Nabilone

Structural formula
	1: 1 mixture of the ( enantiomers ): ; (6a R , 10a R ) form (top) and ; (6a S , 10a S ) form (bottom)
General
Non-proprietary name	Nabilone
other names	(6a R * , 10a R * ) -3- (1,1-Dimethyl heptyl) -6,6a, 7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9 H -dibenzo [ b , d ] pyran-9-one; (±) - trans -3- (1,1-dimethylheptyl) -6,6a, 7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9 H -dibenzo [ b , d ] pyran -9-on; Latin : nabilonum;
Molecular formula	C 24 H 36 O 3
Brief description	white solid
External identifiers / databases
EC number	637-087-5
ECHA InfoCard	100.164.824
PubChem	5284592
DrugBank	DB00486
Wikidata	Q419079
Drug information
ATC code	A04 AD11
Drug class	Antiemetics , cannabinoids
properties
Molar mass	372.54 g · mol -1
Physical state	firmly
Melting point	159-160 ° C
solubility	DMSO : ~ 18 g · l −1 , insoluble in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	> 1000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nabilone is a fully synthetic derivative of Δ ⁹ -tetrahydrocannabinol . Nabilone was patented by Eli Lilly in 1975 as a tranquilizer and anti- emetic.

Manufacturing

A multi-step synthesis starting from 3,5-dimethoxybenzaldehyde is described in the literature. The synthesis can also take place by isomerization from the corresponding 6a, 10a-cis product, which in turn is accessible from the condensation of resorcinol derivatives with 4- (1-hydroxy-1-methylethyl) -3-cyclohexen-1-one.

Stereoisomerism

3- (1,1-dimethylheptyl) -6,6a, 7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9 H -dibenzo [ b , d pyran-9-one has] two stereogenic centers. So there can be four stereo isomers . The drug nabilone is a racemate [1: 1 mixture of the (6a R , 10a R ) form and the (6a S , 10a S ) form, which are enantiomeric to one another ]. The other two stereoisomers [(6a R , 10a S ) form and (6a S , 10a R ) form] have no pharmacological significance.

Legal

Nabilone is listed as a narcotic in Appendix III of the German Narcotics Act. It is therefore marketable in Germany and must be prescribed on the narcotic prescription.

indication

Nabilone is approved

in anorexia and cachexia in AIDS patients
as an antiemetic for nausea and vomiting under cytostatics or radiation therapy as part of cancer therapy.

Trade names

Cesamet (USA, GB)
Canemes (AT, DE)

Individual evidence

↑ ^a ^b ^c ^d data sheet Nabilone solid, ≥ 98% (HPLC) from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1097, ISBN 978-0-911910-00-1 .
↑ Entry on nabilone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substance s, 4th edition (2000), Thieme-Verlag Stuttgart, pp. 1381-1382, ISBN 978-1-58890-031-9 .
↑ US Patent 4,171,315 .
↑ US Patent 4054582 .

Web links

FDA label from Cesamet (PDF; 97 kB)

[Sigma-1] ta sheet Nabilone solid, ≥ 98% (HPLC) from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).

[MerckIndex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1097, ISBN 978-0-911910-00-1 .

[ChemIDplus-3] Entry on nabilone in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[A._Kleemann-4] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substance s, 4th edition (2000), Thieme-Verlag Stuttgart, pp. 1381-1382, ISBN 978-1-58890-031-9 .

[5] US Patent 4,171,315 .

[6] US Patent 4054582 .