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Nabilone

HCID 5284592
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
51022-71-0
표준 SMILES
CCCCCCC(C)(C)c1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(=O)C[C@@H]21
InChIKey
GECBBEABIDMGGL-RTBURBONSA-N
분자식
C24H36O3
평균 분자량
372.5 g/mol

개요

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.

이름 및 식별자

우선 이름
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
영어명
NABILONE-DEA SCHEDULE II
분자식
C24H36O3
분자량
372.54

이름 및 동의어

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
이름 더 보기
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]

물성

구조 계산 물성

XLogP
6.4
극성 표면적
46.5 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
6
무거운 원자 수
27
형식 전하
0
복잡도
524

실험 및 물리화학적 성질

Drugs · 4건

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 · 2건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

물리화학적 성질

녹는점
155 · 155-156°C
끓는 점
457.4 · 457.4±45.0 °C(Predicted)
밀도
1.029 · 1.029±0.06 g/cm3(Predicted)
저장 조건
2 · 2-8°C
용해도
18 mg/mL, · DMSO: ~18mg/mL, 가용성
물리적 상태
고체
산도 계수 (pKa)
66 % · pKa in 66% DMF: 13.5(at 25℃)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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

독성 정보

Hepatotoxicity · 1건

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 · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nabilone

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

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

화학 및 산업

약리 정보

ATC Code · 2건

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Pharmacodynamics · 1건

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 · 1건

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 · 1건

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.

관련 반응

11건
반응 기록 만들기
HRID 47126 반응식
HRID 47126생성물로uspto-grants-1979_11
HRID 47127 반응식
HRID 47127생성물로uspto-grants-1979_11
HRID 267859 반응식
HRID 267859생성물로uspto-grants-1976_03
HRID 616615 반응식
HRID 616615생성물로uspto-grants-1978_02
HRID 867128 반응식
HRID 867128생성물로uspto-grants-1978_07
HRID 867129 반응식
HRID 867129생성물로uspto-grants-1978_07
HRID 972941 반응식
HRID 972941생성물로uspto-grants-1977_10
HRID 972943 반응식
HRID 972943생성물로uspto-grants-1977_10
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화합물 노트

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데이터베이스 식별자

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

화학적 성질

White to Off-White Solid

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

2N4O9L084N

NABILONE

Established Pharmacologic Class [EPC] - Cannabinoid

Chemical Structure [CS] - Cannabinoids

Nabilone is a Cannabinoid.

NABILONE

MeSH Pharmacological Classification · 2건

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 · 3건

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

응용 분야

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

상·하류 제품 정보

상류 원료

암모니아(가스)Lithium ion (1+)