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Nabilone

HCID 5284592
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Grundinformationen

CAS
51022-71-0
Standard-SMILES
CCCCCCC(C)(C)c1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(=O)C[C@@H]21
InChIKey
GECBBEABIDMGGL-RTBURBONSA-N
Summenformel
C24H36O3
Durchschnittliche Molmasse
372,5 g/mol

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
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
Englischer Name
NABILONE-DEA SCHEDULE II
Summenformel
C24H36O3
Molmasse
372.54

Namen und Synonyme

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
Weitere Namen anzeigen
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]

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,4
Polarare Oberfläche (TPSA)
46,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
6
Schwere Atome
27
Formalladung
0
Komplexität
524

Experimentelle und physikochemische Eigenschaften

Drugs · 4 Einträge

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 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
155 · 155-156°C
Siedepunkt
457.4 · 457.4±45.0 °C(Predicted)
Dichte
1.029 · 1.029±0.06 g/cm3(Predicted)
storage temp.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nabilone

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

wgk
3
RTECS-Nr.
HP8756000
risk_code
22-36-20/21/22-11

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Eintrag

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.

Zugehörige Reaktionen

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Reaktionsgleichung von HRID 867129
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Datenbank-Bezeichner

CAS
51022-71-0、61617-09-2
PubChem CID
5284592
ChEMBL
CHEMBL2218896
UNII
2N4O9L084N
EC Number
637-087-5
Nikkaji
J335.978F
2 · 2-8°C
Löslichkeit
18 mg/mL, · DMSO: ~18 mg/mL, soluble
Aggregatzustand
solid
pka
66 % · pKa in 66% DMF: 13.5(at 25℃)
Farbe
white
hazard_code
Xn,F
safety_code
36/37/39-45-36/37-16
DEA Controlled Substances
CSCN: 7379CAS SCH: IINARC: N
FDA Pharmacological Classification · 6 Einträge

2N4O9L084N

NABILONE

Established Pharmacologic Class [EPC] - Cannabinoid

Chemical Structure [CS] - Cannabinoids

Nabilone is a Cannabinoid.

NABILONE

MeSH Pharmacological Classification · 2 Einträge

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 Einträge

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

Anwendungen

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

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Ammoniak, wasserfreiLithium ion (1+)