Dexanabinol

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Structural formula
Structure of dexanabiol
General
Non-proprietary name Dexanabinol
other names
  • HU-211
  • Sinnabidiol
  • (6a S , 10a S ) -9- (hydroxymethyl) -6,6-dimethyl-3- (2-methyloctan-2-yl) -6a, 7,10,10a-tetrahydrobenzo [ c ] chromen-1-ol
Molecular formula C 25 H 38 O 3
External identifiers / databases
CAS number 112924-45-5
EC number 675-766-8
ECHA InfoCard 100.201.022
PubChem 107778
ChemSpider 96934
DrugBank DB06444
Wikidata Q962504
Drug information
Drug class

Antiemetic

properties
Molar mass 386,57 g · mol -1
safety instructions
GHS labeling of hazardous substances
08 - Dangerous to health 07 - Warning

Caution

H and P phrases H: 302-312-315-319-332-335-361
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dexanabinol (HU-211) is a synthetic cannabinoid that does not bind to CB 1 and CB 2 receptors . It is a research chemical that is currently not approved for marketing.

chemistry

Dexanabinol is the enantiomer of HU-210 , a very potent cannabinoid. Structurally, it is the mirror image of the side chain homologue of the THC metabolite 11-hydroxy-Δ 9 -tetrahydrocannabinol.

The original synthesis of HU-211 is based on an acid-catalyzed condensation of (+) - myrthenol and 1,1-dimethylheptylresorcinol (3,5-dihydroxy-1- (1,1-dimethylheptyl) benzene).

structure

It was developed in Raphael Mechoulam's group at the Hebrew University in Jerusalem. HU-211 does not bind to known cannabinoid receptors but to NMDA receptor channels and has therefore been tested as a potential drug for traumatic brain injury , but was no more effective than placebo in clinical studies.

literature

  • K. Razdan: The Total Synthesis of Cannabinoids . In: John Apsimon (Ed.): The Total Synthesis of Natural Products . Wiley Interscience, 1981, ISBN 978-0-471-05460-3 , p. 245.

Web links

Individual evidence

  1. Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label of [No public or meaningful name is available] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 14, 2020, is derived from a self-classification by the distributor .
  2. R. Mechoulam, N. Lander, A. Breuer, J. Zahalka: Synthesis of the Individual, Pharmacologically Distinct, Enantiomers of a Tetrahydrocannabinol Derivative . In: Tetrahedron: Asymmetry , 1990, 5, pp. 315-318.
  3. R Zeltser, Z Seltzer, A Eisen, JJ Feigenbaum, R Mechoulam: Suppression of neuropathic pain behavior in rats by a non-psychotropic synthetic cannabinoid with NMDA receptor-blocking properties . In: Pain . 47, No. 1, October 1991, pp. 95-103. PMID 1663228 .
  4. ^ AI Maas, G Murray, H Henney et al .: Efficacy and safety of dexanabinol in severe traumatic brain injury: results of a phase III randomized, placebo-controlled, clinical trial . In: The Lancet Neurology . 5, No. 1, January 2006, pp. 38-45. doi : 10.1016 / S1474-4422 (05) 70253-2 . PMID 16361021 .