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JWH-018

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JWH-018
Legal status
Legal status
Identifiers
  • Naphthalen-1-yl-(1-pentylindol-3-yl)methanone
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard100.163.574 Edit this at Wikidata
Chemical and physical data
FormulaC24H23NO
Molar mass341.45 g/mol g·mol−1
Solubility in waterhydrophobic, n/a mg/mL (20 °C)

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.[2][3][4] 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. [5][6][7]

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 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) is between 1 and 2 milligrams. Some users may be able to use higher dosages of 3-5 mg taken orally or smoked. Dosage is not strictly sensitive to users' general tolerance to THC, anxiety reactions have been noted when as little as 2 mg have been taken, even by users comfortable with taking cannabis. 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.[8]

Substance CYPs hERG Cytotox Genotox Rat Repeat Tox Rat PK
JWH-018 4/6 +ve * [8] Negative [8] Negative [8] Negative [8] Lethargy, Catatonia, Tachyphylaxis, No Organ Pathology [8] Bi-phasic, Well Distributed [8]
  • Denotes positive results and indicates further testing needed to define the issue.

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 [9]
Germany 22nd January 2009 [10]
Latvia 28th November 2009
Lithuania 5th June 2009 [9]
Luxembourg JWH-018 is potentially illegal in Luxembourg, where the government has "adopted an analogue approach by referring to ‘synthetic agonists of cannabinoid receptors’"[9]
Poland [9]
South Korea 1 July 2009 [11]
Sweden 30th July 2009 The bill was accepted on 30th July 2009 and was in effect on 15th September 2009.[12]
Estonia 24th July 2009
Romania 15th February 2010
Russia 22th January 2010
United Kingdom 23rd December 2009 [13]

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. Lawmakers in the state of Kansas[3] are currently considering bills that would ban JWH-018. [14] In February of 2010, two Kansas stores selling an herbal blend containing the product were raided by the FDA, who confiscated all of their JWH-018 stock.[15]

In Feb. 2010, Law makers in MO began considering a ban on K2, which is an herbal blend containing JWH-018.

See also

References

  1. ^ Insert footnote text here
  2. ^ 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)
  3. ^ US patent 6900236, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2005-05-31 
  4. ^ US patent 7241799, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2007-07-10 
  5. ^ Gefährlicher Kick mit Spice (German)
  6. ^ Erstmals Bestandteile der Modedroge „Spice“ nachgewiesen (German)
  7. ^ Spice enthält chemischen Wirkstoff (German)
  8. ^ a b c d e f g JWH-018 Toxicity Results
  9. ^ a b c d [1]
  10. ^ BGBl I Nr. 3 vom 21.01.2009, 22. BtMÄndV vom 19. Januar 2009, S. 49–50.
  11. ^ 최연희 (2 July 2009). "1일부터 '5-메오-밉트' 등 향정신성의약품 지정". 헬스코리아뉴스. Retrieved 18 February 2010.
  12. ^ [2](Swedish)
  13. ^ http://business.timesonline.co.uk/tol/business/law/article6965663.ece
  14. ^ 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/
  15. ^ http://www.pitch.com/2010-02-18/news/kansas-legislature-bans-k2-synthetic-marijuana/
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