化工社化工社 化学情報印刷レポート · 研究参考用
ハルマリン
ハルマリン · 7-メトキシ-1-メチル-3,4-ジヒドロ-β-カルボリン · ジヒドロハルミン · 4,9-ジヒドロ-7-メトキシ-1-メチル-3H-ピリド[3,4-b]インドール · O-メチルハルマロール · 3,4-ジヒドロ-7-メトキシ-1-メチル-9H-ピリド[3,4-b]インドール · 1-メチル-7-メトキシ-3,4-ジヒドロ-β-カルボリン · 3,4-ジヒドロハルミン
識別子と物理属性
| CAS No. | 304-21-2 |
|---|---|
| 分子式 | C13H14N2O |
| 平均分子量 | 214.26 g/mol |
| 単同位体質量 | 214.11061307 g/mol |
| SMILES | COc1ccc2c3c([nH]c2c1)C(C)=NCC3 |
| InChIKey | RERZNCLIYCABFS-UHFFFAOYSA-N |
| PubChem CID | 3564 |
| ChEMBL | CHEMBL340807 |
| ChEBI | CHEBI:28172 |
| EC No. | 206-152-6 |
| DTXSID | DTXSID8041038 |
| 現地名 | ハルマリン |
化学・物理的性質
| XLogP | 2.1 |
|---|---|
| 極性表面積 | 37.4 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 302 |
| 医薬品 | DEA NFLIS-Drug Category -> StimulantsPharmaceuticals -> Listed in ZINC15 |
| Color/Form | Orthorhombic bipyramidal prisms, tablets from methanol, rhombic octahedra from ethanol |
| 溶解度 | Slightly soluble in water, alcohol, etherquite soluble in hot alcohol, dilute acidsSoluble in chloroform, pyridine30.6 [ug/mL] (The mean of the results at pH 7.4)Slightly soluble in waterDMF: 1.4 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 0.25 mg/mlEthanol: 0.5 mg/ml |
| Human Drugs | Pharmaceuticals |
| 融点 | 229-231 °C250 - 251 °C232-234 °C(lit.) |
| Physical Description | Solid |
| Dissociation Constants | pKa = 4.2 |
| Collision Cross Section | 146.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]148.98 Ų [M+Na]+ [CCS Type: TW |
| Other Experimental Properties | Slender needles, moderately soluble in water, alcohol /Hydrochloride dihydrate/ |
| 沸点 | 354.4°C (rough estimate) |
| 比旋光度 | ±0° |
| 密度 | 1.0850 (rough estimate) |
| 屈折率 | 1.6450 (estimate) |
| 貯蔵条件 | -10 to -25°C |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 4.2(at 25℃) |
| 色 | Light orange to Yellow to Green |
| Merck | 14,4613 |
| BRN | 207310 |
| InChI | 1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3 |
| InChIKey | RERZNCLIYCABFS-UHFFFAOYSA-N |
| SMILES | COc1ccc2c3CCN=C(C)c3[nH]c2c1 |
| LogP（分配係数） | 2.251 (est) |
| CAS データベース | 304-21-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Harmaline(304-21-2) |
| EPAの化学物質情報 | 3H-Pyrido[3,4-b]indole, 4,9-dihydro-7-methoxy-1-methyl- (304-21-2) |
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.WarningH302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P270, P301+P317, P308+P316, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (33.3%) |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Natural Pollution Sources | ... from seeds of Peganum harmala L., Zygophyllaceae ... from Banisteria caapi Spruce, Malpighiaceae |
| Human Toxicity Excerpts | /CASE REPORTS/ Peganum harmala, commonly called "Syrian rue," is native to countries around the Mediterranean sea and western United States. Known for its sedative effects when consumed by farm animals, its seeds have stimulant and hallucinogenic effects at low doses (3-4 g when eaten) in humans. Its active ingredients harmaline and harmine have monoamine oxidase inhibitor properties. A 41-year-old female prepared a hot drink by boiling approximately 100 g of P. harmala seeds in water (10-20 times the recommended dose for "calming one's nerves"). Upon presentation to the emergency department, she was unconscious and had hypertension, tachycardia, and tachypnea. Hepatic and renal function markers were grossly elevated. After intubation, she improved with supportive care over the course of five days. Her level of consciousness, renal and hepatic markers gradually returned to normal. Poisoning with high doses of Peganum harmala can be life-threatening, although patients usually recover with supportive therapy alone. |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Neurotoxicity/ Both harmaline and physostigmine are known to produce whole-body tremors in rodents, yet there is little quantitative information on the differential frequency characteristics of these tremors or on other possible motor effects of these drugs. In addition, the degree to which tolerance develops to their tremorogenic effects is uncertain. OBJECTIVES: The purpose of this work was to use a new kind of instrument (the force-plate actometer) to describe quantitatively the frequency characteristics of tremor induced by the two drugs and simultaneously to measure locomotor activity effects. Another aim was to detect any tolerance effects on the tremor or locomotor measurements. Sprague-Dawley rats in four separate groups received harmaline (0, 4.0, 8.0, and 16.0 mg/kg) while another four groups received physostigmine (0, 0.10, 0.25, and 0.50 mg/kg). Dosing continued for 4 consecutive days. Each day, every rat's whole-body tremor and locomotor activity were recorded for 30 min. Fourier analysis of the force-plate recordings was used to quantify tremor and characterize its frequency components. Harmaline induced a dose-related tremor that peaked in the 10 Hz region of the spectrum, while the dose related-tremor of physostigmine was demonstrably of a broader-band frequency composition. While harmaline tremor exhibited pronounced tolerance, physostigmine tremor remained substantial across the 4 days of dosing. Both drugs suppressed locomotor activity, and there was no tolerance on this measure for either drug. In regard to tremor, harmaline and physostigmine induced quantitatively different kinds of tremor, and these differences probably reflect the drugs' different sites of action in the brain (harmaline: inferior olive |
用途
用途
薬理研究用。
用途
薬理、生理作用研究用。
使用
CNS stimulant, antiparkinsonian agent
製法・合成法
純化方法
Recrystallise harmaline from MeOH and sublime it at high vacuum. It has UV in MeOH a