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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 450663987
| IUPAC_name = (5-(2-fluorophenyl)-1-pentylpyrrol-3-yl)-naphthalen-1-ylmethanone
| IUPAC_name = (5-(2-Fluorophenyl)-1-pentylpyrrol-3-yl)-naphthalen-1-ylmethanone
| image = JWH-307.svg
| image = JWH-307.svg
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| CAS_number =

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| ATC_prefix =
<!--Clinical data-->
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| ATC_suffix =
| tradename =
⚫
| PubChem = 16049783
| DrugBank =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
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| C=26|H=24|F=1|N=1|O=1
| pregnancy_category =
| molecular_weight = 385.472 g/mol
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫
| smiles = CCCCCN1C=C(C=C1C2=CC=CC=C2F)C(=O)C3=CC=CC4=CC=CC=C43
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| bioavailability =
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
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| protein_bound =
| legal_US = Schedule I
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| metabolism =
| legal_DE = Anlage II
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| elimination_half-life =
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| routes_of_administration =
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| excretion =

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
<!--Pharmacokinetic data-->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
| bioavailability =
⚫
| protein_bound =
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| metabolism =
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
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| elimination_half-life =
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
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| excretion =
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status = Legal
<!--Identifiers-->
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| routes_of_administration =
| CAS_number_Ref = {{cascite|correct|??}}
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| CAS_number = 914458-26-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 06QTR14ONW
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| ATC_prefix =
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| ATC_suffix =
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| PubChem = 16049783
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID = 13178178

<!--Chemical data-->
⚫
| C=26 | H=24 | F=1 | N=1 | O=1
⚫
| smiles = CCCCCN1C=C(C=C1C2=CC=CC=C2F)C(=O)C3=CC=CC4=CC=CC=C43
| StdInChI = 1S/C26H24FNO/c1-2-3-8-16-28-18-20(17-25(28)23-13-6-7-15-24(23)27)26(29)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3
| StdInChIKey = WYNZPDDTQGVCLZ-UHFFFAOYSA-N
}}
}}


'''JWH-307''' is an [[analgesic]] drug used in scientific research, which acts as a [[cannabinoid]] agonist at both the [[cannabinoid receptor 1|CB<sub>1</sub>]] and [[cannabinoid receptor 2|CB<sub>2</sub>]] [[Receptor (biochemistry)|receptors]]. It is somewhat selective for the CB<sub>2</sub> subtype, with a [[Dissociation constant|Ki]] of 7.7nM at CB<sub>1</sub> vs 3.3nM at CB<sub>2</sub>.<ref>Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB<sub>1</sub> and CB<sub>2</sub> receptors. ''Bioorganic & Medicinal Chemistry Letters'' 2006; 16:5432-5435.</ref> It was discovered by, and named after, Dr. [[John W. Huffman]].
'''JWH-307''' is an [[analgesic]] drug used in scientific research, which acts as a [[cannabinoid]] agonist at both the [[cannabinoid receptor 1|CB<sub>1</sub>]] and [[cannabinoid receptor 2|CB<sub>2</sub>]] [[Receptor (biochemistry)|receptors]]. It is somewhat selective for the CB<sub>2</sub> subtype, with a [[Dissociation constant|K<sub>i</sub>]] of 7.7&nbsp;nM at CB<sub>1</sub> vs 3.3&nbsp;nM at CB<sub>2</sub>.<ref>Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB<sub>1</sub> and CB<sub>2</sub> receptors. ''Bioorganic & Medicinal Chemistry Letters'' 2006; 16:5432-5435.</ref> It was discovered by, and named after, [[John W. Huffman]]. JWH-307 was detected as an ingredient in [[synthetic cannabis]] smoking blends in 2012, initially in Germany.<ref>{{cite journal | vauthors = Ernst L, Krüger K, Lindigkeit R, Schiebel HM, Beuerle T | title = Synthetic cannabinoids in "spice-like" herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market | journal = Forensic Science International | volume = 222 | issue = 1–3 | pages = 216–22 | date = October 2012 | pmid = 22748479 | doi = 10.1016/j.forsciint.2012.05.027 }}</ref><ref>{{cite journal | vauthors = Kneisel S, Auwärter V | title = Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction | journal = Journal of Mass Spectrometry | volume = 47 | issue = 7 | pages = 825–35 | date = July 2012 | pmid = 22791249 | doi = 10.1002/jms.3020 | bibcode = 2012JMSp...47..825K }}</ref>


In the United States, CB<sub>1</sub> receptor agonists of the 3-(1-naphthoyl)pyrrole class such as JWH-307 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>
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{{cannabinoid-stub}}


==References==
== See also ==
* [[JWH-147]]
<references/>


== References ==
{{reflist}}


{{Cannabinoids}}
{{Cannabinoids}}
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{{cannabinoid-stub}}



[[Category:Naphthoylpyrroles]]
[[Category:Naphthoylpyrroles]]
[[Category:Organofluorides]]
[[Category:JWH cannabinoids]]
[[Category:2-Fluorophenyl compounds]]
[[Category:CB1 receptor agonists]]
[[Category:CB2 receptor agonists]]
[[Category:Pentyl compounds]]

Latest revision as of 09:18, 5 September 2024

JWH-307
Legal status
Legal status
Identifiers
  • (5-(2-Fluorophenyl)-1-pentylpyrrol-3-yl)-naphthalen-1-ylmethanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H24FNO
Molar mass385.482 g·mol−1
3D model (JSmol)
  • CCCCCN1C=C(C=C1C2=CC=CC=C2F)C(=O)C3=CC=CC4=CC=CC=C43
  • InChI=1S/C26H24FNO/c1-2-3-8-16-28-18-20(17-25(28)23-13-6-7-15-24(23)27)26(29)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3
  • Key:WYNZPDDTQGVCLZ-UHFFFAOYSA-N
  (verify)

JWH-307 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 7.7 nM at CB1 vs 3.3 nM at CB2.[1] It was discovered by, and named after, John W. Huffman. JWH-307 was detected as an ingredient in synthetic cannabis smoking blends in 2012, initially in Germany.[2][3]

In the United States, CB1 receptor agonists of the 3-(1-naphthoyl)pyrrole class such as JWH-307 are Schedule I Controlled Substances.[4]

See also

[edit]

References

[edit]
  1. ^ Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors. Bioorganic & Medicinal Chemistry Letters 2006; 16:5432-5435.
  2. ^ Ernst L, Krüger K, Lindigkeit R, Schiebel HM, Beuerle T (October 2012). "Synthetic cannabinoids in "spice-like" herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market". Forensic Science International. 222 (1–3): 216–22. doi:10.1016/j.forsciint.2012.05.027. PMID 22748479.
  3. ^ Kneisel S, Auwärter V (July 2012). "Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction". Journal of Mass Spectrometry. 47 (7): 825–35. Bibcode:2012JMSp...47..825K. doi:10.1002/jms.3020. PMID 22791249.
  4. ^ 21 U.S.C. § 812: Schedules of controlled substances
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