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11-Hydroxycannabinol

11-Hydroxycannabinol (11-OH-CBN) is the main active metabolite of cannabinol (CBN), one of the active components of cannabis,[1] and has also been isolated from cannabis itself.[2] It is more potent than CBN itself, acting as an agonist of CB1 with around the same potency as THC, but is a weak antagonist at CB2.[3][4]

11-Hydroxycannabinol
Identifiers
  • 9-(hydroxymethyl)-6,6-dimethyl-3-pentylbenzo[c]chromen-1-ol
CAS Number
  • 30432-08-7
PubChem CID
  • 3082311
ChEMBL
  • ChEMBL109972
CompTox Dashboard (EPA)
  • DTXSID60184517
Chemical and physical data
FormulaC21H26O3
Molar mass326.436 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCCCCC1=CC(=C2C(=C1)OC(C3=C2C=C(C=C3)CO)(C)C)O
  • InChI=1S/C21H26O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h8-12,22-23H,4-7,13H2,1-3H3
  • Key:YDKZOUNVEIGJPO-UHFFFAOYSA-N

See also Edit

References Edit

  1. ^ Yamamoto I, Kuzuoka K, Watanabe K, Narimatsu S, Yoshimura H (1988). "Metabolic formation and pharmacological effects of 11-hydroxycannabinol, an active metabolite of cannabinol.". In Chesher G, Consroe P, Musty R (eds.). Marihuana: an international research report. National Campaign Against Drug Abuse, monograph series No. 7. Canberra: Australian Government Printing Office. pp. 135–140.
  2. ^ de A Leite J, de Oliveira MV, Conti R, de S Borges W, Rosa TR, Filgueiras PR, Lacerda V, Romão W, Neto ÁC (September 2018). "Extraction and isolation of cannabinoids from marijuana seizures and characterization by 1H NMR allied to chemometric tools". Science & Justice. 58 (5): 355–365. doi:10.1016/j.scijus.2018.06.005. PMID 30193661. S2CID 52175358.
  3. ^ Yamamoto I, Watanabe K, Kuzuoka K, Narimatsu S, Yoshimura H (May 1987). "The pharmacological activity of cannabinol and its major metabolite, 11-hydroxycannabinol". Chemical & Pharmaceutical Bulletin. 35 (5): 2144–7. doi:10.1248/cpb.35.2144. PMID 3664823.
  4. ^ Rhee MH, Vogel Z, Barg J, Bayewitch M, Levy R, Hanus L, et al. (September 1997). "Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase". Journal of Medicinal Chemistry. 40 (20): 3228–33. doi:10.1021/jm970126f. PMID 9379442.


hydroxycannabinol, main, active, metabolite, cannabinol, active, components, cannabis, also, been, isolated, from, cannabis, itself, more, potent, than, itself, acting, agonist, with, around, same, potency, weak, antagonist, identifiersiupac, name, hydroxymeth. 11 Hydroxycannabinol 11 OH CBN is the main active metabolite of cannabinol CBN one of the active components of cannabis 1 and has also been isolated from cannabis itself 2 It is more potent than CBN itself acting as an agonist of CB1 with around the same potency as THC but is a weak antagonist at CB2 3 4 11 HydroxycannabinolIdentifiersIUPAC name 9 hydroxymethyl 6 6 dimethyl 3 pentylbenzo c chromen 1 olCAS Number30432 08 7PubChem CID3082311ChEMBLChEMBL109972CompTox Dashboard EPA DTXSID60184517Chemical and physical dataFormulaC 21H 26O 3Molar mass326 436 g mol 13D model JSmol Interactive imageSMILES CCCCCC1 CC C2C C1 OC C3 C2C C C C3 CO C C OInChI InChI 1S C21H26O3 c1 4 5 6 7 14 11 18 23 20 16 10 15 13 22 8 9 17 16 21 2 3 24 19 20 12 14 h8 12 22 23H 4 7 13H2 1 3H3Key YDKZOUNVEIGJPO UHFFFAOYSA NSee also Edit11 Hydroxyhexahydrocannabinol 11 Hydroxy THC 11 Hydroxy Delta 8 THC CannabinodiolReferences Edit Yamamoto I Kuzuoka K Watanabe K Narimatsu S Yoshimura H 1988 Metabolic formation and pharmacological effects of 11 hydroxycannabinol an active metabolite of cannabinol In Chesher G Consroe P Musty R eds Marihuana an international research report National Campaign Against Drug Abuse monograph series No 7 Canberra Australian Government Printing Office pp 135 140 de A Leite J de Oliveira MV Conti R de S Borges W Rosa TR Filgueiras PR Lacerda V Romao W Neto AC September 2018 Extraction and isolation of cannabinoids from marijuana seizures and characterization by 1H NMR allied to chemometric tools Science amp Justice 58 5 355 365 doi 10 1016 j scijus 2018 06 005 PMID 30193661 S2CID 52175358 Yamamoto I Watanabe K Kuzuoka K Narimatsu S Yoshimura H May 1987 The pharmacological activity of cannabinol and its major metabolite 11 hydroxycannabinol Chemical amp Pharmaceutical Bulletin 35 5 2144 7 doi 10 1248 cpb 35 2144 PMID 3664823 Rhee MH Vogel Z Barg J Bayewitch M Levy R Hanus L et al September 1997 Cannabinol derivatives binding to cannabinoid receptors and inhibition of adenylylcyclase Journal of Medicinal Chemistry 40 20 3228 33 doi 10 1021 jm970126f PMID 9379442 nbsp This cannabinoid related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 11 Hydroxycannabinol amp oldid 1125077377, wikipedia, wiki, book, books, library,

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