ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト:[email protected]AIアクセス:llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
  1. ホーム
  2. /化合物

ナビロン

Nabilone

HCID 5284592
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
51022-71-0
標準SMILES
CCCCCCC(C)(C)c1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(=O)C[C@@H]21
InChIKey
GECBBEABIDMGGL-RTBURBONSA-N
分子式
C24H36O3
平均分子量
372.5 g/mol

概要

Nabilone is a DEA Schedule II controlled substance. Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence. It is a Hallucinogenic substances substance.

名称と識別子

優先名称
Nabilone
IUPAC
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
現地名
ナビロン
英語名
NABILONE-DEA SCHEDULE II
分子式
C24H36O3
分子量
372.54

名称と別名

NabiloneCesamet51022-71-0NabilonaNabilonum2N4O9L084NCPD 109514CPD-109514DTXSID8023341(6AR,10AR)-1-HYDROXY-6,6-DIMETHYL-3-(2-METHYLOCTAN-2-YL)-6H,6AH,7H,8H,9H,10H,10AH-BENZO[C]ISOCHROMEN-9-ONELY 109514(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo(c)isochromen-9-one
名称をさらに表示
ナビロンlilly109514Nabilone solutiontrans-(+-)-hydroxy-NABILONE-DEA SCHEDULE IINabilone (1 mg/mL in Acetonitrile)d)pyran-9-one,3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-9h-dibenzo((6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6,6a,7,8,10,10a-hexahydrobenzo[c]chromen-9-onetrans-6,6-Dimethyl-3-(1,1-dimethylheptyl)-1-hydroxy-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one9H-Dibenzo[b,d]pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6aR,10aR)-rel-
RefChem:56613A04AD11DTXCID5014739541-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo(c)chromen-9-one(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-oneNabilone (1.0 mg/mL in Acetonitrile)Nabilonum [Latin]Nabilona [Spanish]

物性

構造計算による物性

XLogP
6.4
極性表面積
46.5 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
6
重原子数
27
形式電荷
0
複雑度
524

実験および物理化学的性質

Drugs · 4 件

DEA NFLIS-Drug Category -> Cannabinoids

DEA Schedule II Controlled Substance -> Hallucinogenic substances

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP6.8
Solubility4.93e-04 g/L
Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

物理化学的性質

融点
155 · 155-156°C
沸点
457.4 · 457.4±45.0 °C(Predicted)
比重(密度)
1.029 · 1.029±0.06 g/cm3(Predicted)
貯蔵温度
2 · 2-8°C
溶解性
18 mg/mL、可溶 · DMSO: ~18 mg/mL、可溶
外見
個体
酸解離定数(Pka)
66 % · pKa in 66% DMF: 13.5(at 25℃)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationDEA schedule II controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Hepatotoxicity · 1 件

Serum aminotransferase elevations during nabilone therapy are not common, generally mild and similar to the rate in controls who are receiving cancer chemotherapy. There have been no convincing cases of clinically apparent liver injury attributable to nabilone published in the literature and, thus, significant liver injury from nabilone must be exceeding rare, if it occurs at all.

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nabilone

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

安全データ

wgk
3
rtecs
HP8756000
risk_code
22-36-20/21/22-11
hazard_code
Xn,F
safety_code
36/37/39-45-36/37-16
DEA Controlled Substances

化学と産業

薬理情報

ATC Code · 2 件

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Pharmacodynamics · 1 件

Nabilone is a cannabinoid with therapeutic uses. It is an analog of dronabinol (also known as tetrahydrocannabinol or THC), the psychoactive ingredient in cannabis. Although structurally distinct from THC, nabilone mimics THC's structure and pharmacological activity through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, however it is considered to be twice as active as Δ⁹-THC.

Mechanism of Action · 1 件

Nabilone is an orally active synthetic cannabinoid which, like other cannabinoids, has complex effects on the central nervous system (CNS). It has been suggested that the antiemetic effect of nabilone is caused by interaction with the cannabinoid receptor system, i.e., the CB (1) receptor, which is a component of the endocannabinoid system of the body. The endocannabinoid system is widely distributed throughout the central and peripheral nervous system (via the Cannabinoid Receptors CB1 and CB2) and plays a role in many physiological processes such as inflammation, cardiovascular function, learning, pain, memory, stress and emotional regulation, and the sleep/wake cycle among many others. CB1 receptors are found in both the central and peripheral nervous system, and are most abundant in the hippocampus and amygdala, which are the areas of the brain responsible for short-term memory storage and emotional regulation. CB2 receptors are mainly located in the peripheral nervous system and can be found on lymphoid tissue where they are involved in regulation of immune function.

Biological Half-LifeThe plasma half-life (T1/2) values for nabilone and total radioactivity of identified and unidentified metabolites are about 2 and 35 hours, respectively.
Metabolism/Metabolites · 1 件

Hepatic. Two metabolic pathways have been suggested. The major pathway probably involves the direct oxidation of Nabilone to produce hydroxylic and carboxylic analogues. These compounds are thought to account for the remaining plasma radioactivity when carbinol metabolites have been extracted.

関連反応

11 件
反応記録を作成
HRID 47126 の反応式
HRID 47126生成物としてuspto-grants-1979_11
HRID 47127 の反応式
HRID 47127生成物としてuspto-grants-1979_11
HRID 267859 の反応式
HRID 267859生成物としてuspto-grants-1976_03
HRID 616615 の反応式
HRID 616615生成物としてuspto-grants-1978_02
HRID 867128 の反応式
HRID 867128生成物としてuspto-grants-1978_07
HRID 867129 の反応式
HRID 867129生成物としてuspto-grants-1978_07
HRID 972941 の反応式
HRID 972941生成物としてuspto-grants-1977_10
HRID 972943 の反応式
HRID 972943生成物としてuspto-grants-1977_10
1 / 2 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
51022-71-0、61617-09-2
PubChem CID
5284592
ChEMBL
CHEMBL2218896
UNII
2N4O9L084N
EC Number
637-087-5
Nikkaji
J335.978F
色
白い

化学的性質

化学的特性White to Off-White Solid

CSCN: 7379CAS SCH: IINARC: N
FDA Pharmacological Classification · 6 件

2N4O9L084N

NABILONE

Established Pharmacologic Class [EPC] - Cannabinoid

Chemical Structure [CS] - Cannabinoids

Nabilone is a Cannabinoid.

NABILONE

MeSH Pharmacological Classification · 2 件

Drugs used to prevent NAUSEA or VOMITING.

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

Absorption, Distribution and Excretion · 3 件

Nabilone appears to be completely absorbed from the human gastrointestinal tract when administered orally. Following oral administration of a 2 mg dose of radiolabeled nabilone, peak plasma concentrations of approximately 2 ng/mL nabilone and 10 ng equivalents/mL total radioactivity are achieved within 2.0 hours.

The route and rate of the elimination of nabilone and its metabolites are similar to those observed with other cannabinoids, including delta-9-THC (dronabinol). When nabilone is administered intravenously, the drug and its metabolites are eliminated mainly in the feces (approximately 67%) and to a lesser extent in the urine (approximately 22%) within 7 days. Of the 67% recovered from the feces, 5% corresponded to the parent compound and 16% to its carbinol metabolite. Following oral administration about 60% of nabilone and its metabolites were recovered in the feces and about 24% in urine. Therefore, it appears that the major excretory pathway is the biliary system.

The apparent volume of distribution of nabilone is about 12.5 L/kg.

Cellular LocationsMembrane

応用分野

使用A labelled synthetic cannabinoid with antiemetic, antiglaucoma, and CNS activity. Antiemetic. Controlled substance (hallucinogen).

上流・下流製品情報

上流原料

アンモニアリチウムイオン