JWH-307: Difference between revisions

JWH-307
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule I;
Identifiers
	IUPAC name (5-(2-Fluorophenyl)-1-pentylpyrrol-3-yl)-naphthalen-1-ylmethanone;
CAS Number	914458-26-7 ;
PubChem CID	16049783;
ChemSpider	13178178;
UNII	06QTR14ONW;
CompTox Dashboard (EPA)	DTXSID60581542 ;
Chemical and physical data
Formula	C26H24FNO
Molar mass	385.482 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1C=C(C=C1C2=CC=CC=C2F)C(=O)C3=CC=CC4=CC=CC=C43;
	InChI 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)

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Revision as of 14:20, 24 March 2024

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 K_i 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]

References

^ 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.
^ 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.
^ 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.
^ 21 U.S.C. § 812: Schedules of controlled substances

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

[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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[2]

[3]

[4]

@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
 {{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
@@ Line 12: / Line 13: @@
 | legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
 | legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
-| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
+| legal_US = Schedule I
+| legal_DE = Anlage II
-| legal_status = <small>{{Abbreviation|GER|Germany}}:</small> [[Drugs controlled by the German Betäubungsmittelgesetz|Anlage II]]
 | routes_of_administration =
@@ Line 26: / Line 27: @@
 | CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 914458-26-7
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 06QTR14ONW
 | ATC_prefix =
 | ATC_suffix =
@@ Line 35: / Line 38: @@
 <!--Chemical data-->
 | C=26 | H=24 | F=1 | N=1 | O=1
-| molecular_weight = 385.472 g/mol
 | smiles = CCCCCN1C=C(C=C1C2=CC=CC=C2F)C(=O)C3=CC=CC4=CC=CC=C43
-| InChI             = 1/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
-| InChIKey          = WYNZPDDTQGVCLZ-UHFFFAOYAK
 | 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 was detected as an ingredient in [[synthetic cannabis]] smoking blends in 2012, initially in Germany.<ref>{{Cite journal
+'''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>
-| last1 = Ernst | first1 = L.
-| last2 = Krüger | first2 = K.
-| last3 = Lindigkeit | first3 = R.
-| last4 = Schiebel | first4 = H. M.
-| last5 = Beuerle | first5 = T.
-| title = Synthetic cannabinoids in "spice-like" herbal blends: First appearance of JWH-307 and recurrence of JWH-018 on the German market
-| doi = 10.1016/j.forsciint.2012.05.027
-| journal = Forensic Science International
-| year = 2012
-| pmid = 22748479
-| pmc = | volume=222 | issue=1–3 | pages=216–22
-}}</ref><ref>{{Cite journal
-| last1 = Kneisel | first1 = S.
-| last2 = Auwärter | first2 = V.
-| doi = 10.1002/jms.3020
-| 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 = 825–835
-| year = 2012
-| pmid = 22791249
-| pmc =
-}}</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>
-==See also==
+== See also ==
 * [[JWH-147]]
-==References==
+== References ==
+{{reflist}}
-<references/>
 {{Cannabinoids}}
@@ Line 80: / Line 58: @@
 [[Category:Naphthoylpyrroles]]
 [[Category:JWH cannabinoids]]
-[[Category:Organofluorides]]
+[[Category:Fluoroarenes]]
+[[Category:CB1 receptor agonists]]
+[[Category:CB2 receptor agonists]]
+[[Category:Pentyl compounds]]