HU-210
Encyclopedia
HU-210 is a synthetic cannabinoid that was first synthesized
in 1988 from (1R,5S)-Myrtenol by the group led by Professor Raphael Mechoulam
at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC
from cannabis
and has an extended duration of action. HU-210 is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ8- tetrahydrocannabinol, in some references it is called 1,1-dimethylheptyl- 11-hydroxytetrahydrocannabinol. The abbreviation HU stands for Hebrew University.
The (+) enantiomer
of HU-210 has almost all of the cannabinoid activity, with the (-) enantiomer HU-211 being inactive as a cannabinoid but instead acts as an NMDA antagonist having neuroprotective effects.
Per a 2005 article in the Journal of Clinical Investigation
, HU-210 promotes proliferation, but not differentiation
, of cultured embryonic hippocampal NS
/PC
s likely via a sequential activation of CB1 receptors
, G(i/o) proteins, and ERK signaling
. It was also indicated by this increased neural growth to entail antianxiety and antidepressant
effects.
HU-210, alongside other synthetic cannabinoids like WIN 55,212-2
and JWH-133
, is implicated in preventing the inflammation caused by Amyloid beta
proteins involved in Alzheimer's Disease
, in addition to preventing cognitive impairment and loss of neuronal markers. This anti-inflammatory action is induced through the activation of cannabinoid receptor
s which prevents microglia
l activation that elicits the inflammation. Additionally, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.
HU-210 is a potent analgesic
with many of the same effects as natural THC.
, HU-210 was discovered in Spice Gold
products seized at the US border in January 2009. Over 100 pounds of Spice products were seized based on this finding. HU-210 was also detected in three Spice products in the UK, as reported in June 2009.
To view states affected, see JWH-018
.
To view national schedule, see: List of Schedule I drugs (US), http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm
Chemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...
in 1988 from (1R,5S)-Myrtenol by the group led by Professor Raphael Mechoulam
Raphael Mechoulam
Raphael Mechoulam is an Israeli professor of Medicinal Chemistry and Natural Products at the Hebrew University of Jerusalem in Israel...
at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC
THC
THC commonly refers to tetrahydrocannabinol, the main active chemical compound in Cannabis.THC may also refer to:* Tan Holdings Corporation...
from cannabis
Cannabis
Cannabis is a genus of flowering plants that includes three putative species, Cannabis sativa, Cannabis indica, and Cannabis ruderalis. These three taxa are indigenous to Central Asia, and South Asia. Cannabis has long been used for fibre , for seed and seed oils, for medicinal purposes, and as a...
and has an extended duration of action. HU-210 is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ8- tetrahydrocannabinol, in some references it is called 1,1-dimethylheptyl- 11-hydroxytetrahydrocannabinol. The abbreviation HU stands for Hebrew University.
The (+) enantiomer
Enantiomer
In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
of HU-210 has almost all of the cannabinoid activity, with the (-) enantiomer HU-211 being inactive as a cannabinoid but instead acts as an NMDA antagonist having neuroprotective effects.
Per a 2005 article in the Journal of Clinical Investigation
Journal of Clinical Investigation
The Journal of Clinical Investigation is a biomedical journal, with a 2010 impact factor of 14.152. The journal makes its research articles — including access to articles back to 1924 — freely available online....
, HU-210 promotes proliferation, but not differentiation
Cellular differentiation
In developmental biology, cellular differentiation is the process by which a less specialized cell becomes a more specialized cell type. Differentiation occurs numerous times during the development of a multicellular organism as the organism changes from a simple zygote to a complex system of...
, of cultured embryonic hippocampal NS
Neural stem cell
Neural stem cells are the self-renewing, multipotent cells that generate the main phenotypes of the nervous system. In 1989, Sally Temple described multipotent, self-renewing progenitor and stem cells in the subventricular zone of the mouse brain . In 1992, Brent A...
/PC
Progenitor cell
A progenitor cell is a biological cell that, like a stem cell, has a tendency to differentiate into a specific type of cell, but is already more specific than a stem cell and is pushed to differentiate into its "target" cell...
s likely via a sequential activation of CB1 receptors
Cannabinoid receptor type 1
The cannabinoid receptor type 1, often abbreviated to CB1, is a G protein-coupled cannabinoid receptor located in the brain. It is activated by endocannabinoid neurotransmitters including anandamide and by the compound THC, found in the psychoactive drug cannabis.-Expression:The CB1 receptor is...
, G(i/o) proteins, and ERK signaling
MAPK/ERK pathway
The MAPK/ERK pathway is a chain of proteins in the cell that communicates a signal from a receptor on the surface of the cell to the DNA in the nucleus of the cell. The signal starts when a growth factor binds to the receptor on the cell surface and ends when the DNA in the nucleus expresses a...
. It was also indicated by this increased neural growth to entail antianxiety and antidepressant
Antidepressant
An antidepressant is a psychiatric medication used to alleviate mood disorders, such as major depression and dysthymia and anxiety disorders such as social anxiety disorder. According to Gelder, Mayou &*Geddes people with a depressive illness will experience a therapeutic effect to their mood;...
effects.
HU-210, alongside other synthetic cannabinoids like WIN 55,212-2
WIN 55,212-2
WIN 55,212-2 is a chemical described as an aminoalkylindole derivative, that produces effects similar to those of cannabinoid derivatives such as THC but has an entirely different chemical structure....
and JWH-133
JWH-133
JWH-133 is a potent selective CB2 receptor agonist, with a Ki of 3.4nM and selectivity of around 200x for CB2 over CB1 receptors. It was discovered by, and named after, John W...
, is implicated in preventing the inflammation caused by Amyloid beta
Amyloid beta
Amyloid beta is a peptide of 36–43 amino acids that is processed from the Amyloid precursor protein. While it is most commonly known in association with Alzheimer's disease, it does not exist specifically to cause disease...
proteins involved in Alzheimer's Disease
Alzheimer's disease
Alzheimer's disease also known in medical literature as Alzheimer disease is the most common form of dementia. There is no cure for the disease, which worsens as it progresses, and eventually leads to death...
, in addition to preventing cognitive impairment and loss of neuronal markers. This anti-inflammatory action is induced through the activation of cannabinoid receptor
Cannabinoid receptor
The cannabinoid receptors are a class of cell membrane receptors under the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid receptors contain seven transmembrane spanning domains...
s which prevents microglia
Microglia
Microglia are a type of glial cell that are the resident macrophages of the brain and spinal cord, and thus act as the first and main form of active immune defense in the central nervous system . Microglia constitute 20% of the total glial cell population within the brain...
l activation that elicits the inflammation. Additionally, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.
HU-210 is a potent analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
with many of the same effects as natural THC.
Recreational use
According to the U.S. Customs and Border ProtectionU.S. Customs and Border Protection
U.S. Customs and Border Protection is a federal law enforcement agency of the United States Department of Homeland Security charged with regulating and facilitating international trade, collecting import duties, and enforcing U.S. regulations, including trade, customs and immigration. CBP is the...
, HU-210 was discovered in Spice Gold
Spice (drug)
Synthetic cannabis is a psychoactive herbal and chemical product which, when consumed, mimics the effects of cannabis. It is best known by the brand names K2 and Spice, both of which have largely become genericized trademarks used to refer to any synthetic cannabis product...
products seized at the US border in January 2009. Over 100 pounds of Spice products were seized based on this finding. HU-210 was also detected in three Spice products in the UK, as reported in June 2009.
United States
HU-210 is a schedule I controlled substance under the Controlled Substances Act.To view states affected, see JWH-018
JWH-018
JWH-018 or AM-678 is an analgesic chemical from the naphthoylindole family, which acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2...
.
To view national schedule, see: List of Schedule I drugs (US), http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm
Other HU Cannabinoids
- HU-211
- HU-243
- HU-308HU-308HU-308 is a drug which acts as a cannabinoid agonist. It is highly selective for the CB2 receptor subtype, with a selectivity of over 5000x for CB2 vs CB1. The synthesis and characterization took place in the laboratory of Prof. Mechoulam at the Hebrew University of Jerusalem in the late 1990s...
- HU-320HU-320HU-320 is a drug related to cannabidiol, which has strong antiinflammatory and immunosuppressive properties while demonstrating no psychoactive effects....
- HU-331HU-331HU-331 is a quinone anticarcinogenic drug synthesized from cannabidiol, a cannabinoid in the Cannabis sativa plant. It showed a great efficacy against oncogenic human cells. HU-331 does not cause arrest in cell cycle, cell apoptosis or caspase activation...
- HU-336HU-336HU-336 is a strongly antiangiogenic compound, significantly inhibiting angiogenesis at concentrations as low as 300nM. It inhibits angiogenesis by directly inducing apoptosis of vascular endothelial cells without changing the expression of pro- and antiangiogenic cytokines and their receptors....
- HU-345HU-345HU-345 is a drug which is able to inhibit aortic ring angiogenesis more potently than its parent compound cannabinol....