HU-210 is a

synthetic cannabinoid Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids ( THC, CBD and many others) in cannabis plants attach. These novel psychoactive substances should not be confused with synthe ...

that was first synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the

Hebrew University The Hebrew University of Jerusalem (HUJI; he, הַאוּנִיבֶרְסִיטָה הַעִבְרִית בִּירוּשָׁלַיִם) is a public university, public research university based in Jerusalem, Israel. Co-founded by Albert Einstein ...

. HU-210 is 100 to 800 times more potent than natural

THC Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC' ...

from

cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: '' Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternative ...

and has an extended duration of action. HU-210 has a binding affinity of 0.061nM at CB1 and 0.52nM at CB2 in cloned human cannabinoid receptors. Compared to Delta-9-THC of 40.7nM at CB1. 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.

Effects and research

HU-210, the (–)

enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...

of 11-OH-D⁸-THC-DMH, has almost all of the cannabinoid activity, while the (+) enantiomer, known as HU-211, is inactive as a

cannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

and instead acts as an NMDA antagonist having neuroprotective effects. HU-210 promotes proliferation, but not differentiation, of cultured embryonic hippocampal neural stem and progenitor cells likely via a sequential activation of CB₁ receptors, G_i/o proteins, and ERK signaling. It was also indicated by this increased

neural In biology, the nervous system is the highly complex part of an animal that coordinates its actions and sensory information by transmitting signals to and from different parts of its body. The nervous system detects environmental changes ...

growth to entail antianxiety and

antidepressant Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common Side effect, side-effects of antidepressants include Xerostomia, dry mouth, weig ...

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 Amyloid beta (Aβ or Abeta) denotes peptides of 36–43 amino acids that are the main component of the amyloid plaques found in the brains of people with Alzheimer's disease. The peptides derive from the amyloid precursor protein (APP), which is ...

proteins involved in

Alzheimer's disease Alzheimer's disease (AD) is a neurodegenerative disease that usually starts slowly and progressively worsens. It is the cause of 60–70% of cases of dementia. The most common early symptom is difficulty in remembering recent events. As ...

, in addition to preventing cognitive impairment and loss of neuronal markers. This anti-inflammatory action is induced through the activation of cannabinoid receptors, which prevents

microglia Microglia are a type of neuroglia (glial cell) located throughout the brain and spinal cord. Microglia account for about 7% of cells found within the brain. As the resident macrophage cells, they act as the first and main form of active immune de ...

l activation that elicits the inflammation. In addition, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models. HU-210 is a potent

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

with many of the same effects as natural THC. HU-210 has an oral LD50 of 5,000mg/kg in rats and 14,200mg/kg in rabbits. HU-210 has an LDLO (Lowest Lethal Dose amount) of 143mg/kg in humans. Caffeine has an LD50 estimated to be 150–200 milligrams per kilogram. Delta-8-THC LD50 has not been confirmed. In a 1973 study monkeys and dogs given 9,000mg/kg of Delta-8-THC was nonlethal.

Chemistry

HU-210 is the

of HU-211 (

Dexanabinol Dexanabinol (HU-211 or ETS2101) is a synthetic cannabinoid derivative in development by e-Therapeutics plc. It is the "unnatural" enantiomer of the potent cannabinoid agonist HU-210. Unlike other cannabinoid derivatives, HU-211 does not act as a ...

). The original synthesis of HU-210 is based on an acid-catalyzed condensation of (–)- Myrtenol and 1,1-Dimethylheptylresorcinol (3,5-Dihydroxy-1-(1,1-dimethylheptyl)benzol). HU-210 synthesis

Legal status

HU-210 is not listed in the schedules set out by the

United Nations The United Nations (UN) is an intergovernmental organization whose stated purposes are to maintain international peace and security, develop friendly relations among nations, achieve international cooperation, and be a centre for harmoni ...

Single Convention on Narcotic Drugs The Single Convention on Narcotic Drugs, 1961 (Single Convention, 1961 Convention, or C61) is an international treaty that controls activities (cultivation, production, supply, trade, transport) of specific narcotic drugs and lays down a syste ...

from 1961 nor their

Convention on Psychotropic Substances The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 February ...

from 1971, so the signatory countries to these international drug control treaties are not required by said treaties to control HU-210.

New Zealand

HU-210 is banned in New Zealand as of 8 May 2014.

United States

HU-210 is not listed in the list of scheduled controlled substances in the USA. It is therefore not scheduled at the federal level in the United States, but it is possible that HU-210 could legally be considered an analog of Delta-9-THC (which is one of the substances controlled in Schedule I as "tetrahydrocannabinols"), and therefore sales or possession could potentially be prosecuted under the Federal Analogue Act. A brief profile of HU-210 written and published by the

Drug Enforcement Administration The Drug Enforcement Administration (DEA; ) is a United States federal law enforcement agency under the U.S. Department of Justice tasked with combating drug trafficking and distribution within the U.S. It is the lead agency for domestic en ...

(DEA) in 2009 (but subsequently removed from the DEA's website several years later) stated that HU-210 is a Schedule I controlled substance under the

Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States ...

due to being similar to

. This indicates that the DEA might legally consider HU-210 to be an analogue of Delta-8-THC for the purposes of applying the Federal Analog Act to those that handle HU-210. An elucidation of the rationale for the DEA's claim was not presented, no references were cited, and the claim was eventually removed from the DEA's website. A version of the document (updated in 2013), now in PDF form, exists on the DEA Office of Diversion Control's website. Claimed in this possibly misleading though definitive sounding document, with the same lack of detailed explanation or citation, is:

Alabama

HU-210 is a Schedule I controlled substance in

Alabama (We dare defend our rights) , anthem = " Alabama" , image_map = Alabama in United States.svg , seat = Montgomery , LargestCity = Huntsville , LargestCounty = Baldwin County , LargestMetro = Greater Birmingham , area_total_km2 = 135,7 ...

Florida

HU-210 is a Schedule I

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Single ...

, categorized as a

hallucinogen Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorize ...

, making it illegal to buy, sell, or possess in the state of

Florida Florida is a state located in the Southeastern region of the United States. Florida is bordered to the west by the Gulf of Mexico, to the northwest by Alabama, to the north by Georgia, to the east by the Bahamas and Atlantic Ocean, and ...

without a license.

Vermont

Effective January 1, 2016, HU-210 is a regulated drug in Vermont designated as a "Hallucinogenic Drug."

Other HU Cannabinoids

* HU-211 * HU-239 * HU-243 * HU-308 * HU-320 * HU-331 *

HU-336 HU-336 is a strongly antiangiogenic compound, significantly inhibiting angiogenesis at concentrations as low as 300 nM. It inhibits angiogenesis by directly inducing apoptosis of vascular endothelial cells without changing the expression of ...

HU-345 HU-345 (cannabinol quinone) is a drug that is able to inhibit aortic ring angiogenesis more potently than its parent compound cannabinol (CBN). It exhibits no psychoactive effects on the body. HU-345 can be derived through the oxidative degra ...