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Delta-9-Tetrahydrocannabinolic Acid B: A Mechanism for its Formation in Cannabis.
Cannabis Cannabinoid Res. 2023 02; 8(1):1-4.CC

Abstract

There appears to be consensus among Cannabis biologists that delta-9-tetrahydrocannabinolic acid A (THCA-A) is the exclusive product of the enzyme THCA synthase. This then leaves an open question for formation of the THCA-A structural isomer, delta-9-tetrahydrocannabinolic acid B (THCA-B), discovered as a minor product in Cannabis in 1969. With no reasonable biochemical pathway to explain the presence of THCA-B in Cannabis, a synthetic route was next considered. Using established literature precedent, a photochemical mechanism has been proposed for the conversion of THCA-A to cannabidiolic acid (CBDA), followed by conversion of CBDA to THCA-B employing bond-breaking and bond-forming reactions.

Authors+Show Affiliations

PerkinElmer Health Sciences, Inc., Waltham, Massachusetts, USA.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

35290744

Citation

Filer, Crist N.. "Delta-9-Tetrahydrocannabinolic Acid B: a Mechanism for Its Formation in Cannabis." Cannabis and Cannabinoid Research, vol. 8, no. 1, 2023, pp. 1-4.
Filer CN. Delta-9-Tetrahydrocannabinolic Acid B: A Mechanism for its Formation in Cannabis. Cannabis Cannabinoid Res. 2023;8(1):1-4.
Filer, C. N. (2023). Delta-9-Tetrahydrocannabinolic Acid B: A Mechanism for its Formation in Cannabis. Cannabis and Cannabinoid Research, 8(1), 1-4. https://doi.org/10.1089/can.2021.0216
Filer CN. Delta-9-Tetrahydrocannabinolic Acid B: a Mechanism for Its Formation in Cannabis. Cannabis Cannabinoid Res. 2023;8(1):1-4. PubMed PMID: 35290744.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Delta-9-Tetrahydrocannabinolic Acid B: A Mechanism for its Formation in Cannabis. A1 - Filer,Crist N, Y1 - 2022/03/15/ PY - 2022/3/16/pubmed PY - 2023/2/10/medline PY - 2022/3/15/entrez KW - Cannabis KW - THCA-B KW - photochemistry KW - tetrahydrocannabinolic acid B SP - 1 EP - 4 JF - Cannabis and cannabinoid research JO - Cannabis Cannabinoid Res VL - 8 IS - 1 N2 - There appears to be consensus among Cannabis biologists that delta-9-tetrahydrocannabinolic acid A (THCA-A) is the exclusive product of the enzyme THCA synthase. This then leaves an open question for formation of the THCA-A structural isomer, delta-9-tetrahydrocannabinolic acid B (THCA-B), discovered as a minor product in Cannabis in 1969. With no reasonable biochemical pathway to explain the presence of THCA-B in Cannabis, a synthetic route was next considered. Using established literature precedent, a photochemical mechanism has been proposed for the conversion of THCA-A to cannabidiolic acid (CBDA), followed by conversion of CBDA to THCA-B employing bond-breaking and bond-forming reactions. SN - 2378-8763 UR - https://www.unboundmedicine.com/medline/citation/35290744/Delta_9_Tetrahydrocannabinolic_Acid_B:_A_Mechanism_for_its_Formation_in_Cannabis_ DB - PRIME DP - Unbound Medicine ER -
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