JWH-007 is an

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 ...

chemical from the naphthoylindole family, which acts 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 ...

agonist at both the CB₁ and CB₂ receptors. It was first reported in 1994 by a group including the noted cannabinoid chemist

John W. Huffman John William Huffman (1932–2022) was a professor of organic chemistry at Clemson University who first synthesised novel cannabinoids. His research, funded by the National Institute on Drug Abuse, was focused on making a drug to target endocanna ...

. It was the most active of the first group of ''N''-

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...

naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of the ''N''-morpholinylethyl compounds

pravadoline Pravadoline (WIN 48,098) is an antinflammatory and analgesic drug with an IC50 of 4.9 μM and a ''K''i of 2511 nM at CB1, related in structure to nonsteroidal anti-inflammatory drugs (NSAIDs) such as indometacin. It was developed in ...

(WIN 48,098),

JWH-200 JWH-200 (WIN 55,225) is an analgesic chemical from the aminoalkylindole family that acts as a cannabinoid receptor agonist. Its binding affinity, ''K''i at the CB1 receptor is 42 nM, around the same as that of THC, but its analgesic potenc ...

(WIN 55,225) and

WIN 55,212-2 WIN 55,212-2 is a chemical described as an aminoalkylindole derivative, which produces effects similar to those of cannabinoids such as tetrahydrocannabinol (THC) but has an entirely different chemical structure. WIN 55,212-2 is a potent canna ...

by the

Sterling Winthrop Sterling Drug was an American global pharmaceutical company, also known as Sterling Winthrop, Inc. in its last years (after the merger with Winthrop-Stearns Inc. which itself resulted from the merger of ''Winthrop Chemical Company Inc.'' and '' ...

group. Several other ''N''-alkyl substituents were found to be active by Huffman's team including the ''n''-

butyl In organic chemistry, butyl is a four- carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, gi ...

, ''n''-

hexyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

, 2- heptyl, and

cyclohexyl Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

ethyl groups, but it was subsequently determined that the 2-methyl group on the

indole Indole is an aromatic heterocyclic organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other c ...

ring is not required for CB₁ binding, and tends to increase affinity for CB₂ instead. Consequently, the 2- desmethyl derivative of JWH-007, JWH-018, has slightly higher

binding affinity In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usually a mo ...

for CB₁, with an optimum binding of 9.00 nM at CB₁ and 2.94 nM at CB₂, and JWH-007 displayed optimum binding of 9.50 nM at CB₁ and 2.94 nM at CB₂. Another drug similarly named JHW-007 (not JWH) is a cocaine analog (the di-''para''-fluoro

benztropine Benzatropine ( INN), known as benztropine in the United States and Japan, is a medication used to treat movement disorders like parkinsonism and dystonia, as well as extrapyramidal side effects of antipsychotics, including akathisia. It is not u ...

, being essentially a hybrid between benzatropine and

difluoropine Difluoropine (O-620) is a stimulant drug synthesised from tropinone, which acts as a potent and selective dopamine reuptake inhibitor. Difluoropine is unique among the tropane-derived dopamine reuptake inhibitors in that the active stereoisomer ...

; with fluorine groups in the former or being descarbmethoxy in the latter) and atypical

dopamine reuptake inhibitor A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular ...

, but is distinct from and not the same as this JWH-007.

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-007 are Schedule I Controlled Substances. JWH-007 was banned in Sweden on 1 October 2010 as a hazardous good harmful to health, after being identified as an ingredient in "herbal" synthetic cannabis products. JWH-007 is illegal in

Poland Poland, officially the Republic of Poland, is a country in Central Europe. It is divided into 16 administrative provinces called voivodeships, covering an area of . Poland has a population of over 38 million and is the fifth-most populou ...

since 08.06.2010 on the basis of 'Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii' published in Dz.U. 2011 nr 105 poz. 614 As of October 2015 JWH-007 is a controlled substance in China.

References

{{Cannabinoidergics Designer drugs JWH cannabinoids Naphthoylindoles CB1 receptor agonists CB2 receptor agonists

Legal status

See also

References