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{{drugbox
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{{Drugbox| verifiedrevid = 400141290
| UNII_Ref = {{fdacite|correct|FDA}}
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| UNII = 03S640ADSK verifiedrevid = 400141290
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|IUPAC_name = [(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
|IUPAC_name = [(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

Revision as of 22:37, 30 June 2011

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 mass437.571 g/mol 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

Levonantradol (CP 50,556-1) is a synthetic cannabinoid analog of dronabinol (Marinol) developed by Pfizer in the 1980s. It is around 30x 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]

See also

References

  1. ^ Little PJ, Compton DR, Johnson MR, Melvin LS, Martin BR. Pharmacology and stereoselectivity of structurally novel cannabinoids in mice. Journal of Pharmacology and Experimental Therapeutics 1988; 247:1046–1051.
  2. ^ Tramer MR, Carroll D, Campbell FA, Reynolds DJ, Moore RA, McQuay HJ. Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review. British Medical Journal 2001 Jul 7;323(7303):16-21.
  3. ^ Campbell FA, Tramer MR, Carroll D, Reynolds DJ, Moore RA, McQuay HJ. Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review. British Medical Journal. 2001 Jul 7;323(7303):13-6.
  4. ^ Ben Amar M. Cannabinoids in medicine: A review of their therapeutic potential. Journal of Ethnopharmacology. 2006 Apr 21;105(1-2):1-25.
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