2-Ethoxymethyl Salvinorin B
Encyclopedia
2-Ethoxymethyl salvinorin B (symmetry, 2-EtOMe-Sal B) is a semi-synthetic analogue
of the natural product salvinorin A
, with a longer duration of action of around 3 hours (compared to less than 30 minutes for salvinorin A), and increased affinity and intrinsic activity
at the κ-opioid receptor
. Like the related compound herkinorin
, 2-ethoxymethyl salvinorin B is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation, as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum
, salvinorin A is present in larger quantities.
2-Ethoxymethyl salvinorin B has a Ki of 0.32 nM at the κ-opioid receptor, and around 3,000 times selectivity over the μ- and δ-opioid receptors, making it one of the most potent
and selective
kappa agonists yet discovered. In animal studies it fully substituted for salvinorin A and the synthetic kappa agonist U-69593, and was active at doses as low as 0.005 mg/kg. Human bioassays found the compound to be active at 50 μg.
Analog (chemistry)
In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
of the natural product salvinorin A
Salvinorin A
Salvinorin A is the main active psychotropic molecule in Salvia divinorum, a Mexican plant which has a long history of use as an entheogen by indigenous Mazatec shamans...
, with a longer duration of action of around 3 hours (compared to less than 30 minutes for salvinorin A), and increased affinity and intrinsic activity
Intrinsic activity
Intrinsic activity or efficacy refers to the relative ability of a drug-receptor complex to produce a maximum functional response. This must be distinguished from the affinity, which is a measure of the ability of the drug to bind to its molecular target, and the EC50, which is a measure of the...
at the κ-opioid receptor
Receptor (biochemistry)
In biochemistry, a receptor is a molecule found on the surface of a cell, which receives specific chemical signals from neighbouring cells or the wider environment within an organism...
. Like the related compound herkinorin
Herkinorin
Herkinorin is an opioid analgesic that is an analogue of the natural product Salvinorin A. It was discovered in 2005 during structure-activity relationship studies into neoclerodane diterpenes, the family of chemical compounds of which Salvinorin A is a member.Unlike Salvinorin A which is a...
, 2-ethoxymethyl salvinorin B is made from salvinorin B, which is most conveniently made from salvinorin A by deacetylation, as while both salvinorin A and salvinorin B are found in the plant Salvia divinorum
Salvia divinorum
Salvia divinorum is a psychoactive plant which can induce dissociative effects and is a potent producer of "visions" and other hallucinatory experiences...
, salvinorin A is present in larger quantities.
2-Ethoxymethyl salvinorin B has a Ki of 0.32 nM at the κ-opioid receptor, and around 3,000 times selectivity over the μ- and δ-opioid receptors, making it one of the most potent
Potency (pharmacology)
In the field of pharmacology, potency is a measure of drug activity expressed in terms of the amount required to produce an effect of given intensity. A highly potent drug evokes a larger response at low concentrations, while a drug of lower potency evokes a small response at low concentrations...
and selective
Functional Selectivity
Functional selectivity is the ligand-dependent selectivity for certain signal transduction pathways in one and the same receptor. This can be present when a receptor has several possible signal transduction pathways...
kappa agonists yet discovered. In animal studies it fully substituted for salvinorin A and the synthetic kappa agonist U-69593, and was active at doses as low as 0.005 mg/kg. Human bioassays found the compound to be active at 50 μg.