Adhyperforin

Chemical compound

none

Legal statusLegal status

In general: Over-the-counter (OTC)

Identifiers

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

CAS Number

143183-63-5^N

PubChem CID

9963735

ChemSpider

25066875^N

UNII

EC9K3C78V8

ChEMBL

ChEMBL388948^Y

Chemical and physical dataFormulaC₃₆H₅₄O₄Molar mass550.824 g·mol⁻¹3D model (JSmol)

Interactive image

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

InChI

InChI=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^N
Key:DHPDSOCOUJHGHE-ACJQSPJVSA-N^N

^NY (what is this?) (verify)

Adhyperforin is a phytochemical found in the members of the plant genus Hypericum including St. John's Wort.^[1] It has a very similar pharmacological profile to hyperforin and acts as a TRPC6 ion channel activator,^[1] thereby inhibiting the reuptake of various neurotransmitters including serotonin, norepinephrine, dopamine, GABA, and glutamate.^[1] Adhyperforin is found in St. John's Wort in levels approximately 1/10 those of hyperforin.^[1]

References

^ ^a ^b ^c ^d Jensen AG, Hansen SH, Nielsen EO (2001). "Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity". Life Sci. 68 (14): 1593–1605. doi:10.1016/S0024-3205(01)00946-8. PMID 11263672.

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine^‡ Gepirone Indeloxazine Flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAsTooltip Tricyclic antidepressants	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Amoxapine Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine
TeCAsTooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Isoniazid^# Linezolid^# Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tedizolid Tranylcypromine Reversible: Caroxazone^‡ Mixed: Bifemelane
MAO_ATooltip Monoamine oxidase A-selective	Reversible: Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_BTooltip Monoamine oxidase B-selective	Irreversible: Selegiline

Adjunctive therapies
Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous
Ademetionine (SAMe) GABAkine neurosteroids (brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

TRP channel modulators

TRPA

Activators

4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ^12,14-prostaglandin J2
α-Sanshool (ginger, Sichuan and melegueta peppers)
Acrolein
Allicin (garlic)
Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
AM404
ASP-7663
Bradykinin
Cannabichromene (cannabis)
Cannabidiol (cannabis)
Cannabigerol (cannabis)
Cinnamaldehyde (cinnamon)
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (cumin)
Curcumin (turmeric)
Dehydroligustilide (celery)
Diallyl disulfide
Dicentrine (Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (ginger)
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (celery, Angelica acutiloba)
Linalool (Sichuan pepper, thyme)
Methylglyoxal
Methyl salicylate (wintergreen)
N-Methylmaleimide
Nicotine (tobacco)
Oleocanthal (olive oil)
Paclitaxel (Pacific yew)
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (Dorrigo pepper)
Shogaols (ginger, Sichuan and melegueta peppers)
Tear gases
Tetrahydrocannabinol (cannabis)
Tetrahydrocannabiorcol
Thiopropanal S-oxide (onion)
Umbellulone (Umbellularia californica)
WIN 55,212-2

Blockers

TRPC

Activators	Adhyperforin (St John's wort) Diacyl glycerol GSK1702934A Hyperforin (St John's wort) Substance P
Blockers	DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-Amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid