Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Use dmy dates|date=August 2020}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 437691572
| verifiedrevid = 437691572
| IUPAC_name = 1-([(1E)-3-pentylinden-1-ylidine]methyl)naphthalene
| IUPAC_name = 1-([(1''E'')-3-Pentylinden-1-ylidine]methyl)naphthalene
| image = JWH-176.svg
| image = JWH-176.svg
| width = 180
| width = 180
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = Class B
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = Schedule I
| legal_status = Legal
| legal_status =
| routes_of_administration =
| routes_of_administration =


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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 619294-62-1
| CAS_number = 619294-62-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VA60GT97BB
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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<!--Chemical data-->
<!--Chemical data-->
| C=25 | H=24
| C=25 | H=24
| smiles = CCCCCC1=C\C(=C/c2cccc3ccccc32)c2ccccc21
| molecular_weight = 324.457 g/mol
⚫
| StdInChI = 1S/C25H24/c1-2-3-4-11-21-18-22(25-16-8-7-15-24(21)25)17-20-13-9-12-19-10-5-6-14-23(19)20/h5-10,12-18H,2-4,11H2,1H3/b22-17+
| smiles = CCCCCc(c3)c1ccccc1c3=Cc2cccc4ccccc24
⚫
| StdInChIKey = FPESBQVTVSBBSE-OQKWZONESA-N
⚫
| StdInChI = 1S/C25H24/c1-2-3-4-11-21-18-22(25-16-8-7-15-24(21)25)17-20-13-9-12-19-10-5-6-14-23(19)20/h5-10,12-18H,2-4,11H2,1H3/b22-17-
⚫
| StdInChIKey = FPESBQVTVSBBSE-XLNRJJMWSA-N
}}
}}


'''JWH-176''' is an [[analgesic]] drug which acts as a [[cannabinoid receptor agonist]]. Its [[Dissociation constant#Protein-ligand binding|binding affinity]] at the CB<sub>1</sub> receptor is only 26.0nM, making it more potent than [[THC]] itself,<ref>Huffman JW, Padgett LW. Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes. ''Current Medicinal Chemistry'', 2005; 12: 1395-1411.</ref> however JWH-176 is particularly notable in that it is a [[hydrocarbon]] containing no [[heteroatom]]s. This demonstrates that reasonably high-affinity [[cannabinoid]] binding and agonist effects can be produced by compounds with no [[hydrogen bonding]] capacity at all, relying merely on [[Van der Waals force|Van der Waals]] interactions to bind to the receptor.<ref>Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. {{ISBN|3-540-22565-X}}</ref> It was discovered by, and named after, Dr. [[John W. Huffman]].
'''JWH-176''' is an [[analgesic]] drug which acts as a [[cannabinoid receptor agonist]]. Its [[Dissociation constant#Protein-ligand binding|binding affinity]] at the CB<sub>1</sub> receptor is 26.0&nbsp;nM, making it more potent than [[THC]] itself,<ref name="pmid15974991">{{cite journal | vauthors = Huffman JW, Padgett LW | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | journal = Current Medicinal Chemistry | volume = 12 | issue = 12 | pages = 1395–411 | date = 2005 | pmid = 15974991 | doi = 10.2174/0929867054020864 }}</ref> however JWH-176 is particularly notable in that it is a [[hydrocarbon]] containing no [[heteroatom]]s. This demonstrates that reasonably high-affinity [[cannabinoid]] binding and agonist effects can be produced by compounds with no [[hydrogen bonding]] capacity at all, relying merely on [[Van der Waals force|Van der Waals]] and possibly hydrophobic interactions to bind to the receptor.<ref>{{cite book | vauthors = Pertwee RG | title = Cannabinoids | series = Handbook of Experimental Pharmacology | volume = 168 | pages = 269 | publisher = Springer | isbn = 3-540-22565-X }}</ref> It was discovered by, and named after, [[John W. Huffman]].


==Stereochemistry==
==Stereochemistry==
⚫
JWH-176 is the (''E'')-stereoisomer of 1-([3-pentylinden-1-ylidine]methyl)naphthalene, whereas '''JWH-171''' is the mixture of the (''E'')- and (''Z'')-isomers.<ref>{{cite book | vauthors = Huffman JW, Padgett LW | chapter = Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes |url=https://books.google.com/books?id=N_luK703FKEC|title=Frontiers in Medicinal Chemistry | volume = 4 | veditors = Rahman A, Iqbal Choudhary M, Reitz AB |date=2010-12-10|pages = 661–687 (681) |isbn = 978-1-60805-346-9 | doi = 10.2174/978160805207310904010661 }}</ref>
[[File:JWH-171.svg|95px|thumb|left|JWH-171]]
:[[File:JWH-171.svg|95px|thumb|left|JWH-171]]{{clear-left}}
⚫
'''JWH-176''' is the ''E'' stereoisomer of 1-([3-pentylinden-1-ylidine]methyl)naphthalene, whereas '''JWH-171''' is the mixture of the ''E'' and ''Z'' isomers.<ref>{{cite book |isbn=978-1608052073|url=https://books.google.com/books?id=N_luK703FKEC|title=Frontiers in Medicinal Chemistry , Volume (4)|last1=Rahman|first1=Atta-ur|last2=Iqbal Choudhary|first2=M|last3=Reitz|first3=Allen B|date=2010-12-10|page=681}}</ref> <br><br><br><br>


==Legal status==
In the United States, CB<sub>1</sub> receptor agonists of the 1-(1-naphthylmethylene)indene class such as JWH-176 and JWH-171 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>

As of 23 December 2009, any compound structurally derived from 1–(1–naphthylmethyl)indene by substitution at the 3–position of the indene ring by an alkyl group is a Class B drug in the United Kingdom.<ref>{{ Cite legislation UK | type = si | si = The Misuse of Drugs Act 1971 (Amendment) Order 2009 | year = 2009 | number = 3209 }}</ref>


==See also==
==See also==
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{{Cannabinoids}}
{{Cannabinoids}}
{{cannabinoid-stub}}


[[Category:Cannabinoids]]
[[Category:JWH cannabinoids]]
[[Category:JWH cannabinoids]]
[[Category:Naphthalenes]]
[[Category:1-Naphthyl compounds]]
[[Category:Indenes]]
[[Category:Indenes]]
[[Category:Polycyclic aromatic hydrocarbons]]
[[Category:Polycyclic aromatic hydrocarbons]]
[[Category:CB1 receptor agonists]]

Latest revision as of 21:05, 20 June 2023

JWH-176
Legal status
Legal status
Identifiers
  • 1-([(1E)-3-Pentylinden-1-ylidine]methyl)naphthalene
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H24
Molar mass324.467 g·mol−1
3D model (JSmol)
  • CCCCCC1=C\C(=C/c2cccc3ccccc32)c2ccccc21
  • InChI=1S/C25H24/c1-2-3-4-11-21-18-22(25-16-8-7-15-24(21)25)17-20-13-9-12-19-10-5-6-14-23(19)20/h5-10,12-18H,2-4,11H2,1H3/b22-17+
  • Key:FPESBQVTVSBBSE-OQKWZONESA-N
  (verify)

JWH-176 is an analgesic drug which acts as a cannabinoid receptor agonist. Its binding affinity at the CB1 receptor is 26.0 nM, making it more potent than THC itself,[1] however JWH-176 is particularly notable in that it is a hydrocarbon containing no heteroatoms. This demonstrates that reasonably high-affinity cannabinoid binding and agonist effects can be produced by compounds with no hydrogen bonding capacity at all, relying merely on Van der Waals and possibly hydrophobic interactions to bind to the receptor.[2] It was discovered by, and named after, John W. Huffman.

Stereochemistry[edit]

JWH-176 is the (E)-stereoisomer of 1-([3-pentylinden-1-ylidine]methyl)naphthalene, whereas JWH-171 is the mixture of the (E)- and (Z)-isomers.[3]

JWH-171

Legal status[edit]

In the United States, CB1 receptor agonists of the 1-(1-naphthylmethylene)indene class such as JWH-176 and JWH-171 are Schedule I Controlled Substances.[4]

As of 23 December 2009, any compound structurally derived from 1–(1–naphthylmethyl)indene by substitution at the 3–position of the indene ring by an alkyl group is a Class B drug in the United Kingdom.[5]

See also[edit]

References[edit]

  1. ^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
  2. ^ Pertwee RG. Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. Springer. p. 269. ISBN 3-540-22565-X.
  3. ^ Huffman JW, Padgett LW (10 December 2010). "Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes". In Rahman A, Iqbal Choudhary M, Reitz AB (eds.). Frontiers in Medicinal Chemistry. Vol. 4. pp. 661–687 (681). doi:10.2174/978160805207310904010661. ISBN 978-1-60805-346-9.
  4. ^ 21 U.S.C. § 812: Schedules of controlled substances
  5. ^ "The Misuse of Drugs Act 1971 (Amendment) Order 2009", legislation.gov.uk, The National Archives, SI 2009/3209
source: https://en.wikipedia.org/w/index.php?title=JWH-176&diff=1161131386&oldid=851954041

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