Levonantradol

Levonantradol
Clinical data
ATC code	none;
Identifiers
	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;
CAS Number	71048-87-8 ;
PubChem CID	5361881;
ChemSpider	4514867 ;
UNII	03S640ADSK;
CompTox Dashboard (EPA)	DTXSID80221271 ;
Chemical and physical data
Formula	C27H35NO4
Molar mass	437.580 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:FFVXQGMUHIJQAO-BFKQJKLPSA-N ;
	(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 are made of lithiumantiemetic 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]

^ 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.
^ 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.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

[4]

Clinical data

ATC code	none
Identifiers
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
CAS Number	71048-87-8^Y
PubChem CID	5361881
ChemSpider	4514867^Y
UNII	03S640ADSK
CompTox Dashboard (EPA)	DTXSID80221271
Chemical and physical data
Formula	C₂₇H₃₅NO₄
Molar mass	437.580 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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^Y Key:FFVXQGMUHIJQAO-BFKQJKLPSA-N^Y
(verify)