Tetrahydrocannabinolic acid

Source: Wikipedia, the free encyclopedia.
Not to be confused with
11-nor-9-Carboxy-THC
.
Tetrahydrocannabinolic acid
Skeletal formula of tetrahydrocannabinolic acid
Ball-and-stick model of the tetrahydrocannabinolic molecule
Clinical data
Other names2-Carboxy-THC; THCA, 2-COOH-THC
ATC code
  • none
Identifiers
  • (6aR,10aR)-1-Hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylic acid
JSmol)
  • CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1C(=O)O)O

Tetrahydrocannabinolic acid (THCA, 2-COOH-THC;

conjugate base tetrahydrocannabinolate) is a precursor of tetrahydrocannabinol (THC), an active component of cannabis.[1]

THCA is found in variable quantities in fresh, undried cannabis, but is progressively

cannabis edibles.[1]

Uses

THCA is rarely directly used, but its presence is commonly analyzed when cannabis or hemp-based products are screened for THC; some countries require that it be measured in such screens.[2][3]: 32 

THCA in its isolated form is available for purchase in select medical and recreational cannabis dispensaries in the form of a white crystalline powder. It can be smoked or vaporized in typical smoking devices, such as a bong or dab rig (device used for vaporizing hash oil). These methods convert the THCA to THC and so are used for their psychoactive effects. THCA is also sometimes encapsulated and taken as a supplement for a variety of illnesses, although there are currently no established medical applications.[4]

Pharmacological effects

Conversion of THCA to

reagents used in biochemistry experiments are contaminated with THC due to THCA's instability.[5]

A study found THCA and unheated

U937 macrophages and peripheral blood macrophages, an inhibition that persisted over a longer period of time, whereas after prolonged exposure time THC and heated extract tend to induce the TNFα level. THCA and THC show distinct effects on phosphatidylcholine specific phospholipase C (PC-PLC) activity, as THCA and unheated extracts inhibit the PC-PLC activity in a dose-dependent manner, but THC only induced PC-PLC activity at high concentrations, suggest THCA and THC exert their immuno-modulating effects via different metabolic pathways.[6]

The

CB2 receptor antagonist that increased cell proliferation. It is suggested that in a nonpsychoactive treatment for IBD, THCA should be used rather than CBD.[7]

THCA binds to and activates

PPARγ with higher potency than its decarboxylated products.[8]

THCA shows a similar

DUID). THCA was detected in the urine and blood serum samples of several cannabis consumers in concentrations of up to 10.8 ng/mL in urine and 14.8 ng/mL in serum. The concentration of THCA was below the THC concentration in most serum samples, resulting in molar ratios of THCA/THC of approximately 5.0–18.6%. Where a short elapsed time between the last intake and blood sampling was assumed, the molar ratio was 18.6% in the serum.[10]

Chemistry

It has two isomers, THCA-A, in which the carboxylic acid group is in the 1 position, between the hydroxy group and the carbon chain, and THCA-B, in which the carboxylic acid group is in the 3 position, following the carbon chain.[11]: 20  The crystal structures of both THCA-A (colourless prisms, orthorhombic P212121) and THCA-B (also colourless prisms, orthorhombic P212121) have been reported.[12][13]

In the past THCA was thought to be formed in plants by

cyclization of cannabidiolic acid but due to studies in the late 1990s it became apparent that its precursor is cannabigerolic acid, which goes through oxidocyclization through the actions of the enzyme THCA-synthase.[3]
: 14 

It is unstable, and slowly decarboxylates into THC during storage, and the THC itself slowly degrades to CBN, which has potential immunosuppressive and anti-inflammatory activities.[1] When heated or burned, as when cannabis is smoked or included in baked goods, the decarboxylation is rapid but not complete; THCA is detectable in people who smoke or otherwise consume cannabis.[1]

Legal status

THCA is not scheduled by the United Nations' Convention on Psychotropic Substances.[14]

United States

THCA is not

possession could potentially be prosecuted under the Federal Analogue Act.[16] In practice, because THCA spontaneously decarboxylates to form THC, no real sample of purified THCA will be completely free of THC. Thus, any laboratory analysis of THCA using any technique involving significant heat will generate THC in the handling and analytical process. Further, both the Farm Bill and the USDA specify that analytical testing of samples for total THC must use "post-decarboxylation or other similarly reliable methods".[17][18]

See also

References

  1. ^
    PMID 28861488
    .
  2. PMID 15734104
    .
  3. ^
    ISBN 978-92-1-148242-3. Archived from the original
    (PDF) on 29 August 2017.
  4. ^ Hanna A (2018-01-26). "What Is THCA Crystalline?". High Times. Retrieved 2020-02-04.
  5. ^
    PMID 28861508
    .
  6. PMID 16504929
    .
  7. PMID 29082314
    .
  8. PMID 28853159
    .
  9. PMID 21985215
    .
  10. PMID 17219606
    .
  11. ISBN 978-1-59259-947-9
    .
  12. S2CID 231804940
    .
  13. PMID 1138526
    .
  14. ^ "Convention on Psychotropic Substances". 1971. Archived from the original on 2014-03-17. Retrieved 2015-09-21.
  15. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-29.
  16. ^ "Federal Controlled Substance Analogue Act Summary". Erowid Analog Law Vault.
  17. ^ "7 CFR § 990.25 - Standards of performance for detecting total delta-9 tetrahydrocannabinol (THC) concentration levels". LII / Legal Information Institute. Retrieved 2023-07-05.
  18. ^ "AGRICULTURE IMPROVEMENT ACT OF 2018" (PDF). Congress Public Law Library. Retrieved July 4, 2023.
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