MN-25

MN-25
Clinical data
Other names	N-[(S)-Fenchyl]-1-[2-(morpholin-4-yl)ethyl]-7-methoxyindole-3-carboxamide
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name 7-methoxy-1-(2-morpholin-4-ylethyl)-N-[(1R,3S,4S)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide;
JSmol)	Interactive image;
	SMILES COC1=C(N(CCN2CCOCC2)C=C3C(N[C@H]4[C@@]5(C)CC[C@H](C5)C4(C)C)=O)C3=CC=C1;
	InChI InChI=1S/C26H37N3O3/c1-25(2)18-8-9-26(3,16-18)24(25)27-23(30)20-17-29(11-10-28-12-14-32-15-13-28)22-19(20)6-5-7-21(22)31-4/h5-7,17-18,24H,8-16H2,1-4H3,(H,27,30)/t18-,24-,26+/m1/s1 ; Key:VQGDMQICNRCQEH-UFKXBGGNSA-N ;
	(verify)

MN-25 (UR-12) is a drug invented by

CB₁ receptors with a K_i of 245 nM. The indole 2-methyl derivative has the ratio of affinities reversed however, with a K_i of 8 nM at CB₁ and 29 nM at CB₂,^[3]^[4] which contrasts with the usual trend of 2-methyl derivatives having increased selectivity for CB₂ (cf. JWH-018 vs JWH-007, JWH-081 vs JWH-098).^[5]^[6]

Chemically, it is closely related to another indole-3-carboxamide synthetic cannabinoid, Org 28611, but with a different cycloalkyl substitution on the carboxamide, and the cyclohexylmethyl group replaced by morpholinylethyl, as in JWH-200 or A-796,260. Early compounds such as these have subsequently led to the development of many related indole-3-carboxamide cannabinoid ligands.^[7]^[8]^[9]^[10]

References

^ WO application 0158869, Leftheris K, Zhao R, Chen BC, Kiener P, Wu H, Pandit CR, Wrobleski S, Chen P, Hynes J, Longphre M, Norris DJ, Spergel S, Tokarski J, "Cannabinoid Receptor Modulators, Their Processes of Preparation, and use of Cannabinoid Receptor Modulators for Treating Respiratory and Non-Respiratory Diseases", published 16 August 2001, assigned to Bristol-Myers Squibb
hdl:2027/spo.5550190.0011.610
.

PMID 12161142
.

PMID 12747783
.

PMID 15974991
.

PMID 18473928
.

doi:10.1039/c0md00022a
.

PMID 20634067
.

PMID 21074434
.

PMID 21885167
.

Further reading

Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, et al. (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–402.
PMID 12161142
.

Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity". Journal of Medicinal Chemistry. 53 (1): 295–315.
PMID 19921781
.

Chin CL, Tovcimak AE, Hradil VP, Seifert TR, Hollingsworth PR, Chandran P, et al. (January 2008). "Differential effects of cannabinoid receptor agonists on regional brain activity using pharmacological MRI". British Journal of Pharmacology. 153 (2): 367–79.
PMID 17965748
.

Retrieved from "https://en.wikipedia.org/w/index.php?title=MN-25&oldid=1193903096"

[1] WO application 0158869, Leftheris K, Zhao R, Chen BC, Kiener P, Wu H, Pandit CR, Wrobleski S, Chen P, Hynes J, Longphre M, Norris DJ, Spergel S, Tokarski J, "Cannabinoid Receptor Modulators, Their Processes of Preparation, and use of Cannabinoid Receptor Modulators for Treating Respiratory and Non-Respiratory Diseases", published 16 August 2001, assigned to Bristol-Myers Squibb

[2] hdl:2027/spo.5550190.0011.610
.

[3] PMID 12161142
.

[4] PMID 12747783
.

[5] PMID 15974991
.

[6] PMID 18473928
.

[7] :10.1039/c0md00022a
.

[p20634067-8] PMID 20634067
.

[p21074434-9] PMID 21074434
.

[10] PMID 21885167
.

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

See also

References

Further reading