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Revision as of 01:41, 1 November 2010
Pharmaceutical compoundIdentifiers | |
---|---|
IUPAC name
| |
CAS Number | |
PubChem CID | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.163.574 |
Chemical and physical data | |
Formula | C24H23NO |
Molar mass | 341.45 g/mol g·mol |
Solubility in water | hydrophobic, n/a mg/mL (20 °C) |
JWH-018 (1-pentyl-3-(1-naphthoyl)indole) 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. It produces effects in animals similar to those of THC, a cannabinoid naturally present in cannabis, leading to its use in synthetic cannabis.
History
Dr. John W. Huffman, an organic chemist at Clemson University, synthesizes analogues and metabolites of Δ-tetrahydrocannabinol (THC), the principal active component of cannabis. JWH-018 is one of these analogues, with studies showing an affinity for the cannabinoid brain (CB1) receptor five times greater than that of THC. Cannabinoid receptors are found in mammalian brain and spleen tissue; however, the structural details of the active sites are currently unknown.
On December 15, 2008, it was reported by the German pharmaceutical company THC Pharm, that JWH-018 was found as one of the active components in at least three versions of the herbal blend Spice, which has been sold as an incense, in a number of countries around the world since 2002. An analysis of samples acquired four weeks after the German prohibition of JWH-018 took place found that the compound had been replaced with JWH-073.
Common dosage
The usual dosage for individual consumption varies greatly per individual but is typically between 3 and 20 milligrams. When smoked (as opposed to consumed orally) the amount needed may be as little as 1 mg or lower, however the observed effects have a shorter duration.
Pharmacology
Mechanism of Action
JWH-018 is a full agonist of both the CB1 and CB2 cannabinoid receptors.
Pharmacokinetics
For JWH-018, the indole-N-dealkyl metabolite could be detected as well as the hydroxylated metabolite. The highest signals could be observed for the hydroxylated N-desalkyl metabolites. Hydroxylation took place in the side chain and in both aromatic systems, the naphthalene and the indol part, which could be shown by mass shift of the corresponding fragments and by MS experiments. Human metabolites were similar although most metabolism took place on the indole ring and pentyl side chain, and the hydroxylated metabolites were extensively conjugated with glucuronide.
Addiction
At least one case of psychological dependence (as distinct from physical addiction) has been reported. The user consumed JWH-018 daily for eight months. Withdrawal symptoms were similar to those experienced as a result of psychological cannabis dependence. JWH-018 has been shown to cause profound changes in CB1 receptor density following administration, causing desensitization to its effects more rapidly than related cannabinoids.
Toxicity
Compared to THC, which is a partial agonist at CB1 receptors, JWH-018 (and many of its analogues) are full agonists. This means that users may experience far more intense effects compared to smoking cannabis. THC has been shown to inhibit GABA neurotransmission in the brain via several pathways. JWH-018 may cause intense anxiety, agitation, and even seizures or convulsions by inhibiting GABA neurotransmission more efficiently than THC. Cannabinoid receptor full agonists may present serious dangers to the user when overdosed.
A study published March 2010 in the "Journal Of Occupational Medicine and Toxicology" have shown that JWH-018 has similar negative health effects of those found with standard Cannabis consumption because inhalation of smoke from burned organic materials can cause various health problems. JWH-018 depending on method of consumption has very similar effects. One of the researchers involved in the new study is Dr. Anthony Scalzo, a toxicologist at Saint Louis University. He told The Associated Press that he has seen more than 30 cases of Missouri teenagers having agitation, elevated heart rates, vomiting and other health effects not normally associated with moderate to low Cannabis consumption; however, he noted that these are all symptoms that can be seen at high dosages of marijuana.
Usage
JWH-018 produces effects very similar to cannabis but is considerably more potent than similar amounts of cannabis. The drug does not show up in drug test results for cannabis, but its metabolites can be detected in human urine by GC-MS-screening and LC-MS/MS.
John W. Huffman has opined that JWH-018 has no medical use, stating, "It's like LSD, the only thing it is good for is getting you high."
According to the writer Kevin Keck, who sampled various brands of herbal incense containing JWH-018 for research on the subject, "A small amount does produce visual distortions and a marijuana-like buzz. I can easily understand how individuals with little or no experience in navigating this psychic terrain could experience extreme panic attacks that prompt them to seek medical attention...It is not a problem that responsible people use , it is a serious problem that naïve and foolish people use . It is the same problem that surrounds alcohol and any other number of legal prescription drugs."
Legal status
Several countries have placed legal restrictions on the compound.
Country | Date of Ban | Notes | |
---|---|---|---|
Austria | 18 December 2008 | The Austrian Ministry of Health announced on 18 December 2008 that Spice would be controlled under Paragraph 78 of their drug law on the grounds that it contains an active substance which affects the functions of the body, and the legality of JWH-018 is under review. | |
Belarus | 1 January 2010 | ||
Canada | June 3, 2010 | The Chemical JWH-018 is not controlled in Canada . Also note the Most current CDSA can be found here | |
France | February 24, 2009 | ||
Germany | 22 January 2009 | ||
Ireland | 11 May 2010 | An immediate ban was announced on 11 May 2010 by Minister for Health Mary Harney. | |
Italy | 2 July 2010 | ||
Latvia | 28 November 2009 | ||
Poland | |||
South Korea | 1 July 2009 | ||
Sweden | 30 July 2009 | The bill was accepted on 30 July 2009 and was in effect on 15 September 2009. | |
Estonia | 24 July 2009 | ||
Romania | 15 February 2010 | ||
Russia | 22 January 2010 | ||
Ukraine | 31 May 2010 | ||
United Kingdom | 23 December 2009 |
United States
JWH-018 is currently not federally controlled in the U.S., but the Drug Enforcement Administration labeled it a "drug and chemical of concern" in 2009. March 2009: DEA Microgram Bulletin "INTELLIGENCE ALERT".
While remaining legal under federal law, JWH-018 is banned in 15 states as of 10/16/2010. Oklahoma and Illinois have also passed legislation banning JWH-018, and there it will become illegal on 11/1/2010 and 1/1/2011 respectively:
State | Status | Notes | |
---|---|---|---|
Alabama | Illegal | On April 22, 2010, HB 697 passed the Alabama legislature, banning the possession of the following substances:
1) Trade name HU-210 2) Trade name JWH-018 3) Trade name JWH-073 4) Salvia divinorum or salvinorum A. That is, all parts of the plant presently classified botanically as salvia divinorum, whether growing or not, the seeds thereof, any extract from any part of such plant, and every compound, manufacture, salts, derivative, mixture, or preparation of such plant, its seeds or extracts. | |
Alaska | Legislation proposed | http://www.ktuu.com/news/ktuu-assembly-members-working-to-ba-101910,0,3903545.story | |
American Samoa | Unregulated | ||
Arizona | Unregulated | ||
Arkansas | Illegal | On July 2, 2010, the sale of (but not possession of) K2-like products containing JWH-018 and JWH-073 were temporarily banned during an emergency meeting of the Arkansas State Board of Health, citing concerns regarding the safety of these products. Twenty-six suspected medical incidents involving the use of synthetic marijuana products have been reported to Arkansas' Poison Control Center, by comparison there were 40,000 incidents for alcohol.
On October 26, 2010 the ban was made permanent making use, sale, or possession a misdemeanor with up to $500 fine and a month in jail. | |
California | Unregulated | ||
Colorado | Unregulated | ||
Connecticut | Unregulated | ||
Delaware | Unregulated | ||
District of Columbia | Unregulated | ||
Florida | Legislation Proposed | ||
Georgia | Illegal | K2 Spice is now illegal in Georgia. JWH-018 is illegal in Georgia as of July 15, 2010.
| |
Guam | Unregulated | ||
Hawaii | Illegal | possessing it in Hawaii became a felony on August 1, 2010 | |
Idaho | Illegal | Added to controlled substances list for Idaho on 10/15/2010
| |
Illinois | Legislation Passed, Impending Enaction Date: January 1, 2011 | To be effective on 1/1/2011, House Bill 6459 signed into law 7/26/2010 to add to the state list of controlled substances Illinois House Bill 6459 Sites JWH-018 as a Schedule 1 substance. | |
Indiana | Municipal Restrictions | Sale, use and/or possession is illegal or restricted in the cities of Fort Wayne, Auburn, Greenwood, Kendallville, New Haven, Ligonier, Linton; the towns of Hammond, Avilla, Porter, and Shipshewana; and, Allen, Boone, Daviess, Henry, Knox, Morgan, Steuben, Tippecanoe and Vigo Counties. Muncie, Albany, Daleville, Eaton, Gaston, Selma, Yorktown and Delaware counties. | |
Iowa | Illegal | As of July 21, 2010, the Iowa Board of Pharmacy voted to reclassify JWH-018 and other synthetic cannabinoids as Schedule I controlled substances. This is a temporary emergency ban. | |
Kansas | Illegal | In February 2010, two Kansas stores selling an herbal blend containing the product were raided by the DEA, who confiscated all of their JWH-018 stock.
A new law in Kansas has passed that will ban designer cannabinoids JWH-018, JWH-073, HU-210 along with stimulant BZP and TFMPP. | |
Kentucky | Illegal | In a vote taken on April 1, 2010, 79-10 voted to blanket ban all synthetic cannabinoid agonists, making it a class A misdemeanor to manufacture or traffic. Governor Steve Beshear signed HB265 into law on April 13, 2010. | |
Louisiana | Illegal | As of June 18, 2010, Louisiana passed bill HB 173 banning JWH-018, JWH-073, and CP 47,497 as well as most of the herbal ingredients found in incense blends. The Legislature also passed HB 121 and SB 37, which include synthetic cannabinoids. According to the Louisiana State Constitution, "All laws enacted during a regular session of the legislature shall take effect on August fifteenth of the calendar year in which the regular session is held... However, any bill may specify an earlier or later effective date." None of the bills specify a different date. | |
Maine | Unregulated | ||
Maryland | Legislation Proposed | A bill banning JWH-018 and JWH-073 for Baltimore County only will be submitted by the 2nd District Councilman on September 7, 2010. | |
Massachusetts | Unregulated | ||
Michigan | Illegal | Bill passed by Rep. Rick Jones, R-Grand Ledge banning sales and possession of Synthetic Cannaboids (JWH-018, JWH-073, JWH-015, JWH-200, JWH-250, HU-210, CP47,497). Synthetic Cannaboids are a Schedule 1 controlled substance. | |
Minnesota | Municipal Restrictions | Sale, possession and use is illegal or restricted in the cities of Duluth, Hermantown and Princeton, although the city attorneys office in Duluth has decided not to enforce the ban pending a lawsuit brought by local merchants. | |
Mississippi | Illegal | Bill passed by governor Hailey Barbour on September 3, 2010 banning sales and possession statewide. | |
Missouri | Illegal | As of March 28, 2010, The Missouri House approved its version of a bill, by a 142-10 vote, that would outlaw synthetic compounds that mimic the effects of marijuana.
As of April 4, 2010, the bill is awaiting Senate approval. The bill passed final approval and has been sent to the governor. If signed it will take effect on Aug 28th, 2010. The bill has passed and the ban takes effect 28 August. Text of bill can be found here: | |
Montana | Unregulated | ||
Nebraska | Unregulated | ||
Nevada | Unregulated | ||
New Hampshire | Unregulated | ||
New Jersey | Unregulated | ||
New Mexico | Unregulated | ||
New York | Legislation Proposed | ||
North Carolina | Legislation Proposed | ||
North Dakota | Illegal | As of February 25, 2010, the North Dakota Board of Pharmacy issued an emergency order banning the substance. That emergency order was made permanent at an April meeting. | |
Northern Marianas Islands | Unregulated | ||
Ohio | Unregulated | ||
Oklahoma | Legislation Passed, Impending Enaction Date: November 1, 2010 | To be effective on 11/1/2010, House Bill 3241 signed into law 4/28/2010 to add to the state list of controlled substances | |
Oregon | Illegal | Illegal as of 10/15/2010 http://kdrv.com/news/local/192107 | |
Pennsylvania | Legislation Proposed | The Pennsylvania House has passed a bill to ban synthetic cannabinoid chemicals http://www.philly.com/inquirer/local/pa/20100930_Pa__House_passes_bill_to_outlaw_synthetic_marijuana.html | |
Puerto Rico | Unregulated | ||
Rhode Island | Unregulated | ||
South Carolina | Unregulated | ||
South Dakota | Unregulated | ||
Tennessee | Illegal | The governor signed bills (SB2982 and HB2968) on 05/26/2010 banning JWH-018 and several other substances. The substances became illegal on July 1, 2010 per law. | |
Texas | Municipal Restrictions | No state regulation, but possession and use is illegal or restricted in the cities of Allen, Cleburne, Commerce(Must be 21), Conroe, Dallas, Denton (city, not county), Duncanville, Ennis, Frisco,Gladewater, Greenville, Irving, Kilgore, Longview, Mansfield, McKinney, Mineral Wells, Overton, Plano, Port Arthur, Troup, Tyler, Sulphur Springs, Van Alstyne, Watauga, Whitehouse and White Oak. | |
Utah | Legislation Proposed | As of March 28, 2010, A bill creating a state drug advisory panel that could recommend the outlawing of spice is awaiting Gov. Gary Herbert's signature. On May 12, 2010, Salt Lake City police officers conducted a city-wide crackdown asking local shopkeepers to voluntarily remove it from their shelves. There have also been reports of police giving open container tickets for spice found in cars. On September 14, 2010, spice was banned in Ogden, Utah. As of September 20, 2010 Spice was banned in Roy, Utah Spice ban in Cache, Rich and Box Elder counties | |
Vermont | Unregulated | ||
Virginia | Legislation Proposed | jwh-018 only. | |
Virgin Islands | Unregulated | ||
Washington | Unregulated | ||
West Virginia | Unregulated | ||
Wisconsin | Municipal Restrictions | Sale, possession and use is illegal or restricted in the Cities of Eau Claire, La Crosse, Waukesha, and Milwaukee. | |
Wyoming | Unregulated |
See also
References
- Aung, M. M. (2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding". Drug and Alcohol Dependence. 60 (2): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
{{cite journal}}
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ignored (|author=
suggested) (help) - US patent 6900236, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2005-05-31
- US patent 7241799, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2007-07-10
- ^ B.K. Atwood et. al., "JWH018, a common constituent of 'Spice' herbal blends, is a potent and efficacious cannabinoid CB1 receptor agonist." British Journal of Pharmacology, Vol. 160, No. 3. 585-593. 2010.
- "Clemson University :: Department of Chemistry". Clemson.edu. Retrieved 2010-08-23.
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has numeric name (help) - Gefährlicher Kick mit Spice Template:De icon
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- Spice enthält chemischen Wirkstoff Template:De icon
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- Studies on the metabolism of JWH-018 and of a homologue of CP 47,497, pharmacologically active ingredients of different misused incense (“Spice”) using GC-MS and LC-MSn techniques - T. Kraemer, K.Y. Rust, M.R. Meyer, D.K. Wissenbach, D. Bregel, M. Hopf, H.H. Maurer, J. Wilske (Institute of Legal Medicine, Saarland University, 66421 Homburg, Germany
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{{cite journal}}
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ignored (help)CS1 maint: multiple names: authors list (link) - Zimmermann, US; Winkelmann, PR; Pilhatsch, M; Nees, JA; Spanagel, R; Schulz, K (2009). "Withdrawal Phenomena and Dependence Syndrome After the Consumption of "Spice Gold"". Dtsch Arztebl Int. 106 (27): 464–467. doi:10.3238/arztebl.2009.0464. PMC 2719097. PMID 19652769.
- Nora Laaris et. al., "Δ9-tetrahydrocannabinol is a full agonist at CB1 receptors on GABA neuron axon terminals in the hippocampus." Neuropharmacology, Vol. 59, No. 1-2, 121-127. 2010.
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- European Monitoring Centre for Drugs and Drug Addiction. "Understanding the Spice Phenomenon." 2009. ISBN 978-92-9168-411-3.
- "Fake Weed "K2" Can Cause Hallucinations". CBS News. 2010-03-04. Retrieved 2010-08-31.
- Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/jms.1558, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
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instead. - Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/j.forsciint.2010.04.003, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
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instead. - "Synthetic Cannabis Mimic Found in Herbal Incense" (Document). High Times. Jan 28, 2009.
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ignored (help) - (Document). Creative Loafing. August 24, 2010.
{{cite document}}
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ignored (help) - "Controlled Drugs and Substances Act". Laws.justice.gc.ca. 2010-08-16. Retrieved 2010-08-23.
- ^ "EMCDDA | Drug profile: Synthetic cannabinoids and 'Spice'". Emcdda.europa.eu. 2010-08-17. Retrieved 2010-08-23.
- http://www.afssaps.fr/var/afssaps_site/storage/original/application/d23d05edc58479d91c803b496017f073.pdf
- BGBl I Nr. 3 vom 21.01.2009, 22. BtMÄndV vom 19. Januar 2009, S. 49–50.
- Many head shop products banned - Irish Times.
- http://www.politicheantidroga.it/comunicazione/comunicati/2010/luglio/spice,-n-joy-e-mefedrone-da-oggi-stupefacenti.aspx Template:It icon
- 최연희 (2 July 2009). "1일부터 '5-메오-밉트' 등 향정신성의약품 지정". 헬스코리아뉴스. Retrieved 18 February 2010.
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- "Rules Pertaining to Synthetic Marijuana Products" (PDF). Arkansas Department of Health. July 2, 2010. Retrieved July 10, 2010.
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- "Lawmakers hope to snuff out fake pot | Chattanooga Times Free Press". Timesfreepress.com. Retrieved 2010-08-23.
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{{cite web}}
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- |title=New law: Ammended Illinois Law | http://www.ilga.gov/legislation/fulltext.asp?DocName=09600HB6459ham001&GA=96&LegID=52487&SessionId=76&SpecSess=0&DocTypeId=HB&DocNum=6459&GAID=10&Session=.
{{cite web}}
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(help) - "Council sets $2,500 fine for use of K2 - News-Sentinel". www.news-sentinel.com. August 2010.
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- "10RS HB265". Lrc.ky.gov. Retrieved 2010-08-23.
- "2010 Regular Session - Instrument Information". Legis.state.la.us. 2010-06-25. Retrieved 2010-08-23.
- "2010 Regular Session - Instrument Information". Legis.state.la.us. 2010-06-30. Retrieved 2010-08-23.
- "2010 Regular Session - Instrument Information". Legis.state.la.us. 2010-02-07. Retrieved 2010-08-23.
- http://www.legis.state.la.us/lss/lss.asp?doc=206415
- http://www.legislature.mi.gov/documents/2009-2010/billanalysis/Senate/htm/2009-SFA-6038-F.htm
- "Synthetic Pot Now Illegal in Duluth - Citypages Minneapolis News, Events". http://blogs.citypages.com. August 2010.
{{cite web}}
: External link in
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- "Princeton becomes 2nd Minn. city to ban synthetic marijuana - St. Cloud Times". www.sctimes.com. September 2010.
- "Despite Ban, K2 on Shelves - Northlands Newscenter". www.northlandsnewscenter.com. October 2010.
- "Spice University - Herbal Incense - K2 - K2 Spice: Missouri close to ban of K2 Incense Spice". K2spice.blogspot.com. 2010-04-04. Retrieved 2010-08-23.
- BY SARAH D. WIRE/The Associated Press (2010-05-14). "Missouri lawmakers approve bill banning K2". Columbia Missourian. Retrieved 2010-08-23.
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- "Text of Bill" (PDF). house.mo.gov. Retrieved 2010-10-05.
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{{cite web}}
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(help); Text "http://e-lobbyist.com/gaits/OK/HB3241" ignored (help) - "Tennessee General Assembly » Legislation". Wapp.capitol.tn.gov. Retrieved 2010-08-23.
- ^ Kellar, Brad (2010-08-25). "Council votes to ban sales of K2 in city » Local News » The Herald Banner, Greenville, TX". Heraldbanner.com. Retrieved 2010-09-01.
- Campbell, Elizabeth. "Cleburne, Watauga, Frisco and Plano target synthetic marijuana products including K2 | New". Star-telegram.com. Retrieved 2010-08-23.
- "Duncanville joins growing list of cities to ban fake-marijuana products such as K2 | Texas Cable News | TXCN.com | News for Texas | Local News: TV". TXCN.com. 2010-08-05. Retrieved 2010-08-23.
- "Dallas City Council approves ban on 'fake weed' | News for Dallas, Texas | Dallas Morning News". Dallas News. 2010-08-12. Retrieved 2010-08-23.
- "Longview city council bans K-2 - KLTV 7 News Tyler, Longview, Jacksonville |". Kltv.com. Retrieved 2010-08-23.
- "Spice scare: Utah legislation calls for substance review - The Herald Journal: News". News.hjnews.com. Retrieved 2010-08-23.
- "Unified police on mission to get rid of Spice". ksl.com. 2010-05-12. Retrieved 2010-08-23.
- ((http://www.standard.net/topics/drugs/2010/09/14/ogden-bans-spice-its-first-utah-city-prohibit-purchase-manufacture-use-posse.htlm
- ((http://www.fox13now.com/news/kstu-ban-on-spice-by-bear-river-health,0,5330664.story))
- "Others look to ban K2 use and sale similar to Eau Claire - WQOW 18". www.wqow.com. September 2010.
- . October 22, 2010 http://www.620wtmj.com/news/local/105317778.html.
{{cite web}}
: Missing or empty|title=
(help) - "Council OKs ban on synthetic marijuana". jsonline.com. October 12, 2010.
External links
- JWH-018 Report Psychonaut Web Mapping Research Project