adhyperforin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477242567

| IUPAC_name = (1R,5S,6R,7S)-4-Hydroxy-6-methyl-5-(2-methylbutanoyl)-1,3,7-tris(3-methyl-2-buten-1-yl)-6-(4-methyl-3-penten-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

| image = Adhyperforin2DACS.svg

| image2 = Adhyperforin3Dan2.gif

| width = 250

| tradename =

| legal_status = OTC

| routes_of_administration = Oral

| CAS_number_Ref = {{cascite|changed|CAS}}

| CAS_number = 143183-63-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = EC9K3C78V8

| ATC_prefix = none

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 388948

| PubChem = 9963735

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 25066875

| smiles = CCC(C)C(=O)C12C(=C(C(=O)C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)CC=C(C)C)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C36H54O4/c1-12-27(10)30(37)36-32(39)29(18-16-25(6)7)31(38)35(33(36)40,21-19-26(8)9)22-28(17-15-24(4)5)34(36,11)20-13-14-23(2)3/h14-16,19,27-28,39H,12-13,17-18,20-22H2,1-11H3/t27?,28-,34+,35+,36-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DHPDSOCOUJHGHE-ACJQSPJVSA-N

| C=36 | H=54 | O=4

}}

Adhyperforin is a phytochemical found in the members of the plant genus Hypericum including St. John's Wort.{{cite journal | doi = 10.1016/S0024-3205(01)00946-8 | vauthors = Jensen AG, Hansen SH, Nielsen EO | title = Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity. | journal = Life Sci. | volume = 68 | issue = 14 | pages = 1593–1605 | year = 2001 | pmid = 11263672 }} It has a very similar pharmacological profile to hyperforin and acts as a TRPC6 ion channel activator, thereby inhibiting the reuptake of various neurotransmitters including serotonin, norepinephrine, dopamine, GABA, and glutamate. Adhyperforin is found in St. John's Wort in levels approximately 1/10 those of hyperforin.