Kanaboid

Kanabinoidi su klasa spojeva koja obuhvata fitokanabinoide (kisik-sadržavajuće C₂₁ aromatske ugljikovodike u biljci kanabis) i hemijske spojeve koji oponašaju dejstvo fitokanabinoida ili imaju sličnu strukturu (npr. endokanabinoidi, u nervnom i imunskom sistemu životinja, koji aktiviraju kanabinoidne receptore).^[1] Najpoznatiji kanabinoid je delta-9-tetrahidrokanabinol (∆⁹THC, THC- primarni psihoaktivni spoj kanabisa).^[2]^[3]

Sintetski kanabinoidi obuhvataju mnoštvo odvojenih klasa hemijskih spojeva: klasični kanabinoidi koji su strukturno srodni sa THC-om, neklasični kanabinoidi kao što su aminoalkilindoli, 1,5-diarilpirazoli, kvinolini i arilsulfonamidi, kao i eikosanoidi srodni sa endokanabinoidima.^[2]

Kanabinoidni receptori uredi

Prije 1980-ih pretpostavljalo se da kanabinoidi proizvode njihove fiziološke i efekte na ponašanje putem nespecifične interakcije sa ćelijskim membranama, umjesto specifičnim interakcija sa za membranu vezanim receptorima. Otkriće prvih kanabinoidnih receptora tokom 1980-ih doprinijelo je rješenju te debate. Ti receptori su široko zastupljeni kod životinja, a nađeni su kod sisara, ptica, riba i reptila. Di sada su poznata dva tipa kanabinoidnih receptora, zvanih CB₁ i CB₂, a^[1] smatra se da postoje još nekoliko kanabinoidnih receptora.^[4]

Fitokanabinoidi uredi

Tip	Skelet	Ciklizacija
Tip kanabigerola CBG
Kanabihromenski tip CBC
Kanabidiolni tip CBD
Tetrahidrokanabinolni- i kanabinolni tip THC, CBN	Hemijska struktura kanabinoida tipa CBN.
Kanabielsoinski tip CBE
iso- Tetrahidrokanabinolni- tip izo-THC
Kanabiciklolni tip CBL
Kanabicitranski tip CBT
Glavne klase prirodnih kanabinoida

Fitokanabinoidi, prirodni kanabinoidi, biljni kanabinoidi i klasični kanabinoidi su klasa kanabinoida za koju se poznato da se prirodno javlja u znatnim količinama u biljci kanabis. Koncentrirani su u viskoznim smolama (rezinima), koje nastaje u žljezdanim strukturama poznatim kao trihomi. Pored kanabinoida, smolom su bogati i terpeni, koji su u znatnoj meri odgovorni za miris biljke kanabisa.

Fitokanabinoidi su skoro nerastvorivii u vodi, ali su rastvorivi u lipidima, alkoholima, i drugim nepolarnim organskim rastvaračima. Međutim, kao i fenoli, oni formiraju u većoj mjeri u vodi rastvorljive fenolatne soli u jako alkalinim uvjetima.

Svi prirodni kanabinoidi su izvedeni dekarboksilacijom njihovih odgovarajućih 2-karboksilnih kiselina (2-COOH-) (ovaj proces je kataliziran toplotom, svjetlošću ili alkalnom sredinom).

Tipovi uredi

Iz biljke konoplje izolovano je više od 85 kanabinoida ^[5] Glavne klase prirodnih kanabinoida prikazana su u tabeli sa desne strane. Sve klase su izvedene iz kanabigerolnog tipa spojeva i razlikuju se uglavnom u načinu ciklizacije tog prekursora.

Tetrahidrokanabinol (THC), kanabidiol (CBD) i kanabinol (CBN) su najzastupljeniji i najbolje istraženi prirodni kanabinoidi. Drugi uobičajeni kanabinoidi su:

CBG – Kanabigerol
CBC– Kanabihromen
CBL – Kanabiciklol
CBV – Kanabivarin
THCV – Tetrahidrokanabivarin
CBDV – Kanabidivarin
CBCV – Kanabihromevarin
CBGV – Kanabigerovarin
CBGM – Kanabigerol monoetil-eter

Tetrahidrokanabinol uredi

Tetrahidrokanabinol (THC) je primarna psihoaktivna komponenta biljke. Olakšava umjerenu bol (analgetik) i ima neurozaštitna svojstva. THC ima približnono jednak afinitet za receptore CB₁ i CB₂.^[6]

Delta-9-tetrahidrokanabinol (Δ⁹-THC, THC) i delta-8-tetrahidrokanabinol (Δ⁸THC), oponašaju dejstvo anandamida, neurotransmitera koji se prirodno proizvodi u tijelu. Molekule THC-a proizvode upotrebno stanje kanabisa vezivanjem za CB₁ kanabinoidne receptore mozga.

Kanabidiol uredi

Kanabidiol (CBD) nije jako psihoaktivan sam po sebi, a smatralo se da nema uticaja na psihoaktivnost THC-a.^[7] Međutim, nedavne studije su pokazale da su pušači kanabisa sa visokim CBD/THC odnosom manje skloni da dožive šizofreniji slične simptome.^[8] Ti nalazi podržani su psihološkim testovima, u kojima participanti doživljavaju manje intenzivne psihozolike efekte kad se THC intravenozno primjenjuje sa CBD-om (mjereno putem PANSS-ovog testa).^[9] Kanabidiol nema afiniteta za receptore CB₁ i CB₂, ali deluje kao indirektni antagonist kanabinoidnih agonista.^[10] Nedavno je utvrđeno da je on antagonist mogućeg novog kanabinoidnog receptora, GPR55, GPCR koji je eksprimiran u nucleus caudatus i putamenu.^[11] Za kanabidiol je također pokazano da djeluje kao agonist receptora 5-HT_1A,^[12] na koji način deluje kao antidepresant,^[13]^[14] anksiolitik,^[14]^[15] i neurozaštitnik.^[16]^[17]

Kanabinol uredi

Kanabinol (CBN) je primarni proizvod degradacije THC-a, i obično ga ima malo u svježim biljkama. Sadržaj CBN-a povećava se sa degradacijom THC-a tokom skladištenja i sa izlaganjem svjetlosti i zraku. Veoma blago je psihoaktivan. Njegov afinitet za receptor CB₂ veći je nego za receptor CB₁.^[18]

Endokanabinoidi uredi

Anandamid, jedan od endogenih liganda receptora CB₁ i CB₂

Endokanabinoidi su supstance proizvedene u tijelu koje aktiviraju kanabinoidne receptore. Nakon otkrića prvog kanabinoidnog receptora (1988.), započeta je potragu za endogenim ligandima tog receptora.

Tipovi endokanabinoidnih liganda uredi

Arahidonoil etanolamid (Anandamid ili AEA)
2-arahidonoil glicerol (2-AG)
2-arahidonil gliceril etar (noladin eter)
N--arahidonoil-dopamin (NADA)
Virodhamin (OAE)

Prirodni kanabinoidi uredi

Kanabigerolni tip CBG)
Kanabigerol (E)-CBG-C₅	Kanabigerol monometil etar (E)-CBGM-C₅ A	Kanabinerolna kiselina A (Z)-CBGA-C₅ A	Kanabigerovarin (E)-CBGV-C₃
Kanabigerolna kiselina A (E)-CBGA-C₅ A	Kanabigerolna kiselina A monometil eter (E)-CBGAM-C₅ A	Kanabigerovarinska kiselina A (E)-CBGVA-C₃ A
Kanabihromenski tip (CBC)
(±)-Kanabihromen CBC-C₅	(±)-Kanabihromenska kiselina A CBCA-C₅ A	(±)-Kanabivarihromen, (±)-Kanabihromevarin CBCV-C₃	(±)-Kanabihromevarinska kiselina A CBCVA-C₃ A
Kanabidiolni tip (CBD)
(−)-Kanabidiol CBD-C₅	Kanabidiol monometil etar CBDM-C₅	Kanabidiol-C₄ CBD-C₄	(−)-Kanabidivarin CBDV-C₃	Kanabidiorkol CBD-C₁
Kanabidiolna kiselina CBDA-C₅	Kanabidivarinska kiselina CBDVA-C₃
Kanabinodiolni tip (CBND)
Kanabinodiol CBND-C₅	Kanabinodivarin CBND-C₃
Tetrahidrokanabinolni tip (THC)
Δ⁹-Tetrahidrokanabinol Δ⁹-THC-C₅	Δ⁹-Tetrahidrokanabinol-C₄ Δ⁹-THC-C₄	Δ⁹-Tetrahidrokanabivarin Δ⁹-THCV-C₃	Δ⁹-Tetrahidrokanabiorkol Δ⁹-THCO-C₁
Δ⁹-Tetrahidro- kanabinolna kiselina A Δ⁹-THCA-C₅ A	Δ⁹-Tetrahidro- kanabinolna kiselina B Δ⁹-THCA-C₅ B	Δ⁹-Tetrahidro- kanabinolna kiselina C₄ A i/ili B Δ⁹-THCA-C₄ A and/or B	Δ⁹-Tetrahidro- kanabivarinska kiselina A Δ⁹-THCVA-C₃ A	Δ⁹-Tetrahidro- kanabiorkolna kiselina A i/ili B Δ⁹-THCOA-C₁ A i/ili B
(−)-Δ⁸-trans-(6aR,10aR)- Δ⁸-Tetrahidrokanabinol Δ⁸-THC-C₅	(−)-Δ⁸-trans-(6aR,10aR)- Tetrahidrokanabinolna kiselina A Δ⁸-THCA-C₅ A	(−)-(6aS,10aR)-Δ⁹- Tetrahidrokanabinol *(−)-cis-Δ⁹-THC-C₅*
Kanabinolni tip (CBN)
Kanabinol CBN-C₅	Kanabinol-C₄ CBN-C₄	Kanabivarin CBN-C₃	Kanabinol-C₂ CBN-C₂	Kanabiorkol CBN-C₁
Kanabinolna kiselina A CBNA-C₅ A	Kanabinol metil etar CBNM-C₅
Kanabitriolni tip (CBT)
(−)-(9R,10R)-trans- Kanabitriol *(−)-trans-CBT-C₅*	(+)-(9S,10S)-Kanabitriol *(+)-trans-CBT-C₅*	(±)-(9R,10S/9S,10R)- Kanabitriol *(±)-cis-CBT-C₅*	(−)-(9R,10R)-trans- 10-O-Etil-kanabitriol *(−)-trans-CBT-OEt-C₅*	(±)-(9R,10R/9S,10S)- Kanabitriol-C₃ *(±)-trans-CBT-C₃*
8,9-Dihydroxy-Δ^6a(10a)- tetrahidrokanabinol 8,9-Di-OH-CBT-C₅	Kanabidiolna kiselina A kanabitriolni estar CBDA-C₅ 9-OH-CBT-C₅ estar	(−)-(6aR,9S,10S,10aR)- 9,10-Dihidroksi- heksahidrokanabinol, Kanabiripsol Kanabiripsol-C₅	(−)-6a,7,10a-Trihidroksi- Δ⁹-tetrahidrokanabinol (−)-Kanabitetrol	10-Okso-Δ^6a(10a)- tetrahidrokanabinol -{OTHC
Kanabielsoinski tip (CBE)
(5aS,6S,9R,9aR)- Kanabielsoin CBE-C₅	(5aS,6S,9R,9aR)- C₃-Kanabielsoin CBE-C₃	(5aS,6S,9R,9aR)- Kanabielsoinska kiselina A CBEA-C₅ A	(5aS,6S,9R,9aR)- Kanabielsoinska kiselina B CBEA-C₅ B	(5aS,6S,9R,9aR)- C₃-Kanabielsoinska kiselina B CBEA-C₃ B
Kanabiglendol-C₃ OH-izo-HHCV-C₃	Dehidrokanabifuran DCBF-C₅	Kanabifuran CBF-C₅
Izokanabinoidi
(−)-Δ⁷-trans-(1R,3R,6R)- Isotetrahydrocannabinol	(±)-Δ⁷-1,2-cis- (1R,3R,6S/1S,3S,6R)- Isotetrahydro- cannabivarin	(−)-Δ⁷-trans-(1R,3R,6R)- Isotetrahydrocannabivarin
Kanabiciklolni tip (CBL)
(±)-(1aS,3aR,8bR,8cR)- Kanabiciklol CBL-C₅	(±)-(1aS,3aR,8bR,8cR)- Kanabiciklolna kiselina A CBLA-C₅ A	(±)-(1aS,3aR,8bR,8cR)- Kanabiciklovarin CBLV-C₃
Kanabicitranski tip (CBT)
Kanabicitran CBT-C₅
Kanabihromanonski tip (CBCN)
Kanabihromanon CBCN-C₅	Kanabihromanon-C3 CBCN-C₃	Kanabikoumaronon CBCON-C₅

Reference uredi

^ ^a ^b Pacher P, Batkai S, Kunos G (2006). "The endocannabinoid system as an emerging target of pharmacotherapy". Pharmacol Rev. 58 (3): 389–462. doi:10.1124/pr.58.3.2. PMC 2241751. PMID 16968947.
^ ^a ^b Lambert DM, Fowler CJ (2005). "The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications". J. Med. Chem. 48 (16): 5059–87. doi:10.1021/jm058183t. PMID 16078824.
^ Pertwee, Roger, ured. (2005). Cannabinoids. Springer-Verlag. str. 2. ISBN 978-3-540-22565-2.
^ Begg M, Pacher P, Bátkai S, Osei-Hyiaman D, Offertáler L, Mo FM, Liu J, Kunos G (2005). "Evidence for novel cannabinoid receptors". Pharmacol. Ther. 106 (2): 133–45. doi:10.1016/j.pharmthera.2004.11.005. PMID 15866316.
^ El-Alfy, Abir T. et. al. "Antidepressant-like effect of [Delta]9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L." Pharmacology Biochemistry and Behavior. 2010 Jun;95(4). ISSN 0091-3057}}
^ Huffman, JW (2000). "The search for selective ligands for the CB₂ receptor". Curr. Pharm. Des. 6 (13): 1323–37. doi:10.2174/1381612003399347. PMID 10903395.
^ "Behavioural Pharmacology - Abstract: Volume 16(5-6) September 2005 p 487-496 Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids". 04. 2020. Pristupljeno 24. 6. 2007. Nepoznati parametar |fix-attempted= zanemaren (pomoć); Nepoznati parametar |bot= zanemaren (pomoć); Provjerite vrijednost datuma u parametru: |date= (pomoć)
^ Morgan CJ, Curran HV (2008). "Effects of cannabidiol on schizophrenia-like symptoms in people who use cannabis". The British journal of psychiatry : the journal of mental science. 192 (4): 306–7. doi:10.1192/bjp.bp.107.046649. PMID 18378995.
^ "Should I Smoke Dope?". Pristupljeno 24. 5. 2008.
^ Mechoulam, R.; M. Peters; Murillo-Rodriguez (21. 8. 2007). "Cannabidiol - recent advances". Chemistry & Biodiversity. 4 (8): 1678–1692. doi:10.1002/cbdv.200790147. PMID 17712814.^{[mrtav link]}|date=04. 2019 |bot=InternetArchiveBot |fix-attempted=yes }}
^ Ryberg E; Larsson N; Sjögren S; et al. (2007). "The orphan receptor GPR55 is a novel cannabinoid receptor". British Journal of Pharmacology. 152 (7): 1092–101. doi:10.1038/sj.bjp.0707460. PMC 2095107. PMID 17876302.
^ Russo EB, Burnett A, Hall B, Parker KK (2005). "Agonistic properties of cannabidiol at 5-HT1a receptors". Neurochemical Research. 30 (8). doi:10.1007/s11064-005-6978-1. PMID 16258853. ISBN 1106400569781 pogrešan ISBN.
^ Zanelati T, Biojone C, Moreira F, Guimarães F, Joca S (2009). "Antidepressant-like effects of cannabidiol in mice: possible involvement of 5-HT receptors". British Journal of Pharmacology. 159 (1): 122–8. doi:10.1111/j.1476-5381.2009.00521.x. PMC 2823358. PMID 20002102.
^ ^a ^b Resstel LB, Tavares RF, Lisboa SF, Joca SR, Corrêa FM, Guimarães FS (2009). "5-HT1A receptors are involved in the cannabidiol-induced attenuation of behavioural and cardiovascular responses to acute restraint stress in rats". British Journal of Pharmacology. 156 (1): 181–8. doi:10.1111/j.1476-5381.2008.00046.x. PMC 2697769. PMID 19133999.
^ Campos AC, Guimarães FS (2008). "Involvement of 5HT1A receptors in the anxiolytic-like effects of cannabidiol injected into the dorsolateral periaqueductal gray of rats". Psychopharmacology. 199 (2). doi:10.1007/s00213-008-1168-x. PMID 18446323. ISBN 2130081168 pogrešan ISBN.
^ Mishima K; Hayakawa K; Abe K; et al. (2005). "Cannabidiol prevents cerebral infarction via a serotonergic 5-hydroxytryptamine1A receptor-dependent mechanism". Stroke; a Journal of Cerebral Circulation. 36 (5): 1077–82. doi:10.1161/01.STR.0000163083.59201.34. PMID 15845890.^{[mrtav link]}|date=09. 2018 |bot=InternetArchiveBot |fix-attempted=yes }}
^ Hayakawa K; Mishima K; Nozako M; et al. (2007). "Repeated treatment with cannabidiol but not Delta9-tetrahydrocannabinol has a neuroprotective effect without the development of tolerance". Neuropharmacology. 52 (4): 1079–87. doi:10.1016/j.neuropharm.2006.11.005. PMID 17320118.^{[trajno mrtav link]}
^ Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK (2000). "Novel cannabinol probes for CB₁ and CB₂ cannabinoid receptors". Journal of medicinal chemistry. 43 (20): 3778–85. doi:10.1021/jm0001572. PMID 11020293.

Dopunska literatura uredi

de Meijer EP, Bagatta M, Carboni A, Crucitti P, Moliterni VM, Ranalli P, Mandolino G (2003). "The inheritance of chemical phenotype in Cannabis sativa L". Genetics. 163 (1): 335–46. PMC 1462421. PMID 12586720. Pristupljeno 5. 4. 2011.
Devane, WA; Hanuš L; Breuer A; et al. (1992). "Isolation and structure of a brain constituent that binds to the cannabinoid receptor". Science. 258 (5090): 1946–9. doi:10.1126/science.1470919. PMID 1470919.
Elsohly MA, Slade D (2005). "Chemical constituents of marijuana: the complex mixture of natural cannabinoids". Life Sci. 78 (5): 539–48. doi:10.1016/j.lfs.2005.09.011. PMID 16199061.
Hanuš L, Gopher A, Almog S, Mechoulam R (1993). "Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor". J. Med. Chem. 36 (20): 3032–4. doi:10.1021/jm00072a026. PMID 8411021.
Hanuš, L.; Krejčí, Z. (1975). "Isolation of two new cannabinoid acids from Cannabis sativa L. of Czechoslovak origin". Acta Univ. Olomuc., Fac. Med. 74: 161–166. Referenca sadrži prazan nepoznati parametar: |author-name-separator= (pomoć)
Hanuš, L.; Krejčí, Z.; Hruban, L. (1975). "Isolation of cannabidiolic acid from Turkish variety of cannabis cultivated for fibre". Acta Univ. Olomuc., Fac. Med. 74: 167–172. Referenca sadrži prazan nepoznati parametar: |author-name-separator= (pomoć)
Köfalvi, Attila, ured. (2010). Cannabinoids and the Brain. Springer. doi:10.1007/978-0-387-74349-3. ISBN 978-1-4419-4493-1.CS1 održavanje: ref=harv (link)
Turner, C. E.; Mole, M. L.; Hanuš, L.; ElSohly, H. N. (1981). "Constituents of Cannabis sativa L. XIX. Isolation and structure elucidation of cannabiglendol. A novel cannabinoid from an Indian variant" (PDF). J. Nat. Prod. 44 (1): 27–33. doi:10.1021/np50013a005. Referenca sadrži prazan nepoznati parametar: |author-name-separator= (pomoć)
Pertwee, Roger, ured. (2005). Cannabinoids. Springer-Verlag. str. 2. ISBN 978-3-540-22565-2.CS1 održavanje: ref=harv (link)

Vanjski linkovi uredi

Commons ima datoteke na temu: Kanaboid

Šablon:Kanabinoidi

{Farmakomodulacija}} Šablon:Modulatori kanala potencijalnog prolaznog receptora

[pmid16968947-1] Pacher P, Batkai S, Kunos G (2006). "The endocannabinoid system as an emerging target of pharmacotherapy". Pharmacol Rev. 58 (3): 389–462. doi:10.1124/pr.58.3.2. PMC 2241751. PMID 16968947.

[lambert-2] Lambert DM, Fowler CJ (2005). "The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications". J. Med. Chem. 48 (16): 5059–87. doi:10.1021/jm058183t. PMID 16078824.

[3] Pertwee, Roger, ured. (2005). Cannabinoids. Springer-Verlag. str. 2. ISBN 978-3-540-22565-2.

[pmid15866316-4] Begg M, Pacher P, Bátkai S, Osei-Hyiaman D, Offertáler L, Mo FM, Liu J, Kunos G (2005). "Evidence for novel cannabinoid receptors". Pharmacol. Ther. 106 (2): 133–45. doi:10.1016/j.pharmthera.2004.11.005. PMID 15866316.

[5] El-Alfy, Abir T. et. al. "Antidepressant-like effect of [Delta]9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L." Pharmacology Biochemistry and Behavior. 2010 Jun;95(4). ISSN 0091-3057}}

[6] Huffman, JW (2000). "The search for selective ligands for the CB₂ receptor". Curr. Pharm. Des. 6 (13): 1323–37. doi:10.2174/1381612003399347. PMID 10903395.

[behaviouralpharm-7] "Behavioural Pharmacology - Abstract: Volume 16(5-6) September 2005 p 487-496 Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids". 04. 2020. Pristupljeno 24. 6. 2007. Nepoznati parametar |fix-attempted= zanemaren (pomoć); Nepoznati parametar |bot= zanemaren (pomoć); Provjerite vrijednost datuma u parametru: |date= (pomoć)

[pmid18378995-8] Morgan CJ, Curran HV (2008). "Effects of cannabidiol on schizophrenia-like symptoms in people who use cannabis". The British journal of psychiatry : the journal of mental science. 192 (4): 306–7. doi:10.1192/bjp.bp.107.046649. PMID 18378995.

[televisionexperiment-9] "Should I Smoke Dope?". Pristupljeno 24. 5. 2008.

[recentadvances-10] Mechoulam, R.; M. Peters; Murillo-Rodriguez (21. 8. 2007). "Cannabidiol - recent advances". Chemistry & Biodiversity. 4 (8): 1678–1692. doi:10.1002/cbdv.200790147. PMID 17712814.^{[mrtav link]}|date=04. 2019 |bot=InternetArchiveBot |fix-attempted=yes }}

[11] Ryberg E; Larsson N; Sjögren S; et al. (2007). "The orphan receptor GPR55 is a novel cannabinoid receptor". British Journal of Pharmacology. 152 (7): 1092–101. doi:10.1038/sj.bjp.0707460. PMC 2095107. PMID 17876302.

[pmid16258853-12] Russo EB, Burnett A, Hall B, Parker KK (2005). "Agonistic properties of cannabidiol at 5-HT1a receptors". Neurochemical Research. 30 (8). doi:10.1007/s11064-005-6978-1. PMID 16258853. ISBN 1106400569781 pogrešan ISBN.

[pmid20002102-13] Zanelati T, Biojone C, Moreira F, Guimarães F, Joca S (2009). "Antidepressant-like effects of cannabidiol in mice: possible involvement of 5-HT receptors". British Journal of Pharmacology. 159 (1): 122–8. doi:10.1111/j.1476-5381.2009.00521.x. PMC 2823358. PMID 20002102.

[pmid19133999-14] Resstel LB, Tavares RF, Lisboa SF, Joca SR, Corrêa FM, Guimarães FS (2009). "5-HT1A receptors are involved in the cannabidiol-induced attenuation of behavioural and cardiovascular responses to acute restraint stress in rats". British Journal of Pharmacology. 156 (1): 181–8. doi:10.1111/j.1476-5381.2008.00046.x. PMC 2697769. PMID 19133999.

[pmid18446323-15] Campos AC, Guimarães FS (2008). "Involvement of 5HT1A receptors in the anxiolytic-like effects of cannabidiol injected into the dorsolateral periaqueductal gray of rats". Psychopharmacology. 199 (2). doi:10.1007/s00213-008-1168-x. PMID 18446323. ISBN 2130081168 pogrešan ISBN.

[pmid15845890-16] Mishima K; Hayakawa K; Abe K; et al. (2005). "Cannabidiol prevents cerebral infarction via a serotonergic 5-hydroxytryptamine1A receptor-dependent mechanism". Stroke; a Journal of Cerebral Circulation. 36 (5): 1077–82. doi:10.1161/01.STR.0000163083.59201.34. PMID 15845890.^{[mrtav link]}|date=09. 2018 |bot=InternetArchiveBot |fix-attempted=yes }}

[pmid17320118-17] Hayakawa K; Mishima K; Nozako M; et al. (2007). "Repeated treatment with cannabidiol but not Delta9-tetrahydrocannabinol has a neuroprotective effect without the development of tolerance". Neuropharmacology. 52 (4): 1079–87. doi:10.1016/j.neuropharm.2006.11.005. PMID 17320118.^{[trajno mrtav link]}

[pmid11020293-18] Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK (2000). "Novel cannabinol probes for CB₁ and CB₂ cannabinoid receptors". Journal of medicinal chemistry. 43 (20): 3778–85. doi:10.1021/jm0001572. PMID 11020293.

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