Levonantradol

Levonantradol
Clinical data
ATC code
  • none
Identifiers
  • [(6S,6aR,9R,10aR)- 9-hydroxy- 6-methyl- 3-[(2R)-5-phenylpentan- 2-yl]oxy- 5,6,6a,7,8,9,10,10a-octahydrophenanthridin- 1-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H35NO4
Molar mass437.580 g·mol−1
3D model (JSmol)
  • O=C(Oc2cc(O[C@H](C)CCCc1ccccc1)cc4c2[C@@H]3C[C@H](O)CC[C@H]3[C@@H](N4)C)C
  • InChI=1S/C27H35NO4/c1-17(8-7-11-20-9-5-4-6-10-20)31-22-15-25-27(26(16-22)32-19(3)29)24-14-21(30)12-13-23(24)18(2)28-25/h4-6,9-10,15-18,21,23-24,28,30H,7-8,11-14H2,1-3H3/t17-,18+,21-,23+,24-/m1/s1 checkY
  • Key:FFVXQGMUHIJQAO-BFKQJKLPSA-N checkY
  (verify)

Levonantradol (CP 50,556-1) is a synthetic cannabinoid analog of dronabinol (Marinol) developed by Pfizer in the 1980s. It is around 30 times more potent than THC, and exhibits antiemetic and analgesic effects via activation of CB1 and CB2 cannabinoid receptors.[1] Levonantradol is not currently used in medicine as dronabinol or nabilone are felt to be more useful for most conditions, however it is widely used in research into the potential therapeutic applications of cannabinoids.[2][3][4]

  1. ^ Little PJ, Compton DR, Johnson MR, Melvin LS, Martin BR (December 1988). "Pharmacology and stereoselectivity of structurally novel cannabinoids in mice". The Journal of Pharmacology and Experimental Therapeutics. 247 (3): 1046–1051. PMID 2849657.
  2. ^ Tramèr MR, Carroll D, Campbell FA, Reynolds DJ, Moore RA, McQuay HJ (July 2001). "Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review". BMJ. 323 (7303): 16–21. doi:10.1136/bmj.323.7303.16. PMC 34325. PMID 11440936.
  3. ^ Campbell FA, Tramèr MR, Carroll D, Reynolds DJ, Moore RA, McQuay HJ (July 2001). "Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review". BMJ. 323 (7303): 13–16. doi:10.1136/bmj.323.7303.13. PMC 34324. PMID 11440935.
  4. ^ Ben Amar M (April 2006). "Cannabinoids in medicine: A review of their therapeutic potential". Journal of Ethnopharmacology. 105 (1–2): 1–25. CiteSeerX 10.1.1.180.308. doi:10.1016/j.jep.2006.02.001. PMID 16540272.