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Tetrahydrocannabiphorol

Tetrahydrocannabiphorol ( THCP ) is a potent phytocannabinoid , a CB 1 and CB 2 receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC), [ 1 ] bu...

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Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC),[1] but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa.[2][3]

THCP is structurally similar to Δ9-THC, the main active component of cannabis, but with the pentyl side chain extended to heptyl. Since it has a longer side chain, its cannabinoid effects are "far higher than Δ9-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB1, approximately 33 times that of Δ9-THC (40 nM at CB1), however this does not mean it's 33x stronger per milligram.[4]

THCP was studied by Roger Adams as early as 1942.[5]

Isomers

Delta-3-THCP

Δ3-THCP

The Δ3/Δ6a(10a) isomer Δ3-THCP was synthesised in 1941, and was found to have around the same potency as Δ3-THC, unlike the hexyl homologue parahexyl which was significantly stronger.[6]

Delta-8-THCP

JWH-091 (Δ8-THCP) , CAS# 51768-60-6

The Δ8 isomer is also known as a synthetic cannabinoid under the code name JWH-091.[7][8] It's unconfirmed whether or not JWH-091 is found naturally in cannabis plants.[9] JWH-091 has approximately double the binding affinity at the CB1 receptor (22 nM ± 3.9 nM) in comparison to Δ9-THC (40.7 nM ± 1.7 nM) or Δ8-THC (44 nM ± 12 nM),[8] but appears significantly lower in vitro than the binding activity of Δ9-THCP (Ki = 1.2 nM)[4]

Natural cannabis occurrence

El isómero Δ 9 del THCP se encuentra de forma natural en las plantas de cannabis , pero en cantidades muy pequeñas. Un estudio de 2021 informó que el contenido de Δ 9 -THCP oscilaba entre 0,0023 % y 0,0136 % (p/p) (aproximadamente 0,02–0,13  mg/g) sin correlación con el porcentaje de THC en cepas de cannabis con predominio de Δ 9 -THC ; dicho estudio no detectó THCP en cepas con predominio de CBD . [ 2 ] [ 10 ]

Véase también

Referencias

  1. ↑ Harvey DJ (marzo de 1985). "Identificación de metabolitos hepáticos de n-heptil-delta-1-tetrahidrocannabinol en el ratón". Xenobiotica; el destino de los compuestos extraños en los sistemas biológicos . 15 (3): 187– 197. doi : 10.3109/00498258509045349 . PMID 2992174 . 
  2. 1 2 Bueno J, Greenbaum EA (febrero de 2021). "(-)- trans -Δ 9 -Tetrahidrocannabiforol Content of Cannabis sativa Inflorescencia from Various Chemotypes". Journal of Natural Products . 84 (2): 531– 536. doi : 10.1021/acs.jnatprod.0c01034 . PMID 33565878 . S2CID 231866062 .  
  3. ^ Linciano P, Russo F, Citti C, Tolomeo F, Paris R, Fulvio F, et al. (diciembre de 2021). "El nuevo contenido de cannabinoides del ácido heptilforólico en diferentes muestras de Cannabis sativa L.". Talanta . 235 122704. doi : 10.1016/j.talanta.2021.122704 . hdl : 11380/1250339 . PMID 34517579 .  
  4. 1 2 Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, et al. (Diciembre de 2019). "Un nuevo fitocannabinoide aislado de Cannabis sativa L. con una actividad cannabimimética in vivo superior al Δ 9 -tetrahidrocannabinol: Δ 9 -Tetrahidrocannabiforol" . Informes científicos . 9 (1): 20335. Código bibliográfico : 2019NatSR...920335C . doi : 10.1038/s41598-019-56785-1 . PMC 6937300 . PMID 31889124 .   
  5. ↑ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Homólogos y análogos del tetrahidrocannabinol con actividad de marihuana. XIII 1 " . Journal of the American Chemical Society . 64 (3): 694– 697. doi : 10.1021/ja01255a061 .
  6. ↑ Adams R, Loewe S, Jelinek C, Wolff H (julio de 1941). "Homólogos de tetrahidrocannabinol con actividad de marihuana. IX". Journal of the American Chemical Society . 63 (7): 1971– 1973. doi : 10.1021/ja01852a052 .
  7. ↑ Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, et al. (septiembre de 1999). "La manipulación de la cadena lateral del tetrahidrocannabinol delimita agonistas, agonistas parciales y antagonistas" . The Journal of Pharmacology and Experimental Therapeutics . 290 (3): 1065– 1079. PMID 10454479 .  
  8. 1 2 Bow EW, Rimoldi JM (2016). "Las relaciones estructura-función de los cannabinoides clásicos: modulación CB1/CB2" . Perspectives in Medicinal Chemistry . 8 : 17–39 . doi : 10.4137/PMC.S32171 . PMC 4927043. PMID 27398024 .  
  9. ↑ Hazekamp A, Fischedick JT, Díez ML, Lubbe A, Ruhaak RL (2010). "Química del cannabis" . Comprehensive Natural Products II . págs. 1033–1084 . doi : 10.1016/B978-008045382-8.00091-5 . ISBN  978-0-08-045382-8.
  10. ↑ Bueno J, Greenbaum EA (2021). "(-)- trans-Δ9-Tetrahidrocannabiforol Content of Cannabis sativa Inflorescencia from Various Chemotypes". Journal of Natural Products . 84 (2): 531– 536. doi : 10.1021/acs.jnatprod.0c01034 . PMID 33565878 . S2CID 231866062 .