CAS 51022-71-0|(−)-nabilone

Introduction：Basic information about CAS 51022-71-0|(−)-nabilone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Chemical & Physical Properties
3. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
4. Safety Information
5. Articles29
6. Synonyms

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	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
InChIKey	GECBBEABIDMGGL-RTBURBONSA-N
SMILES	CCCCCCC(C)(C)c1cc(O)c2c(c1)OC(C)(C)C1CCC(=O)CC21
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

Articles29

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

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