol. 2017 Feb 28;27(2):316-320. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 391.3±15.0 °C at 760 mmHg |
| Melting Point | 219-221 ºC |
| Molecular Formula | C11H8N2 |
| Molecular Weight | 168.195 |
| Flash Point | 182.1±11.7 °C |
| Exact Mass | 168.068741 |
| PSA | 28.68000 |
| LogP | 2.80 |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.785 |
| InChIKey | AIFRHYZBTHREPW-UHFFFAOYSA-N |
| SMILES | c1ccc2c(c1)[nH]c1cnccc12 |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 100 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2520 mg/kg/28D-C
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 2520 mg/kg
- SEX/DURATION :
- male 28 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - testes, epididymis, sperm duct
- TYPE OF TEST :
- DNA adduct
MUTATION DATA - TYPE OF TEST :
- Mutation in mammalian somatic cells
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 150 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 :
- 150 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 | R22 |
| Safety Phrases | S36/37/39-S26-S22 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | UU9350000 |
| 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% |
Articles38
More Articles| Gamma-carboline derivatives with anti-bovine viral diarrhea virus (BVDV) activity. Bioorg. Med. Chem. 16 , 3780, (2008) Based on anti-viral screening of our heteroaromatics derived from thalidomide, the gamma-carboline skeleton has been identified as a superior scaffold structure for compounds with potent anti-bovine v... | |
| 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... | |
| Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: Evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO Bioorg. Med. Chem. 19 , 7416-24, (2011) Monoamine oxidase (MAO) catalyzes the oxidative deamination of biogenic and exogenous amines and its inhibitors have therapeutic value for several conditions including affective disorders, stroke, neu... |
Synonyms
| Pyridoindole |
| CARBAZOLINE |
| b-carboline |
| β-carboline |
| MFCD00004956 |
| betacarboline |
| Norharmane |
| 9H-Pyrido[3,4-b]indole |
| EINECS 205-959-0 |
| Nor Harmane |
| norhaman |
| Norharman |
| beta-carboline |
| 9H-β-Carboline |
| 2-Azacarbazole |
