Cannabisol

Cannabisol
Clinical data
ATC code	None;
Identifiers
	IUPAC name (6aR,10aR,6a'R,10a'R)-2,2'-Methylenebis(6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol);
CAS Number	1384106-31-3;
PubChem CID	102487751;
ChemSpider	58828771;
Chemical and physical data
Formula	C43H60O4
Molar mass	640.949 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1CC4=C(C5=C(C=C4CCCCC)OC([C@H]6[C@H]5C=C(CC6)C)(C)C)O)O;
	InChI InChI=1S/C43H60O4/c1-9-11-13-15-28-23-36-38(32-21-26(3)17-19-34(32)42(5,6)46-36)40(44)30(28)25-31-29(16-14-12-10-2)24-37-39(41(31)45)33-22-27(4)18-20-35(33)43(7,8)47-37/h21-24,32-35,44-45H,9-20,25H2,1-8H3/t32-,33-,34-,35-/m1/s1; Key:PDADLCKRVIFEGH-BAQBVXSRSA-N;

Cannabisol was a cannabis-derived medication in the early 20th century in Sweden. The drug was used to treat depression until the 1950s.^[1] The 1934 Year Book of the American Pharmaceutical Association states, "A 1.2 p.c. solution of standardized cannabinol, the active constituent of Cannabis indica, is given in doses of 8 to 20 drops three times a day for depression."^[2] The Natural Library of Medicine states, "Cannabisol (1), a unique dimer of Δ9-tetrahydrocannabinol (Δ9-THC) with a methylene bridge, was isolated from Cannabis sativa.^[3] This is the first example of a C-bridged dimeric cannabinoid. The structure of 1 was unambiguously deduced by HRESIMS, GCMS, and NMR spectroscopy. A plausible biogenesis of 1 is described."^[4]^[5]

References

↑ Decorte, Tom (11 February 2016). World Wide Weed: Global Trends in Cannabis Cultivation and its Control. Routledge. pp. 53–. ISBN 978-1-134-78521-6. https://books.google.com/books?id=Dv6NCwAAQBAJ&pg=PT53.
↑ Year Book of the American Pharmaceutical Association. Washington, D.C.: American Pharmaceutical Association. 1934. p. 86. https://books.google.com/books?id=2U5LAAAAMAAJ.
↑ "Life, Before and After CBD Became Prominent". Safer Products. https://safercbd.com/cannabisol-the-truth-behind-cbd-and-its-origins/.
↑ "Cannabis sativa". Tetrahedron Letters 53 (28): 3560–3562. July 2012. doi:10.1016/j.tetlet.2012.04.139. PMID 27695140.
↑ "CBD Oil Benefits". https://holisticwatch.com/what-are-the-benefits-of-cbd/. Sunday, March 8, 2020

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[Decorte2016-1] Decorte, Tom (11 February 2016). World Wide Weed: Global Trends in Cannabis Cultivation and its Control. Routledge. pp. 53–. ISBN 978-1-134-78521-6. https://books.google.com/books?id=Dv6NCwAAQBAJ&pg=PT53.

[2] Year Book of the American Pharmaceutical Association. Washington, D.C.: American Pharmaceutical Association. 1934. p. 86. https://books.google.com/books?id=2U5LAAAAMAAJ.

[3] "Life, Before and After CBD Became Prominent". Safer Products. https://safercbd.com/cannabisol-the-truth-behind-cbd-and-its-origins/.

[4] "Cannabis sativa". Tetrahedron Letters 53 (28): 3560–3562. July 2012. doi:10.1016/j.tetlet.2012.04.139. PMID 27695140.

[5] "CBD Oil Benefits". https://holisticwatch.com/what-are-the-benefits-of-cbd/. Sunday, March 8, 2020

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Clinical data

ATC code	None
Identifiers
IUPAC name (6aR,10aR,6a'R,10a'R)-2,2'-Methylenebis(6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol)
CAS Number	1384106-31-3
PubChem CID	102487751
ChemSpider	58828771
Chemical and physical data
Formula	C₄₃H₆₀O₄
Molar mass	640.949 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1CC4=C(C5=C(C=C4CCCCC)OC([C@H]6[C@H]5C=C(CC6)C)(C)C)O)O
InChI InChI=1S/C43H60O4/c1-9-11-13-15-28-23-36-38(32-21-26(3)17-19-34(32)42(5,6)46-36)40(44)30(28)25-31-29(16-14-12-10-2)24-37-39(41(31)45)33-22-27(4)18-20-35(33)43(7,8)47-37/h21-24,32-35,44-45H,9-20,25H2,1-8H3/t32-,33-,34-,35-/m1/s1 Key:PDADLCKRVIFEGH-BAQBVXSRSA-N

Cannabisol

Topic: Chemistry

References