JWH-018: Difference between revisions

JWH-018
Legal status
Legal status	CA: Schedule II;
Identifiers
	IUPAC name Naphthalen-1-yl-(1-pentylindol-3-yl)methanone;
CAS Number	209414-07-3;
PubChem CID	10382701;
CompTox Dashboard (EPA)	DTXSID10175117 ;
ECHA InfoCard	100.163.574
Chemical and physical data
Formula	C24H23NO
Molar mass	341.45 g/mol g·mol−1
Solubility in water	hydrophobic, n/a mg/mL (20 °C)

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Revision as of 18:51, 2 March 2010

JWH-018 (1-pentyl-3-(1-naphthoyl)indole) is an analgesic chemical from the aminoalkylindole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors, with some selectivity for CB₂.^[1]^[2]^[3] It produces effects in animals very similar to those of THC itself, but with a longer duration of action.

History

On December 15th 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. ^[4]^[5]^[6]

Effects

When smoked or ingested (orally), JWH-018 produces a very pleasant, euphoric feeling. Its effects are considered more of a general body high with unusually clear cerebral effects, similar to cannabis with a higher component ratio of sativa over indica. Some users have reported side effects similar to that of cannabis such as nausea, increased heartbeat, and feelings of paranoia and anxiety as a side-effect. JWH-018 has also been described to be an efficient painkiller, numbing pains with stomach and headaches, along with tooth and joint pain.

Common Dosage

The usual dosage for individual consumption (orally) varies greatly per individual but is typically between 3 and 20 milligrams. Dosage is not strictly sensitive to users' general tolerance to THC, however there seems to be a noticeable correlation per individual (unconfirmed) reports. When smoked (as opposed to consumed orally) the amount needed may be lower, however the observed effects have a lesser duration.

Toxicity

A study performed a cytotoxicity assay in human HepG2 hepatocellular carcinoma cells. It was found that JWH-018 showed little cytotoxicity with an IC50 >250 >μM. These results are consistent with the other cell based assays.^[7]

Substance	CYPs	hERG	Cytotox	Genotox	Rat Repeat Tox	Rat PK
JWH-018	4/6 +ve * ^[7]	Negative ^[7]	Negative ^[7]	Negative ^[7]	Lethargy, Catatonia, Tachyphylaxis, No Organ Pathology ^[7]	Bi-phasic, Well Distributed ^[7]

Denotes positive results and indicates further testing needed to define the issue.

Legal status

Several countries have placed legal restrictions on the compound.

Country	Date of Ban	Notes
Austria	18th December 2008	The Austrian Ministry of Health announced on 18th 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	1st January 2010
France		^[8]
Germany	22nd January 2009	^[9]
Latvia	28th November 2009
Lithuania	5th June 2009	^[8]
Luxembourg		JWH-018 is potentially illegal in Luxembourg, where the government has "adopted an analogue approach by referring to ‘synthetic agonists of cannabinoid receptors’"^[8]
Poland		^[8]
South Korea	1 July 2009	^[10]
Sweden	30th July 2009	The bill was accepted on 30th July 2009 and was in effect on 15th September 2009.^[11]
Estonia	24th July 2009
Romania	15th February 2010
Russia	22th January 2010
United Kingdom	23rd December 2009	^[12]

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" [3]. Lawmakers in the state of Kansas[4] are currently considering bills that would ban JWH-018. ^[13]In February of 2010, two Kansas stores selling an herbal blend containing the product were illegally raided by the FDA, who confiscated all of their JWH-018 stock. ^[14]In Feb. 2010, Law makers in MO began considering a ban on K2, which is an herbal blend containing JWH-018. JWH-018 is currently known by it's street name of "Jazzy Jeff."

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. {{cite journal}}: Cite has empty unknown parameter: |month= (help); Unknown parameter |coauthors= 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
^ Gefährlicher Kick mit Spice (German)
^ Erstmals Bestandteile der Modedroge „Spice“ nachgewiesen (German)
^ Spice enthält chemischen Wirkstoff (German)
^ ^a ^b ^c ^d ^e ^f ^g JWH-018 Toxicity Results
^ ^a ^b ^c ^d [1]
^ BGBl I Nr. 3 vom 21.01.2009, 22. BtMÄndV vom 19. Januar 2009, S. 49–50.
^ 최연희 (2 July 2009). "1일부터 '5-메오-밉트' 등 향정신성의약품 지정". 헬스코리아뉴스. Retrieved 18 February 2010.
^ [2](Swedish)
^ http://business.timesonline.co.uk/tol/business/law/article6965663.ece
^ http://www.phoenixnewtimes.com/2010-02-04/news/up-in-smoke-valley-smokers-buy-steal-and-inhale-jwh-018-to-get-high-and-they-say-it-s-working/
^ http://www.pitch.com/2010-02-18/news/kansas-legislature-bans-k2-synthetic-marijuana/

[1] 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. {{cite journal}}: Cite has empty unknown parameter: |month= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)

[2] US patent 6900236, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2005-05-31

[3] US patent 7241799, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2007-07-10

[4] Gefährlicher Kick mit Spice (German)

[5] Erstmals Bestandteile der Modedroge „Spice“ nachgewiesen (German)

[6] Spice enthält chemischen Wirkstoff (German)

[MFTox-7] ^ ^a ^b ^c ^d ^e ^f ^g JWH-018 Toxicity Results

[EMCDDA_Drug_Profiles:_Synthetic_cannabinoids_and_'Spice'-8] [1]

[BGBL_vom_090119-9] BGBl I Nr. 3 vom 21.01.2009, 22. BtMÄndV vom 19. Januar 2009, S. 49–50.

[10] 최연희 (2 July 2009). "1일부터 '5-메오-밉트' 등 향정신성의약품 지정". 헬스코리아뉴스. Retrieved 18 February 2010.

[11] [2](Swedish)

[12] ttp://business.timesonline.co.uk/tol/business/law/article6965663.ece

[13] ttp://www.phoenixnewtimes.com/2010-02-04/news/up-in-smoke-valley-smokers-buy-steal-and-inhale-jwh-018-to-get-high-and-they-say-it-s-working/

[14] ttp://www.pitch.com/2010-02-18/news/kansas-legislature-bans-k2-synthetic-marijuana/

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@@ Line 121: / Line 121: @@
 === 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" [http://www.justice.gov/dea/programs/forensicsci/microgram/mg0309/mg0309.html].  Lawmakers in the state of Kansas[http://www.pitch.com/2010-02-18/news/kansas-legislature-bans-k2-synthetic-marijuana/] are currently considering bills that would ban JWH-018.  <ref>http://www.phoenixnewtimes.com/2010-02-04/news/up-in-smoke-valley-smokers-buy-steal-and-inhale-jwh-018-to-get-high-and-they-say-it-s-working/</ref>In February of 2010, two Kansas stores selling an herbal blend containing the product were illegally raided by the FDA, who confiscated all of their JWH-018 stock.  <ref>http://www.pitch.com/2010-02-18/news/kansas-legislature-bans-k2-synthetic-marijuana/</ref>In Feb. 2010, Law makers in MO began considering a ban on K2, which is an herbal blend containing JWH-018.
+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" [http://www.justice.gov/dea/programs/forensicsci/microgram/mg0309/mg0309.html].  Lawmakers in the state of Kansas[http://www.pitch.com/2010-02-18/news/kansas-legislature-bans-k2-synthetic-marijuana/] are currently considering bills that would ban JWH-018.  <ref>http://www.phoenixnewtimes.com/2010-02-04/news/up-in-smoke-valley-smokers-buy-steal-and-inhale-jwh-018-to-get-high-and-they-say-it-s-working/</ref>In February of 2010, two Kansas stores selling an herbal blend containing the product were illegally raided by the FDA, who confiscated all of their JWH-018 stock.  <ref>http://www.pitch.com/2010-02-18/news/kansas-legislature-bans-k2-synthetic-marijuana/</ref>In Feb. 2010, Law makers in MO began considering a ban on K2, which is an herbal blend containing JWH-018. JWH-018 is currently known by it's street name of "Jazzy Jeff."
 == See also ==