CAS 442-51-3|Harmine
Introduction：Basic information about CAS 442-51-3|Harmine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Harmine | ||
|---|---|---|---|
| CAS Number | 442-51-3 | Molecular Weight | 212.247 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 421.4±40.0 °C at 760 mmHg |
| Molecular Formula | C13H12N2O | Melting Point | 262-264 °C(lit.) |
| MSDS | / | Flash Point | 139.8±17.0 °C |
Names
| Name | harmine |
|---|---|
| Synonym | More Synonyms |
Harmine BiologicalActivity
| Description | Harmine is a natural dual-specificity tyrosine phosphorylation-regulated kinase ((DYRK)) inhibitor with anticancer and anti-inflammatory activities. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling Pathways >>Neuronal Signaling >>5-HT ReceptorSignaling Pathways >>Protein Tyrosine Kinase/RTK >>DYRKSignaling Pathways >>Cell Cycle/DNA Damage >>RAD51Research Areas >>CancerNatural Products >>AlkaloidResearch Areas >>Neurological Disease |
| Target | 5-HT2A Receptor:397 nM (Ki) DYRK1A RAD51 |
| In Vitro | Harmine is an inhibitor of 5-HT2A, with an Ki of 397 nM[1]. Harmine inhibits tau phosphorylation by DYRK1A by selected DANDYs, with an IC50 of 190 nM[2].Harmine negatively regulates HR by interfering Rad51 recruitment, resulting in severe cytotoxicity in hepatoma cells. Furthermore, NHEJ inhibitor Nu7441 markedly sensitizes Hep3B cells to the anti-proliferative effects of Harmine[3]. |
| In Vivo | It is shown that brain water content is significantly increased in the TBI group. Treatment with Harmine significantly reduces the tissue water content at 1, 3 and 5 days, compared with the TBI group. Harmine treatment significantly reduces the escape latency at 3 and 5 days, compared with the TBI group. Post-TBI administration of Harmine significantly improves the motor function recovery of the rats at 1, 3 and 5 days following TBI, compared with the TBI group without Harmine treatment. The neuronal survival rate in the Harmine-treated group is significantly increased, compared with the TBI group. Administration of Harmine results in marked elevation in the expression of GLT-1, compared with the TBI group. The administration of Harmine significantly reduces the expression of caspase 3, compared with the TBI group[4]. |
| Animal Admin | Rats[4] A total of 150 male Sprague-Dawley rats (age, 10-12 weeks; weighing, 280-320 g; are used in the present study. The rats are randomly divided into three groups: Sham-operated group (sham; n=15); the TBI group (TBI; n=35) and the TBI + Harmine-treated group (Harmine; n=35). Harmine is administered immediately following TBI (i.p, 30 mg/kg per day) for up to 5 days. The sham and TBI groups receive equal volumes of 0.9% saline solution (i.p.). The rats are grouped as follows for examination of behavioral recovery: Sham, n=3; TBI, n=7; and Harmine, n=7. Following TBI, the NSS is evaluated at 1, 3 and 5 days. Each rat is assessed by an observer who is blinded to the animal treatment[4]. |
| References | [1]. Glennon RA, et al. Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors. Drug Alcohol Depend. 2000 Aug 1;60(2):121-32. [2]. Neumann F, et al. DYRK1A inhibition and cognitive rescue in a Down syndrome mouse model are induced by new fluoro-DANDY derivatives. Sci Rep. 2018 Feb 12;8(1):2859. [3]. Zhang L, et al. Harmine suppresses homologous recombination repair and inhibits proliferation of hepatoma cells. Cancer Biol Ther. 2015;16(11):1585-92. [4]. Zhong Z, et al. Treatment with harmine ameliorates functional impairment and neuronal death following traumatic brain injury. Mol Med Rep. 2015 Dec;12(6):7985-91. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 421.4±40.0 °C at 760 mmHg |
| Melting Point | 262-264 °C(lit.) |
| Molecular Formula | C13H12N2O |
| Molecular Weight | 212.247 |
| Flash Point | 139.8±17.0 °C |
| Exact Mass | 212.094955 |
| PSA | 37.91000 |
| LogP | 3.17 |
| Vapour Pressure | 0.0±1.0 mmHg at 25°C |
| Index of Refraction | 1.706 |
| InChIKey | BXNJHAXVSOCGBA-UHFFFAOYSA-N |
| SMILES | COc1ccc2c(c1)[nH]c1c(C)nccc12 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intramuscular
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 3 mg/kg
- TOXIC EFFECTS :
- Behavioral - sleep Behavioral - tremor Gastrointestinal - nausea or vomiting
- REFERENCE :
- AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 200 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 243 mg/kg
- TOXIC EFFECTS :
- Behavioral - excitement Skin and Appendages - hair
- REFERENCE :
- PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 10,1171,1976
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 50 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 10 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 200 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Lungs, Thorax, or Respiration - dyspnea
- REFERENCE :
- AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 60 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - excitement Behavioral - ataxia
- REFERENCE :
- NEPHBW Neuropharmacology. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.9- 1970- Volume(issue)/page/year: 10,15,1971
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - guinea pig
- DOSE/DURATION :
- 100 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Amphibian - frog
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- QJPPAL Quarterly Journal of Pharmacy & Pharmacology. (London, UK) V.2-21, 1929-48. For publisher information, see JPPMAB. Volume(issue)/page/year: 9,37,1936 *** REVIEWS *** TOXICOLOGY REVIEW PISDDJ Pacific Information Service on Street Drugs. (J.K. Brown, School of Pharmacy, Univ. of the Pacific, Stockton, CA 95211) V.1- 1972(?)- Volume(issue)/page/year: 5(3-6),-,1977 TOXICOLOGY REVIEW CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 12,1,1978
Safety Information
| Hazard Codes | Xn:Harmful |
|---|---|
| Risk Phrases | R20/21/22;R36 |
| Safety Phrases | S22-S24/25-S36/37-S26 |
| RIDADR | 1544 |
| WGK Germany | 3 |
| RTECS | UV0175000 |
| Packaging Group | III |
| Hazard Class | 6.1 |
| 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% |
Synonyms
| 9H-Pyrido(3,4-b)indole, 7-methoxy-1-methyl- |
| Yajeine |
| Banisterine |
| Harmine |
| 7-Methoxy-1-methyl-9H-β-carboline |
| Telepathin |
| Yagein |
| Garmin |
| Telepathien |
| Harmin |
| Yageine |
| 9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl- |
| 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole |
| EINECS 207-131-4 |
| Telepathine |
| BANISTERINE MONOHYDRATE |
| 7-Methoxy-1-methyl-9H-pyrido(3,4-b)indole |
| MFCD00150055 |
