(−)-nabilone
Names
[ CAS No. ]:
51022-71-0
[ Name ]:
(−)-nabilone
[Synonym ]:
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
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
[ 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
Articles
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...