(−)-nabilone

Modify Date: 2024-01-02 20:30:44

(−)-nabilone Structure
(−)-nabilone structure
Common Name (−)-nabilone
CAS Number 51022-71-0 Molecular Weight 372.541
Density 1.0±0.1 g/cm3 Boiling Point 457.4±45.0 °C at 760 mmHg
Molecular Formula C24H36O3 Melting Point 155-156ºC
MSDS USA Flash Point 145.4±22.2 °C
Symbol GHS07
GHS07
Signal Word Warning

 Names

Name (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
Synonym More Synonyms

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 457.4±45.0 °C at 760 mmHg
Melting Point 155-156ºC
Molecular Formula C24H36O3
Molecular Weight 372.541
Flash Point 145.4±22.2 °C
Exact Mass 372.266449
PSA 46.53000
LogP 7.05
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.517
Storage condition 2-8°C
Water Solubility DMSO: ~18 mg/mL, soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HP8756000
CHEMICAL NAME :
9H-Dibenzo(b,d)pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hy droxy- 6,6-dimethyl-, trans-(+-)-
CAS REGISTRY NUMBER :
51022-71-0
LAST UPDATED :
199403
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C24-H36-O3
MOLECULAR WEIGHT :
372.60
WISWESSER LINE NOTATION :
T B666 DV IOTT&J H1 H1 LX6&1&1 NQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1000 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 9,185,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1000 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - tremor Behavioral - Straub tail
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 9,185,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>5 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - somnolence (general depressed activity) Behavioral - ataxia
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 9,185,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>1 mg/kg
TOXIC EFFECTS :
Behavioral - general anesthetic Behavioral - food intake (animal) Behavioral - ataxia
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 9,185,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>10 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal)
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 9,185,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
>1 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - ataxia
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 9,185,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
205 mg/kg/29W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Related to Chronic Data - death
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 9,185,1987 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
348 mg/kg
SEX/DURATION :
female 14-22 day(s) after conception lactating female 20 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 48,A120,1979

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases 36/37/39-45
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS HP8756000

 Articles29

More Articles
Oral nabilone capsules in the treatment of chemotherapy-induced nausea and vomiting and pain.

Expert Opin. Investig. Drugs 17(1) , 85-95, (2008)

Nabilone has been approved to treat chemotherapy-induced nausea and vomiting. Recent studies have explored cannabinoids in pain management.To review the evidence for the use of cannabinoids in general...

A randomized, double-blinded, crossover pilot study assessing the effect of nabilone on spasticity in persons with spinal cord injury.

Arch. Phys. Med. Rehabil. 91(5) , 703-7, (2010)

To determine whether nabilone, a synthetic cannabinoid, alleviates spasticity in people with spinal cord injury (SCI).A double-blind, placebo-controlled crossover study.Outpatient rehabilitation clini...

An open-label comparison of nabilone and gabapentin as adjuvant therapy or monotherapy in the management of neuropathic pain in patients with peripheral neuropathy.

Pain Pract. 11(4) , 353-68, (2011)

Neuropathic pain (NeP) is prevalent in patients with peripheral neuropathy (PN), regardless of etiology. We sought to compare the efficacy of the cannabinoid nabilone as either monotherapy or adjuvant...

 Synonyms

9H-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-
UNII:2N4O9L084N
trans-(±)-3-(1,1-Dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one
Compound 109514
nabilone
Nabilonum
(6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-one
9H-Dibenzo[b,d]pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6aR,10aR)-
(6aR,10aR)-nabilone
Cesamet
Nabilon
Nabilone (USAN/INN)
(6aR,10aR)-3-(1,1-Dimethylheptyl)-1-hydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-on
(6aR,10aR)-3-(1,1-diméthylheptyl)-1-hydroxy-6,6-diméthyl-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromén-9-one
Cesamet (TN)
(6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-(2-methyl-2-octanyl)-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-one
Nabilona
(6aR,10aR)-3-(1,1-dimethylheptyl)-1-hydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-one