69636-83-5

Usage

Uses

Used in Pharmaceutical Industry:
α-Cannabispiranol is used as a therapeutic agent for its potential to alleviate pain and inflammation, as well as to regulate mood disorders. Its interaction with cannabinoid receptors suggests a role in the treatment of various conditions that could benefit from such modulation.
Used in Research and Development:
α-Cannabispiranol serves as a subject of study in the exploration of cannabinoids, driving advancements in understanding their medicinal applications and safety profiles. This research is crucial for the development of new pharmaceuticals and therapeutic strategies based on the unique properties of α-Cannabispiranol.

Upstream product

• 61262-81-5 cannabispirone 
• 880-87-5 5,7-dimethoxyindan-1-one 
• 83088-36-2 5-methoxy-7-methoxyethoxymethyloxy-1-(3,3-ethylenedioxybutyl)indan-1-carbonitrile 
• 76842-65-4 rac-2',3'-dihydro-5',7'-dimethoxyspiro[cyclohex-2-ene-1,1'-[1H]inden]-4-one 
• 76842-66-5 C₁₆H₂₀O₄ 
• 83088-39-5 5-methoxy-7-methoxyethoxymethyloxy-1-(3,3-ethylenedioxybutyl)indan-1-carbaldehyde 
• 76842-69-8 5-methoxy-7-methoxyethoxymethyloxyindan-1-spiro-1'-cyclohex-2'-en-4'-one 
• 83088-41-9 5-methoxy-7-methoxyethoxymethyloxy-1-(3-oxobutyl)indan-1-carbaldehyde 
• 76842-62-1 5,7-dimethoxy-1-(3,3-ethylenedioxybutyl)indan-1-carbonitrile 
• 76842-63-2 5,7-dimethoxy-1-(3,3-ethylenedioxybutyl)indan-1-carbaldehyde 
• 76842-72-3 5-methoxy-7-methoxyethoxymethyloxyindan-1-carbonitrile 
• 76842-64-3 5,7-dimethoxy-1-(3-oxobutyl)indan-1-carbaldehyde 
• 76842-74-5 O-methylcannabispiradienone 
• 76842-71-2 5-methoxy-7-methoxyethoxymethyloxyindan-1-one 

Relevant academic research and scientific papers

Total Synthesis of the Spirans of Cannabis: Cannabispiradienone, Cannabispirenone-A and -B, Cannabispirone, α- and β-Cannabispiranols and the Dihydrophenanthrene Cannithrene-1

O-Methylcannabispirenone has been synthesised (57percent overall from 3,5-dimethoxycinnamic acid) via 5,7-dimethoxyindanone, p-tolylsulphonylmethyl isocyanide conversion into the 1-nitrile, alkylation with 1-iodo-3,3-ethylenedioxybutane, deacetalisation, and spirocyclisation. 5,7-Dimethoxyindanone is 7-deprotected by boron trichloride with high selectivity, and re-protected as the methoxyethoxymethyl ether: following the above route, finally deprotecting by boron trichloride, gives cannabispirenone-A (2) in 21percent overall yield.O-Methylcannabispirenone can be demethylated to give (2) by lithium 1,1-dimethylethanethiolate: demethylation with boron tribromide gives cannabispirenone-B (3).Hydrogenation of synthetic cannabispirenone-A gives cannabispirone (4), reduced by borohydride to the epimeric α-(6) and β-(5) cannabispiranols, separated by h.p.l.c.Dehydrogenation of O-methylcannabispirenone with dichlorodicyanobenzoquinone, followed by lithium 1,1-dimethylethanethiolate demethylation, gives cannabispiradienone (1).Under acidic conditions, the latter undergoes dienone-phenol rearrangement to give cannithrene-1 (8), thus completing the total synthesis of the spiro-cannabinoid group of natural products discussed in the preceding paper.The unsubstituted cannabispirenone parent has also been synthesised.

SYNTHESIS OF THE FIVE NATURAL CANNABIS SPIRANS

An efficient route to the O-protected spirenones (2c) and (2d) is described: from these, the five known natural spirans of cannabis, i.e. cannabispiradienone (1a), cannabispirenone-A (2a), cannabispirenone-B (2b), cannabispirone (3a) and cannabispiranol (4a), are synthesised.

Cannabis. XIII. Two new spiro-compounds, cannabispirol and acetyl cannabispirol

Two new spiro-compounds, cannabispirol and acetyl cannabispirol, were isolated along with cannabispirone and cannabispirenone from the Japanese domestic cannabis and these structures were elucidated. The biogenetic relationship of spiro-compounds and cannabinoids was also discussed.