CBD-DMH

CBD-DMH
IUPAC ime
	5-(1,1-Dimetilheptil)-2-[(1R,6R)-3-metil-6-(1-metiletenil)-2-cikloheksen-1-il]-1,3-benzenediol
Identifikatori
CAS broj	97452-63-6
ATC kod	None
PubChem	CID 126670
Sinonimi	1,1-dimetilheptilkanabidiol; 5-(1,1-dimetilheptil)-2-(3-metil-6-(1-metiletenil)-2-cikloheksen-1-il)-1,3-benzenediol; 5-(1,1-dimetilheptil)kanabidiol; 5-(1,1-dimetilheptil)kanabidiol, (1S-trans)-izomer
Hemijski podaci
Formula	C25H38O2
Molarna masa	370.57
	SMILES CCCCCCC(C)(C)C1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O; ;
	InChI InChI=InChI=1S/C25H38O2/c1-7-8-9-10-13-25(5,6)19-15-22(26)24(23(27)16-19)21-14-18(4)11-12-20(21)17(2)3/h14-16,20-21,26-27H,2,7-13H2,1,3-6H3/t20-,21+/m0/s1 ; Key:MPJURNPNPDQYSY-LEWJYISDSA-N ;

Kanabidiol-dimetilheptil (CBD-DMH ili DMH-CBD) je sintetički homolog kanabidiola u kome je pentilni lanac zamenjen dimetilheptilnim lancom. Poznato je nekoliko izomera ovog jedinjenja. Izomer koji je najčešće korišćen u istraživanjima je (−)-CBD-DMH. On ima istu stereohemiju kao i prirodni kanabidiol, ali 1,1-dimetilheptilni bočni lanac. Ovo jedinjenje nije psihoaktivno i deluje prvenstveno kao anandamidni inhibitor preuzimanja. Ono je potentnije od kanabidiola kao antikonvulsant i ima približno istu potentnost kao antiinflamatorno sredstvo.^[1]^[2]^[3]^[4]^[5] Neočekivano je utvrđeno da veštački enantiomer (+)-CBD-DMH, koji ima reverznu stereohemiju od kanabidiola, direktno deluje kao agonist kanabinoidnog receptora sa K_i od 17.4nM na CB₁ i 211nM na CB₂, i proizvodi tipične kanabinoidne efekte u studijama na životinjama.^[6]

Još jedno blisko srodno jedinjenje je poznato. Ono ima dvostruku vezu u cikloheksenskom prstenu pomerenu na 1,6-poziciju umesto 2,3-pozicije (i.e. analogno je sintetičkim THC analozima, poput paraheksila). Kod tog jedinjenja je izopropenilna grupa zasićena do izopropilne, i ono ima 1,2-dimetilheptilni bočni lanac. Ovo jedinjenje je sintetisano Birčovom redukcijom iz 1,2-dimetilheptilnog analoga kanabidiola. Ono isto tako proizvodi potentne kanabinoidima slične efekte kod životinja, ali ima tri hiralna centra i sastoji se od smeše osam stereoizomera, koji nisu pojedinačno izučavanji, te nije poznato koji su enantiomeri aktivni.^[7]^[8]

Vidi još

Reference

^ Leite, J. R.; Carlini, E. A.; Lander, N.; Mechoulam, R. (1982). „Anticonvulsant effects of the (-) and (+)isomers of cannabidiol and their dimethylheptyl homologs”. Pharmacology. 24 (3): 141—146. PMID 7071126. doi:10.1159/000137588.
^ Bisogno, Tiziana; Hanuš, Lumír; De Petrocellis, Luciano; Tchilibon, Susanna; Ponde, Datta E.; Brandi, Ines; Moriello, Aniello Schiano; Davis, John B.; Mechoulam, Raphael; Di Marzo, Vincenzo (2001). „Molecular targets for cannabidiol and its synthetic analogues: Effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide”. British Journal of Pharmacology. 134 (4): 845—852. PMC 1573017 . PMID 11606325. doi:10.1038/sj.bjp.0704327.
^ Fride, Ester; Ponde, Datta; Breuer, Aviva; Hanuš, Lumir (2005). „Peripheral, but not central effects of cannabidiol derivatives: Mediation by CB1 and unidentified receptors”. Neuropharmacology. 48 (8): 1117—1129. PMID 15910887. S2CID 16531395. doi:10.1016/j.neuropharm.2005.01.023.
^ Ben-Shabat, Shimon; Hanuš, Lumír O.; Katzavian, Galia; Gallily, Ruth (2006). „New Cannabidiol Derivatives: Synthesis, Binding to Cannabinoid Receptor, and Evaluation of Their Antiinflammatory Activity”. Journal of Medicinal Chemistry. 49 (3): 1113—1117. PMID 16451075. doi:10.1021/jm050709m.
^ Juknat, Ana; Kozela, Ewa; Kaushansky, Nathali; Mechoulam, Raphael; Vogel, Zvi (2016). „Anti-inflammatory effects of the cannabidiol derivative dimethylheptyl-cannabidiol – studies in BV-2 microglia and encephalitogenic T cells”. Journal of Basic and Clinical Physiology and Pharmacology. 27 (3): 289—296. PMID 26540221. S2CID 4829497. doi:10.1515/jbcpp-2015-0071.
^ Hanu?, Lum�r O.; Tchilibon, Susanna; Ponde, Datta E.; Breuer, Aviva; Fride, Ester; Mechoulam, Raphael (2005). „Enantiomeric cannabidiol derivatives: Synthesis and binding to cannabinoid receptors”. Organic & Biomolecular Chemistry. 3 (6): 1116. PMID 15750656. doi:10.1039/B416943C. replacement character у |first1= на позицији 4 (помоћ)
^ Razdan RK, Pars HG, Thompson WR, Granchelli FE (1974). „Lithium-ammonia reduction of tetrahydrocannabinols”. Tetrahedron Letters. 15 (49–50): 4315—4318. doi:10.1016/S0040-4039(01)92152-5.
^ Razdan, K. (1981). „The Total Synthesis of Cannabinoids”. Ур.: Apsimon, John. The Total Synthesis of Natural Products. Wiley Interscience. стр. 245. ISBN 978-0-471-05460-3. OCLC 19487018.

Literatura

Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799.

Spoljašnje veze

[1] Leite, J. R.; Carlini, E. A.; Lander, N.; Mechoulam, R. (1982). „Anticonvulsant effects of the (-) and (+)isomers of cannabidiol and their dimethylheptyl homologs”. Pharmacology. 24 (3): 141—146. PMID 7071126. doi:10.1159/000137588.

[2] Bisogno, Tiziana; Hanuš, Lumír; De Petrocellis, Luciano; Tchilibon, Susanna; Ponde, Datta E.; Brandi, Ines; Moriello, Aniello Schiano; Davis, John B.; Mechoulam, Raphael; Di Marzo, Vincenzo (2001). „Molecular targets for cannabidiol and its synthetic analogues: Effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide”. British Journal of Pharmacology. 134 (4): 845—852. PMC 1573017 . PMID 11606325. doi:10.1038/sj.bjp.0704327.

[3] Fride, Ester; Ponde, Datta; Breuer, Aviva; Hanuš, Lumir (2005). „Peripheral, but not central effects of cannabidiol derivatives: Mediation by CB1 and unidentified receptors”. Neuropharmacology. 48 (8): 1117—1129. PMID 15910887. S2CID 16531395. doi:10.1016/j.neuropharm.2005.01.023.

[4] Ben-Shabat, Shimon; Hanuš, Lumír O.; Katzavian, Galia; Gallily, Ruth (2006). „New Cannabidiol Derivatives: Synthesis, Binding to Cannabinoid Receptor, and Evaluation of Their Antiinflammatory Activity”. Journal of Medicinal Chemistry. 49 (3): 1113—1117. PMID 16451075. doi:10.1021/jm050709m.

[5] Juknat, Ana; Kozela, Ewa; Kaushansky, Nathali; Mechoulam, Raphael; Vogel, Zvi (2016). „Anti-inflammatory effects of the cannabidiol derivative dimethylheptyl-cannabidiol – studies in BV-2 microglia and encephalitogenic T cells”. Journal of Basic and Clinical Physiology and Pharmacology. 27 (3): 289—296. PMID 26540221. S2CID 4829497. doi:10.1515/jbcpp-2015-0071.

[6] Hanu?, Lum�r O.; Tchilibon, Susanna; Ponde, Datta E.; Breuer, Aviva; Fride, Ester; Mechoulam, Raphael (2005). „Enantiomeric cannabidiol derivatives: Synthesis and binding to cannabinoid receptors”. Organic & Biomolecular Chemistry. 3 (6): 1116. PMID 15750656. doi:10.1039/B416943C. replacement character у |first1= на позицији 4 (помоћ)

[7] Razdan RK, Pars HG, Thompson WR, Granchelli FE (1974). „Lithium-ammonia reduction of tetrahydrocannabinols”. Tetrahedron Letters. 15 (49–50): 4315—4318. doi:10.1016/S0040-4039(01)92152-5.

[8] Razdan, K. (1981). „The Total Synthesis of Cannabinoids”. Ур.: Apsimon, John. The Total Synthesis of Natural Products. Wiley Interscience. стр. 245. ISBN 978-0-471-05460-3. OCLC 19487018.

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