View source for Chemistry:AM-938

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 448104384
| IUPAC_name = (6S,6aR,9R,10aR)-9-(hydroxymethyl)-6-(3-hydroxyprop-1-ynyl)-6-
| image = AM-938 Structure.svg 
| width = 240
<!--Clinical data-->
| tradename = 
| legal_status = 
| routes_of_administration = 
<!--Pharmacokinetic data-->
| metabolism = 
| elimination_half-life = 
| excretion = 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 303113-08-8  
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NPU5SWP5ZS
| PubChem = 10646208
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8821567
| smiles = Oc2cc(cc1O[C@@](C#CCO)([C@@H]3CC[C@H](C[C@H]3c12)CO)C)C(C)(C)CCCCCC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C27H40O4/c1-5-6-7-8-12-26(2,3)20-16-23(30)25-21-15-19(18-29)10-11-22(21)27(4,13-9-14-28)31-24(25)17-20/h16-17,19,21-22,28-30H,5-8,10-12,14-15,18H2,1-4H3/t19-,21-,22-,27+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FFRHKSZKZQWCOY-UOTIDGTBSA-N
<!--Chemical data-->
| C=27 | H=40 | O=4
}}

'''AM-938''' (part of the AM cannabinoid series)  is an [[Biology:Analgesic|analgesic]] drug which is a cannabinoid receptor agonist. It is a derivative of [[Chemistry:HU-210|HU-210]] which has been substituted with a 6β-(3-hydroxyprop-1-ynyl) group. This adds a "southern" aliphatic hydroxyl group to the molecule as seen in the CP-series of nonclassical cannabinoid drugs, and so AM-938 represents a hybrid structure between the classical and [[Chemistry:CP 47,497#See also|nonclassical]] [[Chemistry:Cannabinoid|cannabinoid]] families,<ref>{{cite book | first = Roger | last = Pertwee | name-list-style = vanc | title = Cannabinoids | series = Handbook of Experimental Pharmacology | volume = 168 | page = 269 | publisher = Springer | isbn = 3-540-22565-X }}</ref> with the 6-hydroxyalkyl chain rigidified with a [[Chemistry:Triple bond|triple bond]]. This gives AM-938 a greater degree of selectivity, so while it is still a potent agonist at both [[Biology:Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Biology:Cannabinoid receptor 2|CB<sub>2</sub>]], it is reasonably selective for CB<sub>2</sub>, with a [[Chemistry:Dissociation constant|K<sub>i</sub>]] of 0.3nM at CB<sub>2</sub> and 1.2nM at CB<sub>1</sub>, a selectivity of around 4x.<ref>{{cite journal | vauthors = Tius MA, Hill WA, Zou XL, Busch-Petersen J, Kawakami JK, Fernandez-Garcia MC, Drake DJ, Abadji V, Makriyannis A | display-authors = 6 | title = Classical/non-classical cannabinoid hybrids; stereochemical requirements for the southern hydroxyalkyl chain | journal = Life Sciences | year = 1995 | volume = 56 | issue = 23–24 | pages = 2007–12 | pmid = 7776825 | doi = 10.1016/0024-3205(95)00182-6 }}</ref><ref>{{cite journal | vauthors = Drake DJ, Jensen RS, Busch-Petersen J, Kawakami JK, Concepcion Fernandez-Garcia M, Fan P, Makriyannis A, Tius MA | display-authors = 6 | title = Classical/nonclassical hybrid cannabinoids: southern aliphatic chain-functionalized C-6beta methyl, ethyl, and propyl analogues | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 19 | pages = 3596–608 | date = September 1998 | pmid = 9733485 | doi = 10.1021/jm960677q }}</ref>

== See also ==
* [[Chemistry:AM-4030|AM-4030]] - double bond instead of a triple bond
* [[Chemistry:AM-919|AM-919]] - saturated rather than a triple bond
* [[Chemistry:HU-243|HU-243]] - "southern" side chain replaced by methyl unit

== References ==
{{reflist}}

{{cannabinoids}}

[[Category:Benzochromenes]]
[[Category:Primary alcohols]]
[[Category:Phenols]]


{{Sourceattribution|AM-938}}